Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H29ClO4 |
| Molecular Weight | 416.938 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)O[C@@]1(CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O
InChI
InChIKey=UWFYSQMTEOIJJG-FDTZYFLXSA-N
InChI=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
| Molecular Formula | C24H29ClO4 |
| Molecular Weight | 416.938 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Cyproterone acetate is a steroid drug which was developed by Schering A.G (now Bayer). Cyproterone acetate was approved in Canada, Asia, Latin America and Europe for the treatment of sever acne under the name Diane-35 (ethinyl estradiol) and its mechanism of action in this condition is explained by competitive inhibition of androgen receptor AR. In Canada cyproterone acetate is widely used as a contraceptive, however its usage is associated with liver toxicity and clots formation. In the UK the drug is marketed for the treatment of prostate cancer (Cyproterone acetate brand name).
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1871 |
4.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | DIANE-35 Approved UseDIANE-35 (cyproterone acetate and ethinyl estradiol) is indicated for the treatment of women with severe acne, with associated symptoms of androgenization, including seborrhea and mild hirsutism. |
|||
| Primary | CYPROTERONE ACETATE Approved UseCyproterone Acetate tablets are used in men to treat prostate cancer |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
406 ng/mL |
300 mg 1 times / week steady-state, intramuscular dose: 300 mg route of administration: Intramuscular experiment type: STEADY-STATE co-administered: |
CYPROTERONE ACETATE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
70 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6458025 |
300 mg 1 times / week steady-state, intramuscular dose: 300 mg route of administration: Intramuscular experiment type: STEADY-STATE co-administered: |
CYPROTERONE ACETATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.9 day |
300 mg 1 times / week steady-state, intramuscular dose: 300 mg route of administration: Intramuscular experiment type: STEADY-STATE co-administered: |
CYPROTERONE ACETATE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, Mean age 72.6 years Health Status: unhealthy Age Group: Mean age 72.6 years Sex: M Sources: |
Other AEs: Hot flushes, Gynaecomastia... Other AEs: Hot flushes (30%) Sources: Gynaecomastia (19.5%) Headache (12.3%) Skin and subcutaneous tissue disorders NEC (6.8%) |
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
Disc. AE: Depression, Weight increase... Other AEs: Amenorrhea, Weight gain... AEs leading to discontinuation/dose reduction: Depression Other AEs:Weight increase Headache Libido decreased Fatigue (6.7%) Amenorrhea (32.6%) Sources: Weight gain |
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: M+F Sources: |
|
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 12.3% | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, Mean age 72.6 years Health Status: unhealthy Age Group: Mean age 72.6 years Sex: M Sources: |
| Gynaecomastia | 19.5% | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, Mean age 72.6 years Health Status: unhealthy Age Group: Mean age 72.6 years Sex: M Sources: |
| Hot flushes | 30% | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, Mean age 72.6 years Health Status: unhealthy Age Group: Mean age 72.6 years Sex: M Sources: |
| Skin and subcutaneous tissue disorders NEC | 6.8% | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, Mean age 72.6 years Health Status: unhealthy Age Group: Mean age 72.6 years Sex: M Sources: |
| Weight gain | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
|
| Amenorrhea | 32.6% | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
| Fatigue | 6.7% Disc. AE |
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
| Depression | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
| Headache | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
| Libido decreased | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
| Weight increase | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://molpharm.aspetjournals.org/content/83/6/1257 Page: - |
no [Inhibition 10 uM] | |||
Sources: https://molpharm.aspetjournals.org/content/83/6/1257 Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/34/2/203 Page: - |
yes [IC50 4.3 uM] | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes | |||
Sources: https://dmd.aspetjournals.org/content/33/11/1576 Page: - |
yes | |||
Page: - |
yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pdf.hres.ca/dpd_pm/00011374.PDF#page=10 Page: 10.0 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action. | 2014 |
|
| Bisphenol A affects androgen receptor function via multiple mechanisms. | 2013-05-25 |
|
| Anabolic-androgenic steroids induce apoptosis and NOS2 (nitric-oxide synthase 2) in adult rat Leydig cells following in vivo exposure. | 2012-12 |
|
| Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. | 2011-08 |
|
| Regulation and dysregulation of vitellogenin mRNA accumulation in daphnids (Daphnia magna). | 2011-01-25 |
|
| Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies. | 2011-01-13 |
|
| Relative progestational and androgenic activity of four progestins used for male hormonal contraception assessed in vitro in relation to their ability to suppress LH secretion in the castrate male rat. | 2010-10-26 |
|
| Testosterone-induced modulation of nitric oxide-cGMP signaling pathway and androgenesis in the rat Leydig cells. | 2010-09 |
|
| Abrupt regression of a meningioma after discontinuation of cyproterone treatment. | 2010-09 |
|
| Prolactinoma induced by estrogen and cyproterone acetate in a male-to-female transsexual. | 2010-08 |
|
| Fatal fulminant hepatitis in a chimpanzee (Pan troglodytes) receiving cyproterone acetate. | 2009-12 |
|
| [A case of Budd-Chiari syndrome induced by ethinylestradiol and cyproterone acetate]. | 2009-12 |
|
| Increased thrombin-activatable fibrinolysis inhibitor antigen levels as a clue for prothrombotic state in polycystic ovary syndrome. | 2008-09 |
|
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008-04 |
|
| Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors. | 2007-09-01 |
|
| Venous thromboembolism and cyproterone acetate in men with prostate cancer: a study using the General Practice Research Database. | 2007-06 |
