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

General Information of Drug (ID: DR1336)
Drug Name
Pregnenolone
Synonyms
Pregnenolona [INN-Spanish]; Pregnenolone [INN:BAN]; Pregnenolonum [INN-Latin]; Pregnetan; Pregneton; Pregnolon; Prenolon; Prestwick3_000546; Arthenolone; Enelone; Natolone; Prestwick_859; Regnosone; Skinostelon; delta5-Pregnenolone; pregnenolone; (3BETA)-3-HYDROXYPREGN-5-EN-20-ONE; 145-13-1; 3-beta-Hydroxypregn-5-en-20-one; 3beta-Hydroxy-5-pregnen-20-one; 3beta-Hydroxypregn-5-en-20-one; 5-Pregnen-3-beta-ol-20-one; 5-Pregnen-3beta-ol-20-one; 5-Pregnenolone; Bina-Skin; NSC 1616; Pregn-5-en-20-one, 3-hydroxy-, (3beta)-; UNII-73R90F7MQ8
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 316.5 Topological Polar Surface Area 37.3
Heavy Atom Count 23 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
8955
PubChem SID
3095 ; 5056 ; 841801 ; 3136425 ; 7847211 ; 7889910 ; 8143499 ; 8156371 ; 10321800 ; 11466574 ; 11467694 ; 11486248 ; 12157331 ; 14850333 ; 24702313 ; 24887880 ; 24899008 ; 25621392 ; 29227585 ; 46506718 ; 47275669 ; 47646662 ; 48094643 ; 48318548 ; 48394039 ; 49698547 ; 50019742 ; 50111369 ; 50952978 ; 53790378 ; 56463239 ; 57325339 ; 85165262 ; 87574922 ; 90451278 ; 92125557 ; 92298073 ; 92309191 ; 92712002 ; 93167037 ; 93576762 ; 103557063 ; 103845983 ; 103914285 ; 104319171 ; 121363228 ; 124812051 ; 124892396 ; 126630318 ; 126656995
ChEBI ID
CHEBI:16581
CAS Number
145-13-1
TTD Drug ID
D0B4RU
Formula
C21H32O2
Canonical SMILES
CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI
1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-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-Hydroxypregnenolone sulfate DM004820
152971
Multi-steps Reaction - Hydrolyzationn; sulfation 1 [4]
Pregnenolone sulfate metabolite DM004821
105074
Conjugation - Sulfation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005186 Pregnenolone 17-Hydroxypregnenolone sulfate Multi-steps Reaction - Hydrolyzationn; sulfation SULT2B1 [4]
MR005187 Pregnenolone Pregnenolone sulfate metabolite Conjugation - Sulfation SULT2B1 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Homo sapiens
3BHS2_HUMAN
1.1.1.145
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[2]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[4]
Sulfotransferase 2B1 (SULT2B1) DME0384 Homo sapiens
ST2B1_HUMAN
2.8.2.2
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Km = 0.0028 microM
3BHS1_HUMAN
[2]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Km = 0.0028 microM
3BHS2_HUMAN
[2]
Sulfotransferase 2A1 (SULT2A1) DME0074 Km = 0.0018 microM
ST2A1_HUMAN
[4]
Sulfotransferase 2B1 (SULT2B1) DME0384 Km = 0.0018 microM
ST2B1_HUMAN
[4]
References
1 ClinicalTrials.gov (NCT01409096) Study Using Pregnenolone to Treat Bipolar Depression.
2 Structure/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity. J Biol Chem. 2002 Nov 8;277(45):42795-801.
3 Cytochrome P450 expression and regulation in CYP3A4/CYP2D6 double transgenic humanized mice. Drug Metab Dispos. 2008 Feb;36(2):435-41.
4 Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). J Steroid Biochem Mol Biol. 2001 Jun;77(4-5):261-9.

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