Methyltestosterone

Methyltestosterone
Systematic (IUPAC) name

17b-hydroxy-17a-methylandrost-4-ene-3-one
Clinical data
Trade names	Virilon
AHFS/Drugs.com	monograph
Routes of administration	oral
Legal status
Legal status	CA: Schedule IV US: Schedule III ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Liver
Biological half-life	6-8 hours
Excretion	90% urine / 10% feces
Identifiers
CAS Number	58-18-4^Y
ATC code	G03BA02 (WHO)
PubChem	CID 6010
IUPHAR/BPS	6945
DrugBank	DB06710^N
ChemSpider	5788^Y
UNII	V9EFU16ZIF^Y
ChEBI	CHEBI:27436^N
ChEMBL	CHEMBL1395^Y
Chemical data
Formula	C₂₀H₃₀O₂
Molar mass	302.451
SMILES O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2CC3)C)(C)CC4
InChI 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^Y Key:GCKMFJBGXUYNAG-HLXURNFRSA-N^Y
^NY (what is this?) (verify)

Methyltestosterone (brand names:^[1] Android, Androral, Oraviron, Testred, Virilon), also known as 17α-methyltestosterone, is a 17α-alkylated anabolic steroid used to treat males with a testosterone deficiency.^[2] It bears close structural similarity to testosterone, but has a methyl group at C17 in order to increase oral bioavailability. Due to aromatization to the metabolization-resistant estrogen 17α-methylestradiol, methyltestosterone has relatively high estrogenicity and hence side effects such as gynecomastia.^[3]^[4]

Confiscated methyltestosterone.

References

↑ "Methyltestosterone Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2012-02-13.
↑ "Truestar health".
↑ Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN 978-3-540-79088-4.
↑ Andrea R. Genazzani (17 January 2006). Postmenopausal Osteoporosis: Hormones & Other Therapies. Taylor & Francis US. pp. 243–. ISBN 978-1-84214-311-7.

Anabolic steroids (A14)

Androstane (carbon 19 present)	Adrenosterone Androisoxazole Bolasterone (Myagen) Bolazine Boldione Boldenone undecylenate (Equipoise) 4-Chlordehydromethyltestosterone (Turinabol) 4-Hydroxytestosterone Calusterone Clostebol Danazol Desoxymethyltestosterone (Madol) DHT Drostanolone (Masteron) Enestebol Epitiostanol Fluoxymesterone (Halotestin) Formebolone Furazabol (Miotolan) Hydroxystenozole Mebolazine Mesabolone Mestanolone Mesterolone (Proviron) Metandienone (methandrostenolone) Methandriol Metenolone Methenolone enanthate (Primobolan) Methasterone (Superdrol) Methyltestosterone Methyldiazirinol Oxandrolone (Anavar) Oxymetholone (Anadrol) Oxymesterone Prostanozol Quinbolone (Anabolicum Vister) Roxibolone Silandrone Stanozolol (Strombafort Winstrol) Stenbolone Testosterone`s (Sustamed Sustanon) 1-Testosterone Thiomesterone

Estrene (carbon 19 absent)	Bolenol Ethyldienolone Ethylestrenol Mibolerone (Cheque Drops) Metribolone (R1881) Nandrolone (Deca Durabolin) Norboletone (Genabol) Norclostebol Norethandrolone Normethandrone (methylestrenolone) Oxabolone cipionate Propetandrol Tetrahydrogestrinone (The Clear) Trenbolone (Fina) Trestolone

Prohormones	1-Androstenediol 1,4-Androstadienedione 4-Androstenediol 4-Androstenedione 19-Norandrostenediol 19-Norandrostenedione DHEA

Androgenics

Receptor
(ligands)