|
| Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. | 2007-04 |
|
| Ligand-specific dynamics of the androgen receptor at its response element in living cells. | 2007-03 |
|
| Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element. | 1998-12 |
|
| Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines. | 1998-02-12 |
|
| Follow-up study of children with precocious puberty treated with cyproterone acetate. Ad hoc Committee for CPA. | 1997-09 |
|
| Severe hepatitis and liver failure induced by cyproterone acetate. | 1996-10 |
|
| Lactotroph hyperplasia in an estrogen treated male-to-female transsexual patient. | 1996-09 |
|
| Carcinogenicity of cyproterone acetate in the mouse. | 1996-07 |
|
| [Fatal sub-fulminant hepatitis caused by cyproterone acetate. A new case]. | 1996 |
|
| Cyproterone acetate in the treatment of advanced prostatic cancer: retrospective analysis of liver toxicity in the long-term follow-up of 89 patients. | 1996 |
|
| Hepatocellular carcinoma after treatment with cyproterone acetate combined with ethinyloestradiol. | 1995-02-18 |
|
| Hepatocellular carcinoma during hormonotherapy for prostatic cancer. | 1994-10 |
|
| [Fatal hepatitis caused by cyproterone acetate]. | 1994-03-01 |
|
| Fatal fulminant hepatitis from cyproterone acetate. | 1994-03 |
|
| Double-blind placebo crossover study of cyproterone acetate in the treatment of the paraphilias. | 1993-10 |
|
| Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures. | 1993-03 |
|
| [Fatal subfulminant hepatitis caused by cyproterone acetate]. | 1991 |
|
| Severe hepatitis caused by cyproterone acetate. | 1990-05 |
|
| Induction of dorsolateral prostate adenocarcinomas and other accessory sex gland lesions in male Wistar rats by a single administration of N-methyl-N-nitrosourea, 7,12-dimethylbenz(a)anthracene, and 3,2'-dimethyl-4-aminobiphenyl after sequential treatment with cyproterone acetate and testosterone propionate. | 1990-02-01 |
|
| Characterization of adenocarcinomas of the dorsolateral prostate induced in Wistar rats by N-methyl-N-nitrosourea, 7,12-dimethylbenz(a)anthracene, and 3,2'-dimethyl-4-aminobiphenyl, following sequential treatment with cyproterone acetate and testosterone propionate. | 1990-02-01 |
|
| [Hepatitis after treatment with cyproterone acetate. Apropos of a case]. | 1990 |
|
| Fulminant hepatitis due to cyproterone acetate. | 1989-01-28 |
|
| Pulmonary embolism after short-term treatment of acne vulgaris with ovulation suppressor agents. | 1986-10-06 |
|
| Comparison of diethylstilbestrol, cyproterone acetate and medroxyprogesterone acetate in the treatment of advanced prostatic cancer: final analysis of a randomized phase III trial of the European Organization for Research on Treatment of Cancer Urological Group. | 1986-09 |
|
| Cardiovascular side effects of diethylstilbestrol, cyproterone acetate, medroxyprogesterone acetate and estramustine phosphate used for the treatment of advanced prostatic cancer: results from European Organization for Research on Treatment of Cancer trials 30761 and 30762. | 1986-02 |
|
| The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. | 1985-03 |
|
| Follow-up of prolactin levels in long-term oestrogen-treated male-to-female transsexuals with regard to prolactinoma induction. | 1985-02 |
|
| Effects of cyproterone acetate on adrenal steroidogenesis in vitro. | 1984 |
|
| Androgen antagonists in androgen target tissues. | 1984 |
|
| Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. | 1983-10 |
|
| Teratogenic effects of cyproterone acetate and medroxyprogesterone treatment during the pre- and postimplantation period of mouse embryos. I. | 1982-02 |
|
| [Prevention of testosterone-vasopressin induced necrosis of the kidney cortex by cyproterone acetate]. | 1979-07 |
|
| Cyproterone acetate-promoted prevention of renal cortical necrosis following testosterone and vasopressin administration. | 1979-02 |
|
| Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. | 1973-03 |
Patents
Sample Use Guides
Acne: 1 tablet containing 2 mg cyproterone acetate and 0.035 mg ethinyl estradiol is taken daily for 21 consecutive days beginning on day 1 of the menstrual cycle. The tablets are then discontinued for 7 days and the cycle repeats. Prostatic cancer: the usual dose range is from 1 tablet once a day (100mg) up to 1 tablet three times a day (300mg).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14718041
Primary explants (approx. 1 mm3) of prostate tissue from patients with benign prostatic hyperplasia were treated with 10 nM dihydrotestosterone, 50 pM diethylstilbestrol and 100 nM cyproterone acetate to test steroids action on oxytocin secretion.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:40 GMT 2025
by
admin
on
Mon Mar 31 17:48:40 GMT 2025
|
| Record UNII |
4KM2BN5JHF
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
FDA ORPHAN DRUG |
3884
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
||
|
NCI_THESAURUS |
C146993
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
22054
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | RxNorm | ||
|
207-048-3
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
766
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
100000090321
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
81430
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
DTXSID5020366
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
SUB01539MIG
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
D017373
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
m4041
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | Merck Index | ||
|
3592
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
50743
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
9880
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
2865
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
4KM2BN5JHF
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
C1059
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
CYPROTERONE ACETATE
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
CHEMBL139835
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
DB04839
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY | |||
|
427-51-0
Created by
admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> AGONIST |
BINDING
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|