Structure

InChI Key DQCKKXVULJGBQN-XFWGSAIBSA-N
Smiles O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
InChI
InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H23NO4
Molecular Weight 341.41
AlogP 1.53
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 70.0
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Opioid receptors; mu/kappa/delta antagonist ANTAGONIST DailyMed
Protein: Opioid receptors; mu/kappa/delta

Description: Mu-type opioid receptor

Organism : Homo sapiens

P35372 ENSG00000112038
Protein: Opioid receptors; mu/kappa/delta

Description: Delta-type opioid receptor

Organism : Homo sapiens

P41143 ENSG00000116329
Protein: Opioid receptors; mu/kappa/delta

Description: Kappa-type opioid receptor

Organism : Homo sapiens

P41145 ENSG00000082556
Assay Description Organism Bioactivity Reference
Tested for potent reversible agonist activity on electrically stimulated guinea pig ileal longitudinal muscle preparation Cavia porcellus 50.0 nM
Opioid agonistic activity was measured in guinea pig ileum Cavia porcellus 25.0 %
Tested for the binding affinity against the Mu opioid receptor in guinea pig brain using [3H]-DAMGO Cavia porcellus 0.23 nM
Binding affinity was determined against Mu opioid receptor using [3H]naltrexone as radioligand Cavia porcellus 0.56 nM
Compound was tested for the inhibition of [35S]GTP-gamma-S, binding in Guinea pig Caudate stimulated by the opioid receptor agonist Mu-DAMGO Cavia porcellus 0.93 nM
Tested for binding affinity towards mu receptor in presence of [3H]NAL radioligand None 0.56 nM
Binding affinity determined on Opioid receptor mu 1 in Guinea pig brain membranes using radioligand [3H]DAMGO Cavia porcellus 1.39 nM
Displacement of 0.5 nM [3H]bremazocine from guinea pig brain membrane opioid receptor kappa with 100 nM DAGO and 100 nM DPDPE Cavia porcellus 9.5 nM
Inhibition of opioid receptor kappa by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane Cavia porcellus 9.5 nM
Displacement of [3H]bremazocine from opioid receptor kappa of guinea pig membrane. Cavia porcellus 9.5 nM
Binding affinity was measured by the displacement of [3H]- EK in guinea pig brain membrane of opioid receptor kappa Cavia porcellus 20.0 nM
Displacement of [3H]U-69593 from human recombinant Opioid receptor kappa 1 on CHO cell membranes. None 0.4 nM
Binding affinity in recombinant human Opioid receptor kappa 1 transfected into chinese hamster ovary cells by displacing [3H]U-69593 radioligand Homo sapiens 0.4 nM
Binding affinity against Opioid receptor mu 1 in Guinea pig brain membranes using [3H]DAMGO Cavia porcellus 0.75 nM
Binding affinity towards Opioid receptor mu 1 of guinea pig brain membranes using radioligand 0.25 nM [3H]DAMGO Cavia porcellus 0.17 nM
Binding affinity was determined in a crude membrane preparation from guinea pig brain by displacement of [3H]DAMGO from Opioid receptor mu 1 Cavia porcellus 0.8 nM
Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig brain membrane of Opioid receptor mu 1 Cavia porcellus 0.8 nM
Compound was evaluated for binding affinity at Opioid receptor mu 1 in guinea pig brain membranes Cavia porcellus 0.8 nM
Binding affinity against Opioid receptor mu 1 of guinea pig brain membranes using 0.5 nM of [3H]naloxone as radioligand Cavia porcellus 0.37 nM
Inhibition of [35S]GTP-gamma-S, binding in guinea pig caudate stimulated by DAMGO (Opioid receptor mu 1) Cavia porcellus 0.93 nM
Inhibition of [35S]GTP-gamma-S, binding from Opioid receptor mu 1 in Guinea pig Caudate stimulated by DAMGO Cavia porcellus 0.93 nM
Inhibition of binding of [3H]DAMGO to Opioid receptor mu 1 in guinea pig membranes Cavia porcellus 1.39 nM
Inhibitory binding constant in guinea pig brain homogenate was reported at mu site at a temperature 25 degree Centigrade labeled with [3H](D-Ala2-MePhe4,Gly-ol5)enkephalin(1 nM) Cavia porcellus 1.08 nM
Agonistic activity towards Opioid receptor delta 1 Homo sapiens 5.44 nM
Stimulation of [35S]GTP-gamma-S, binding at human recombinant Opioid receptor delta 1 transfected into CHO cells. None 5.44 Ke nM-1
Compound was evaluated for the binding affinity to opioid receptor kappa using [3H]EK as radioligand in guinea pig brain membrane Cavia porcellus 198.0
The compound was tested for antagonist activity by selective inhibition of [35S]GTP-gamma-S, binding to Opioid receptor mu 1 in Guinea pig caudate stimulated by DAMGO[mu] Cavia porcellus 0.93 nM
Displacement of [3H]C1-DPDPE from human recombinant Opioid receptor delta 1 on CHO cell membranes. None 10.8 nM
Binding affinity for human Opioid receptor delta 1 transfected into chinese hamster ovary cells by displacing [3H]CI-DPDPE radioligand Homo sapiens 10.8 nM
Effective concentration agonistic activity towards Opioid receptor mu 1 Homo sapiens 0.59 nM
Stimulation of DAMGO binding in recombinant human Opioid receptor mu 1 transfected into CHO cells None 0.59 Ke nM-1
Inhibition of total opioid receptor by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane Cavia porcellus 5.7 nM
Displacement of [3H]diprenorphine from k-E297A-receptor expressed in HEK 293 cells None 1.8 nM
Displacement of [3H]diprenorphine from k-Y312A-receptor expressed in HEK 293 cells None 12.7 nM
