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
SMILES
C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
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
| Molecular Formula | C20H30O2 |
| Molecular Weight | 302.451 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB06710Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/methyltestosterone.html
Sources: http://www.drugbank.ca/drugs/DB06710
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17218080 |
1.9 µM [IC50] | ||
Target ID: CHEMBL1871 Sources: http://www.drugbank.ca/drugs/DB06710 |
0.125 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TESTRED Approved Use1. 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 Date1973 |
|||
| Primary | TESTRED Approved Use1. 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 Date1973 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of organotin compounds on pubertal male rats. | 2004-10-01 |
|
| Reproductive disorders in pubertal and adult phase of the male rats exposed to vinclozolin during puberty. | 2004-07 |
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| Hereditary angioedema: the rewards of studying a rare disease. | 2004-07 |
|
| 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. | 2004-06-24 |
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| Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry. | 2004-06-18 |
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| 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. | 2004-05 |
|
| Interlaboratory comparison of four in vitro assays for assessing androgenic and antiandrogenic activity of environmental chemicals. | 2004-05 |
|
| 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. | 2004-04-28 |
|
| Aromatase modulation alters gonadal differentiation in developing zebrafish (Danio rerio). | 2004-04-14 |
|
| The role of androgens in female sexual dysfunction. | 2004-04 |
|
| Hot flashes and androgens: a biological rationale for clinical practice. | 2004-04 |
|
| Testosterone-stimulated weanlings as an alternative to castrated male rats in the Hershberger anti-androgen assay. | 2004-04 |
|
| Fish full life-cycle testing for androgen methyltestosterone on medaka (Oryzias latipes). | 2004-03 |
|
| Prediction of whole-body metabolic clearance of drugs through the combined use of slices from rat liver, lung, kidney, small intestine and colon. | 2004-03 |
|
| Oxandrolone treatment of childhood hereditary angioedema. | 2004-03 |
|
| Application of the revised EU criteria for the confirmation of anabolic steroids in meat using GC-MS. | 2004-03 |
|
| Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2004-02 |
|
| Are sex steroids involved in the sexual growth dimorphism in Eurasian perch juveniles? | 2004-02 |
|
| Mechanistic basis for estrogenic effects in fathead minnow (Pimephales promelas) following exposure to the androgen 17alpha-methyltestosterone: conversion of 17alpha-methyltestosterone to 17alpha-methylestradiol. | 2004-01-07 |
|
| Gonad development and vitellogenin production in zebrafish (Danio rerio) exposed to ethinylestradiol and methyltestosterone. | 2003-12-10 |
|
| Estratest and Estratest HS (esterified estrogens and methyltestosterone) therapy: a summary of safety surveillance data, January 1989 to August 2002. | 2003-12 |
|
| Spermatogenetic disorders in adult rats exposed to tributyltin chloride during puberty. | 2003-12 |
|
| Photoaffinity labeling identification of thyroid hormone-regulated glucocorticoid-binding peptides in rat liver endoplasmic reticulum: an oligomeric protein with high affinity for 16beta-hydroxylated stanozolol. | 2003-12 |
|
| Effects of environmental salinity and 17alpha-methyltestosterone on growth and oxygen consumption in the tilapia, Oreochromis mossambicus. | 2003-12 |
|
| OECD validation of the Hershberger assay in Japan: phase 2 dose response of methyltestosterone, vinclozolin, and p,p'-DDE. | 2003-12 |
|
| 17alpha-methyltestosterone: 28-day oral toxicity study in the rat based on the "Enhanced OECD Test Guideline 407" to detect endocrine effects. | 2003-11-05 |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003-10 |
|
| Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003-09 |
|
| Androgens stimulate sex change in protogynous grouper, Epinephelus coioides: spawning performance in sex-changed males. | 2003-07 |
|
| UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay. | 2003-07 |
|
| Evaluation of the rodent Hershberger assay using three reference endocrine disrupters (androgen and antiandrogens). | 2003-06-23 |
|
| Vitellogenin synthesis via androgens in primary cultures of tilapia hepatocytes. | 2003-06-15 |
|
| 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. | 2003-06 |
|
| [A case of locally advanced prostate cancer with low serum testosterone associated with intake of an androgenic medicine]. | 2003-05 |
|
| Effects of oxytocin on semen release response in African catfish (Clarias gariepinus). | 2003-05 |
|
| Lack of estrogenic or (anti-)androgenic effects of d-phenothrin in the uterotrophic and Hershberger assays. | 2003-04-22 |
|
| Species, sex and inter-individual differences in DNA repair induced by nine sex steroids in primary cultures of rat and human hepatocytes. | 2003-04-20 |
|
| Effects of tributyltin chloride on the reproductive system in pubertal male rats. | 2003-04 |
|
| Neuroendocrine and behavioral effects of high-dose anabolic steroid administration in male normal volunteers. | 2003-04 |
|
| 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. | 2003-03 |
|
| Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills. | 2003-02-05 |
|
| Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. | 2003-02-01 |
|
| Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats. | 2003-02 |
|
| Syntheses of steroid-based molecularly imprinted polymers and their molecular recognition study with spectrometric detection. | 2003-01-15 |
|
| 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 |
|
| Effects of 17 alpha-methyltestosterone on uterine morphology and heat shock protein expression are mediated through estrogen and androgen receptors. | 2002-11 |
|
| Transdermal testosterone gel (Cellegy). | 2002-11 |
|
| [Sex-difference on flutamide metabolism in rat liver microsomal cytochrome P450 1A2]. | 2002-08 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6863484
Estradiol production was significantly stimulated in explants of normal human term placenta cultured in the presence of 0.01 mM methyltestosterone.
| Substance Class |
Chemical
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V9EFU16ZIF
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DEA NO. |
4000
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NDF-RT |
N0000000146
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QG03EK01
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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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QG03EA01
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LIVERTOX |
627
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NCI_THESAURUS |
C243
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G03EA01
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N0000175824
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N0000008241
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G03EK01
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399
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3356
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27436
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D008777
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CHEMBL1395
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V9EFU16ZIF
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DB06710
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6010
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58-18-4
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6904
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139965
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100000085467
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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. | ||
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200-366-3
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1438001
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DTXSID1033664
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SUB08876MIG
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C648
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3365
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9701
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m7467
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METHYLTESTOSTERONE
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LABELED -> NON-LABELED |
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METABOLIC ENZYME -> SUBSTRATE |
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LABELED -> NON-LABELED |
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TARGET -> AGONIST |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
MORE ACTIVE METABOLITE THEN METHYLTESTOSTERONE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
URINE
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PARENT -> IMPURITY |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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