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
[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
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 |
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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 |
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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 |
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Effects of an oral contraceptive combination with or without androgen on mammary tissues: a study in rats. | 2000 Jul-Aug |
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Effects of endocrine disruptors on prosobranch snails (Mollusca: Gastropoda) in the laboratory. Part III: Cyproterone acetate and vinclozolin as antiandrogens. | 2001 Dec |
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Effects of 17alpha-methyltestosterone on seminal vesicle development and semen release response in the African catfish, Clarias gariepinus. | 2001 Nov |
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Neuropsychological effects of methyltestosterone in women using menopausal hormone replacement. | 2001 Sep |
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Differential effects of oral estrogen versus oral estrogen-androgen replacement therapy on body composition in postmenopausal women. | 2002 Apr |
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Validation of the determination of oxymetholone in human plasma analysis using gas chromatography-mass spectrometry. Application to pharmacokinetic studies. | 2002 Jul 25 |
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Transdermal testosterone gel (Cellegy). | 2002 Nov |
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Anabolic androgenic steroids induce age-, sex-, and dose-dependent changes in GABA(A) receptor subunit mRNAs in the mouse forebrain. | 2002 Sep |
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Methyl-testosterone induces male-typical ventilatory behavior in response to putative steroidal pheromones in female round gobies (Neogobius melanostomus). | 2002 Sep |
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Transformations of testosterone and related steroids in Absidia glauca culture. | 2003 |
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Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats. | 2003 Feb |
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Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. | 2003 Feb 1 |
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Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills. | 2003 Feb 5 |
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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 |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003 Sep |
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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 Jan 7 |
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Reproductive disorders in pubertal and adult phase of the male rats exposed to vinclozolin during puberty. | 2004 Jul |
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Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry. | 2004 Jun 18 |
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Fish full life-cycle testing for androgen methyltestosterone on medaka (Oryzias latipes). | 2004 Mar |
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Effects of organotin compounds on pubertal male rats. | 2004 Oct 1 |
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
Created
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Record UNII |
V9EFU16ZIF
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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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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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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PRIMARY | Merck Index | ||
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METHYLTESTOSTERONE
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V9EFU16ZIF
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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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