ChemicalBook > CAS DataBase List > Cyproterone acetate

Cyproterone acetate

Product Name
Cyproterone acetate
CAS No.
427-51-0
Chemical Name
Cyproterone acetate
Synonyms
ANDROCUR;CYPROSTAT;CIPROTERONE ACETATE;SH-714;nsc-81430;Cyproviron;cyprosteroneacetate;CYPROTERONE ACETATE;CYPROFERONE ACETATE;cyproteron-racetate
CBNumber
CB7338955
Molecular Formula
C24H29ClO4
Formula Weight
416.94
MOL File
427-51-0.mol
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Cyproterone acetate Property

Melting point:
200-201°C
Boiling point:
528.8°C (rough estimate)
Density 
1.0677 (rough estimate)
refractive index 
1.4429 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol.
form 
Solid
color 
White to Off-White
λmax
281nm(MeOH)(lit.)
Merck 
14,2774
InChIKey
UWFYSQMTEOIJJG-KIXORDEXNA-N
SMILES
C[C@@]12C(=CC(=O)[C@@H]3C[C@H]13)C(Cl)=C[C@@]1([H])[C@]3([H])CC[C@@](C(=O)C)(OC(=O)C)[C@@]3(C)CC[C@]21[H] |&1:1,6,8,12,14,18,26,30,r|
EPA Substance Registry System
3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1.beta.,2.beta.)- (427-51-0)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-40-36/37/38
Safety Statements 
22-36-26
WGK Germany 
3
RTECS 
GZ2230000
HS Code 
29372900
Hazardous Substances Data
427-51-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2809
Product name
Cyproterone acetate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material, certified reference material
Packaging
50MG
Price
$344
Updated
2024/03/01
Sigma-Aldrich
Product number
C3412
Product name
Cyproterone acetate
Purity
≥98%
Packaging
250mg
Price
$305
Updated
2024/03/01
Sigma-Aldrich
Product number
C3283000
Product name
Cyproterone acetate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
c3283000
Price
$220
Updated
2024/03/01
TCI Chemical
Product number
C2942
Product name
Cyproterone Acetate
Purity
>98.0%(HPLC)
Packaging
1g
Price
$107
Updated
2024/03/01
TCI Chemical
Product number
C2942
Product name
Cyproterone Acetate
Purity
>98.0%(HPLC)
Packaging
200mg
Price
$36
Updated
2024/03/01
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Cyproterone acetate Chemical Properties,Usage,Production

Description

Cyproterone acetate (CPA) is an androgen receptor antagonist. It binds to human androgen receptors (Ki = 14 nM) and inhibits dihydrotestosterone-induced androgen receptor activation in CV-1 cells (IC50 = 26 nM). CPA (30 mg/kg) decreases ventral prostate weight in castrated immature rats. It also suppresses accessory sexual glands and fertility in adult male rats when administered at a dose of 10 mg/kg. CPA (0.3 μM) also induces apoptosis in primary adult female rat hepatocytes. Formulations containing cyproterone acetate have been used in the treatment of androgenization in females.

Chemical Properties

Crystalline Solid

Originator

Androcur ,Schering,W. Germany,1973

Uses

Cyproterone acetate (CPA) has been shown to exert gestagenic and glucocorticoid effects. Because it inhibits the negative diencephalic pituitary testicular feedback system, it lowers luteinizing hormone (LH) and testosterone production and plasma levels. cyproterone acetate is both an anti-androgen and a progestogen. CPA is used in combined birth control pills, in the treatment of androgen-dependent skin and hair conditions such as acne (Combined with estrogen), seborrhea, excessive hair growth, and scalp hair loss, high androgen levels, in transgender hormone therapy, to treat prostate cancer, to reduce sex drive in sex offenders or men with paraphilias or hypersexuality, to treat early puberty, and for other uses. It is used both at low doses and at higher doses.

Definition

ChEBI: Cyproterone acetate is a steroid ester resulting from the formal condensation of the carboxy group of acetic acid with the 17-hydroxy group of cyproterone. It is an antiandrogenic drug which has recently been recognized to promote the occurrence and growth of intracranial meningiomas. It has a role as an androgen antagonist, a progestin and a geroprotector. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a chlorinated steroid, a steroid ester and an acetate ester. It is functionally related to a cyproterone.

