Normethandrone

Last updated
Normethandrone
Methylestrenolone.svg
Clinical data
Trade names Metalutin, others
Other namesNormetandrone; Methylestrenolone; Methyloestrenolone; Methylnortestosterone; Normethyltestosterone; Normethandrolone; Normethisterone; Methylnandrolone; NMT; 17α-Methyl-19-nortestosterone; 17α-Methylestr-4-en-17β-ol-3-one; P-6051; RU-598; NSC-10039
Routes of
administration 		By mouth
Drug class Progestogen; Progestin; Androgen; Anabolic steroid
ATC code
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.440 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H28O2
Molar mass 288.431 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CCC4=CC(=O)CC[C@H]34
  • InChI=1S/C19H28O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16+,17-,18-,19-/m0/s1
  • Key:ZXSWTMLNIIZPET-ZOFHRBRSSA-N

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. [1] [2] [3] [4] It is taken by mouth. [5]

Contents

Side effects of normethandrone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [6] It can also cause liver damage. [7] Normethandrone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. [5] It is also a synthetic AAS and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone (DHT). [4] [8] It has some estrogenic activity as well and no other important hormonal activity. [9] [1] [3]

Normethandrone was introduced for medical use by 1957. [10] It is available only in a few countries, including Brazil, Indonesia, and Venezuela, and is available only in combination with methylestradiol or estradiol valerate. [2] [1]

Medical uses

Normethandrone is used in combination with an estrogen, either methylestradiol or estradiol valerate, in the treatment of amenorrhea and menopausal symptoms in women. [1] [2] [11] It has also been used to treat dysmenorrhea in women. [12] Normethandrone has been used successfully to inhibit libido in men with sexual deviance. [13] Although normethandrone can be classified as an AAS and has strong such effects at sufficiently high doses, it is not typically used as such and is instead used medically only as a progestin. [3] [1] [4] This is because it is so highly progestogenic in comparison. [4]

Androgen replacement therapy formulations and dosages used in women
RouteMedicationMajor brand namesFormDosage
Oral Testosterone undecanoate Andriol, JatenzoCapsule40–80 mg 1x/1–2 days
Methyltestosterone Metandren, EstratestTablet0.5–10 mg/day
Fluoxymesterone HalotestinTablet1–2.5 mg 1x/1–2 days
NormethandroneaGinecosideTablet5 mg/day
Tibolone LivialTablet1.25–2.5 mg/day
Prasterone (DHEA) b–Tablet10–100 mg/day
Sublingual Methyltestosterone MetandrenTablet0.25 mg/day
Transdermal Testosterone IntrinsaPatch150–300 μg/day
AndroGelGel, cream1–10 mg/day
Vaginal Prasterone (DHEA) IntrarosaInsert6.5 mg/day
Injection Testosterone propionate aTestovironOil solution25 mg 1x/1–2 weeks
Testosterone enanthate Delatestryl, Primodian DepotOil solution25–100 mg 1x/4–6 weeks
Testosterone cypionate Depo-Testosterone, Depo-TestadiolOil solution25–100 mg 1x/4–6 weeks
Testosterone isobutyrate aFemandren M, FolivirinAqueous suspension25–50 mg 1x/4–6 weeks
Mixed testosterone esters ClimacteronaOil solution150 mg 1x/4–8 weeks
Omnadren, SustanonOil solution50–100 mg 1x/4–6 weeks
Nandrolone decanoate Deca-DurabolinOil solution25–50 mg 1x/6–12 weeks
Prasterone enanthate aGynodian DepotOil solution200 mg 1x/4–6 weeks
Implant Testosterone TestopelPellet50–100 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.
Androgen/anabolic steroid dosages for breast cancer
RouteMedicationFormDosage
Oral Methyltestosterone Tablet30–200 mg/day
Fluoxymesterone Tablet10–40 mg 3x/day
Calusterone Tablet40–80 mg 4x/day
NormethandroneTablet40 mg/day
Buccal Methyltestosterone Tablet25–100 mg/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection) Testosterone propionate Oil solution50–100 mg 3x/week
Testosterone enanthate Oil solution200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution250 mg 1x/week
Methandriol Aqueous suspension100 mg 3x/week
Androstanolone (DHT) Aqueous suspension300 mg 3x/week
Drostanolone propionate Oil solution100 mg 1–3x/week
Metenolone enanthate Oil solution400 mg 3x/week
Nandrolone decanoate Oil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms

Normethandrone is marketed in combination with methylestradiol in the form of oral tablets containing 5 mg normethandrone and 0.3 mg methylestradiol. [11] [14]

Side effects

Normethandrone has been associated with symptoms of masculinization and hepatotoxicity. [6] [7] [15]

