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 ℞ (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
PubChem (CID)	6010
IUPHAR/BPS	6945
DrugBank	DB06710
ChemSpider	5788
UNII	V9EFU16ZIF
ChEBI	CHEBI:27436
ChEMBL	CHEMBL1395
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 Key:GCKMFJBGXUYNAG-HLXURNFRSA-N
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Methyltestosterone (brand names Android, Androral, Metandren, Oraviron, Testred, Virilon),^[1] 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.^[2] 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.^[3][4]

Confiscated methyltestosterone.

History

Methyltestosterone was first synthesized in 1935, and was the first 17α-alkylated AAS to be synthesized.^[5]

See also

• List of androgens/anabolic steroids
• Ethyltestosterone
• Topterone
• 17α-Methylprogesterone
• Ethinyl estradiol
• Metandienone
• Methylestradiol
• Normethandrone

References

1. "Methyltestosterone Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2012-02-13.
2. "Truestar health".
3. Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN 978-3-540-79088-4.
4. Andrea R. Genazzani (17 January 2006). Postmenopausal Osteoporosis: Hormones & Other Therapies. Taylor & Francis US. pp. 243–. ISBN 978-1-84214-311-7.
5. Shahidi NT (2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clin Ther. 23 (9): 1355–90. PMID 11589254.