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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O2
Molecular Weight 302.451
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLTESTOSTERONE

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=GCKMFJBGXUYNAG-HLXURNFRSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H30O2
Molecular Weight 302.451
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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. The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. Methyltestosterone is marketed under the brand names Android, Androral, Metandren, Oraviron, Testred, Virilon.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.9 µM [IC50]
0.125 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TESTRED
Primary
TESTRED

Cmax

ValueDoseCo-administeredAnalytePopulation
95.9 ng/mL
50 mg single, oral
METHYLTESTOSTERONE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
275.2 ng × h/mL
50 mg single, oral
METHYLTESTOSTERONE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.39 h
50 mg single, oral
METHYLTESTOSTERONE serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Replacement therapy in androgen-deficient males is 10 to 50 mg of methylTESTOSTERone daily. The dosage of methylTESTOSTERone for androgen therapy in breast carcinoma in females is from 50-200 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Estradiol production was significantly stimulated in explants of normal human term placenta cultured in the presence of 0.01 mM methyltestosterone.
Substance Class Chemical
Record UNII
V9EFU16ZIF
Record Status Validated (UNII)
Record Version