Agonists	4-Chlordehydromethyltestosterone 4-Hydroxytestosterone 5α-Androst-1-ene-3,17-dione 7β-Hydroxyepiandrosterone 11-Ketotestosterone 17-((1-Oxoheptyl)oxy)androstan-3-one 17-((1-Oxopentyl)oxy)androstan-3-one 17-(1-Oxopropoxy)androstan-3-one 17β-Hydroxyandrost-2-ene-2-carbonitrile 19-Norandrostenediol 19-Norandrostenedione 19-Norandrosterone 19-Nordehydrotestosterone Δ¹-Androstenediol Δ¹-Testosterone Δ^1,4-Androstenedione Δ⁴-Androstenediol Δ⁴-Androstenedione Δ^4-Tibolone Δ⁴-Androstenediol Δ⁴-Androstenedione Adrenosterone Androisoxazole Androstanolone Bolandiol Bolasterone Bolazine Boldenone Boldione Bolenol Bolmantalate Calusterone Cl-4AS-1 Clostebol Cloxotestosterone Cortexolone 17α-propionate Danazol Desogestrel Desoxymethyltestosterone DHEA DHEA sulfate Dihydrotestosterone Drostanolone Enestebol Epitiostanol Ethisterone Ethyldienolone Ethylestrenol Fluoxymesterone Formebolone Furazabol Hexabolan Hydroxystenozole Levonorgestrel Mebolazine Medroxyprogesterone acetate Mepitiostane Mesabolone Mestanolone Mesterolone Metandienone/Methandrostenolone Metenolone Metenolone acetate Metenolone enanthate Methandriol Methandriol propionate Methasterone Methylestrenolone Methyltestosterone Metribolone Mibolerone Nandrolone Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexane carboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone undecyclate Norboletone Norclostebol Norethandrolone Norethisterone Norgestrel Oxabolone Oxabolone cypionate Oxandrolone Oxendolone Oxymesterone Oxymetholone Penmesterol Propetandrol Quinbolone Quingestanol acetate Roxibolone Silandrone Stanozolol Stenbolone Stenbolone acetate Testolactone Testosterone Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone ketolaurate Testosterone nicotinate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tetrahydrogestrinone Thiomesterone Tibolone Tiomesterone Trenboloneca Trenbolone acetate Trestolone

Mixed (SARMs)	AC-262,356 Andarine BMS-564,929 Enobosarm (ostarine) LGD-2226 LGD-3303 LGD-4033 RAD140 S-23 S-40503 TFM-4AS-1

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Abiraterone Abiraterone acetate Apalutamide AZD-3514 Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) Benorterone Bicalutamide BMS-641,988 BOMT Canrenoic acid Canrenone Chlormadinone acetate Cimetidine Cioteronel Clometerone Cyproterone Cyproterone acetate Delanterone DDT (via metabolite p,p’-DDE) Dieldrin Dienogest Drospirenone Endosulfan Enzalutamide EPI-001 Epitestosterone Fenarimol Flutamide Galeterone Guggulsterone Hydroxyflutamide Inocoterone Ketoconazole Lavender oil Linuron Megestrol acetate Mespirenone Methiocarb Metogest Mifepristone Nilutamide Nomegestrol Nordinone Norgestimate ODM-201 ONC1-13B ORM-15341 Osaterone Oxendolone PF-998425 Potassium canrenoate Prochloraz Procymidone R-2956 Rosterolone RU-58642 RU-58841 Spironolactone Topilutamide (fluridil) Topterone Valproic acid Vinclozolin VT-464 Zanoterone

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics

Estrogenics

Receptor
(ligands)

ER (α, β)

Agonists	(R)-DPN (S)-DPN (R,R)-THC (S,S)-THC 2,8-DHHHC 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8β-VE₂ 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-IE₂ 16α-LE₂ (Cpd1471) Δ⁴-Androstenedione Δ⁵-Androstenediol 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others) Anethole Anol Atrimustine Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Cloxestradiol Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate) Coumestans (e.g., coumestrol, psoralidin) DHEA DHEA-S Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol dipropionate Diosgenin Doisynoestrol (fenocycline) Doisynolic acid DY-131 (GSK-9089) Endosulfan Epiestriol Epimestrol ERB-196 (WAY-202196) Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate) Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrobin (DBE) Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Estropronicate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol 3-isopropylsulfonate Etynodiol diacetate Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methylestradiol Miroestrol Moxestrol Nilestriol Noretynodrel Orestrate Paroxypropione Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Promestriene Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quadrosilan Quinestradol Quinestrol SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) WAY-166818 WAY-200070

Mixed (SERMs)	2-Hydroxyestrone 27-Hydroxycholesterol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Broparestrol Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC Fulvestrant ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 XCT-790 ZK-164015 ZK-191703

GPER

Agonists	7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Fulvestrant (ICI-182,780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCB (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalenone

Antagonists	Estriol G-15 G-36 MIBE

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, aromatase, and 27-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate 16-Hydroxy-DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione 16-Hydroxyandrostenedione Testosterone

Indirect	Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin) Calcitriol (vitamin D) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoids • Mineralocorticoids • Progestogenics

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