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| CAS No.: | 427-51-0 |
|---|---|
| Name: | Cyproterone acetate |
| Molecular Structure: | |
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| Formula: | C24H29ClO4 |
| Molecular Weight: | 416.945 |
| Synonyms: | SH 714;Cyproteron-r acetate;6-Chloro-1beta,2beta-dihydro-17-hydroxy-3H-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate;Cyproteroneacetate;Cyproterone acetate (JAN/USAN);Cyproviron;1,2-alpha-Methylene-6-chloro-(sup 4,6)-pregnadiene-17-alpha-ol-3,20-dione 17-alpha-acetate;6-Chloro-delta(sup 6)-1,2-alpha-methylene-17-alpha-hydroxyprogesterone acetate;3H-Cyclopropa[1,2]pregna-1,4,6-triene-3, 20-dione, 17- (acetyloxy)-6-chloro-1,2-dihydro-, (1.beta., 2.beta.)-;6-Chloro-delta-6-1,2alpha-methylene-17alpha-hydroxyprogesterone acetate;17-alpha-Acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dione;1,2-alpha-Methylene-6-chloro-pregna-4,6-diene-3,20-dione 17-alpha-acetate;Cyproterone acetate [USAN:JAN];Cyproterone 17-O-acetate;6-Chloro-1-beta,2-beta-dihydro-17-hydroxy-3H-cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione 17-acetate;SH 80714;3H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 6-chloro-1-beta,2-beta-dihydro-17-hydroxy-, acetate;6-Chloro-17-hydroxy-1.alpha.,2.alpha.-methylenepregna-4, 6-diene-3,20-dione acetate;Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1.alpha.,2.alpha.-methylene-, acetate;Cyproterone 17.alpha.-acetate;1, 2.alpha.-Methylene-6-chloro-(sup 4,6)-pregnadiene-17.alpha.-ol-3, 20-dione 17alpha-acetate;Progesterone, 6-chloro-6-dehydro-17-hydroxy-1.alpha.,2.alpha.-methylene-, acetate;Cyproterone 17alpha-acetate;3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20- dione,17-(acetyloxy)-6-chloro-1,2-dihydro-,(1a,2a)-;Cyproteron acetate;Cyprosterone acetate;Androcur;6-chloro-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate; |
| EINECS: | 207-048-3 |
| Density: | 1.27 g/cm3 |
| Melting Point: | 200-201 °C |
| Boiling Point: | 525.9 °C at 760 mmHg |
| Flash Point: | 177.6 °C |
| Appearance: | Crystalline solid |
| Hazard Symbols: |
 Xn,  Xi
|
| Risk Codes: | 20/21/22-40-36/37/38 |
| Safety: | 22-36-26 |
| PSA: | 60.44000 |
| LogP: | 4.60760 |
6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione
trimethylsulfoxonium iodide
cyproterone acetate
| Conditions | Yield |
|---|---|
| Stage #1: 6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione; trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 5 - 20℃; for 29.5h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃; | 51.51% |
6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate
cyproterone acetate
| Conditions | Yield |
|---|---|
| Stage #1: 6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate With 2,4,6-trimethyl-pyridine for 0.333333h; Heating / reflux; Stage #2: With hydrogenchloride In diethyl ether; water pH=7; Product distribution / selectivity; | |
| With sodium acetate In methanol; N,N-dimethyl-formamide at 60℃; for 8h; Temperature; |
cyproterone acetate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 2: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
cyproterone acetate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: sulfuric acid / N,N-dimethyl-formamide / 2 h / pH 2 2: chloroform / 58 °C 3: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 °C 4: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 5: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
1,4,6-triene-3,20-dione-17α-hydroxyprogesterone
cyproterone acetate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: orthoformic acid triethyl ester / dichloromethane / 5 h / 30 °C 2: N,N-dimethyl-formamide / 3 h / 42 °C 3: sulfuric acid / N,N-dimethyl-formamide / 2 h / pH 2 4: chloroform / 58 °C 5: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 °C 6: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 7: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
cyproterone acetate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 3 h / 42 °C 2: sulfuric acid / N,N-dimethyl-formamide / 2 h / pH 2 3: chloroform / 58 °C 4: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 °C 5: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 6: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: chloroform / 58 °C 2: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 °C 3: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 4: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 °C 2: acetic anhydride; acetic acid; hydrogenchloride / water / 11 h / 0 - 27 °C 3: sodium acetate / N,N-dimethyl-formamide; methanol / 8 h / 60 °C View Scheme |
cyproterone acetate
| Conditions | Yield |
|---|---|
| With sodium carbonate In methanol; N,N-dimethyl-formamide at 50 - 55℃; for 5h; |
cyproterone acetate
6-chloro-1α,2α-methylene-4,6,16-pregnatriene-3,20-dione
| Conditions | Yield |
|---|---|
| 89% |
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EPA Genetic Toxicology Program.
Cyproterone acetate, with the CAS NO.427-51-0, is also called 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. Cyproterone acetate is very soluble in dichloromethane, soluble in methyl alcohol, freely soluble in acetone, sparingly soluble in dehydrated alcohol, and insoluble in water. Cyproterone acetate is a medicine which is used in prostate cancer.
Physical properties about Cyproterone acetate are: (1)ACD/LogP: 4.216; (2)ACD/LogD (pH 5.5): 4.22; (3)ACD/LogD (pH 7.4): 4.22; (4)ACD/BCF (pH 5.5): 942.43; (5)ACD/BCF (pH 7.4): 942.43; (6)ACD/KOC (pH 5.5): 4683.45; (7)ACD/KOC (pH 7.4): 4683.45; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.582 ; (11)Molar Refractivity: 109.164 cm3; (12)Molar Volume: 327.087 cm3; (13)Polarizability: 43.276 10-24cm3; (14)Surface Tension: 48.9609985351563 dyne/cm; (15)Density: 1.275 g/cm3; (16)Flash Point: 177.633 °C; (17)Enthalpy of Vaporization: 80.007 kJ/mol; (18)Boiling Point: 525.853 °C at 760 mmHg
Uses of Cyproterone acetate: Cyproterone acetate is used in the treatment of prostate cancer. It blocks the effects of hormones that may worsen certain types of prostate cancer. Tablet forms of this medicine must not be taken by women.
When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Wear suitable protective clothing;
3. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure: (1)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;
(2)InChIKey=UWFYSQMTEOIJJG-FDTZYFLXSA-N;
(3)SmilesC1=2[C@@]([C@@H]3[C@@H](C(=O)C2)C3)([C@@H]2[C@H]([C@H]3[C@]([C@@](OC(C)=O)(C(C)=O)CC3)(C)CC2)C=C1Cl)C
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| man | LDLo | oral | 171mg/kg/17W- (171mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: LIVER FUNCTION TESTS IMPAIRED | Israel Journal of Medical Sciences. Vol. 30, Pg. 238, 1994. |
| man | TDLo | oral | 514mg/kg/7W-I (514mg/kg) | LIVER: LIVER FUNCTION TESTS IMPAIRED LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" | Australian and New Zealand Journal of Medicine. Vol. 26, Pg. 724, 1996. |
| mouse | LD50 | intraperitoneal | 3300mg/kg (3300mg/kg) | Drugs in Japan Vol. 6, Pg. APP-4, 1982. | |
| mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. APP-4, 1982. | |
| mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. APP-4, 1982. | |
| rat | LD50 | intraperitoneal | 565mg/kg (565mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 349, 1982. | |
| rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. APP-4, 1982. | |
| rat | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. APP-4, 1982. |
