ZOLMITRIPTAN

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N02CC03
UNII 2FS66TH3YW
EPA CompTox DTXSID8045933

Structure

InChI Key ULSDMUVEXKOYBU-ZDUSSCGKSA-N
Smiles CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12
InChI
InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H21N3O2
Molecular Weight 287.36
AlogP 1.92
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 57.36
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Serotonin 1b (5-HT1b) receptor agonist AGONIST FDA
Protein: Serotonin 1d (5-HT1d) receptor
Description: 5-hydroxytryptamine receptor 1D
Organism : Homo sapiens
P28221 ENSG00000179546
Protein: Serotonin 1b (5-HT1b) receptor
Description: 5-hydroxytryptamine receptor 1B
Organism : Homo sapiens
P28222 ENSG00000135312
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 14
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - 7 - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - 0 - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
16 3 2 1-4 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103
Assay Description Organism Bioactivity Reference
Binding affinity against 5-hydroxytryptamine 1 receptor using rabbit jugular vein assay in the absence of endothelium None 1.8 nM
In vitro binding affinity was determined towards cloned human 5-hydroxytryptamine 1A receptor using [3H]8-OH-DPAT radioligand None 124.0 nM
Binding affinity for cloned human 5-hydroxytryptamine 1A receptor Homo sapiens 78.6 nM
In vitro binding affinity was determined towards cloned human 5-hydroxytryptamine 1B receptor using [3H]5-CT radioligand None 4.2 nM
Binding affinity in CHO-K1 cells transfected with human recombinant 5-hydroxytryptamine 1B receptor None 6.166 nM
Effective concentration determined by measuring inhibition of forskolin-stimulated c-AMP formation at 5-hydroxytryptamine 1B receptor stably transfected in CHO cell lines None 15.7 nM
In vitro binding affinity was determined towards cloned human 5-hydroxytryptamine 1D receptor using [3H]5-CT radioligand None 0.76 nM
Binding affinity in CHO-K1 cells transfected with human 5-hydroxytryptamine 1D receptor None 2.818 nM
Binding affinity against 5-hydroxytryptamine 1D receptor beta using rabbit saphenous vein assay. None 1.5 nM
Binding affinity to recombinant human 5-hydroxytryptamine 1D receptor alpha None 0.92 nM
Binding affinity against 5-hydroxytryptamine 1D receptor beta using rabbit saphenous vein assay. None 1.5 nM
Binding affinity for cloned human 5-hydroxytryptamine 1D receptor beta None 4.0 nM
Binding affinity against Alpha-2 adrenergic receptor in rat cortex using [3H]-idazoxan as radioligand None 7.0 nM
Binding affinity against dopamine receptor D1 in rat striatum using [3H]SCH-23390 as radioligand None 0.3 nM
Binding affinity against Dopamine receptor D2 in rat striatum using [3H]-spiperone as radioligand None 0.04 nM
Inhibition of human FAAH at 1 uM Homo sapiens 13.55 %
Cardiovascular toxicity in human coronary arteries assessed as induction of vasoconstriction after 30 mins Homo sapiens 40.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 95.98 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 102.48 %
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 3.79 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.38 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.51 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.59 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 13.79 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.65 %
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 0.25 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 7.85 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 25.69 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.111 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.24 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.04 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.04 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.24 %

Cross References

Resources Reference
ChEBI 10124
ChEMBL CHEMBL1185
DrugBank DB00315
DrugCentral 2869
FDA SRS 2FS66TH3YW
Human Metabolome Database HMDB0014460
Guide to Pharmacology 60
KEGG C07218
PubChem 60857
SureChEMBL SCHEMBL33336
ZINC ZINC000000015515
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