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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

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

HIDE SMILES / InChI

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

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
Effects of an oral contraceptive combination with or without androgen on mammary tissues: a study in rats.
2000 Jul-Aug
Effects of three vertebrate hormones on the growth, development, and reproduction of the tomato moth, Lacanobia oleracea L. (Lepidoptera: Noctuidae).
2001 Aug
Cerebrospinal fluid and behavioral changes after methyltestosterone administration: preliminary findings.
2001 Feb
Preliminary observations on differing psychological effects of conjugated and esterified estrogen treatments.
2001 Mar
Effects of androgens on social behavior and morphology of alternative reproductive males of the Azorean rock-pool blenny.
2001 Mar
Methyltestosterone pharmacokinetics and oral bioavailability in rainbow trout (Oncorhynchus mykiss).
2001 May
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
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
Determination of natural corticosteroids in urine samples from sportsmen.
2001 Sep 15
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
Validation of the determination of oxymetholone in human plasma analysis using gas chromatography-mass spectrometry. Application to pharmacokinetic studies.
2002 Jul 25
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
Studies of masculinization, detoxification, and oxidative stress responses in guppies (Poecilia reticulata) exposed to effluent from a pulp mill.
2002 May
Estratest and Estratest HS (esterified estrogens and methyltestosterone) therapy: a summary of safety surveillance data, January 1989 to August 2002.
2003 Dec
Effects of environmental salinity and 17alpha-methyltestosterone on growth and oxygen consumption in the tilapia, Oreochromis mossambicus.
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
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases.
2003 Sep
Are sex steroids involved in the sexual growth dimorphism in Eurasian perch juveniles?
2004 Feb
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
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
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
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
by admin
on Mon Mar 31 18:22:58 GMT 2025
Edited
by admin
on Mon Mar 31 18:22:58 GMT 2025
Record UNII
V9EFU16ZIF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
17-METHYLTESTOSTERONE
MI  
Preferred Name English
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
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
17?-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
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
NDF-RT N0000000146
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
WHO-VATC QG03EK01
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
WHO-VATC QG03BA02
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
WHO-ATC G03BA02
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
CFR 21 CFR 310.528
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
WIKIPEDIA Designer-drugs-Methyltestosterone
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
WHO-VATC QG03EA01
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
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
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
Code System Code Type Description
INN
399
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
DRUG CENTRAL
3356
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
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
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY RxNorm
NSC
139965
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PRIMARY
SMS_ID
100000085467
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLTESTOSTERONE
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
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
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
RS_ITEM_NUM
1438001
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PRIMARY
EPA CompTox
DTXSID1033664
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PRIMARY
EVMPD
SUB08876MIG
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
NCI_THESAURUS
C648
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
HSDB
3365
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
NSC
9701
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
MERCK INDEX
m7467
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
METHYLTESTOSTERONE
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
FDA UNII
V9EFU16ZIF
Created by admin on Mon Mar 31 18:22:58 GMT 2025 , Edited by admin on Mon Mar 31 18:22:58 GMT 2025
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
METABOLIC ENZYME -> SUBSTRATE
LABELED -> NON-LABELED
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE ACTIVE -> PARENT
MORE ACTIVE METABOLITE THEN METHYLTESTOSTERONE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
URINE
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY