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Normethandrone

From Wikipedia, the free encyclopedia
Chemical compound

Not to be confused withNormethadone orNorethandrolone.
Pharmaceutical compound
Normethandrone
Clinical data
Trade namesMetalutin, 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 classProgestogen;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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.007.440Edit this at Wikidata
Chemical and physical data
FormulaC19H28O2
Molar mass288.431 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 asmethylestrenolone ormethylnortestosterone and sold under the brand nameMetalutin among others, is aprogestin andandrogen/anabolic steroid (AAS) medication which is used in combination with anestrogen in the treatment ofamenorrhea andmenopausalsymptoms in women.[1][2][3][4] It is takenby mouth.[5]

Side effects of normethandrone includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.[6] It can also causeliver damage.[7] Normethandrone is a progestin, or asyntheticprogestogen, and hence is anagonist of theprogesterone receptor, thebiological target of progestogens likeprogesterone.[5] It is also asynthetic AAS and hence is anagonist of theandrogen receptor, thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[4][8] It has someestrogenic activity as well and no other importanthormonal activity.[9][1][3]

Normethandrone was introduced for medical use by 1957.[10] It is available only in a few countries, includingBrazil,Indonesia, andVenezuela, and is available only in combination withmethylestradiol orestradiol valerate.[2][1]

Medical uses

[edit]

Normethandrone is used in combination with anestrogen, eithermethylestradiol orestradiol valerate, in the treatment ofamenorrhea andmenopausalsymptoms in women.[1][2][11] It has also been used to treatdysmenorrhea in women.[12] Normethandrone has been used successfully to inhibitlibido in men withsexual 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
OralTestosterone undecanoateAndriol, JatenzoCapsule40–80 mg 1x/1–2 days
MethyltestosteroneMetandren, EstratestTablet0.5–10 mg/day
FluoxymesteroneHalotestinTablet1–2.5 mg 1x/1–2 days
NormethandroneaGinecosideTablet5 mg/day
TiboloneLivialTablet1.25–2.5 mg/day
Prasterone (DHEA)b–Tablet10–100 mg/day
SublingualMethyltestosteroneMetandrenTablet0.25 mg/day
TransdermalTestosteroneIntrinsaPatch150–300 μg/day
AndroGelGel, cream1–10 mg/day
VaginalPrasterone (DHEA)IntrarosaInsert6.5 mg/day
InjectionTestosterone propionateaTestovironOil solution25 mg 1x/1–2 weeks
Testosterone enanthateDelatestryl, Primodian DepotOil solution25–100 mg 1x/4–6 weeks
Testosterone cypionateDepo-Testosterone, Depo-TestadiolOil solution25–100 mg 1x/4–6 weeks
Testosterone isobutyrateaFemandren M, FolivirinAqueous suspension25–50 mg 1x/4–6 weeks
Mixed testosterone estersClimacteronaOil solution150 mg 1x/4–8 weeks
Omnadren, SustanonOil solution50–100 mg 1x/4–6 weeks
Nandrolone decanoateDeca-DurabolinOil solution25–50 mg 1x/6–12 weeks
Prasterone enanthateaGynodian DepotOil solution200 mg 1x/4–6 weeks
ImplantTestosteroneTestopelPellet50–100 mg 1x/3–6 months
Notes:Premenopausal women produce about 230 ± 70 μgtestosterone 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
OralMethyltestosteroneTablet30–200 mg/day
FluoxymesteroneTablet10–40 mg 3x/day
CalusteroneTablet40–80 mg 4x/day
NormethandroneTablet40 mg/day
BuccalMethyltestosteroneTablet25–100 mg/day
Injection (IMTooltip intramuscular injection orSCTooltip subcutaneous injection)Testosterone propionateOil solution50–100 mg 3x/week
Testosterone enanthateOil solution200–400 mg 1x/2–4 weeks
Testosterone cypionateOil solution200–400 mg 1x/2–4 weeks
Mixed testosterone estersOil solution250 mg 1x/week
MethandriolAqueous suspension100 mg 3x/week
Androstanolone (DHT)Aqueous suspension300 mg 3x/week
Drostanolone propionateOil solution100 mg 1–3x/week
Metenolone enanthateOil solution400 mg 3x/week
Nandrolone decanoateOil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionateOil solution50–100 mg/week
Note: Dosages are not necessarily equivalent.Sources: See template.

