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

General Information of Drug (ID: DR0593)
Drug Name
Epoprostenol
Synonyms
Epoprostenolum; DCR9Z582X0; Epoprostenol [USAN:INN]; Epoprostenolum [INN-Latin]; KAQKFAOMNZTLHT-OZUDYXHBSA-N; KB-IV-24; PGI(sub 2); Prostacyclin I2; Prostaglandin 12; Prostaglandin X; U 53,217; Vasocyclin; epoprostenol; prostacyclin; prostaglandin I2; 35121-78-9; 6,9-alpha-Epoxy-11-alpha,15(S)-dihydroxyprosta-5(Z),13(E)-dien-1-oic acid; 6,9S-epoxy-11R,15S-dihydoxy-5Z,13E-prostadienoic acid; 63859-31-4; BRN 1690090; CHEBI:15552; PG-I2; PGI2; PGX; UNII-DCR9Z582X0
Indication Pulmonary hypertension [ICD11: BB01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 352.5 Topological Polar Surface Area 87
Heavy Atom Count 25 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5282411
PubChem SID
4266019 ; 7979800 ; 7980285 ; 8143216 ; 11038504 ; 14900947 ; 26754810 ; 26754811 ; 39315859 ; 47291286 ; 47662474 ; 48110621 ; 48415947 ; 50110786 ; 57358657 ; 77700624 ; 85788539 ; 92309912 ; 93166672 ; 99300826 ; 103326666 ; 113857140 ; 127327695 ; 127327696 ; 127335056 ; 127335057 ; 127335058 ; 127335059 ; 127335060 ; 135000098 ; 135651541 ; 137003054 ; 142047542 ; 164756785 ; 175267334 ; 179150361 ; 224259470 ; 226399315 ; 250134198 ; 252216120 ; 252378175 ; 252455636
ChEBI ID
ChEBI:15552
CAS Number
35121-78-9
TTD Drug ID
D0V0IX
Formula
C20H32O5
Canonical SMILES
CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)O2)O)O
InChI
1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChIKey
KAQKFAOMNZTLHT-OZUDYXHBSA-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
6,15-Diketo-13,14-dihydro-PGF1alpha DM001924
174013
Oxidation - Hydroxylation 1 [3]
6-Keto-PGF1alpha DM001925
5280888
Unclear 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000911 Epoprostenol 6,15-Diketo-13,14-dihydro-PGF1alpha Oxidation - Hydroxylation Unclear [3]
MR000912 Epoprostenol 6-Keto-PGF1alpha Unclear Unclear [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
References
1 Epoprostenol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells. Arterioscler Thromb Vasc Biol. 2005 Feb;25(2):321-6.
3 Integrated pharmacokinetics and pharmacodynamics of epoprostenol in healthy subjects Br J Clin Pharmacol. 2012 Dec;74(6):978-89. doi: 10.1111/j.1365-2125.2012.04301.x.
4 In search of pulmonary hypertension treatments: Effect of 17-estradiol on PGI(2) pathway in human pulmonary artery. Prostaglandins Leukot Essent Fatty Acids. 2021 Sep;172:102321. doi: 10.1016/j.plefa.2021.102321.

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