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
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 |
---|---|---|
Evaluation of high-dose estrogen and high-dose estrogen plus methyltestosterone treatment on cognitive task performance in postmenopausal women. | 2002 |
|
Effects of the association of androgen/estrogen on the bladder and urethra of castrated rats. | 2002 |
|
Steroid-induced cataract: other than in the whole animal system, in the lens culture system, androgens, estrogens and progestins as well as glucocorticoids produce a loss of transparency of the lens. | 2002 |
|
Concept evaluation: androgen-stimulated immature intact male rats as an assay for antiandrogens. | 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 |
|
Functional genomics and sexual differentiation in amphibians. | 2002 Dec |
|
Effects of acute 17alpha-methyltestosterone, acute 17beta-estradiol, and chronic 17alpha-methyltestosterone on dopamine, norepinephrine and serotonin levels in the pituitary, hypothalamus and telencephalon of rainbow trout (Oncorhynchus mykiss). | 2002 Dec |
|
Solid-state photodimerization of steroid enones. | 2002 Dec 13 |
|
Activation of the growth hormone/insulin-like growth factor axis by treatment with 17 alpha-methyltestosterone and seawater rearing in the tilapia, Oreochromis mossambicus. | 2002 Jul |
|
Validation of the determination of oxymetholone in human plasma analysis using gas chromatography-mass spectrometry. Application to pharmacokinetic studies. | 2002 Jul 25 |
|
Structural specificity of steroids in stimulating DNA synthesis and protooncogene expression in primary rat hepatocyte cultures. | 2002 May |
|
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 |
|
Effects of 17 alpha-methyltestosterone on uterine morphology and heat shock protein expression are mediated through estrogen and androgen receptors. | 2002 Nov |
|
Transdermal testosterone gel (Cellegy). | 2002 Nov |
|
Effect on growth and reproduction of hormone immersed and masculinized fighting fish Betta splendens. | 2002 Nov 1 |
|
Androgens and the development of the vagina. | 2002 Oct |
|
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 |
|
Detection of environmental androgens: a novel method based on enzyme-linked immunosorbent assay of spiggin, the stickleback (Gasterosteus aculeatus) glue protein. | 2002 Sep |
|
[Cholestatic jaundice and pruritus]. | 2002 Sep 18 |
|
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 tributyltin chloride on the reproductive system in pubertal male rats. | 2003 Apr |
|
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 |
|
Gonad development and vitellogenin production in zebrafish (Danio rerio) exposed to ethinylestradiol and methyltestosterone. | 2003 Dec 10 |
|
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats. | 2003 Feb |
|
Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. | 2003 Feb 1 |
|
Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills. | 2003 Feb 5 |
|
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 |
|
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 |
|
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 |
|
Effects of oxytocin on semen release response in African catfish (Clarias gariepinus). | 2003 May |
|
17alpha-methyltestosterone: 28-day oral toxicity study in the rat based on the "Enhanced OECD Test Guideline 407" to detect endocrine effects. | 2003 Nov 5 |
|
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
|
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003 Sep |
|
Aromatase modulation alters gonadal differentiation in developing zebrafish (Danio rerio). | 2004 Apr 14 |
|
Evaluation of the rodent Hershberger assay using three reference endocrine disrupters (androgen and antiandrogens). | 2004 Jan-Feb |
|
Reproductive disorders in pubertal and adult phase of the male rats exposed to vinclozolin during puberty. | 2004 Jul |
|
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 |
|
Prediction of whole-body metabolic clearance of drugs through the combined use of slices from rat liver, lung, kidney, small intestine and colon. | 2004 Mar |
|
Application of the revised EU criteria for the confirmation of anabolic steroids in meat using GC-MS. | 2004 Mar |
|
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DEA NO. |
4000
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
NDF-RT |
N0000000146
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-VATC |
QG03EK01
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-VATC |
QG03BA02
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-ATC |
G03BA02
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
CFR |
21 CFR 310.528
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WIKIPEDIA |
Designer-drugs-Methyltestosterone
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-VATC |
QG03EA01
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
LIVERTOX |
627
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
NCI_THESAURUS |
C243
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-ATC |
G03EA01
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
NDF-RT |
N0000175824
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
NDF-RT |
N0000008241
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
||
|
WHO-ATC |
G03EK01
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
399
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
3356
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
27436
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
D008777
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
CHEMBL1395
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
V9EFU16ZIF
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
DB06710
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
6010
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
58-18-4
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
6904
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | RxNorm | ||
|
139965
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
100000085467
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
METHYLTESTOSTERONE
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
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. | ||
|
200-366-3
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
1438001
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
DTXSID1033664
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
SUB08876MIG
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
C648
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
3365
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
9701
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
m7467
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | Merck Index | ||
|
METHYLTESTOSTERONE
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY | |||
|
V9EFU16ZIF
Created by
admin on Fri Dec 15 16:14:49 GMT 2023 , Edited by admin on Fri Dec 15 16:14:49 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)