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Cyproterone

HCID 5284537
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2098-66-0
Standard SMILES
CC(=O)[C@@]1(O)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@@]21C
InChIKey
DUSHUSLJJMDGTE-ZJPMUUANSA-N
Molecular formula
C22H27ClO3
Average molar mass
374.9 g/mol
Monoisotopic mass
374.1648724

Overview

Cyproterone is a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a chlorinated steroid. It has a role as an androgen antagonist. It derives from a hydride of a pregnane.

Names & identifiers

Preferred name
Cyproterone
IUPAC
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
English name
Cyproterone
Molecular formula
C22H27ClO3
Molecular weight
374.9

Names & synonyms

cyproterone2098-66-0CiproteronaCyproteronumDTXSID3022873CiproteroneCiproterona ServycalE61Q31EK2FNSC-758636DTXCID102873CHEBI:507423'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 6-chloro-1,2-dihydro-17-hydroxy-, (1beta,2beta)-
Show more names
cyproteronSH-80881BAY 94-8367Cyproterone-d5ro-17-hydroxy-Cyproterone USP/EP/BPCyproterone Acetate Impurity F
Med Cyproterone(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo(9.7.0.0^(2,8).0^(3,5).0^(12,16))octadeca-7,9-dien-6-one(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0^{2,8}.0^{3,5}.0^{12,16}]octadeca-7,9-dien-6-one3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 6-chloro-1,2-dihydro-17-hydroxy-, (1beta,2beta)-SH-881RefChem:130164G03HA01(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one

Database identifiers

CAS
2098-66-0

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
26
Formal charge
0
Complexity
797

Experimental & physicochemical properties

Solubility6.65e-03 g/L
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physicochemical properties

Melting point
208 · 208-210°C
Boiling point
521 · 521.0±50.0 °C(Predicted)
Density
1.29 · 1.29±0.1 g/cm3(Predicted)
storage temp.
Refrigerator
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
12.86 · 12.86±0.70(Predicted)
color
Off-White to Yellow
FDA UNII
61 Q31EK2F · E61Q31EK2F
ATC code
3 HA01 · G03HA01
Symbol(GHS)
8 · GHS08

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesCarc. 2 (100%)

Toxicology

Hepatotoxicity · 1 item

Cyproterone has been associated with serum enzyme elevations during therapy in 10% to 14% of patients, but these elevations are usually transient and mild and often resolve even without dose modification. More importantly, cyproterone has been associated with many instances of clinically apparent liver injury with jaundice. The time to onset has ranged from a few months to as long as a year, but typically arises within 3 to 6 months of starting treatment. The liver injury is almost always hepatocellular with moderate to marked elevations in serum aminotransferase levels and minimal increases in alkaline phosphatase. Mixed and more cholestatic injury occurs occasionally and may have a more favorable prognosis. Importantly, the hepatocellular injury associated with cyproterone use is often severe and the mortality rate of patients presenting with jaundice is at least 10% (these patients frequently being elderly men with advanced prostate cancer and not qualifying for emergency liver transplantation). Immunoallergic features (fever, rash, eosinophilia) are uncommon, as are autoantibodies. Some patients, however, appear to respond to corticosteroid therapy and rare instances of autoimmune-hepatitis like injury have been attributed to cyproterone. Improvement is usually seen within 1 to 2 weeks of stopping cyproterone and resolution within 1 to 3 months. Nevertheless, many examples of progressive liver injury leading to death from hepatic failure despite prompt discontinuation of therapy have been reported. In rare cases, recovery has been incomplete and patients have had residual evidence of chronic liver disease or cirrhosis.

Chemistry & industry

Pharmacology

ATC Code · 3 items

G03HA01

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

MeSH Pharmacological ClassificationCompounds which inhibit or antagonize the biosynthesis or actions of androgens.
Cellular LocationsCytoplasm

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >750
Applications · 3 items

Usesinsecticide

UsesCyproterone is used to control sexual attraction in men in cases of sexual deviations, as well as for inoperable prostate gland carcinoma. In women, it is used for severe cases of androgenization, and in children with idiopathic premature sexual maturity.

UsesAn antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsexuals.

Suppliers44 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Related reactions

3 records
New reaction record
HRID 848444 reaction equation
HRID 848444As reactantuspto-grants-1981_10
HRID 1156954 reaction equation
HRID 1156954As reactantuspto-grants-1982_06
HRID 2049021 reaction equation
HRID 2049021As reactantuspto-grants-1980_04

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
5284537
DTXSID
DTXSID3022873
ChEMBL
CHEMBL142130
ChEBI
CHEBI:50742
UNII
E61Q31EK2F
EC Number
690-915-7
Nikkaji
J34.128B
Signal word
Danger
Hazard statements
351 · H351-H360
Precautionary statements
201 · P201-P202-P281-P308+P313-P405-P501
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

CYPROTERONE

DILI Positive

Oral, Intramuscular

DOI:10.1016/j.drudis.2019.09.022

Safety data

Signal word
Danger
Symbol(GHS)
GHS08
Hazard statements
H351-H360
Precautionary statements
P201-P202-P281-P308+P313-P405-P501
Dayang Chem (Hangzhou) Co.,Ltd.
+86-0571-88938639 17705817739 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
深圳市简一生物科技有限公司0755-84826604 · [email protected]
孟成科技(上海)有限公司400-820-6829 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Standardpharm Co. Ltd.86-714-3992388 · [email protected]
BOC Sciences16314854226 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
广州佳途科技股份有限公司020-81960175-877 18933936954 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 400821072 · [email protected]
美化生物科技有限公司15175972705
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
广州市桐晖药业有限公司020-66392521-118 18922260391 · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海贝万塔生物科技有限公司021-67187366 19901745723 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 17389186172 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
重庆卡兰医药有限公司[email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
上海择睿生物科技有限公司021-54580889 18321124657 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]
陕西缔都化学有限公司17691182729 17392216275 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]

Additional notes

DefinitionChEBI: Cyproterone is a 20-oxo steroid, a 17alpha-hydroxy steroid, a chlorinated steroid, a 3-oxo-Delta(4) steroid and a tertiary alpha-hydroxy ketone. It has a role as an androgen antagonist. It derives from a hydride of a pregnane.