Pharmacology

Pharmacodynamics

Normethandrone shows high progestogenic activity. [5] With sublingual administration in women, it has at least 150 times the potency of sublingual progesterone and 50 times the potency of sublingual ethisterone. [5] It also has 10 times the potency of injected progesterone via this route. [5] The oral potency of normethandrone in terms of endometrial transformation is similar to that of norethisterone. [16] [17] It has been reported to inhibit ovulation in women. [18]

In addition to its progestogenic activity, normethandrone has anabolic and androgenic activity and can produce effects associated with this activity. [1] [4] It has a high ratio of anabolic to androgenic activity. [19] The anabolic potency of normethandrone is similar to that of norethandrolone and is much greater than that of nandrolone or metandienone. [8] It is also greater than that of ethylestrenol. [8] Normethandrone has been found to increase nitrogen retention, a measure of anabolic effect, at a dosage of 30 mg/day. [20] Analogously to nandrolone and norethandrolone, 5α-dihydronormethandrone, the 5α-reduced metabolite of normethandrone, shows reduced affinity for the androgen receptor relative to normethandrone. [21] [22] Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone. [21]

Normethandrone has estrogenic activity via aromatization into methylestradiol. [3]

Relative affinities (%) of normethandrone and metabolites
Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Normethandrone75–125125–150<11–5<1 ? ?
5α-Dihydronormethandrone 15–2550–75 ?<1 ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, and aldosterone for the MR Tooltip mineralocorticoid receptor. Sources: See template.

Pharmacokinetics

Normethandrone is metabolized by aromatase into methylestradiol in small quantities, similarly to methyltestosterone and metandienone. [3] [23] [24] The metabolites of normethandrone have not been well-studied, but 5α-dihydronormethandrone is a likely metabolite formed by 5α-reductase. [25] [26]

The pharmacokinetics of normethandrone have been reviewed. [27]

Chemistry

Normethandrone, also known as 17α-methyl-19-nortestosterone or as 17α-methylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone; 19-NT). It is specifically the 17α-methyl derivative of nandrolone as well as the 17α-methyl variant of norethandrolone (17α-ethyl-19-NT) and norethisterone (17α-ethynyl-19-NT). [28]

Synthesis

Chemical syntheses of normethandrone have been published. [27]

History

Normethandrone has been marketed for medical use since 1957. [10] The combination of normethandrone and methylestradiol was introduced by at least 1966. [14]

Society and culture

Generic names

Normethandrone has not been assigned an INN Tooltip International Nonproprietary Name or other formal name designations. [28] [29] [2] It is also known as methylestrenolone, methylnortestosterone, normethandrolone, and normethisterone. [28] [29] [2]

Brand names

Brand names of normethandrone include Batynid, Ginecosid, Ginecoside, Gynomin, Lutenin, Matronal, Mediol, Metalutin, Methalutin, Orgasteron, Orosteron, and Renodiol. [28] [29] [2] [1] [30] [11]

Availability

Normethandrone is marketed in Brazil, Indonesia, and Venezuela in combination with methylestradiol or estradiol valerate. [2] [1]

Related Research Articles

<span class="mw-page-title-main">Progestogen</span> Steroid hormone that activates the progesterone receptor

Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. The progestogens are named for their function in maintaining pregnancy, although they are also present at other phases of the estrous and menstrual cycles.

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Marion Jones, Barry Bonds, and Dwain Chambers.

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

<span class="mw-page-title-main">Ethisterone</span> Chemical compound

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Noretynodrel</span> Chemical compound

Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.

<span class="mw-page-title-main">Methylestradiol</span> Chemical compound

Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication. Methylestradiol is taken by mouth.

<span class="mw-page-title-main">Dimethandrolone</span> Chemical compound

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Methylhydroxynandrolone</span> Chemical compound

Methylhydroxynandrolone, also known as 4-hydroxy-17α-methyl-19-nortestosterone (HMNT), as well as 4,17β-dihydroxy-17α-methylestr-4-en-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of nandrolone (19-nortestosterone) which was never marketed. It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use. The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement". MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">5α-Dihydronorethisterone</span> Chemical compound

5α-Dihydronorethisterone is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues.

<span class="mw-page-title-main">17α-Allyl-19-nortestosterone</span> Chemical compound

17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.

<span class="mw-page-title-main">5α-Dihydronormethandrone</span> Chemical compound

5α-Dihydronormethandrone, also known as 17α-methyl-4,5α-dihydro-19-nortestosterone or as 17α-methyl-5α-estran-17β-ol-3-one, is an androgen/anabolic steroid and a likely metabolite of normethandrone formed by 5α-reductase. Analogously to nandrolone and its 5α-reduced metabolite 5α-dihydronandrolone, 5α-DHNMT shows reduced affinity for the androgen receptor relative to normethandrone. Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

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