Methyltestosterone

"Android (drug)" redirects here. For the drug used in the treatment of anemia, see Androyd.

Methyltestosterone

Clinical data
Trade names	Agoviron, Android, Metandren, Oraviron, Oreton, Testovis, Testred, Virilon, others
Other names	RU-24400; NSC-9701; 17α-Methyltestosterone; 17α-Methylandrost-4-en-17β-ol-3-one [1] [2] [3]
AHFS/Drugs.com	Monograph
Pregnancy category	AU:D
Routes of administration	By mouth, buccal, sublingual [4] [5] [6]
Drug class	Androgen; Anabolic steroid
ATC code	G03BA02 ( WHO ) G03EK01 ( WHO )
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C5 (Anabolic steroids) [7] CA: Schedule IV US: Schedule III In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	~70% [8]
Protein binding	98% [9]
Metabolism	Liver
Elimination half-life	150 minutes (~2.5–3 hours) [8] [10]
Duration of action	1–3 days [9]
Excretion	Urine: 90% [9] Feces: 6% [9] [11]
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	58-18-4  Y
PubChem CID	6010
IUPHAR/BPS	6945
DrugBank	DB06710  Y
ChemSpider	5788  Y
UNII	V9EFU16ZIF
KEGG	D00408  Y
ChEBI	CHEBI:6892  Y
ChEMBL	ChEMBL1395  Y
CompTox Dashboard (EPA)	DTXSID1033664
ECHA InfoCard	100.000.333
Chemical and physical data
Formula	C20H30O2
Molar mass	302.458 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C
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
(verify)

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. ^{[4] [5] [12] [13] [14]} It is taken by mouth or held in the cheek or under the tongue. ^{[4] [13] [14] [6]}

Side effects of methyltestosterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. ^[4] It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and liver damage. ^[4] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). ^{[4] [15]} It has moderate androgenic effects and moderate anabolic effects, which make it useful for producing masculinization. ^{[4] [16]}

Methyltestosterone was discovered in 1935 and was introduced for medical use in 1936. ^{[6] [17] [18] [19] [4]} It was made shortly after the discovery of testosterone and was one of the first synthetic AAS to be developed. ^{[6] [17] [18]} In addition to its medical use, methyltestosterone is used to improve physique and performance, although it is not as commonly used as other AAS for such purposes due to its androgenic effects, estrogenic effects, and risk of liver damage. ^[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit. ^[4]

Uses

Medical

Methyltestosterone is or has been used in the treatment of delayed puberty, hypogonadism, cryptorchidism, and erectile dysfunction in males, and in low doses to treat menopausal symptoms (specifically for osteoporosis, hot flashes, and to increase libido and energy), postpartum breast pain and engorgement, and breast cancer in women. ^{[4] [5] [12]} It is specifically approved in the United States for the treatment of hypogonadism and delayed puberty in males and the treatment of advanced inoperable breast cancer in females. ^[13] It was also approved in low doses in combination with esterified estrogens for the treatment of moderate to severe vasomotor symptoms associated with menopause in women in the United States, but this formulation was discontinued and hence is no longer used. ^[14]

Methyltestosterone is less effective in inducing masculinization than testosterone, but is useful for maintaining established masculinization in adults. ^[20]

The dosages of methyltestosterone used are 10 to 50 mg/day in men for common medical uses like hypogonadism and delayed puberty as well as physique- and performance-enhancing purposes and 2.5 mg/day in women for menopausal symptoms. ^[4] Higher dosages of 50 to 200 mg/day have been used to treat women with inoperable breast cancer that has failed to respond to other therapies, although such dosages are associated with severe irreversible virilization. ^[4]

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Androgen replacement therapy formulations and dosages used in men

Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone a	–	Tablet	400–800 mg/day (in divided doses)
	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg/2–4× day (with meals)
	Methyltestosteroneb	Android, Metandren, Testred	Tablet	10–50 mg/day
	Fluoxymesterone b	Halotestin, Ora-Testryl, Ultandren	Tablet	5–20 mg/day
	Metandienone b	Dianabol	Tablet	5–15 mg/day
	Mesterolone b	Proviron	Tablet	25–150 mg/day
Sublingual	Testosterone b	Testoral	Tablet	5–10 mg 1–4×/day
	Methyltestosteroneb	Metandren, Oreton Methyl	Tablet	10–30 mg/day
Buccal	Testosterone	Striant	Tablet	30 mg 2×/day
	Methyltestosteroneb	Metandren, Oreton Methyl	Tablet	5–25 mg/day
Transdermal	Testosterone	AndroGel, Testim, TestoGel	Gel	25–125 mg/day
		Androderm, AndroPatch, TestoPatch	Non-scrotal patch	2.5–15 mg/day
		Testoderm	Scrotal patch	4–6 mg/day
		Axiron	Axillary solution	30–120 mg/day
	Androstanolone (DHT)	Andractim	Gel	100–250 mg/day
Rectal	Testosterone	Rektandron, Testosteronb	Suppository	40 mg 2–3×/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection)	Testosterone	Andronaq, Sterotate, Virosterone	Aqueous suspension	10–50 mg 2–3×/week
	Testosterone propionate b	Testoviron	Oil solution	10–50 mg 2–3×/week
	Testosterone enanthate	Delatestryl	Oil solution	50–250 mg 1x/1–4 weeks
		Xyosted	Auto-injector	50–100 mg 1×/week
	Testosterone cypionate	Depo-Testosterone	Oil solution	50–250 mg 1x/1–4 weeks
	Testosterone isobutyrate	Agovirin Depot	Aqueous suspension	50–100 mg 1x/1–2 weeks
	Testosterone phenylacetate b	Perandren, Androject	Oil solution	50–200 mg 1×/3–5 weeks
	Mixed testosterone esters	Sustanon 100, Sustanon 250	Oil solution	50–250 mg 1×/2–4 weeks
	Testosterone undecanoate	Aveed, Nebido	Oil solution	750–1,000 mg 1×/10–14 weeks
	Testosterone buciclate a	–	Aqueous suspension	600–1,000 mg 1×/12–20 weeks
Implant	Testosterone	Testopel	Pellet	150–1,200 mg/3–6 months
Notes: Men produce about 3 to 11 mg of testosterone per day (mean 7 mg/day in young men). Footnotes:a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template.

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Androgen replacement therapy formulations and dosages used in women

Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg 1x/1–2 days
	Methyltestosterone	Metandren, Estratest	Tablet	0.5–10 mg/day
	Fluoxymesterone	Halotestin	Tablet	1–2.5 mg 1x/1–2 days
	Normethandrone a	Ginecoside	Tablet	5 mg/day
	Tibolone	Livial	Tablet	1.25–2.5 mg/day
	Prasterone (DHEA) b	–	Tablet	10–100 mg/day
Sublingual	Methyltestosterone	Metandren	Tablet	0.25 mg/day
Transdermal	Testosterone	Intrinsa	Patch	150–300 μg/day
		AndroGel	Gel, cream	1–10 mg/day
Vaginal	Prasterone (DHEA)	Intrarosa	Insert	6.5 mg/day
Injection	Testosterone propionate a	Testoviron	Oil solution	25 mg 1x/1–2 weeks
	Testosterone enanthate	Delatestryl, Primodian Depot	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone cypionate	Depo-Testosterone, Depo-Testadiol	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone isobutyrate a	Femandren M, Folivirin	Aqueous suspension	25–50 mg 1x/4–6 weeks
	Mixed testosterone esters	Climacterona	Oil solution	150 mg 1x/4–8 weeks
		Omnadren, Sustanon	Oil solution	50–100 mg 1x/4–6 weeks
	Nandrolone decanoate	Deca-Durabolin	Oil solution	25–50 mg 1x/6–12 weeks
	Prasterone enanthate a	Gynodian Depot	Oil solution	200 mg 1x/4–6 weeks
Implant	Testosterone	Testopel	Pellet	50–100 mg 1x/3–6 months
Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes:a = Mostly discontinued or unavailable. b = Over-the-counter. Sources: See template.

