Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1697)
Drug Name
AY-27,255
Synonyms
Vinpocetine; Apovincaminate d'ethyle [French]; Apovincaminic acid ethyl ester; Bravinton; Cavinton; Ceractin; Ethyl (+)-apovincaminate; Ethyl (+)-cis-apovincaminate; Ethyl apovincamin-22-oate; Ethyl apovincaminate; RGH 4405; RGH-4405; TCV-3B; Vinpocetinum [INN-Latin]; cis-Apovincaminic acid ethyl ester; vinpocetine; (+)-Apovincaminic acid ethyl ester; (+)-cis-Apovincaminic acid ethyl ester; 3-alpha,16-alpha-Apovincaminic acid ethyl ester; 42971-09-5; AY 27,255; EINECS 256-028-0; Eburnamenine-14-carboxylic acid ethyl ester; UNII-543512OBTC
Indication Haemorrhagic stroke [ICD11: 8B20] Phase 2/3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 350.5 Topological Polar Surface Area 34.5
Heavy Atom Count 26 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
443955
PubChem SID
855619 ; 3727081 ; 7848434 ; 7980299 ; 10299443 ; 10321872 ; 11341598 ; 11361781 ; 11364294 ; 11366856 ; 11369418 ; 11371881 ; 11374568 ; 11377580 ; 11466296 ; 11467416 ; 11485054 ; 11486071 ; 11487183 ; 11489345 ; 11490776 ; 11492889 ; 11495214 ; 14802886 ; 14925387 ; 17405811 ; 24278182 ; 26612408 ; 26680355 ; 26759739 ; 36887098 ; 47216903 ; 47365339 ; 47440398 ; 47810892 ; 47959906 ; 48334637 ; 48334638 ; 48416699 ; 48483328 ; 49698412 ; 49964760 ; 50103960 ; 50103961 ; 50103962 ; 50103963 ; 50113284 ; 53778363 ; 53790458 ; 56424092
ChEBI ID
CHEBI:32297
CAS Number
42971-09-5
TTD Drug ID
D06BCB
Formula
C22H26N2O2
Canonical SMILES
CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
InChI
1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1
InChIKey
DDNCQMVWWZOMLN-IRLDBZIGSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Apovincaminic acid DM006047
160154
Oxidation - Hydrolyzationn; dealkylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006510 AY-27,255 Apovincaminic acid Oxidation - Hydrolyzationn; dealkylation CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
References
1 ClinicalTrials.gov (NCT02878772) Vinpocetine Inhibits NF-κB-dependent Inflammation in Acute Ischemic Stroke Patients.
2 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Vinpocetine, cognition, and epilepsy

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.