U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/methyltestosterone.html

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TESTRED

Approved Use

1. Males Androgens are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone: 1. Primary hypogonadism (congenital or acquired) — testicular failure due to cryptorchidism, bilateral torsions, orchitis, vanishing testis syndrome; or orchidectomy. 2. Hypogonadotropic hypogonadism (congenital or acquired) — idiopathic gonadotropin or LHRH deficiency, or pituitary hypothalamic injury from tumors, trauma, or radiation. If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty. 3. Androgens may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every 6 months to assess the effect of treatment on the epiphyseal centers. 2. Females Androgens may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are 1 to 5 years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has also been used in premenopausal women with breast cancer who have benefitted from oophorectomy and are considered to have a hormone-responsive tumor.

Launch Date

1973
Primary
TESTRED

Approved Use

1. Males Androgens are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone: 1. Primary hypogonadism (congenital or acquired) — testicular failure due to cryptorchidism, bilateral torsions, orchitis, vanishing testis syndrome; or orchidectomy. 2. Hypogonadotropic hypogonadism (congenital or acquired) — idiopathic gonadotropin or LHRH deficiency, or pituitary hypothalamic injury from tumors, trauma, or radiation. If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty. 3. Androgens may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every 6 months to assess the effect of treatment on the epiphyseal centers. 2. Females Androgens may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are 1 to 5 years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has also been used in premenopausal women with breast cancer who have benefitted from oophorectomy and are considered to have a hormone-responsive tumor.

Launch Date

1973
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
95.9 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLTESTOSTERONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
275.2 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLTESTOSTERONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.39 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLTESTOSTERONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone.
2001 Aug
17alpha-methyl testosterone is a competitive inhibitor of aromatase activity in Jar choriocarcinoma cells and macrophage-like THP-1 cells in culture.
2001 Dec
Estradiol and para-chlorophenylalanine downregulate the expression of brain aromatase and estrogen receptor-alpha mRNA during the critical period of feminization in tilapia (Oreochromis mossambicus).
2001 Nov
Effects of 17alpha-methyltestosterone on seminal vesicle development and semen release response in the African catfish, Clarias gariepinus.
2001 Nov
Mass spectrometry of steroid glucuronide conjugates. II-Electron impact fragmentation of 3-keto-4-en- and 3-keto-5alpha-steroid-17-O-beta glucuronides and 5alpha-steroid-3alpha,17beta-diol 3- and 17-glucuronides.
2001 Sep
Neuropsychological effects of methyltestosterone in women using menopausal hormone replacement.
2001 Sep
Determination of natural corticosteroids in urine samples from sportsmen.
2001 Sep 15
Determination of nandrolone and metabolites in urine samples from sedentary persons and sportsmen.
2001 Sep 25
Concept evaluation: androgen-stimulated immature intact male rats as an assay for antiandrogens.
2002 Apr
Osteoporosis and beta-thalassemia major: role of the IGF-I/IGFBP-III axis.
2002 Apr
Androgen effects on bone and muscle.
2002 Apr
Differential effects of oral estrogen versus oral estrogen-androgen replacement therapy on body composition in postmenopausal women.
2002 Apr
[Sex-difference on flutamide metabolism in rat liver microsomal cytochrome P450 1A2].
2002 Aug
Effect of methyl testosterone administration on plasma viscosity in postmenopausal women.
2002 Aug
Validation of the determination of oxymetholone in human plasma analysis using gas chromatography-mass spectrometry. Application to pharmacokinetic studies.
2002 Jul 25
Effects of dehydroepiandrosterone on rat apolipoprotein AI gene expression in the human hepatoma cell line, HepG2.
2002 Mar
Increased 21-hydroxylase and shutdown of C(17,20) lyase activities in testicular tissues of the grouper (Epinephelus coioides) during 17alpha-methyltestosterone-induced sex inversion.
2002 May
Morphological sex reversal upon short-term exposure to endocrine modulators in juvenile fathead minnow (Pimephales promelas).
2002 May 10
Effects of 17 alpha-methyltestosterone on uterine morphology and heat shock protein expression are mediated through estrogen and androgen receptors.
2002 Nov
Effect on growth and reproduction of hormone immersed and masculinized fighting fish Betta splendens.
2002 Nov 1
Anabolic androgenic steroids induce age-, sex-, and dose-dependent changes in GABA(A) receptor subunit mRNAs in the mouse forebrain.
2002 Sep
Mechanisms of anabolic androgenic steroid modulation of alpha(1)beta(3)gamma(2L) GABA(A) receptors.
2002 Sep
Methyl-testosterone induces male-typical ventilatory behavior in response to putative steroidal pheromones in female round gobies (Neogobius melanostomus).
2002 Sep
Effects of environmental endocrine disruptors on the sex differentiation in Korean rockfish, Sebastes schlegeli.
2003
Transformations of testosterone and related steroids in Absidia glauca culture.
2003
In vivo biotransformation of 17 alpha-methyltestosterone in the horse revisited: identification of 17-hydroxymethyl metabolites in equine urine by capillary gas chromatography/mass spectrometry.
2003
Neuroendocrine and behavioral effects of high-dose anabolic steroid administration in male normal volunteers.
2003 Apr
Species, sex and inter-individual differences in DNA repair induced by nine sex steroids in primary cultures of rat and human hepatocytes.
2003 Apr 20
Lack of estrogenic or (anti-)androgenic effects of d-phenothrin in the uterotrophic and Hershberger assays.
2003 Apr 22
Estratest and Estratest HS (esterified estrogens and methyltestosterone) therapy: a summary of safety surveillance data, January 1989 to August 2002.
2003 Dec
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.
2003 Feb
Syntheses of steroid-based molecularly imprinted polymers and their molecular recognition study with spectrometric detection.
2003 Jan 15
Androgens stimulate sex change in protogynous grouper, Epinephelus coioides: spawning performance in sex-changed males.
2003 Jul
UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay.
2003 Jul
Comparative effects of oral esterified estrogens with and without methyltestosterone on endocrine profiles and dimensions of sexual function in postmenopausal women with hypoactive sexual desire.
2003 Jun
Vitellogenin synthesis via androgens in primary cultures of tilapia hepatocytes.
2003 Jun 15
Tibolone is not converted by human aromatase to 7alpha-methyl-17alpha-ethynylestradiol (7alpha-MEE): analyses with sensitive bioassays for estrogens and androgens and with LC-MSMS.
2003 Mar
[A case of locally advanced prostate cancer with low serum testosterone associated with intake of an androgenic medicine].
2003 May
Effects of oxytocin on semen release response in African catfish (Clarias gariepinus).
2003 May
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
The role of androgens in female sexual dysfunction.
2004 Apr
Hot flashes and androgens: a biological rationale for clinical practice.
2004 Apr
Effects of a model androgen (methyl testosterone) and a model anti-androgen (cyproterone acetate) on reproductive endocrine endpoints in a short-term adult mummichog (Fundulus heteroclitus) bioassay.
2004 Apr 28
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004 Feb
Hereditary angioedema: the rewards of studying a rare disease.
2004 Jul
Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry.
2004 Jun 18
Androgenic and estrogenic effects of the synthetic androgen 17alpha-methyltestosterone on sexual development and reproductive performance in the fathead minnow (Pimephales promelas) determined using the gonadal recrudescence assay.
2004 Jun 24
Fish full life-cycle testing for androgen methyltestosterone on medaka (Oryzias latipes).
2004 Mar
Effect of the combination of methyltestosterone and esterified estrogens compared with esterified estrogens alone on apolipoprotein CIII and other apolipoproteins in very low density, low density, and high density lipoproteins in surgically postmenopausal women.
2004 May
Interlaboratory comparison of four in vitro assays for assessing androgenic and antiandrogenic activity of environmental chemicals.
2004 May
Patents

