Cyproterone Acetate

Possibly Marketed Outside US

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

[H][C@@]12C[C@]1([H])[C@@]3(C)C(=CC2=O)C(Cl)=C[C@@]4([H])[C@]5([H])CC[C@](OC(C)=O)(C(C)=O)[C@@]5(C)CC[C@]34[H]

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

HIDE SMILES / InChI

Molecular Formula	C24H29ClO4
Molecular Weight	416.938
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167	Antagonist 2,778		4.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Severe acne 1	Curative		Approved 8,429	DIANE-35
Prostate cancer 178	Primary		Approved 8,429	CYPROTERONE ACETATE

C_max

Value	Dose	Co-administered	Analyte	Population
406 ng/mL	300 mg 1 times / week steady-state, intramuscular		CYPROTERONE ACETATE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
70 ng × h/mL	300 mg 1 times / week steady-state, intramuscular		CYPROTERONE ACETATE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.9 day	300 mg 1 times / week steady-state, intramuscular		CYPROTERONE ACETATE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
200 mg 1 times / day multiple, oral Recommended	unhealthy, Mean age 72.6 years n = 293	Other AEs: Hot flushes, Gynaecomastia...
100 mg 1 times / day multiple, oral Recommended	unhealthy, adult n = 76	Disc. AE: Depression, Weight increase... Other AEs: Amenorrhea, Weight gain...
600 mg 1 times / day multiple, oral Highest studied dose	unhealthy, children
300 mg 1 times / day multiple, oral Recommended	unhealthy

Showing 1 to 4 of 4 entries

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AEs

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AE	Significance	Dose	Population
Headache	12.3%	200 mg 1 times / day multiple, oral Recommended	unhealthy, Mean age 72.6 years n = 293
Gynaecomastia	19.5%	200 mg 1 times / day multiple, oral Recommended	unhealthy, Mean age 72.6 years n = 293
Hot flushes	30%	200 mg 1 times / day multiple, oral Recommended	unhealthy, Mean age 72.6 years n = 293
Skin and subcutaneous tissue disorders NEC	6.8%	200 mg 1 times / day multiple, oral Recommended	unhealthy, Mean age 72.6 years n = 293
Weight gain		100 mg 1 times / day multiple, oral Recommended	unhealthy, adult n = 76

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 706 OATP1B1 788 CYP2C8 911 CYP2C19 1,478 P-gp 1,461 MRP2 383		CYP1A2 701 CYP2E1 128

Drug as perpetrator

Show entries

Target	Modality	Activity
OATP1B1 803	inhibitor 3,277	no [Inhibition 10 uM]
OATP1B3 715	inhibitor 3,277	no
P-gp 1,650	inhibitor 3,277	yes [IC50 4.3 uM]
CYP1A2 1,692	inducer 1,573	yes
CYP2C19 1,553	inhibitor 3,277	yes

Showing 1 to 5 of 12 entries

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Drug as victim

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,737	substrate 3,367	yes

Showing 1 to 1 of 1 entries

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PubMed

Show entries

Title	Date	PubMed
Teratogenic effects of cyproterone acetate and medroxyprogesterone treatment during the pre- and postimplantation period of mouse embryos. I.	1982 Feb	6461082
Severe hepatitis caused by cyproterone acetate.	1990 May	2140997
Hepatitis due to cyproterone acetate.	1992	1389539
[Fatal hepatitis caused by cyproterone acetate].	1994 Mar-Apr	7817350
Altered cognitive function in men treated for prostate cancer with luteinizing hormone-releasing hormone analogues and cyproterone acetate: a randomized controlled trial.	2002 Sep	12175403

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Patents

Sample Use Guides

In Vivo Use Guide

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

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.