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

General Information of Drug (ID: DR0213)
Drug Name
Bimatoprost
Synonyms
Bimatoprost; LS-181817; Latisse; Lumigan; Lumigan (TN); QXS94885MZ; bimatoprostum; (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide; (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide; 155206-00-1; 5-Heptenamide, 7-(3,5-dihydroxy-2-(3-hydrdoxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-, (1R-(1alpha(Z),2beta(1E,3S*),3alpha,5alpha))-; AC1NSJUW; AGN 192024; AGN-192024; CHEBI:51230; UNII-QXS94885MZ
Indication Glaucoma [ICD11: 9C61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 415.6 Topological Polar Surface Area 89.8
Heavy Atom Count 30 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5311027
PubChem SID
7978793 ; 11056218 ; 11528907 ; 12015127 ; 14855657 ; 14880018 ; 17396891 ; 17403938 ; 39340757 ; 46505334 ; 50126297 ; 50464908 ; 56464316 ; 71851420 ; 90342416 ; 90342418 ; 99443334 ; 103770946 ; 114155088 ; 126592972 ; 126666993 ; 134223006 ; 134338457 ; 135256698 ; 135649995 ; 137005798 ; 142063913 ; 152134985 ; 152344136 ; 160964244 ; 162180462 ; 174548912 ; 175266561 ; 175437834 ; 179150000 ; 210279322 ; 210281645 ; 223392784 ; 223660297 ; 223704349 ; 224493205 ; 226412773 ; 250184579 ; 251912536 ; 251915515 ; 252214992 ; 252448483 ; 252822160
ChEBI ID
CHEBI:51230
CAS Number
155206-00-1
TTD Drug ID
D0Q2XF
Formula
C25H37NO4
Canonical SMILES
CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
InChI
1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
InChIKey
AQOKCDNYWBIDND-FTOWTWDKSA-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
17-Phenyl-Trinor-PGF2alpha DM001421
5283081
Hydrolysis - Hydrolysis 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000365 Bimatoprost 17-Phenyl-Trinor-PGF2alpha Hydrolysis - Hydrolysis Unclear [3]
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
References
1 Bimatoprost was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Product monograph: LUMIGAN RC (Bimatoprost).
3 The hydrolysis of the prostaglandin analog prodrug bimatoprost to 17-phenyl-trinor PGF2alpha by human and rabbit ocular tissue J Ocul Pharmacol Ther. 2003 Apr;19(2):97-103. doi: 10.1089/108076803321637627.

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