Displacement of [3H]diprenorphine from opioid receptor kappa 1 expressed in HEK 293 cells None 4.2 nM
Tested for the binding affinity against the opioid receptor in guinea pig brain using [3H]bremazocine Cavia porcellus 3.8 nM
Inhibition of 0.5 nM [3H]bremazocine binding to guinea pig brain membrane opioid receptors Cavia porcellus 5.7 nM
Displacement of [3H]bremazocine from opioid receptor of guinea pig membrane Cavia porcellus 5.7 nM
Inhibitory concentration against Opioid receptor kappa 1 using [3H]- U-69,593 radioligand Cavia porcellus 0.5 nM
Tested for the binding affinity against the Kappa opioid receptor in guinea pig brain using [3H]U-69593 Cavia porcellus 0.53 nM
Binding affinity against Opioid receptor kappa 1 using [3H]ethylketocyclazocine as radioligand. None 3.9 nM
In vito concentration required to displace [3H]BRM (Kd = 1.0 nM and concentration is 1.8 nM) from opioid receptor kappa 2 in guinea brain membranes. Cavia porcellus 5.97 nM
In vito concentration required to displace [3H]BRM (Kd = 1.0 nM and concentration is 1.8 nM) from opioid receptor kappa 2 in guinea brain membranes. Cavia porcellus 47.2 nM
inhibition of 1.0 nM [3H]- DAGO binding to guinea pig brain membrane opioid receptor mu Cavia porcellus 0.73 nM
Inhibition of opioid receptor mu by displacing 1 nM [3H]DAGO in guinea pig brain membrane Cavia porcellus 0.73 nM
Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig brain membrane of opioid receptor mu Cavia porcellus 0.8 nM
Inhibition of [3H]naloxone binding to opioid receptor in presence of NaCl None 0.62 nM
Displacement of [3H]- diprenorphine from delta-W284E-receptor expressed in HEK 293 cells None 55.7 nM
Displacement of [3H]- diprenorphine from delta-receptor expressed in HEK 293 cells None 44.7 nM
Binding activity against Opioid receptor kappa 1 using [3H]U-69593 as radioligand in guinea pig membranes. Cavia porcellus 4.71 nM
Binding affinity at Opioid receptor kappa 1 by displacement of [3H]U-69593 in guinea pig brain membranes Cavia porcellus 2.2 nM
Binding affinity determined on Opioid receptor kappa 1 in Guinea pig brain membranes using radioligand [3H]U-69593 Cavia porcellus 4.71 nM
Binding affinity against Kappa Opioid receptor in Guinea pig brain membranes using [3H]-DAMGO+EKC Cavia porcellus 36.0 nM
Compound was evaluated for the binding affinity to Opioid receptor mu using [3H]DAMGO as radioligand in guinea pig brain membrane Cavia porcellus 7.6
In vito concentration required to displace [3H]DAGO (Kd = 0.7 nM and concentration is 1.7 nM) from opioid receptor mu in rat brain membranes. None 4.04 nM
Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig brain membrane of opioid receptor delta Cavia porcellus 36.0 nM
Compound was evaluated for the binding affinity to opioid receptor delta using [3H]DADLE as radioligand in guinea pig brain membrane Cavia porcellus 364.0
Binding affinity towards guinea pig Opioid receptor kappa 1 using radioligand [3H]U-69593 Cavia porcellus 0.31 nM
Binding affinity was determined towards opioid receptor kappa 1 using [3H]U-69593 as radioligand Cavia porcellus 0.31 nM
Binding affinity was determined against Opioid receptor kappa 1<br>using [3H]ethylketocyclazocine as radioligand Cavia porcellus 3.9 nM
Binding affinity was determined as ability to displace [3H]-U-69, radioligand from Opioid receptor kappa 1 Cavia porcellus 4.71 nM
Binding affinity was determined in a crude membrane preparation from guinea pig brain by displacement of [3H]U-69593 from Opioid receptor kappa 1 Cavia porcellus 1.1 nM
Binding affinity was measured by the displacement of [3H]- EK in guinea pig brain membrane of Opioid receptor kappa 1 Cavia porcellus 20.0 nM
Compound was evaluated for binding affinity of Opioid receptor kappa 1 in guinea pig brain membranes Cavia porcellus 20.0 nM
In vito concentration required to displace [3H]DAGO (Kd = 0.7 nM and concentration is 1.7 nM) from opioid receptor mu in rat brain membranes. None 1.18 nM
In vito concentration required to displace [3H]cyclofoxy (Kd = 0.8 nM and concentration is 1.3 nM) from mu and kappa2 receptor in rat brain membranes. Rattus norvegicus 6.77 nM
In vito concentration required to displace [3H]cyclofoxy (Kd = 0.8 nM and concentration is 1.3 nM) from mu and kappa2 receptor in rat brain membranes. Rattus norvegicus 2.57 nM
In vito concentration required to displace [3H]DADLE (Kd = 1.6 nM and concentration is 1.9 nM) from high affinity delta-site in rat brain membranes. None 221.0 nM
In vito concentration required to displace [3H]-DADLE (Kd = 12.2 nM and concentration is 2.1 nM) from low affinity delta-site in rat brain membranes. None 5.57 nM
In vito concentration required to displace [3H]DADLE (Kd = 1.6 nM and concentration is 1.9 nM) from high affinity delta-site in rat brain membranes. None 101.0 nM
In vito concentration required to displace [3H]DADLE (Kd = 12.2 nM and concentration is 2.1 nM) from low affinity delta-site in rat brain membranes. None 4.75 nM
Binding affinity against Opioid receptor kappa 1 of guinea pig brain membranes using 1 nM of (-)-[3H]ethylketazocine as radioligand Cavia porcellus 4.8 nM
Compound was tested for the inhibition of [35S]GTP-gamma-S, binding to Opioid receptor kappa 1 Cavia porcellus 2.05 nM