Sample Use Guides

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.
Name Type Language
METHYLTESTOSTERONE
EP   HSDB   INN   MART.   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
CDB-110
Code English
NSC-9701
Code English
17-METHYLTESTOSTERONE
MI  
Common Name English
METHYLTESTOSTERONE [ORANGE BOOK]
Common Name English
METHYLTESTOSTERONE [USP MONOGRAPH]
Common Name English
TESTRED
Brand Name English
METANDREN
Brand Name English
RU-24400
Code English
.ALPHA.-METHYLTESTOSTERONE
Common Name English
OXANDROLONE IMPURITY, METHYLTESTOSTERONE- [USP IMPURITY]
Common Name English
METHYLTESTOSTERONE [MART.]
Common Name English
METHYLTESTOSTERONE CIII
USP-RS  
Common Name English
17β-Hydroxy-17-methylandrost-4-en-3-one
Systematic Name English
METHYLTESTOSTERONE [JAN]
Common Name English
METHYLTESTOSTERONE [USP-RS]
Common Name English
ANDROST-4-EN-3-ONE, 17-HYDROXY-17-METHYL-, (17.BETA.)-
Common Name English
METHYLTESTOSTERONE [HSDB]
Common Name English
NSC-139965
Code English
ORETON
Brand Name English
Methyltestosterone [WHO-DD]
Common Name English
L-589.372
Code English
17-METHYLTESTOSTERONE [MI]
Common Name English
17.ALPHA.-METHYLTESTOSTERONE
Common Name English
L 589.372
Code English
ANDROID
Brand Name English
RU 24400
Code English
METHYLTESTOSTERONE [VANDF]
Common Name English
METHYLTESTOSTERONE [WHO-IP]
Common Name English
U-2842
Code English
methyltestosterone [INN]
Common Name English
METHYLTESTOSTERONUM [WHO-IP LATIN]
Common Name English
VIRILON
Brand Name English
L-589372
Code English
METHYLTESTOSTERONE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
DEA NO. 4000
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NDF-RT N0000000146
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WHO-VATC QG03EK01
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WHO-VATC QG03BA02
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WHO-ATC G03BA02
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CFR 21 CFR 310.528
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WIKIPEDIA Designer-drugs-Methyltestosterone
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WHO-VATC QG03EA01
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LIVERTOX 627
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NCI_THESAURUS C243
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WHO-ATC G03EA01
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NDF-RT N0000175824
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NDF-RT N0000008241
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WHO-ATC G03EK01
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Code System Code Type Description
INN
399
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PRIMARY
DRUG CENTRAL
3356
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PRIMARY
CHEBI
27436
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PRIMARY
MESH
D008777
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PRIMARY
ChEMBL
CHEMBL1395
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PRIMARY
DAILYMED
V9EFU16ZIF
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PRIMARY
DRUG BANK
DB06710
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PRIMARY
PUBCHEM
6010
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PRIMARY
CAS
58-18-4
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PRIMARY
RXCUI
6904
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PRIMARY RxNorm
NSC
139965
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PRIMARY
SMS_ID
100000085467
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLTESTOSTERONE
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PRIMARY Description: Colourless or almost colourless crystals or a white or slightly yellowish white, crystalline powder; odourless. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS; sparingly soluble in ether R. Category: Androgen. Storage: Methyltestosterone should be kept in a well-closed container, protected from light. Definition: Methyltestosterone contains not less than 97.0% and not more than 102.0% of C20H30O2, calculated with reference to the dried substance.
ECHA (EC/EINECS)
200-366-3
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PRIMARY
RS_ITEM_NUM
1438001
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PRIMARY
EPA CompTox
DTXSID1033664
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PRIMARY
EVMPD
SUB08876MIG
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PRIMARY
NCI_THESAURUS
C648
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PRIMARY
HSDB
3365
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PRIMARY
NSC
9701
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PRIMARY
MERCK INDEX
m7467
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PRIMARY Merck Index
WIKIPEDIA
METHYLTESTOSTERONE
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PRIMARY
FDA UNII
V9EFU16ZIF
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PRIMARY