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Androgen/anabolic steroid dosages for breast cancer

Route	Medication	Form	Dosage
Oral	Methyltestosterone	Tablet	30–200 mg/day
	Fluoxymesterone	Tablet	10–40 mg 3x/day
	Calusterone	Tablet	40–80 mg 4x/day
	Normethandrone	Tablet	40 mg/day
Buccal	Methyltestosterone	Tablet	25–100 mg/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection)	Testosterone propionate	Oil solution	50–100 mg 3x/week
	Testosterone enanthate	Oil solution	200–400 mg 1x/2–4 weeks
	Testosterone cypionate	Oil solution	200–400 mg 1x/2–4 weeks
	Mixed testosterone esters	Oil solution	250 mg 1x/week
	Methandriol	Aqueous suspension	100 mg 3x/week
	Androstanolone (DHT)	Aqueous suspension	300 mg 3x/week
	Drostanolone propionate	Oil solution	100 mg 1–3x/week
	Metenolone enanthate	Oil solution	400 mg 3x/week
	Nandrolone decanoate	Oil solution	50–100 mg 1x/1–3 weeks
	Nandrolone phenylpropionate	Oil solution	50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Non-medical

Methyltestosterone is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters, although it is not commonly used relative to other AAS for such purposes. ^[4]

Available forms

See also: Esterified estrogens/methyltestosterone and Conjugated estrogens/methyltestosterone

Methyltestosterone is typically used as an oral medication. ^[6] It is also available under the brand names Metandren and Oreton Methyl for use specifically by buccal or sublingual administration. ^{[6] [21]} Methyltestosterone is available in the form of 2, 5, 10, and 25 mg oral tablets. ^{[22] [23]} It was also available in combination with estrogens as esterified estrogens/methyltestosterone (0.625 mg/1.25 mg, 1.25 mg/2.5 mg) and conjugated estrogens/methyltestosterone (0.625 mg/5.0 mg, 1.25 mg/10 mg). ^[22]

Contraindications

Methyltestosterone should be used with caution in women and children, as it can cause irreversible virilization. ^[4] Due to its estrogenicity, methyltestosterone can also accelerate epiphyseal closure and thereby produce short stature in children and adolescents. ^[4] It can worsen symptoms in men with benign prostatic hyperplasia. ^[4] Methyltestosterone should not be used in men with prostate cancer, as androgens can accelerate tumor progression. ^[4] The drug should be used with caution in patients with pre-existing hepatotoxicity, due to its own potential for hepatotoxicity. ^[4]

Side effects

See also: Anabolic steroid § Adverse effects

Adverse effects of methyltestosterone include androgenic side effects like oily skin, acne, seborrhea, increased facial/body hair growth, scalp hair loss, increased aggressiveness and sex drive, and spontaneous erections, as well as estrogenic side effects like breast tenderness, gynecomastia, fluid retention, and edema. ^{[4] [24]} In women, methyltestosterone can cause partially irreversible virilization, for instance voice deepening, hirsutism, clitoromegaly, breast atrophy, and muscle hypertrophy, as well as menstrual disturbances and reversible infertility. ^{[4] [24]} In men, the drug may also cause hypogonadism, testicular atrophy, and reversible infertility at sufficiently high dosages. ^{[4] [24]}

Methyltestosterone can sometimes cause hepatotoxicity, for instance elevated liver enzymes, cholestatic jaundice, peliosis hepatis, hepatomas, and hepatocellular carcinoma, with extended use. ^{[4] [24] [25]} It can also have adverse effects on the cardiovascular system. ^[4] AAS like methyltestosterone stimulate erythropoiesis (red blood cell production) and increase hematocrit levels and at high dosages can cause polycythemia (overproduction of red blood cells), which can greatly increase the risk of thrombic events such as embolism and stroke. ^[4] With long-term treatment, AAS can increase the risk of benign prostatic hyperplasia and prostate cancer. ^[4] Violent and even homicidal behavior, hypomania/mania, depression, suicidality, delusions, and psychosis have all been associated with very high dosages of AAS. ^[26]

Interactions

Aromatase inhibitors can be used to reduce or prevent the estrogenic effects of methyltestosterone and 5α-reductase inhibitors can be used to reduce its virilizing effects and thereby improve its ratio of anabolic to androgenic activity and reduce its rate of androgenic side effects. ^[4]

Pharmacology

Pharmacodynamics

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Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids

Medication	Ratioa
Testosterone	~1:1
Androstanolone (DHT)	~1:1
Methyltestosterone	~1:1
Methandriol	~1:1
Fluoxymesterone	1:1–1:15
Metandienone	1:1–1:8
Drostanolone	1:3–1:4
Metenolone	1:2–1:30
Oxymetholone	1:2–1:9
Oxandrolone	1:3–1:13
Stanozolol	1:1–1:30
Nandrolone	1:3–1:16
Ethylestrenol	1:2–1:19
Norethandrolone	1:1–1:20
Notes: In rodents. Footnotes:a = Ratio of androgenic to anabolic activity. Sources: See template.