In vito concentration required to displace 9 (Kd = 1.6 nM and concentration is 1.8 nM) from opioid receptor kappa 1 in guinea brain membranes. Cavia porcellus 2.81 nM
Inhibition of [35S]GTP-gamma-S, binding in guinea pig caudate stimulated by U69,593 in Opioid receptor kappa 1 Cavia porcellus 2.05 nM
Inhibition of [35S]GTP-gamma-S, binding from Opioid receptor kappa 1 in Guinea pig Caudate stimulated by U69,593 Cavia porcellus 2.05 nM
Inhibition of [3H]U-69593 binding to Opioid receptor kappa 1 of guinea pig membranes Cavia porcellus 4.71 nM
Inhibition of binding of [3H]U69, 593 to Opioid receptor kappa 1 in guinea pig membranes Cavia porcellus 4.71 nM
Inhibitory binding constant in guinea pig brain homogenate was reported at Opioid receptor kappa 1 at temperature 25 degree Celsius labeled with (-)-[3H]immazocine (0.1 nM). Cavia porcellus 8.5 nM
Opioid receptor kappa 1 apparent binding constant from guinea pig cerebellum using [3H]diprenorphine binding assay Cavia porcellus 8.7 nM
Tested for binding affinity towards kappa receptor in presence of [3H]EKC radioligand Cavia porcellus 6.0 nM
Binding affinity for Opioid receptor kappa 1 was determined by inhibition of binding of [3H]U-69593 (1.2-2.2 nM) to guinea pig brain membranes Cavia porcellus 7.0 nM
The compound was tested for antagonist activity by selective inhibition of [35S]GTP-gamma-S, binding in Guinea pig caudate stimulated by U69,593 to Opioid receptor kappa 1 Cavia porcellus 2.06 nM
Inhibition of [3H]DPDPE binding to guinea pig brain membrane Opioid receptor delta 1 at 1.0 nM Cavia porcellus 15.0 nM
Inhibition of Opioid receptor delta 1 by displacing 1 nM [3H]DPDPE in guinea pig brain membrane Cavia porcellus 15.0 nM
Binding activity against Opioid receptor delta 1 using [3H]DADLE as radioligand in rat brain membranes. None 94.9 nM
Binding affinity at opioid receptor delta 1 by displacement of [3H]DADLE in rat brain membrane None 7.5 nM
Inhibitory concentration was determined against delta-opioid receptor using [3H]- DPDPE radioligand Cavia porcellus 10.0 nM
Tested for the binding affinity against the Delta opioid receptor in guinea pig brain using [3H]DPDPE Cavia porcellus 10.0 nM
Binding affinity determined on Opioid receptor delta 1 in Guinea pig brain membranes using radioligand [3H]DADLE Cavia porcellus 94.9 nM
Binding affinity was determined as ability to displace [3H]DADLE radioligand from Opioid receptor delta 1 None 94.9 nM
Inhibitory concentration was determined against Opioid receptor mu 1 using [3H]- DAMGO radioligand Cavia porcellus 0.2 nM
Binding affinity against Delta Opioid receptor in Guinea pig brain membranes using [3H]DAMGO+DADLE Cavia porcellus 20.0 nM
Binding affinity towards Opioid receptor delta 1 of guinea pig brain membranes using radioligand 0.2 nM [3H]Naltrindole Cavia porcellus 11.0 nM
Binding affinity was determined towards Opioid receptor delta 1 using [3H]naltrindole as radioligand Cavia porcellus 11.0 nM
Binding affinity was determined in a crude membrane preparation from guinea pig brain by displacement of [3H]DPDPE from Opioid receptor delta 1 Cavia porcellus 11.0 nM
Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig brain membrane of Opioid receptor delta 1 Cavia porcellus 36.0 nM
Compound was evaluated for binding affinity at Opioid receptor delta 1 in guinea pig brain membranes Cavia porcellus 36.0 nM
Binding affinity against Opioid receptor delta 1 of guinea pig brain membranes using 1 nM of [3H]DADLE as radioligand Cavia porcellus 9.4 nM
Compound was tested for the inhibition of [35S]GTP-gamma-S, binding in Guinea pig Caudate stimulated by the Opioid receptor delta 1 agonist Delta-SNC80 Cavia porcellus 19.3 nM
Inhibition of [3H]-DADLE binding to Opioid receptor delta 1 of rat brain membranes Rattus norvegicus 94.9 nM
Opioid receptor delta 1 apparent binding constant from rat brain membranes using [3H]DADLE binding assay Rattus norvegicus 6.7 nM
Binding affinity for Opioid receptor delta 1 was determined by inhibition of binding of [3H]DADLE (1.3-2.0 nM) to rat brain membranes None 39.5 nM
In vito concentration required to displace 9 (Kd = 1.6 nM and concentration is 1.8 nM) from opioid receptor kappa 1 in guinea brain membranes. Cavia porcellus 16.8 nM
Agonistic activity towards Opioid receptor kappa 1 Homo sapiens 1.86 nM
Stimulation of U-69,593 binding at human recombinant Opioid receptor kappa 1 transfected into CHO cells. None 1.86 Ke nM-1
Inhibition of [35S]GTP-gamma-S, binding in guinea pig caudate stimulated by SNC80 (Opioid receptor delta 1) Cavia porcellus 19.3 nM
Inhibition of [35S]GTP-gamma-S, binding from Opioid receptor delta 1 in Guinea pig Caudate stimulated by SNC80 Cavia porcellus 19.3 nM
Inhibition of binding of [3H]DADLE to Opioid receptor delta 1 in guinea pig membranes Cavia porcellus 94.9 nM
Inhibitory binding constant in guinea pig brain homogenate was reported at Opioid receptor delta 1 at a a temperature 25 degree Celsius labeled with [3H](D-Ala2-D-Leu5)-enkephalin (0.7 nM) Cavia porcellus 6.6 nM
The compound was tested for antagonist activity by selective inhibition of [35S]GTP-gamma-S, binding in Guinea pig caudate stimulated by SMC-80 (Opioid receptor delta 1) Cavia porcellus 19.3 nM
