6-Chlor-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-trien-3,20-dion-17-acetat
[(2S,3S,5R,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
Grundinformationen
- CAS
427-51-0- Standard-SMILES
CC(=O)O[C@]1(C(C)=O)CCC2C3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)C3CC[C@@]21C- InChIKey
UWFYSQMTEOIJJG-WMANOXGZSA-N- Summenformel
- C24H29ClO4
- Durchschnittliche Molmasse
- 416,9 g/mol
- Monoisotopische Masse
- 416,1754371
Namen und Bezeichner
- Bevorzugter Name
- [(2S,3S,5R,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
- IUPAC
- [(2S,3S,5R,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
- Lokaler Name
- 6-Chlor-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-trien-3,20-dion-17-acetat
- Englischer Name
- Cyproterone acetate
- Summenformel
- C24H29ClO4
- Molmasse
- 416.94
Namen und Synonyme
[(2S,3S,5R,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] acetateSpectrum_000882Spectrum2_001270Spectrum3_000372Spectrum4_000306BSPBio_002123KBioGR_000892KBioSS_001362DivK1c_000206SPECTRUM1500216SPBio_001240HMS500K08
Weitere Namen anzeigen
CIPROTERONE ACETATEANDROCURCYPROSTATSH-714nsc-81430CyprovironcyprosteroneacetateCYPROTERONE ACETATECYPROFERONE ACETATEcyproteron-racetate
KBio1_000206KBio2_001362KBio2_003930KBio2_006498KBio3_001343NINDS_000206HMS1920C08HMS2091I16
Datenbank-Bezeichner
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,6
- Polarare Oberfläche (TPSA)
- 60,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 903
Physikochemische Eigenschaften
- Schmelzpunkt
- 200 · 200-201°C
- Siedepunkt
- 528.8 °C · 528.8°C (rough estimate)
- Dichte
- 1.0677 · 1.0677 (rough estimate)
- Brechungsindex
- 1.4429 · 1.4429 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol.
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Merck
- 14 · 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 chemische Informationen
- 3 · 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)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29372900
- RTECS-Nr.
- GZ2230000
- risk_code
- 20/21/22-40-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 22-36-26
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 427-51-0(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationCarc. 2
Chemie und Industrie
Anwendungen
BeschreibungCyproterone 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.
VerwendenCyproterone 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.
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