Methyltestosterone

Methyltestosterone
Clinical data

Trade names	Android, Androral, Metandren, Oraviron, Testred, Virilon
AHFS/Drugs.com	Monograph
Routes of administration	Oral
ATC code	G03BA02 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Liver
Biological half-life	6-8 hours
Excretion	90% urine / 10% feces
Identifiers
IUPAC name 17α-Methylandrost-4-en-17β-ol-3-one
CAS Number	58-18-4^Y
PubChem CID	6010
IUPHAR/BPS	6945
DrugBank	DB06710^N
ChemSpider	5788^Y
UNII	V9EFU16ZIF
ChEBI	CHEBI:27436^N
ChEMBL	CHEMBL1395^Y
ECHA InfoCard	100.000.333
Chemical and physical data
Formula	C₂₀H₃₀O₂
Molar mass	302.451
3D model (Jmol)	Interactive image
SMILES O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2CC3)C)(C)CC4
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/t15-,16+,17+,18+,19+,20+/m1/s1^Y Key:GCKMFJBGXUYNAG-HLXURNFRSA-N^Y
^NY (what is this?)

Methyltestosterone (brand names Android, Androral, Metandren, Oraviron, Testred, Virilon), also known as 17α-methyltestosterone or as 17α-methylandrost-4-en-17β-ol-3-one, is a synthetic, orally active androgenic-anabolic steroid (AAS) and 17α-methylated derivative of testosterone that is used to treat males with androgen deficiency. It bears close structural similarity to testosterone, but has a methyl group at the C17α position in order to increase oral bioavailability. Due to efficient aromatization into the potent estrogen methylestradiol, methyltestosterone has relatively high estrogenicity and hence potential side effects such as gynecomastia.

Methyltestosterone was first synthesized in 1935, and was the first 17α-alkylated AAS to be synthesized.