Inhibitory concentration was determined against Opioid receptors using [3H]- bremazocine radioligand Cavia porcellus 3.8 nM
Inhibition of [3H]naloxone binding to opioid receptor in presence of NaCl None 0.5 nM
Inhibition of stereospecific [3H]diprenorphine binding to opioid receptors of rat brain homogenates by 50% in the absence of Na None 22.0 nM
Inhibition of stereospecific [3H]diprenorphine binding to opioid receptors of rat brain homogenates by 50% in the presence of Na None 14.0 nM
Inhibition of [3H]diprenorphine binding to rat brain membrane opioid receptors;(T= total opioid receptor family) Rattus norvegicus 0.55 nM
Displacement of [3H]DAMGO from human recombinant Opioid receptor mu 1 on CHO cell membranes. None 0.2 nM
Binding affinity for human Opioid receptor mu 1 transfected into chinese hamster ovary cells by displacing [3H]DAMGO radioligand Homo sapiens 0.2 nM
Evaluated for the inhibition of [3H]naltrexone binding to Opioid receptor mu 1 in rat brain homogenates. None 1.5 nM
Binding activity against Opioid receptor mu 1 using [3H]DAMGO as radioligand in rat brain membranes. None 1.39 nM
Binding affinity at Opioid receptor mu 1 by displacement of [3H]DAMGO in rat brain membrane None 2.4 nM
Inhibition of [3H]DAMGO binding to Opioid receptor mu 1 of rat brain membranes None 1.39 nM
Inhibition of [3H]DAGO binding to rat brain membrane Opioid receptor mu 1 Rattus norvegicus 1.8 nM
Binding affinity for Opioid receptor mu 1 was determined by inhibition of binding of [3H]DAMGO (1.4-3 nM) to rat brain membranes None 2.5 nM
Binding affinity against Opioid receptor mu 1 using [3H]naloxone as radioligand. None 0.56 nM
Binding affinity was determined towards opioid receptor mu1 using [3H]DAMGO as radioligand Cavia porcellus 0.17 nM
Displacement of [3H]- diprenorphine from mu-K303E-receptor expressed in HEK 293 cells None 2.0 nM
Displacement of [3H]- diprenorphine from mu-W318A-receptor expressed in HEK 293 cells None 2.5 nM
Displacement of [3H]- diprenorphine from mu-receptor expressed in HEK 293 cells None 1.6 nM
Inhibition of [3H]DADLE binding to opioid receptor Cavia porcellus 12.0 nM
Inhibition of [3H]fluadom binding to opioid receptor Cavia porcellus 2.6 nM
Binding affinity towards kappa-opioid receptor by displacement of [3H]-EKC at from guinea pig cortical tissue Cavia porcellus 3.9 nM
Binding affinity towards kappa opioid receptor by displacement of [3H]EKC in guinea pig cortical tissue Cavia porcellus 6.0 nM
Binding affinity towards mu-opioid receptor by the displacement of [3H]Nal in rat brain homogenates None 0.56 nM
Binding affinity was determined as ability to displace [3H]DAMGO radioligand from Mu opioid receptor None 1.39 nM
Binding affinity towards mu opioid receptor by displacement of [3H]NAL from rat brain homogenates None 0.56 nM
Ratio of kappa/delta-opioid receptors Binding affinity Homo sapiens 0.04 nM
Ratio of mu/delta-opioid receptors Binding affinity Homo sapiens 0.02 nM
Binding affinity against Opioid receptor mu 1 expressed in CHO cells using [3H]DAMGO as radioligand Homo sapiens 0.11 nM
Binding affinity against Opioid receptor kappa 1 expressed in CHO cells using [3H]U-69593 as radioligand Homo sapiens 0.19 nM
Binding affinity against Opioid receptor delta 1 expressed in CHO cells using [3H]Naltrindole as radioligand Homo sapiens 60.0 nM
Inhibition of [3H]DAMGO binding to human Mu opioid receptor expressed in CHO cells Homo sapiens 0.2 nM
Inhibition of [3H]U-69593 binding to human kappa opioid receptor expressed in CHO cells Homo sapiens 0.4 nM
Inhibition of [3H]C1-DPDPE binding to human delta opioid receptor expressed in CHO cells Homo sapiens 10.8 nM
Displacement of [3H]DAMGO from human recombinant MOR expressed in CHO cells Homo sapiens 0.2 nM
Displacement of [3H]Cl-DPDPE from human recombinant DOR expressed in CHO cells Homo sapiens 10.8 nM
Displacement of [3H]U-69593 from human recombinant KOR expressed in CHO cells Homo sapiens 0.4 nM
Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in CHO cells Homo sapiens 0.2 nM
Displacement of [3H]U-69593 from human recombinant kappa opioid receptor expressed in CHO cells Homo sapiens 0.4 nM
Displacement of [3H]Cl-DPDPE from human recombinant delta opioid receptor expressed in CHO cells Homo sapiens 10.8 nM
Displacement of [3H]DAMGO from mu opioid receptor in guinea pig brain homogenate Cavia porcellus 0.4 nM
Displacement of [3H]U-69593 from kappa opioid receptor in guinea pig brain homogenate Cavia porcellus 0.6 nM
Displacement of [3H]Cl-DPDPE from delta receptor in guinea pig brain homogenate Cavia porcellus 6.5 nM
Activity at human recombinant mu opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTP-gamma-S binding Homo sapiens 0.59 nM
Activity at human recombinant delta opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTP-gamma-S binding Homo sapiens 5.44 nM
Activity at human recombinant kappa opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTP-gamma-S binding Homo sapiens 1.86 nM
Displacement of [3H]diprenorphine from human cloned mu opioid receptor expressed in CHO cells Homo sapiens 1.0 nM
Displacement of [3H]diprenorphine from human cloned kappa opioid receptor expressed in CHO cells Homo sapiens 4.4 nM