Indications

Cyproterone acetate is a progestational antiandrogen that blocks androgen receptor binding and suppresses androgen-sensitive tissues. It is available in a topical form in Europe for the treatment of hirsutism.

Manufacturing Process

2.34 g of 1,2α-methylene-δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate are dissolved in 18.25 cc of ethylene chloride which contains 844 rng of perbenzoic acid. The solution is stored for 16 hours at +5°C and 7 hours at room temperature. It is then diluted with methylene chloride and, with aqueous ferrous sulfate solution, sodium bicarbonate solution and with water washed until neutral.
The organic phase is dried over sodium sulfate and then concentrated to dryness. 1.62 g of the thus obtained crude 1,2α-methylene-6,7α-oxido-δ4- pregnene-17α-ol-3,20-dione-17-acetate are dissolved in 109 cc of glacial acetic acid. This solution is then saturated at room temperature with hydrogen chloride gas and stored for 20 hours, It is then diluted with methylene chloride and washed with water until neutral.
The organic phase is dried over sodium sulfate and then concentrated to dryness. The thus obtained crude 6-chloro-1α-chloromethyl-δ4,6-pregnadiene17α-ol-3,20-dione-17-acetate is heated to boiling in 20 cc of collidine for 20 minutes under nitrogen. After dilution with ether it is washed with 4 N hydrochloric acid and washed with water until neutral.
After drying over sodium sulfate and concentration to vacuum the remaining residue is subjected to chromatography over silica gel. Using a benzene-ethyl acetate mixture (19:1) there is eluated 900 mg of 6-chloro-1,2α-methyleneδ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate, which upon recrystallization from isopropyl ether melts at 200° to 201°C.

Therapeutic Function

Antiandrogen

Mechanism of action

The mechanism of action of Cyproterone acetate at the molecular level has never been described conclusively. Studies have found that in rat ventral prostate nuclei, CPA interferes with androgen binding to the androgen receptor. It is possible that CPA interferes with the translocation of the androgen receptor from the cytoplasm to the nuclear compartment. At the transcription level, the effects of CPA also include a reduction of androgen-dependent cellular functions, such as a reduction of acid phosphatase, prostate-specific androgen, and androgen-dependent enzymes such as 5-a-reductase[1].

Side effects

Vbreast tenderness and swelling. Tiredness and weakness (fatigue). Depression or mood changes. Hot flushes or sweats. Swelling in parts of the body (fluid build up). Weight changes. Liver changes (you will have regular blood tests to check for this). Shortness of breath.

Metabolism

Cyproterone is metabolised by various pathways including hydroxylation and conjugation; about 35% of a dose is excreted in urine, the remainder being excreted in the bile. The principal metabolite, 15β-hydroxycyproterone, has anti-androgenic activity

References

[1] Schr?der F, et al. Cyproterone Acetate-Mechanism of Action and Clinical Effectiveness in Prostate Cancer Treatment. Cancer, 1993; 72: 3810-3815.

Cyproterone acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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Cyproterone acetate Suppliers

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View Lastest Price from Cyproterone acetate manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
Cyproterone acetate 427-51-0
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-19
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cyproterone acetate 427-51-0
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
97%-103%; EP
Supply Ability
100 KG
Release date
2021-05-31
Wuhan Haorong Biotechnology Co.,Ltd
Product
Cyproterone acetate 427-51-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000
Release date
2023-07-27

427-51-0, Cyproterone acetateRelated Search:

1-Methoxy-2-propyl acetate Methyl acetate Tocopheryl acetate Leuprorelin acetate Ethylene glycol monoethyl ether acetate Vinyl acetate Glatiramer acetate POLY(VINYL ACETATE) Isopropyl acetate Sodium acetate 2-Butoxyethyl acetate Ethyl acetate Butyl acetate CHLOROPHOSPHONAZO III Chlormadinone acetate Pregna-4,6-diene-3,20-dione ACETATE Cyproterone Acetate 427-51-0 /Base

