14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 4447
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: CC12CCC(=O)C=C1CCC1C2CCC2(C1CCC2(O)C)C
• Canonical SMILES: O=C1CCC2(C(=C1)CCC1C2CCC2(C1CCC2(C)O)C)C
• InChI: InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3
• InChIKey: GCKMFJBGXUYNAG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: 17-A-methyl testosterone
• Brand Name: Android; Testred; Virilon
• Synonyms: Methyltestosterone

Database IDs

• CAS Number: 58-18-4
• PubChem SID: 160967879
• PubChem CID: 4160

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.086739
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6459997
• LogD (pH = 7.4): 3.646
• Log P: 3.646
• Molar Refractivity: 89.068 cm^3
• Polarizability: 35.103523 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.61
• LOG S: -4.34
• Solubility (Water): 1.39e-02 g/l

DETAILS

DrugBank - DB06710

• Drug Groups: approved
• Description: A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.
• Indication: Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.
• Pharmacology: Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.
• Toxicity: Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
• Biotransformation: Hepatic.; Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
• Absorption: The methyl group aids to increase oral bioavailability.
• Half Life: 6-8 hours
• Protein Binding: 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
• Elimination: 90% urine / 10% feces
• External Links: Wikipedia