Displacement of [3H]diprenorphine from human cloned delta opioid receptor expressed in CHO cells Homo sapiens 14.0 nM
Antagonist activity assessed as inhibition of loperamide-stimulated [35S]GTPgammaS binding to human mu opioid receptor expressed in CHO cells Homo sapiens 4.1 nM
Displacement of [3H]diprenorphine from human cloned mu opioid receptor expressed in CHO cells Homo sapiens 1.0 nM
Displacement of [3H]diprenorphine from human cloned kappa opioid receptor expressed in CHO cells Homo sapiens 4.4 nM
Displacement of [3H]diprenorphine from human cloned delta opioid receptor expressed in CHO cells Homo sapiens 14.0 nM
Antagonist activity against human cloned mu opioid receptor expressed in CHO cells assessed as inhibition of loperamide-stimulated [35S]GTP-gamma-S binding Homo sapiens 4.1 nM
Displacement of [3H]DAMGO from human opioid gamma receptor expressed in CHO cells Homo sapiens 0.23 nM
Displacement of [3H]U-69593 from human opioid kappa receptor expressed in CHO cells Homo sapiens 0.25 nM
Displacement of [3H]naltrindole from human opioid delta receptor expressed in CHO cells Homo sapiens 38.0 nM
Antagonist activity at human opioid kappa receptor expressed in CHO cells assessed as inhibition of U-50488-stimulated [35S]GTP-gamma-S binding Homo sapiens 200.0 nM
Agonist activity at human opioid gamma receptor expressed in CHO cells assessed as inhibition of DAGO-stimulated [35S]GTPgammaS binding Homo sapiens 17.0 nM
Displacement of [3H]DAMGO from human cloned mu opioid receptor Homo sapiens 0.2 nM
Displacement of [3H]U-69593 from human cloned kappa opioid receptor Homo sapiens 0.4 nM
Displacement of [3H]DPDPE from human cloned delta opioid receptor Homo sapiens 10.8 nM
Antagonist activity at human mu opioid receptor expressed in CHO cells by [35S]GTP-gamma-S binding assay Homo sapiens 0.59 nM
Antagonist activity at human kappa opioid receptor expressed in CHO cells by [35S]GTP-gamma-S binding assay Homo sapiens 2.99 nM
Antagonist activity at human delta opioid receptor expressed in CHO cells by [35S]GTP-gamma-S binding assay Homo sapiens 11.06 nM
Displacement of [3H]diprenorphine from human mu opioid receptor expressed in CHO cells in presence of high sodium by SPA Homo sapiens 0.87 nM
Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cells in presence of high sodium by SPA Homo sapiens 5.28 nM
Displacement of [3H]bremazocine from human delta opioid receptor expressed in CHO cells in presence of high sodium by SPA Homo sapiens 16.31 nM
Displacement of [3H]diprenorphine from cloned human mu opioid receptor expressed in CHO cells Homo sapiens 0.87 nM
Displacement of [3H]diprenorphine from cloned human kappa opioid receptor expressed in CHO cells Homo sapiens 5.28 nM
Displacement of [3H]bremazocine from cloned human delta opioid receptor expressed in CHO cells Homo sapiens 16.31 nM
Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells Homo sapiens 0.3 nM
Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO cells Homo sapiens 16.31 nM
Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cells Homo sapiens 0.81 nM
Activity at human mu opioid receptor by [35S]GTPgammaS binding assay Homo sapiens 0.05012 nM
Activity at human delta opioid receptor by [35S]GTPgammaS binding assay Homo sapiens 1.585 nM
Displacement of [3H]etorphine from opioid receptor in rat cerebrum Rattus norvegicus 0.63 nM
Displacement of 3.0 nM [3H]etorphine from opioid receptor in rat cerebrum Rattus norvegicus 2.0 nM
Antagonist activity at mu opioid receptor in Swiss mouse vas deferens assessed as reversal of Sufentanil effect on electrically-induced driven twitch Mus musculus 1.738 nM
Antagonist activity at kappa opioid receptor in Swiss mouse vas deferens assessed as reversal of U50488 effect on electrically-induced driven twitch Mus musculus 18.2 nM
Antagonist activity at delta opioid receptor in Swiss mouse vas deferens assessed as reversal of DSLET effect on electrically-induced driven twitch Mus musculus 38.9 nM
Displacement of [3H]naloxone from monocloned mu opioid receptor expressed in CHO cells None 0.26 nM
Displacement of [3H]NTI from monocloned delta opioid receptor expressed in CHO cells None 117.06 nM
Displacement of [3H]norBNI from monocloned kappa opioid receptor expressed in CHO cells None 5.15 nM
Binding affinity to mu opioid receptor in guinea pig forebrain Cavia porcellus 0.335 nM
Binding affinity to kappa opioid receptor in guinea pig cerebellum Cavia porcellus 0.373 nM
Binding affinity to delta opioid receptor in guinea pig forebrain Cavia porcellus 20.7 nM
Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum Cavia porcellus 0.373 nM
Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain Cavia porcellus 0.325 nM
Displacement of [3H]NTI from delta opioid receptor in guinea pig forebrain Cavia porcellus 20.7 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 40.3 %
Displacement of [3H]DAMGO from mu opioid receptor in Hartley guinea pig brain membrane Cavia porcellus 0.4 nM
Displacement of [3H]DAMGO from delta opioid receptor in Hartley guinea pig brain membrane Cavia porcellus 6.5 nM
Displacement of [3H]U69,593 from kappa opioid receptor in Hartley guinea pig brain membrane Cavia porcellus 0.6 nM
Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells Homo sapiens 0.2 nM
Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO cells Homo sapiens 11.0 nM
Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO cells Homo sapiens 0.4 nM
Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells Homo sapiens 0.11 nM
Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CHO cells Homo sapiens 60.0 nM
Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cells Homo sapiens 0.19 nM
Displacement of [3H]DAMGO from mu opioid receptor expressed in CHO cells None 0.26 nM
Displacement of [3H]NTI from delta opioid receptor expressed in CHO cells None 117.0 nM
Displacement of [3H]norBNI from kappa opioid receptor expressed in CHO cells None 5.15 nM
Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells after 60 mins by scintillation counting Homo sapiens 0.11 nM
Displacement of [3H]naltrindole from human delta opioid receptor expressed in CHO cells after 3 hrs by scintillation counting Homo sapiens 60.0 nM
Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO cells after 60 mins by scintillation counting Homo sapiens 0.19 nM
Agonist activity at human mu opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 16.0 nM
Agonist activity at human delta opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 21.0 nM
Agonist activity at human kappa opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 3.3 nM
Antagonist activity against human mu opioid receptor expressed in CHO cells assessed as inhibition of DAMGO-stimulated [35S]GTPgammaS binding Homo sapiens 4.8 nM
Antagonist activity against human delta opioid receptor expressed in CHO cells assessed as inhibition of SNC80-stimulated [35S]GTPgammaS binding Homo sapiens 130.0 nM
Antagonist activity against human kappa opioid receptor expressed in CHO cells assessed as inhibition of U50488-stimulated [35S]GTPgammaS binding Homo sapiens 130.0 nM
Displacement of [3H]DAMGO from mu opioid receptor expressed in HEK293 cells by visible spectrophotometry None 0.3 nM
Displacement of [3H]DPDPE from delta opioid receptor expressed in HEK293 cells by visible spectrophotometry None 16.31 nM
Displacement of [3H]U69593 from kappa opioid receptor expressed in HEK293 cells by visible spectrophotometry None 0.81 nM
Antagonist activity at mu opioid receptor expressed in HEK293 cells assessed as inhibition of compound 11-induced [35S]GTPgammaS binding None 3.6 nM
Antagonist activity at delta opioid receptor expressed in HEK293 cells assessed as inhibition of compound 14-induced [35S]GTPgammaS binding None 66.8 nM
Antagonist activity at kappa opioid receptor expressed in HEK293 cells assessed as inhibition of compound 16-induced [35S]GTPgammaS binding None 0.042 nM
Displacement of [3H]U69593 from guinea pig cerebellum kappa opioid receptor Cavia porcellus 0.373 nM
Displacement of [3H]NTI from guinea pig forebrain delta opioid receptor Cavia porcellus 20.7 nM
Displacement of [3H]DAMGO from guinea pig forebrain mu opioid receptor Cavia porcellus 0.335 nM
Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain Cavia porcellus 0.335 nM
Displacement of [3H]NTI from delta opioid receptor in guinea pig forebrain Cavia porcellus 0.373 nM
Displacement of [3H]U69,593 from kappa opioid receptor in guinea pig cerebellum Cavia porcellus 44.2 nM
Displacement of [3H]DAMGO from mu opioid receptor in Hartley guinea pig forebrain by liquid scintillation counting Cavia porcellus 0.335 nM
Displacement of [3H]U69493 from kappa opioid receptor in Hartley guinea pig cerebellum by liquid scintillation counter Cavia porcellus 0.373 nM
Displacement of [3H]NTI from delta opioid receptor in Hartley guinea pig forebrain by liquid scintillation counter Cavia porcellus 44.2 nM
Antagonist activity at human mu opioid receptor expressed in CHO cells assessed as [35S]GTPgammaS binding by SPA Homo sapiens 1.995 nM
Antagonist activity at human delta opioid receptor expressed in CHO cells assessed as [35S]GTPgammaS binding by SPA Homo sapiens 25.12 nM
Antagonist activity at human kappa opioid receptor expressed in CHO cells assessed as [35S]GTPgammaS binding by SPA Homo sapiens 10.0 nM
Displacement of [125I]-IBNtxA from MOR-1 expressed in CHO cells None 1.15 nM
Displacement of [125I]-IBNalA from MOR-1 expressed in CHO cells None 2.71 nM
Displacement of [125I]-IBOxyA from MOR-1 expressed in CHO cells None 0.07 nM
Displacement of [3H]-DAMGO from mu opioid receptor in guinea pig forebrain homogenates Cavia porcellus 0.335 nM
Displacement of [3H]-NTI from delta opioid receptor in guinea pig forebrain homogenates Cavia porcellus 20.7 nM
Displacement of [3H]-U69593 from kappa opioid receptor in guinea pig cerebellum homogenates Cavia porcellus 0.373 nM
Displacement of [3H]DAMGO from mouse mu opioid receptor in whole brain without cerebellum Mus musculus 0.265 nM
Displacement of [3H]DPDPE from mouse delta opioid receptor in whole brain without cerebellum Mus musculus 12.27 nM
Displacement of [3H]U69,593 from guinea pig kappa opioid receptor in cerebellum Cavia porcellus 0.702 nM
DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 251.0 nM DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 88.0 nM
DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine) None 18.0 nM DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine) None 7.175 nM
DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 4.083 nM DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 1.657 nM
Displacement of [3H]DAMGO from mu opioid receptor in rat brain homogenate after 1 hr by liquid scintillation counting Rattus norvegicus 0.46 nM
Displacement of [3H]DPDPE from delta opioid receptor in rat brain homogenate after 1 hr by liquid scintillation counting Rattus norvegicus 11.0 nM
Displacement of [3H]U69593 from kappa opioid receptor in rat brain homogenate after 1 hr by liquid scintillation counting Rattus norvegicus 1.07 nM
Displacement of [3H]-DAMGO from mouse MOR expressed in HEK293 cells Mus musculus 0.6457 nM
Displacement of [3H]-DAMGO from mouse MOR/DOR expressed in HEK293 cells Mus musculus 0.871 nM
Displacement of [125I]-BNtxA from Mu-type opioid receptor exon 11-associated truncated six transmembrane domain splice variant in mouse brain membranes after 90 mins Mus musculus 32.7 nM
Agonist activity at mu opioid receptor (unknown origin) expressed CHO cells assessed as stimulation of [35S]-GTP[gammaS] binding Homo sapiens 0.38 nM
Displacement of [3H]NTI from delta opioid receptor (unknown origin) after 1.5 hrs Homo sapiens 95.46 nM
Displacement of [3H]DPN from kappa opioid receptor (unknown origin) after 1.5 hrs Homo sapiens 0.9 nM
Displacement of [3H]naloxone from mu opioid receptor (unknown origin) after 1.5 hrs Homo sapiens 0.34 nM
Agonist activity at mouse mu opioid receptor expressed in CHO cells assessed as stimulation of [35S]-GTPgammaS binding after 1.5 hrs Mus musculus 0.16 nM
Displacement of [3H]-naltrindole from mouse delta opioid receptor expressed in CHO cells after 1.5 hrs Mus musculus 143.5 nM
Displacement of [3H]-diprenorphine from mouse kappa opioid receptor expressed in CHO cells after 1.5 hrs Mus musculus 1.44 nM
Displacement of [3H]-naloxone from mouse mu opioid receptor expressed in CHO cells after 1.5 hrs Mus musculus 0.33 nM
Binding affinity to wild type MOR (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 1.85 nM Binding affinity to wild type MOR (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 3.9 nM
Binding affinity to MOR Y210A mutant (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 0.45 nM Binding affinity to MOR Y210A mutant (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 0.95 nM
Binding affinity to MOR W318A mutant (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 4.91 nM Binding affinity to MOR W318A mutant (unknown origin) expressed in CHO cells after 15 mins by Ca2+ mobilization assay Homo sapiens 10.35 nM
Agonist activity at delta opioid receptor (unknown origin) expressed in CHO cell membranes assessed as stimulation of [35S]-GTPgammaS binding after 1.5 hrs Homo sapiens 4.4 nM
Displacement of [3H]NTI from delta opioid receptor (unknown origin) expressed in CHO cell membranes after 1.5 hrs Homo sapiens 95.5 nM
Displacement of [3H]DPN from kappa opioid receptor (unknown origin) expressed in CHO cell membranes after 1.5 hrs Homo sapiens 0.9 nM
Displacement of [3H]NLX from mu opioid receptor (unknown origin) expressed in CHO cell membranes after 1.5 hrs Homo sapiens 0.26 nM
Agonist activity at kappa opioid receptor (unknown origin) expressed in CHO cell membranes assessed as stimulation of [35S]-GTPgammaS binding after 1.5 hrs Homo sapiens 0.81 nM
Reduction in alcohol intake in alcohol-preferring rat at 3 mg/kg, sc after 30 mins Rattus norvegicus 21.0 %
Antagonist activity at human mu opioid receptor expressed in Gqi5 transfected CHO cells assessed as inhibition of DAMGO-stimulated Ca2+ influx preincubated for 15 mins followed by DAMGO challenge Homo sapiens 8.9 nM
Displacement of [3H]-naloxone from human mu opioid receptor expressed in CHO cells after 1 hr Homo sapiens 0.7 nM
Binding affinity to rat brain opioid receptor Rattus norvegicus 0.5 nM
Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in CHO cell membranes after 60 mins by scintillation counting method Homo sapiens 0.2 nM
Displacement of [3H]U69593 from human recombinant kappa opioid receptor expressed in CHO cell membranes after 60 mins by scintillation counting method Homo sapiens 0.4 nM
Displacement of [3H]Cl-DPDPE from human recombinant delta opioid receptor expressed in CHO cell membranes after 60 mins by scintillation counting method Homo sapiens 10.8 nM
Agonist activity at human recombinant delta opioid receptor expressed in CHO cell membranes after 60 mins by [35S]GTPgammaS binding assay Homo sapiens 5.44 nM
Displacement of [3H]diprenorphine from human recombinant mu opioid receptor expressed in HEK cells after 60 mins Homo sapiens 0.45 nM
Displacement of [3H]naloxane from mouse MOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 0.33 nM
Displacement of [3H]diprenorphine from mouse KOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 1.44 nM
Displacement of [3H]naltrindole from mouse DOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 143.5 nM
Stimulation of mouse MOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 0.16 nM
Agonist activity at mouse KOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 0.81 nM
