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

General Information of Drug (ID: DR1657)
Drug Name
Ulipristal
Synonyms
Uliprisnil; Ulipristal; Ulipristal (USAN/INN); Ulipristal [USAN:INN:BAN]; VA-2914; AMX10182; CDB 3236; Deacetyl CDB 2914; HKDLNTKNLJPAIY-WKWWZUSTSA-N; PGL 4001; SCHEMBL545159; (8S,11R,13S,14S,17R)-17-acetyl-11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-6,7,8,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; 159811-51-5; 6J5J15Q2X8; C28H35NO3; CHEMBL2103846; UNII-6J5J15Q2X8; ellae
Indication Contraception [ICD11: JA65] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 433.6 Topological Polar Surface Area 57.6
Heavy Atom Count 32 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
13559281
PubChem SID
24841789 ; 28676416 ; 35849341 ; 124490307 ; 135271930 ; 160687014 ; 164235293 ; 165245594 ; 172919799 ; 175266288 ; 198993968 ; 223435395 ; 226854508 ; 252228535 ; 252432863 ; 252473760
CAS Number
159811-51-5
TTD Drug ID
D0V4WD
Formula
C28H35NO3
Canonical SMILES
CC(=O)C1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O
InChI
1S/C28H35NO3/c1-17(30)28(32)14-13-25-23-11-7-19-15-21(31)10-12-22(19)26(23)24(16-27(25,28)2)18-5-8-20(9-6-18)29(3)4/h5-6,8-9,15,23-25,32H,7,10-14,16H2,1-4H3/t23-,24+,25-,27-,28-/m0/s1
InChIKey
HKDLNTKNLJPAIY-WKWWZUSTSA-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
Epoxide ulipristal acetate DM002407 N. A. Unclear 1 [3]
PGL4002 DM002409
15908064
Oxidation - Mono-N-Demethylation 1 [3]
Conjugation with glutathione DM002408 N. A. Unclear 2 [3]
PGL-4004 DM002410
15908061
Oxidation - Di-N-Demethylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002470 Ulipristal Epoxide ulipristal acetate Unclear Unclear [3]
MR002471 Ulipristal PGL4002 Oxidation - Mono-N-Demethylation CYP2D6 ... [3]
MR002468 Epoxide ulipristal acetate Conjugation with glutathione Unclear Unclear [3]
MR002469 PGL4002 PGL-4004 Oxidation - Di-N-Demethylation CYP2D6 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Ulipristal was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The clinical pharmacology and pharmacokinetics of ulipristal acetate for the treatment of uterine fibroids. Reprod Sci. 2015 Apr;22(4):476-83.
3 Pharmacokinetics, toxicological and clinical aspects of ulipristal acetate: insights into the mechanisms implicated in the hepatic toxicity Drug Metab Rev. 2021 Aug;53(3):375-383. doi: 10.1080/03602532.2021.1917599.

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