(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl 3-cyclopentylpropanoate

• ChemBase ID: 72786
• Molecular Formular: C27H40O3
• Molecular Mass: 412.6047
• Monoisotopic Mass: 412.29774514
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)OC(=O)CCC1CCCC1)C)C
• Canonical SMILES: O=C(O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)CCC1CCCC1
• InChI: InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
• InChIKey: HPFVBGJFAYZEBE-ZLQWOROUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl 3-cyclopentylpropanoate; (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-cyclopentylpropanoate
• IUPAC Traditional name: testosterone cypionate
• Synonyms: Depovirin; Testosterone 17β-cyclopentanepropionate; Testosterone 17β-cypionate; Testosterone cypionate; (17β)-3-Oxoandrost-4-ene-17-carboxylic Acid; 3-Oxoandrost-4-ene-17β-carboxylic Acid; 17β-Carboxyandrost-4-en-3-one; AD-Acid; AL 3793; CC 14837; Etienic Acid; L 552.803; NSC 226121; SKF 106224; Testosterone-17β-carboxylic Acid; Testosterone 17β-Carboxylic Acid; 17β-羟基-4-雄甾烯-3-酮-17-环戊丙酸酯; 4-雄甾烯-17β-醇-3-酮-17-环戊丙酸酯; 环戊丙酸睾酮; 睾酮-17β-环戊丙酸酯

Database IDs

• CAS Number: 58-20-8; 302-97-6
• EC Number: 200-368-4
• MDL Number: MFCD00053944
• PubChem SID: 24899869; 162037707
• PubChem CID: 441404

CALCULATED PROPERTIES

• Acid pKa: 19.086855
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.1086526
• LogD (pH = 7.4): 6.1086526
• Log P: 6.1086526
• Molar Refractivity: 119.3586 cm^3
• Polarizability: 47.410328 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: XA3066000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-63
• Safety Statements: 22-26-36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350-H361
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Salt Data: Cypionate

DETAILS

Selleck Chemicals - S1700

Research Area: Endocrinology
Biological Activity:
Testosterone cypionate is the oil-soluble 17 (beta)-cyclopentylpropionate ester of the androgenic hormone testosterone. Approximately 7% of testosterone is reduced to 5α-dihydrotestosterone (DHT) by the cytochrome P450 enzyme 5α-reductase, an enzyme highly expressed in male accessory sex organs and hair follicles. Approximately 0.3% of testosterone is converted into estradiol by aromatase (CYP19A1) an enzyme expressed in the brain, liver, and adipose tissues. [1]

Toronto Research Chemicals - T155070

Testosterone 17β-Carboxylic Acid is used in the synthesis of anti-benign prostatic hyperplasia drugs Dutasteride (D735000) and Finasteride.

REFERENCES

• http://en.wikipedia.org/wiki/Testosterone_cypiona
• Brooks, J., et al.: Annu. Drug Data Rep., 14, 996 (1992)
• Lam, J., et al.: Urology, 61, 354 (1992)
• Tarter, T., et al.: Curr. Pharm. Des., 12, 775 (1992)
• Aggarwal, S., et al.: Steroids, 75, 109 (1992)