Available forms

[edit]

Normethandrone is marketed in combination withmethylestradiol in the form oforaltablets containing 5 mg normethandrone and 0.3 mg methylestradiol.[11][14]

Side effects

[edit]
See also:Progestin § Side effects, andAnabolic steroid § Adverse effects

Normethandrone has been associated withsymptoms ofmasculinization andhepatotoxicity.[6][7][15]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Normethandrone shows highprogestogenic activity.[5] Withsublingual administration in women, it has at least 150 times thepotency of sublingualprogesterone and 50 times the potency of sublingualethisterone.[5] It also has 10 times the potency of injected progesterone via this route.[5] The oral potency of normethandrone in terms ofendometrial transformation is similar to that ofnorethisterone.[16][17] It has been reported to inhibitovulation in women.[18]

In addition to its progestogenic activity, normethandrone hasanabolic andandrogenic activity and can produce effects associated with this activity.[1][4] It has a high ratio of anabolic to androgenic activity.[19] The anabolicpotency of normethandrone is similar to that ofnorethandrolone and is much greater than that ofnandrolone ormetandienone.[8] It is also greater than that ofethylestrenol.[8] Normethandrone has been found to increasenitrogen retention, a measure of anabolic effect, at a dosage of 30 mg/day.[20] Analogously to nandrolone andnorethandrolone,5α-dihydronormethandrone, the5α-reducedmetabolite of normethandrone, shows reducedaffinity for theandrogen receptor relative to normethandrone.[21][22] Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone.[21]

Normethandrone hasestrogenic activity viaaromatization intomethylestradiol.[3]

Relative affinities (%) of normethandrone and metabolites
CompoundPRTooltip Progesterone receptorARTooltip Androgen receptorERTooltip Estrogen receptorGRTooltip Glucocorticoid receptorMRTooltip Mineralocorticoid receptorSHBGTooltip Sex hormone-binding globulinCBGTooltip Corticosteroid binding globulin
Normethandrone75–125125–150<11–5<1??
5α-Dihydronormethandrone15–2550–75?<1???
Notes: Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,dexamethasone for theGRTooltip glucocorticoid receptor, andaldosterone for theMRTooltip mineralocorticoid receptor.Sources: See template.

Pharmacokinetics

[edit]

Normethandrone ismetabolized byaromatase intomethylestradiol in small quantities, similarly tomethyltestosterone andmetandienone.[3][23][24] The metabolites of normethandrone have not been well-studied, but5α-dihydronormethandrone is a likely metabolite formed by5α-reductase.[25][26]

Thepharmacokinetics of normethandrone have been reviewed.[27]

Chemistry

[edit]
See also:List of progestogens andList of androgens/anabolic steroids

Normethandrone, also known as 17α-methyl-19-nortestosterone or as 17α-methylestr-4-en-17β-ol-3-one, is asyntheticestranesteroid and a17α-alkylatedderivative ofnandrolone (19-nortestosterone; 19-NT). It is specifically the 17α-methyl derivative of nandrolone as well as the 17α-methyl variant ofnorethandrolone (17α-ethyl-19-NT) andnorethisterone (17α-ethynyl-19-NT).[28]

Synthesis

[edit]

Chemical syntheses of normethandrone have been published.[27]

History

[edit]

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

[edit]

Generic names

[edit]

Normethandrone has not been assigned anINNTooltip International Nonproprietary Name or other formal name designations.[28][29][2] It is also known asmethylestrenolone,methylnortestosterone,normethandrolone, andnormethisterone.[28][29][2]

Brand names

[edit]

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

[edit]

Normethandrone is marketed inBrazil,Indonesia, andVenezuela in combination withmethylestradiol orestradiol valerate.[2][1]

