Details of the Drug

General Information of Drug (ID: DMLMOIJ)

Drug Name
Cyproterone acetate
Synonyms
Cyprosterone acetate; Cyproteron acetate; Cyproteron-R acetate; Cyproterone 17-O-acetate; Cyproterone 17.alpha.-acetate; Cyproterone 17alpha-acetate; Cyproterone acetate [USAN:JAN]; Androcur; CYPROTERONE ACETATE; Cyproteroneacetate; SH 714; SH 80714; SH-714; 3'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1beta,2beta)-; 427-51-0; 4KM2BN5JHF; C24H29ClO4; CCRIS 4385; CHEBI:50743; CHEMBL139835; EINECS 207-048-3; HSDB 3592; MLS000859908; NSC 81430; NSC-81430; UNII-4KM2BN5JHF
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 416.9
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption
The drug is completely absorbed following oral administration []
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [1]
Elimination
1% of drug is excreted from urine in the unchanged form [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 38 hours (oral), and 96 hours (intramuscular adminutesistration) [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 10.27872 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0021 mg/mL [1]
Chemical Identifiers
Formula
C24H29ClO4
IUPAC Name
[(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxo-15-pentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dienyl] acetate
Canonical SMILES
CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)OC(=O)C
InChI
UWFYSQMTEOIJJG-FDTZYFLXSA-N
InChIKey
1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
Cross-matching ID
PubChem CID
9880
ChEBI ID
CHEBI:50743
CAS Number
427-51-0
DrugBank ID
DB04839
INTEDE ID
DR0396
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [5]
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Gene/Protein Processing [6]
Apolipoprotein A-II (APOA2) OTQ3HGTC APOA2_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [7]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [8]
Follitropin subunit beta (FSHB) OTGLS283 FSHB_HUMAN Gene/Protein Processing [9]
Kallikrein-2 (KLK2) OT9RE37R KLK2_HUMAN Gene/Protein Processing [10]
Lutropin subunit beta (LHB) OT5GBOVJ LSHB_HUMAN Gene/Protein Processing [9]
Prostate-specific antigen (KLK3) OTFGSBFJ KLK3_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 BDDCS applied to over 900 drugs
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 Progestogens in menopausal hormone therapy. Prz Menopauzalny. 2015 Jun;14(2):134-43.
5 Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. Gynecol Endocrinol. 2007 Apr;23(4):193-7. doi: 10.1080/09513590701214414.
6 Antiandrogenic therapy can cause coronary arterial disease. Int J Urol. 2005 Oct;12(10):886-91. doi: 10.1111/j.1442-2042.2005.01145.x.
7 Structure-based virtual screening of CYP1A1 inhibitors: towards rapid tier-one assessment of potential developmental toxicants. Arch Toxicol. 2021 Sep;95(9):3031-3048. doi: 10.1007/s00204-021-03111-2. Epub 2021 Jun 28.
8 Receptor-dependent regulation of the CYP3A4 gene. Toxicology. 2002 Dec 27;181-182:199-202.
9 Twenty-one day administration of dienogest reversibly suppresses gonadotropins and testosterone in normal men. J Clin Endocrinol Metab. 2002 May;87(5):2107-13. doi: 10.1210/jcem.87.5.8514.
10 Dramatic suppression of plasma and urinary prostate specific antigen and human glandular kallikrein by antiandrogens in male-to-female transsexuals. J Urol. 2000 Mar;163(3):802-5.