Details of the Drug

General Information of Drug (ID: DMWIDJK)

Drug Name
FORMESTANE
Synonyms
formestane; 566-48-3; 4-Hydroxyandrost-4-ene-3,17-dione; 4-Hydroxyandrostenedione; Lentaron; CGP-32349; Lentaron(R); 4-OH-A; B, Aromatase inhibitor; 4-Hydroxy-4-androstene-3,17-dione; NSC 282175; 17-dione; 4-OHA; CGP 32349; Formestane [INN:BAN]; UNII-PUB9T8T355; CCRIS 7483; ANDROST-4-ENE-3,17-DIONE, 4-HYDROXY-; 4-Hydroxy-delta(sub 4)-androstenedione; BRN 1889793; MLS002153359; MLS000028826; PUB9T8T355; CHEBI:75172
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 302.4
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 18 minutes [2]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.8435 micromolar/kg/day [3]
Vd
The volume of distribution (Vd) of drug is 1.8 L/kg []
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Cardiovascular disorder Not Available AK1 OT614AR3 [4]
Chemical Identifiers
Formula
C19H26O3
IUPAC Name
(8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Canonical SMILES
C[C@]12CCC(=O)C(=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
InChI
InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
InChIKey
OSVMTWJCGUFAOD-KZQROQTASA-N
Cross-matching ID
PubChem CID
11273
ChEBI ID
CHEBI:75172
CAS Number
566-48-3
DrugBank ID
DB08905
TTD ID
D0B6PZ
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1) OT6EBDHM DHB1_HUMAN Gene/Protein Processing [6]
Adenylate kinase isoenzyme 1 (AK1) OT614AR3 KAD1_HUMAN Drug Response [4]
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [7]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [8]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5 The taiwaniaquinoids: a review. J Nat Prod. 2010 Feb 26;73(2):284-98.
6 Mammalian lignans and genistein decrease the activities of aromatase and 17beta-hydroxysteroid dehydrogenase in MCF-7 cells. J Steroid Biochem Mol Biol. 2005 Apr;94(5):461-7.
7 Androgen- and estrogen-receptor mediated activities of 4-hydroxytestosterone, 4-hydroxyandrostenedione and their human metabolites in yeast based assays. Toxicol Lett. 2018 Aug;292:39-45. doi: 10.1016/j.toxlet.2018.04.026. Epub 2018 Apr 24.
8 Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro. Toxicol In Vitro. 2000 Jun;14(3):227-34.