  • cyprosteroneacetate
  • 1,2-alpha-methylene-6-chloro-delta-(sup4,6)-pregnadiene-17-alpha-ol-3,20-dio
  • 1,2-alpha-methylene-6-chloro-delta(sup6)-17-alpha-hydroxyprogesteroneacetat
  • 1,2-alpha-methylene-6-chloro-pregna-4,6-diene-3,20-dione17-alpha-acetate
  • 17-alpha-acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dio
  • 20-dione,6-chloro-17-hydroxy-1-alpha,2-alpha-methylene-pregna-6-diene-3
  • 6)-pregnadiene-17-alpha-ol-3,20-dione17-2-alpha-methylene-6-chloro-(sup4
  • 6-chlor-delta(sup6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronacetat
  • 6-chloro-1,2-alpha-methylene-17-alpha-hydroxy-delta(sup6)-progesteroneaceta
  • 6-chloro-1,2-alpha-methylene-6-dehydro-17-alpha-hydroxyprogesteroneacetate
  • 6-chloro-17-hydroxy-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dioneacet
  • 6-chloro-delta(sup6)-1,2-alpha-methylene-17-alpha-hydroxyprogesteroneacetat
  • CYPROSTAT
  • CYPROTERONE ACETATE
  • CYPROFERONE ACETATE
  • 6-CHLORO-1BETA,2BETA-DIHYDRO-17-HYDROXY-3'H-CYCLOPROPA[1,2]-PREGNA-1,4,6-TRIENE-3,20-DIONE ACETATE
  • 6-chloro-1b,2b-dihydro-17-hydroxy-3'h-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate
  • ANDROCUR
  • 4,6-PREGNADIEN-6-CHLORO-1-ALPHA, 2-ALPHA-METHYLENE-17-OL-3,20-DIONE ACETATE
  • cyproterone17-alpha-acetate
  • cyproteron-racetate
  • nsc-81430
  • Cyproterone D3 Acetate
  • Cyproterone Acetate BP2000,EP2000
  • CIPROTERONE ACETATE
  • 6-chloro-1-beta,2-beta-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate
  • Androcur, Cyprostat
  • 3H-Cyclopropa1,2pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1.beta.,2.beta.)-
  • 6-Chloro-1α,2α-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate
  • CyproteroneAcetateedmfep5
  • CyproteroneAcetateEdmf
  • 6-Chloro-1β,2β-dihydro-17-hydroxy-3μH-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate
  • Androcurone acetate
  • SH-714
  • Cyproterone acetate(Androcur)
  • Cyproviron
  • (1β,2β)-17-(acetyloxy)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
  • Cyproterone acetate for peak identification
  • * Color Pronk (cyproterone)
  • Cyproterone acetate, 98%, an androgen receptor (AR) antagonist
  • Cyproterone acetate CRS
  • Cyproterone acetate for peak identification CRS
  • Cyproterone Acetate &gt
  • Cyproterone 17-O-acetate
  • 6-Chloro-3,20-dioxo-1β,2β-dihydro-3′H-cyclopropa-[1,2]pregna-1,4,6-trien-17-yl acetate
  • (1aR,5aR,5bS,8R,8aS,9aS,9bS,9cS)-8-Acetyl-4-chloro-8a,9b-dimethyl-2-oxo-1a,2,5a,5b,6,7,8,8a,9,9a,9b,9c-dodecahydro-1H-cyclopropa[a]pentaleno[1,2-h]naphthalen-8-yl acetate
  • Cyproterone acetate USP/EP/BP
  • Cyproterone Acetate-13C,d3
  • Cyproterone acetate (C3283000)
  • Cyproterone Acetate D3Q: What is Cyproterone Acetate D3 Q: What is the CAS Number of Cyproterone Acetate D3 Q: What is the storage condition of Cyproterone Acetate D3 Q: What are the applications of Cyproterone Acetate D3
  • Cyproterone acetateQ: What is Cyproterone acetate Q: What is the CAS Number of Cyproterone acetate Q: What is the storage condition of Cyproterone acetate Q: What are the applications of Cyproterone acetate
  • Cyproterone acetate API
  • Cyproterone acetate chloride
  • Cyproterone (+)-bitartrate salt
  • 3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1β,2β)-
  • 4, 6-PREGNADIEN-6-CHLORO-1α, 2α-METHYLENE-17-OL-3, 20-DIONE ACETATE
  • (2aR,3aS,3bS,3cS,5aS,6R,8aS,8bR)-6-acetyl-10-chloro-3b,5a-dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-6-yl acetate
  • 427-51-0