Agonist activity at mouse DOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS binding assay Mus musculus 4.4 nM
Antagonist activity at human MOR expressed in CHO cells assessed as inhibition of DAMGO-induced increase in intracellular Ca2+ level incubated for 15 mins prior to DAMGO addition by microplate reader analysis Homo sapiens 15.5 nM
Flux Assay: As Ca2+ flux is associated with the activation of the MOR, the functional activity of bivalent ligand 1, monovalent ligand 2, and naltrexone was then evaluated in a Ca2+ mobilization assay in hMORCHO cells transfected with chimeric Ca2+ following a published protocol.23 No agonism was observed for any of the tested compounds (data not shown). Thus, they were further assessed for their antagonist properties as the ability to inhibit DAMGO (a MOR agonist) induced Ca2+ flux. Homo sapiens 8.9 nM
Radioligand Binding Assay: A bivalent ligand 1 (FIG. 14) that combines the pharmacophores of naltrexone (a MOR antagonist) and maraviroc (a CCR5 antagonist) into one molecule was designed and synthesized. Herein is reported the characterization of this novel molecular probe in for its binding affinity, Ca2− flux functional activity, and HIV-1 inhibition potency. Bivalent ligand 1 was first characterized in hMOR-expressed CHO cells in the competitive radioligand binding assay as described previously. Homo sapiens 0.7 nM
Displacement of 2-((1E,3E,5E)-5-(1-Ethyl-3,3-dimethyl-5-sulfoindolin-2-ylidene)-penta-1,3-dien-1-yl)-1-(6-((6-((6S,7R,7aR,12bS)-9-hydroxy-7-methoxy-3-methyl-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinoline-6-carboxamido)hexyl)-amino)-6-oxohexyl)-3,3-dimethyl-3H-indol-1-ium-5-sulfonate,2,2,2-Trifluoroacetate Salt from human MOR expressed in HEK293 cells by Cheng-Prusoff analysis Homo sapiens 0.2754 nM
Displacement of [3H]DAMGO from human MOR expressed in HEK293 cells preincubated for 1 hr followed by radioligand addition measured after 1 hr by liquid scintillation counting analysis Homo sapiens 0.1995 nM
Ex vivo inhibition of [3H]-Diprenophine binding to mu opioid receptor in striatum/nucleus accumbens isolated from rat treated with compound at 7 mg/kg, po for 6 hrs measured after 30 mins post [3H]-Diprenophine addition to tissue relative to control Rattus norvegicus 40.0 %
Ex vivo inhibition of [3H]-Diprenophine binding to delta opioid receptor in striatum/nucleus accumbens isolated from rat treated with compound at 7 mg/kg, po for 6 hrs measured after 30 mins post [3H]-Diprenophine addition to tissue relative to control Rattus norvegicus 40.0 %
Ex vivo inhibition of [3H]-Diprenophine binding to kappa opioid receptor in striatum/nucleus accumbens isolated from rat treated with compound at 7 mg/kg, po for 6 hrs measured after 30 mins post [3H]-Diprenophine addition to tissue relative to control Rattus norvegicus 40.0 %
Displacement of [3H]DAMGO from mu opioid receptor in guinea pig brain membrane Cavia porcellus 0.26 nM
Displacement of [3H]DADLE from delta opioid receptor in guinea pig brain membrane Cavia porcellus 10.5 nM
Displacement of [3H]-DPN from recombinant human mu opioid receptor expressed in CHO-K1 cell membranes by radioligand binding assay Homo sapiens 0.1585 nM
Displacement of [3H]-DPN from recombinant human delta opioid receptor expressed in CHO-K1 cell membranes by radioligand binding assay Homo sapiens 6.31 nM
Displacement of [3H]-DPN from guinea pig kappa opioid receptor expressed in CHO-K1 cell membranes by radioligand binding assay Cavia porcellus 0.5012 nM
Displacement of [3H]-NLX from mouse MOR expressed in CHO cells incubated for 1.5 hrs by radioligand binding assay Mus musculus 0.39 nM
Antagonist activity at human MOR transfected in CHO cells co-transfected with Gqi5 assessed as inhibition of DAMGO-induced calcium mobilization incubated for 15 mins prior to DAMGO addition and measured for 90 secs by Fluo-4AM dye based fluorescence analysis Homo sapiens 2.87 nM
Displacement of [3H]NLX from mouse MOR expressed in CHO cell membrane incubated for 90 mins by liquid scintillation spectrophotometry Mus musculus 0.39 nM
Displacement of [3H]-NLX from mouse mu opioid receptor expressed in CHO cells measured after 1.5 hrs by competitive-binding assay Mus musculus 0.4 nM
Antagonist activity at human mu opioid receptor expressed in CHO cells co- expressing Gqi5 assessed as decrease in DAMGO-induced intracellular calcium mobilization incubated for 15 mins followed by DAMGO addition by Fluo-AM dye based fluorescence assay Homo sapiens 8.9 nM
Displacement of [3H]-naloxone from mouse MOR expressed in CHO cells incubated for 1.5 hrs by competitive radioligand binding assay Mus musculus 0.7 nM
Antagonist activity at mouse MOR expressed in CHO cells assessed as inhibition of DAMGO-induced calcium mobilization preincubated for 60 mins measured after 15 mins by calcium mobilization assay Mus musculus 6.62 nM

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Cross References

Resources Reference
ChEBI 7465
ChEMBL CHEMBL19019
DrugBank DB00704
DrugCentral 1765
FDA SRS 5S6W795CQM
Human Metabolome Database HMDB0014842
Guide to Pharmacology 1639
KEGG C07253
PharmGKB PA450588
PubChem 5360515
SureChEMBL SCHEMBL34681
ZINC ZINC000000001773