As an AAS, methyltestosterone is an agonist of the androgen receptor (AR), similarly to androgens like testosterone and dihydrotestosterone (DHT). ^{[4] [24]} It is a substrate for 5α-reductase like testosterone, and so is potentiated analogously in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland via transformation into the more potent AR agonist mestanolone (17α-methyl-DHT). ^{[4] [24]} As such, methyltestosterone has a relatively low ratio of anabolic to androgenic activity, with a similar ratio to that of testosterone (close to 1:1), and this makes it among the most androgenic AAS. ^{[4] [24]} Due to efficient aromatization into the potent and metabolism-resistant estrogen methylestradiol (17α-methylestradiol), methyltestosterone has relatively high estrogenicity and hence potential for estrogenic side effects such as gynecomastia and fluid retention. ^{[17] [27]} The drug possesses negligible progestogenic activity. ^{[4] [24]}

Due to its combined disadvantages of a relatively poor ratio of anabolic to androgenic activity, unusually high estrogenicity, and the potential for hepatotoxicity (as with other 17α-alkylated AAS), methyltestosterone has not been used as commonly as many other AAS either in medicine or for physique- or performance-enhancing purposes. ^[4]

Pharmacokinetics

Absorption

Methyltestosterone has dramatically improved oral bioavailability and metabolic stability relative to testosterone. ^{[4] [24]} This difference is due to the C17α methyl group, which results in steric hindrance and prevents metabolism. ^{[4] [24]} The oral bioavailability of methyltestosterone is about 70%, and it is well-absorbed from the gastrointestinal tract. ^[8] Methyltestosterone can also be taken buccally or sublingually. ^{[4] [8]} Although effective orally, methyltestosterone is more effective by these non-oral routes, which are said to approximately double its bioavailability and require half the oral dosage. ^{[4] [8] [21]}

Circulating levels of methyltestosterone with administration of 1.25 to 2.5 mg/day oral methyltestosterone in women are in the range of 20 to 30 ng/dL. ^[28] For comparison to testosterone, methyltestosterone is at least as potent as an AAS. ^[28] However, due to the large decrease in sex hormone-binding globulin (SHBG) levels and hence increase in free unbound testosterone caused by methyltestosterone, androgenic effects may be greater than reflected merely by methyltestosterone levels. ^[28]

Distribution

Methyltestosterone is highly protein-bound, by approximately 98%. ^[9] The medication has low but significant affinity for human serum sex hormone-binding globulin (SHBG), about 25% of that of testosterone and 5% of that of DHT. ^{[4] [29]}

Metabolism

The biological half-life of methyltestosterone is approximately 3 hours (range 2.5–3.5 hours). ^{[8] [11]} The duration of action of methyltestosterone is said to be 1 to 3 days, and is described as relatively short among AAS. ^{[9] [30]}

Excretion

Methyltestosterone is excreted 90% in the urine as conjugates and other metabolites, and 6% in feces. ^[9]

Chemistry

See also: List of androgens/anabolic steroids § Testosterone derivatives

Methyltestosterone, also known as 17α-methyltestosterone or as 17α-methylandrost-4-en-17β-ol-3-one, is a synthetic, 17α-alkylated androstane steroid and a derivative of testosterone differing from it only in the presence of a methyl group at the C17α position. ^{[1] [2] [4]} Close synthetic relatives of methyltestosterone include metandienone (17α-methyl-δ¹-testosterone) and fluoxymesterone (9α-fluoro-11β-hydroxy-17α-methyltestosterone). ^{[4] [24]}

