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

General Information of Drug (ID: DR0839)
Drug Name
Hydroxyprogesterone caproate
Synonyms
Hydroxyprogesteronum; Hydroxyprogesteronum [INN-Latin]; Idrossiprogesterone [DCIT]; Oxiprogesteronum; Prodix; Prodox; Setaderm; hydroxyprogesterone; 17-Hydroxypregn-4-ene-3,20-dione; 17-Hydroxyprogesterone; 17-alpha-Hydroxyprogesterone; 17ALPHA-HYDROXYPROGESTERONE; 17a-Hydroxyprogesterone; 17alpha-Hydroxy-4-pregnene-3,20-dione; 17alpha-Hydroxy-progesterone; 68-96-2; Pregn-4-ene-3,20-dione, 17-hydroxy-; delta(4)-Pregnene-17alpha-ol-3,20-dione; Gestageno; Gestageno gador; Hidroxiprogesterona; Hidroxiprogesterona [INN-Spanish]; A-Hydroxyprogesterone caproate; Corlutin L.A.; Delalutin; Depo-Proluton; Duraluton; Estralutin; Gesterol LA 250; HYDROXYPROGESTERONE CAPROATE; Hormofort; Hydroxyprogesterone hexanoate; Hylutin; Hyproval; Hyproval-PA; Hyroxon; Idrogestene; Kaprogest; Lutate; Luteocrin; Luteocrin depot; Lutopron; Neolutin; Neolutin forte; Primolut Depot; Progesterone caproate; Progesterone retard pharlon; Proluton Depot; Relutin; Syngynon; Teralutil; 17alpha-Caproyloxypregn-4-ene-3,20-dione; 17alpha-Hydroxyprogesterone caproate; 630-56-8; Proge
Indication Uterine cancer [ICD11: 2C76] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 428.6 Topological Polar Surface Area 60.4
Heavy Atom Count 31 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
169870
PubChem SID
10348 ; 80880 ; 855528 ; 7848012 ; 10257140 ; 12209772 ; 15007174 ; 24895697 ; 46243005 ; 49834232 ; 53788881 ; 56424128 ; 57351759 ; 75144784 ; 81093219 ; 87571349 ; 90473603 ; 93576739 ; 103770831 ; 103823738 ; 113466682 ; 117622268 ; 124576771 ; 124799532 ; 124886752 ; 127764370 ; 131321883 ; 131549786 ; 134976956 ; 137124474 ; 143449668 ; 144207051 ; 144212650 ; 160843844 ; 162092117 ; 163270260 ; 164788675 ; 170465210 ; 174529979 ; 175265862 ; 179316277 ; 184545682 ; 198993584 ; 223439966 ; 226397056 ; 241113174 ; 250112560 ; 252122136 ; 252308498 ; 252401932
ChEBI ID
CHEBI:5812
CAS Number
630-56-8
TTD Drug ID
D00AEQ
Formula
C27H40O4
Canonical SMILES
CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
InChI
1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
InChIKey
DOMWKUIIPQCAJU-LJHIYBGHSA-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-alpha-hydroxyprogesterone DM002987
6238
Hydrolysis - Hydrolyzation 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005143 Hydroxyprogesterone caproate 17alpha- Hydroxyprogesterone Hydrolysis - Hydrolyzation ES [3], [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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Esterases (ES) DMEN229 Homo sapiens Not Available Not Available [3] , [4]
Steroid 21-hydroxylase (CYP21A2) DME0037 Homo sapiens
CP21A_HUMAN
1.14.14.16
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
References
1 Hydroxyprogesterone Caproate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22.
3 Transplacental transfer and metabolism of 17-alpha-hydroxyprogesterone caproate
4 The association among cytochrome P450 3A, progesterone receptor polymorphisms, plasma 17-alpha hydroxyprogesterone caproate concentrations, and spontaneous preterm birth. Am J Obstet Gynecol. 2017 Sep;217(3):369.e1-369.e9.
5 Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2005 Jan;90(1):445-54.
6 The glucuronidation of Delta4-3-Keto C19- and C21-hydroxysteroids by human liver microsomal and recombinant UDP-glucuronosyltransferases (UGTs): 6alpha- and 21-hydroxyprogesterone are selective substrates for UGT2B7. Drug Metab Dispos. 2007 Mar;35(3):363-70.

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