(10S,11S,14S,15S)-14-hydroxy-14,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one

• ChemBase ID: 2706
• Molecular Formular: C19H24O2
• Molecular Mass: 284.39266
• Monoisotopic Mass: 284.17763001
• SMILES: C1CC(=O)C=C2CC[C@@H]3C(=C12)C=C[C@]1([C@H]3CC[C@]1(C)O)C
• Canonical SMILES: O=C1CCC2=C3C=C[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(C)O)C
• InChI: InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1
• InChIKey: CCCIJQPRIXGQOE-XWSJACJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14S,15S)-14-hydroxy-14,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one; (10S,11S,14S,15S)-14-hydroxy-14,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6,16-trien-5-one
• IUPAC Traditional name: metribolona; methyltrienolone
• Synonyms: R1881; Metribolone; 17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one; Methyltrienolone; (17b)-17-Hydroxy-17-methyl-Estra-4,9,11-trien-3-one; NSC 92858; RU 1881; R1881; Methyltrienolone; Metribolone; (17β)-17-Hydroxy-17-methyl-estra-4,9,11-trien-3-one; 3-Oxo-17β-hydroxy-17-methylestra-4,9,11-triene; 17α-Methyl-3-oxo-4,9,11-estratrien-17β-ol; R 1881

Database IDs

• CAS Number: 965-93-5
• MDL Number: MFCD00199021
• PubChem SID: 46505539; 160966155
• PubChem CID: 261000
• CHEMBL: 166444
• Wikipedia Title: Metribolone

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.903393
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.5347936
• LogD (pH = 7.4): 2.5347939
• Log P: 2.5347939
• Molar Refractivity: 86.2929 cm^3
• Polarizability: 32.78173 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.11
• LOG S: -3.93
• Solubility (Water): 3.32e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; DMSO: ≥10 mg/mL; Ethanol; Methanol
• Apperance: light yellow to yellow powder; Pale Yellow Solid
• Melting Point: 165-168°C
• Optical Rotation: [α]/D -48 to -68°

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Drug Control: USDEA Schedule IIIN; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H24O2

DETAILS

DrugBank - DB02998

• Drug Groups: experimental
• Description: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - R0908

Biochem/physiol Actions
Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. R1881, also known as methyltrienolone, is a synthetic androgen. It is the gold standard AR agonist.

Toronto Research Chemicals - M338820

An anabolic steroid.

REFERENCES

• Basu, H., et al.: Cancer Res., 69, 7689 (2009)
• De Gendt, K., et al.: Biol. Reproduct., 81, 1083 (2009)
• Jung, M., et al.: J. Med. Chem., 53, 2779 (2009)