(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 130692
• Molecular Formular: C20H32O2
• Molecular Mass: 304.46688
• Monoisotopic Mass: 304.24023026
• SMILES: C[C@H]1CC(=O)C[C@H]2[C@]1([C@H]1CC[C@]3([C@H]([C@@H]1CC2)CC[C@@H]3O)C)C
• Canonical SMILES: O=C1C[C@H](C)[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1
• InChIKey: UXYRZJKIQKRJCF-TZPFWLJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: proviron
• Synonyms: Mesterolone; (1α,5α,17β)-17-hydroxy-1-methylandrostan-3-one; 1α-Methyl-5α-dihydrotestosterone; 17β-Hydroxy-1α-methyl-5α-androstan-3-one; 1α-Methyl-5α-androstan-17β-ol-3-one; 1α-Methyl-17β-hydroxy-5α-androstan-3-one; Androviron; Mesteranum; Mestoranum; NSC 75054; Proviron; Provirone 25; SH 723; Testiwop; Mesterolone; 1α-甲基雄甾烷-17β-醇-3-酮; 甲氢睾酮

Database IDs

• CAS Number: 1424-00-6
• EC Number: 215-836-3
• MDL Number: MFCD00133082
• PubChem SID: 162224970; 24897174
• PubChem CID: 15020

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6982768
• LogD (pH = 7.4): 3.6982768
• Log P: 3.6982768
• Molar Refractivity: 88.1517 cm^3
• Polarizability: 35.343018 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: BV8063400
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-24/25-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Purity: 97%
• Grade: analytical standard, for drug analysis

DETAILS

Toronto Research Chemicals - M225800

Mesterolone is a synthetic androgen and a dihydrotestosterone derivative. Mesterolone is rarely used for replacement therapies due to its weak androgenic activity.

REFERENCES

• Sisci, D. et al.: Adv. Contracep. Deliv. Sys., 9, 239 (1993)
• Petry, R. et al.: Acta Endocrinol., 59, 497 (1993)
• Stroemme, S.B. et al.: Med. Sci. Sports, 6, 203 (1993)