Details of the Drug

General Information of Drug (ID: DMERWUC)

Drug Name
Organon
Synonyms
Allylestrenol; Allyloestrenol; Allyloestrenolum; Gestanin; Gestanol; Gestanon; Gestanyn; Orageston; Perselin; Turinal; Allilestrenolo [DCIT]; Alilestrenol [INN-Spanish]; Allylestrenol [INN:JAN]; Allylestrenol(jan); Allylestrenolum [INN-Latin]; Gestanon-r; Perselin (TN); Allylestrenol (JAN/INN); (17beta)-17-prop-2-en-1-ylestr-4-en-17-ol; (8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol; 17-(2-Propenyl)estr-4-en-17-ol; 17-Hydroxy-17-alpha-allyl-4-estrene; 17-alpha-Allyl-17-beta-hydroxy-4-estrene; 17-alpha-Allyl-17-beta-hydroxy-delta(sup 4)-estren; 17-alpha-Allyl-3-deoxy-19-nortestosterone; 17-alpha-Allyl-4-oestrene-17-beta-ol; 17-alpha-Allylestr-4-en-17-beta-ol; 17-alpha-Allylhydroxy-19-nor-4-androstene; 17.alpha.-Allyl-17-.beta.-hydroxy-.delta.(sup 4)-estren; 17.alpha.-Allyl-17.beta.-hydroxy-4-estrene; 17.alpha.-Allyl-3-deoxy-19-nortestosterone; 17.alpha.-Allyl-4-destrene-17.beta.-ol; 17.alpha.-Allyl-4-estren-17.beta.-ol; 17.alpha.-Allyl-4-oestrene-17.beta.-ol; 17.alpha.-Allylestr-4-en-17.beta.-ol; 17.alpha.-Allylestrenol; 17alpha-Allyl-17beta-hydroxy-4-estrene; 17alpha-Allyl-19-nor-delta-4-androstene-17beta-ol; 17alpha-Allyl-3-deoxy-19-nortestosterone; 17alpha-Allyl-4-destrene-17beta-ol; 17alpha-Allyl-4-estren-17beta-ol; 17alpha-Allyl-4-oestrene-17beta-ol; 17alpha-Allylestr-4-en-17beta-ol; 17alpha-Allylestrenol; 21-Methylene-19-nor-17-alpha-preg-4-en-17-ol; 3-Deoxy-17-alpha-allyl-19-nortestosterone
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Preclinical [1]
ATC Code
G03DC01: Organon
G03DC: Estren derivatives
G03D: PROGESTOGENS
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 300.5
Logarithm of the Partition Coefficient (xlogp) 5.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C21H32O
IUPAC Name
(8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CCCC[C@H]34
InChI
InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChIKey
ATXHVCQZZJYMCF-XUDSTZEESA-N
Cross-matching ID
PubChem CID
235905
ChEBI ID
CHEBI:31189
CAS Number
432-60-0
UNII
I47VB5DZ8O
DrugBank ID
DB01431
TTD ID
D07PNC
INTEDE ID
DR0068

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glycine transporter GlyT-1 (SLC6A9) TTHJTF7 SC6A9_HUMAN Blocker [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 06 Mental, behavioural or neurodevelopmental disorder
Disease Class ICD-11: 6A20 Schizophrenia
The Studied Tissue Pre-frontal cortex
The Studied Disease Schizophrenia [ICD-11:6A20]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glycine transporter GlyT-1 (SLC6A9) DTT SLC6A9 4.94E-01 -0.09 -0.34
Glycine transporter GlyT-1 (SLC6A9) DTT SLC6A9 1.64E-01 -0.03 -0.17
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.66E-01 4.25E-02 1.20E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.75E-01 5.15E-02 3.64E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties. J Steroid Biochem. 1985 Aug;23(2):165-8.
2 The pipeline and future of drug development in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):904-22.
3 Identification of the human P450 enzymes involved in the in vitro metabolism of the synthetic steroidal hormones Org 4060 and Org 30659. Xenobiotica. 2002 Feb;32(2):109-18.
4 Effect of anti-estrogens on the androgen receptor activity and cell proliferation in prostate cancer cells. Urol Res. 2004 Dec;32(6):406-10. doi: 10.1007/s00240-004-0424-8. Epub 2004 Aug 14.