Derivatives

See also: 17α-Alkylated anabolic steroid § List of 17α-alkylated AAS

Methyltestosterone and ethyltestosterone (17α-ethyltestosterone) are the parent structures of all 17α-alkylated AAS. Major 17α-alkylated AAS include the testosterone derivatives fluoxymesterone, metandienone (methandrostenolone), and methyltestosterone and the DHT derivatives oxandrolone, oxymetholone, and stanozolol. ^{[4] [24]}

Synthesis

A chemical synthesis of methyltestosterone from dehydroepiandrosterone (DHEA) with methandriol as an intermediate proceeds as follows: ^{[31] [32]}

History

Methyltestosterone was first synthesized in 1935 along with methandriol and mestanolone. ^{[33] [34] [6] [17] [18]} It was the second synthetic AAS to be developed, following mesterolone (1α-methyl-DHT) in 1934, and was the first 17α-alkylated AAS to be synthesized. ^{[6] [17] [18]} The drug was introduced for medical use in 1936. ^{[19] [4]}

Society and culture

A confiscated capsule of illicit methyltestosterone.

Generic names

Methyltestosterone is the INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name, USP Tooltip United States Pharmacopeia, BAN Tooltip British Approved Name, and JAN Tooltip Japanese Accepted Name of the drug and its generic name in English and Japanese, while méthyltestostérone is its DCF Tooltip Dénomination Commune Française and French name and metiltestosterone is its DCIT Tooltip Denominazione Comune Italiana and Italian name. ^{[1] [2] [35] [3]} The generic name of the drug is methyltestosterone in Latin, methyltestosteron in German, and metiltestosterona in Spanish. ^{[1] [2] [3]} Methyltestosterone is also known by its former developmental code name NSC-9701. ^{[35] [3]}

Brand names

Brand names under which methyltestosterone is or has been marketed for medical use include Afro, Agovirin, Android, Androral, Mesteron, Metandren, Methitest, Methyltestosterone, Methyl Testosterone, Oraviron, Oreton, Oreton Methyl, Testormon, Testovis, Testred, and Virilon, among others. ^{[1] [2] [3] [36]}

With an estrogen

Main article: Esterified estrogens/methyltestosterone

Methyltestosterone is available at a low-dose in combination with esterified estrogens for the treatment of menopausal symptoms like hot flashes in women under the brand names Covaryx, Essian, Estratest, Menogen, and Syntest. ^{[4] [37]}

Availability

Availability of methyltestosterone in countries throughout the world. Blue is currently or formerly marketed.

United States

See also: List of androgens/anabolic steroids available in the United States

Although it is not commonly used, methyltestosterone is one of the few AAS that remains available for medical use in the United States. ^{[4] [36]} The others are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, oxandrolone, oxymetholone, and fluoxymesterone. ^[36]

Other countries

Methyltestosterone has also been marketed in many other countries throughout the world. ^{[1] [2] [3] [4] [38] [39]}

Legal status

Methyltestosterone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act. ^{[40] [41]}

See also

• Esterified estrogens/methyltestosterone
• Conjugated estrogens/methyltestosterone

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Further reading

• Phillips EH, Ryan S, Ferrari R, Green C (2003). "Estratest and Estratest HS (esterified estrogens and methyltestosterone) therapy: a summary of safety surveillance data, January 1989 to August 2002". Clin Ther. 25 (12): 3027–43. doi:10.1016/s0149-2918(03)90090-7. PMID   14749144.
• Kabat GC, Kamensky V, Heo M, Bea JW, Hou L, Lane DS, Liu S, Qi L, Simon MS, Wactawski-Wende J, Rohan TE (2014). "Combined conjugated esterified estrogen plus methyltestosterone supplementation and risk of breast cancer in postmenopausal women". Maturitas. 79 (1): 70–6. doi:10.1016/j.maturitas.2014.06.006. PMID   25011395.
• El-Desoky el-SI, Reyad M, Afsah EM, Dawidar AA (2016). "Synthesis and chemical reactions of the steroidal hormone 17α-methyltestosterone". Steroids. 105: 68–95. doi:10.1016/j.steroids.2015.11.004. PMID   26639430. S2CID   32620483.

External links

• "Methyltestosterone". William Llewellyn's Anabolic.org. Archived from the original on 2019-12-31. Retrieved 2020-04-01.