[(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

Base Information

• Chemical 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
• CAS No.: 427-51-0
• Molecular Formula: C24H29ClO4
• Molecular Weight: 416.945
• Hs Code.: 29372900
• NSC Number: 756713
• Mol file: 427-51-0.mol

Synonyms:[(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;Spectrum_000882;Spectrum2_001270;Spectrum3_000372;Spectrum4_000306;BSPBio_002123;KBioGR_000892;KBioSS_001362;DivK1c_000206;SPECTRUM1500216;SPBio_001240;HMS500K08;KBio1_000206;KBio2_001362;KBio2_003930;KBio2_006498;KBio3_001343;NINDS_000206;HMS1920C08;HMS2091I16;Pharmakon1600-01500216;CCG-39121;NSC756713;NSC-756713;IDI1_000206;NCGC00178807-01;AS-13021;SBI-0051326.P003;AB00051957_02;SR-05000002038;SR-05000002038-1;BRD-A95207036-001-02-8;BRD-A95207036-001-03-6

Chemical Property of [(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

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 3.78E-11mmHg at 25°C
• Melting Point: 200-201 °C
• Refractive Index: 1.582
• Boiling Point: 525.9 °C at 760 mmHg
• Flash Point: 177.6 °C
• PSA: 60.44000
• Density: 1.27 g/cm³
• LogP: 4.60760
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 416.1754371
• Heavy Atom Count: 29
• Complexity: 903

Purity/Quality:

99.00% ^*data from raw suppliers

Cyproterone Acetate >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40-36/37/38
• Safety Statements: 22-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)OC(=O)C
• Isomeric SMILES: CC(=O)[C@]1(CCC2[C@@]1(CCC3C2C=C(C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C)Cl)C)OC(=O)C
• 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.
• Uses: Used as an antiandrogen. Combinded with estrogen in the treatment of acne The free alcohol is an anti-androgen; cyproterone acetate is both an anti-androgen and a progestogen. Combined with estrogen it is used in the treatment of acne. antiparasitic, fasciolicide
• 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.
• Therapeutic Function: Antiandrogen
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of [(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

There total 14 articles about [(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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.51%

6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione (13698-49-2) + trimethylsulfoxonium iodide (1774-47-6) → cyproterone acetate (427-51-0)

Guidance literature:

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;

With hydrogenchloride; In water; dimethyl sulfoxide; at 0 ℃;

Reference yield:

C24H30Cl2O4 → cyproterone acetate (427-51-0)

Guidance literature:

With sodium carbonate; In methanol; N,N-dimethyl-formamide; at 50 - 55 ℃; for 5h;

Reference yield:

6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate (17183-98-1) → cyproterone acetate (427-51-0)

Guidance literature:

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;

With hydrogenchloride; In diethyl ether; water; pH=7; Product distribution / selectivity;

upstream raw materials:

6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione

trimethylsulfoxonium iodide

6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate

1,4,6-triene-3,20-dione-17α-hydroxyprogesterone

Downstream raw materials:

cyproterone

Refernces

• 1、 -. "Production technology and production device of c`yproterone acetate". Paragraph 0091; 0093. . Retrieved 2019/01/08.
• 2、 -. "Further syntheses of cyproterone acetate". Page/Page column 3; 20; 30. . Retrieved 2010/02/07.