CHLORDIAZEPOXIDE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N05BA02
UNII 6RZ6XEZ3CR
EPA CompTox DTXSID4046022

Structure

InChI Key ANTSCNMPPGJYLG-UHFFFAOYSA-N
Smiles CNC1=Nc2ccc(Cl)cc2C(c2ccccc2)=[N+]([O-])C1
InChI
InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14ClN3O
Molecular Weight 299.76
AlogP 2.95
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 50.46
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 21.0

Pharmacology

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR PubMed Wikipedia
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
- 200-910 - 275-740 74-75
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 4-35
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Cholecystokinin receptor
- 100000 - - -
Membrane receptor
- 100000 - 438 -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 25000-44100 - - -
Assay Description Organism Bioactivity Reference
Binding affinity against rat benzodiazepine (BZD) receptor None 438.0 nM
Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor of rat cerebral cortex membrane None 710.0 nM
Concentration that inhibits binding of 1.5 nM [3H]diazepam to rat brain benzodiazepine receptor None 200.0 nM
Inhibition of [3H]flunitrazepam binding to GABA-A benzodiazepine receptor of rat cerebral cortex Rattus norvegicus 330.0 nM
Inhibition of specific binding of 1.5 nM [3H]diazepam to rat brain benzodiazepine receptors None 200.0 nM
Inhibitory concentration against specific binding of [3H]diazepam to Benzodiazepine receptor in rat brain None 200.0 nM
In vitro for inhibition of [3H]diazepam towards Benzodiazepine receptor from rat None 248.0 nM
In vitro inhibition of [3H]diazepam binding towards Benzodiazepine receptor at 1 uM None 75.0 %
Inhibition of binding of tritiated 3[H]diazepam radioligand to rat brain homogenates None 442.0 nM
Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor in synaptic membranes of rat cerebral cortex Rattus norvegicus 910.0 nM
Percent inhibition of [3H]- Diazepam binding to GABA-A Benzodiazepine receptor of rat frontal cortex membranes Rattus norvegicus 74.0 %
Displacement of 3[H]Flunitrazepam from GABA-A central benzodiazepine receptor of bovine brain membranes Bos taurus 790.0 nM
Inhibition of [3H]flunitrazepam binding to benzodiazepine receptor in bovine brain membrane Bos taurus 790.0 nM
Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-acid A receptor alpha-1-beta-3-gamma-2 Homo sapiens 605.0 nM
Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-1-beta-3-gamma-2 receptor subunits expressed in Xenopus oocytes Homo sapiens 770.0 nM
Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-1-beta-3-gamma-2) stably expressed in L(tk-) cells. None 560.0 nM
Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-acid A receptor alpha-2-beta-3-gamma-2 Homo sapiens 392.0 nM
Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-2-beta-3-gamma-2 receptor subunits expressed in Xenopus oocytes Homo sapiens 460.0 nM
Displacement of [3H]Ro-151788 from human Gamma-aminobutyric acid A receptor alpha-2-beta-3-gamma-2 stably expressed in L(tk-) cells None 460.0 nM
Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-acid A receptor alpha-3-beta-3-gamma-2 Homo sapiens 471.0 nM
Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-3-beta-3-gamma-2 receptor subunits expressed in Xenopus oocytes Homo sapiens 740.0 nM
Binding affinity by displacement of [3H]Ro-151788 from recombinant human gamma-aminobutyric-acid A receptor alpha3,beta3,gamma2 stably expressed in L cells Homo sapiens 275.0 nM
Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-acid A receptor alpha-5-beta-3-gamma-2 Homo sapiens 368.0 nM
Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-5-beta-3-gamma-2 receptor subunits expressed in Xenopus oocytes Homo sapiens 520.0 nM
Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-5-beta-3-gamma-2) stably expressed in L(tk-) cells. None 320.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 4.4 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM Cavia porcellus 35.0 %
Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A receptor alpha-1-beta-3-gamma-2 expressed in L(tk-) cells Homo sapiens 605.0 nM
Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A receptor alpha-2-beta-3-gamma-2 expressed in L(tk-) cells Homo sapiens 392.0 nM
Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A receptor alpha-3-beta-3-gamma-2 expressed in L(tk-) cells Homo sapiens 471.0 nM
Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A receptor alpha-5-beta-3-gamma-2 expressed in L(tk-) cells Homo sapiens 368.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 208.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 15.47 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.48 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 19.46 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 14.44 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 27.16 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.53 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -9.21 %

Cross References

Resources Reference
ChEBI 3611
ChEMBL CHEMBL451
DrugBank DB00475
DrugCentral 594
FDA SRS 6RZ6XEZ3CR
Human Metabolome Database HMDB0014618
Guide to Pharmacology 3370
SureChEMBL SCHEMBL18474
ZINC ZINC000019632917
CONTENTS