References

[edit]
  1. ^abcdefgh"Digital Medicines Information Suite | MedicinesComplete".
  2. ^abcdefg"Gynomin".
  3. ^abcdeFriedl KE (1990). "Reappraisal of the health risks associated with the use of high doses of oral and injectable androgenic steroids".NIDA Research Monograph.102:142–177.PMID 1964199.
  4. ^abcdeKrüskemper HL (22 October 2013).Anabolic Steroids. Elsevier. pp. 10–.ISBN 978-1-4832-6504-9.
  5. ^abcdeFerin J (August 1956). "A new substance with progestational activity; comparative assays in ovariectomized women; clinical results".Acta Endocrinologica.22 (4):303–317.doi:10.1530/acta.0.0220303.PMID 13354223.
  6. ^abLundberg PO (1962). "Migraine Prophylaxis with Progestogens".European Journal of Endocrinology.40 (4 Suppl):S5 –S22.doi:10.1530/acta.0.040S0005.ISSN 0804-4643.
  7. ^abDelorimier AA, Gordan GS, Lowe RC, Carbone JV (August 1965). "Methyltestosterone, Related Steroids, and Liver Function".Archives of Internal Medicine.116 (2):289–294.doi:10.1001/archinte.1965.03870020129023.PMID 14315662.
  8. ^abcBrueggemeier RW (2006). "Sex Hormones (Male): Analogs and Antagonists".Encyclopedia of Molecular Cell Biology and Molecular Medicine. Wiley-VCH Verlag GmbH & Co. KGaA. p. 42.doi:10.1002/3527600906.mcb.200500066.ISBN 3-527-60090-6.
  9. ^Heftmann E (1970).Steroid Biochemistry. Academic Press. p. 72.ISBN 978-0-12-336650-4.Normethandrone (Fig. 49) is a 19-nortestosterone derivative having progestational as well as androgenic and anabolic activity.
  10. ^abOfficial Gazette of the United States Patent Office. U.S. Patent Office. 1957.
  11. ^abcUnlisted Drugs. Pharmaceutical Section, Special Libraries Association. 1982.Batynid. C. Each dragee contains: normethandrone, 5 mg.; and methylestradiol, 0.3 mg. E. (Formerly) Gynaekosid. M. Boehringer Biochemia, Florence. A. Estrogenic; Rx of secondary amenorrhea. R. Notiz Med Farm 32;295, Nov-Dec 81.
  12. ^Begni-Calvet D (1959). "[Two properties of methylestrenolone (17-alpha-methyl-19-nortestosterone): its effectiveness in the treatment of dysmenorrhea, its anabolic action]".Gynécologie Pratique.10:261–272.PMID 13798272.
  13. ^Servais J (1973). "A clinical study of cases of psychosexual disturbances in men treated by a libido inhibitor: Methylestrenolone".Archives of Sexual Behavior.2 (4):387–390.doi:10.1007/BF01541012.ISSN 0004-0002.S2CID 145090184.
  14. ^abAkingba JB, Ayodeji EA (February 1966). "Amenorrhea as a leading symptom of choriocarcinoma".The Journal of Obstetrics and Gynaecology of the British Commonwealth.73 (1):153–155.doi:10.1111/j.1471-0528.1966.tb05137.x.PMID 5948541.S2CID 38008851.
  15. ^Feldman EB, Carter AC (June 1960). "Endocrinologic and metabolic effects of 17 alpha-methyl-19-nortestosterone in women".The Journal of Clinical Endocrinology and Metabolism.20 (6):842–857.doi:10.1210/jcem-20-6-842.PMID 13822027.
  16. ^Horský J, Presl J (1981)."Hormonal Treatment of Disorders of the Menstrual Cycle". In Horský J, Presl J (eds.).Ovarian Function and its Disorders: Diagnosis and Therapy. Developments in Obstetrics and Gynecology. Springer Science & Business Media. pp. 309–332.doi:10.1007/978-94-009-8195-9_11.ISBN 978-94-009-8195-9.
  17. ^Boschann HW (July 1958). "Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications".Annals of the New York Academy of Sciences.71 (5):727–752.Bibcode:1958NYASA..71..727B.doi:10.1111/j.1749-6632.1958.tb54649.x.PMID 13583829.
  18. ^Camerino B, Sala G (1960). "Anabolic Steroids". In Jucker E (ed.).Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Fortschritte der Arzneimittelforschung. Progress in Drug Research. Progres des Recherches Pharmaceutiques. Vol. 2. pp. 71–134.doi:10.1007/978-3-0348-7038-2_2.ISBN 978-3-0348-7040-5.PMID 14448579.{{cite book}}:ISBN / Date incompatibility (help)
  19. ^Kochakian CD (6 December 2012).Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 379–.ISBN 978-3-642-66353-6.
  20. ^Dorfman RI (5 December 2016).Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 68–.ISBN 978-1-4832-7300-6.
  21. ^abOjasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors".Journal of Steroid Biochemistry.27 (1–3):255–269.doi:10.1016/0022-4731(87)90317-7.PMID 3695484.
  22. ^Behre HM, Kliesch S, Lemcke B, von Eckardstein S, Nieschlag E (December 2001). "Suppression of spermatogenesis to azoospermia by combined administration of GnRH antagonist and 19-nortestosterone cannot be maintained by this non-aromatizable androgen alone".Human Reproduction.16 (12):2570–2577.doi:10.1093/humrep/16.12.2570.PMID 11726576.
  23. ^Thieme D, Hemmersbach P (18 December 2009).Doping in Sports. Springer Science & Business Media. pp. 470–.ISBN 978-3-540-79088-4.
  24. ^Llewellyn W (2011).Anabolics. Molecular Nutrition Llc. pp. 444–454, 533.ISBN 978-0-9828280-1-4.
  25. ^Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C (May 2009). "Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine".The Journal of Steroid Biochemistry and Molecular Biology.115 (1–2):44–61.doi:10.1016/j.jsbmb.2009.02.016.PMID 19429460.S2CID 10051396.
  26. ^Schjølberg TH (2013).In Vitro Synthesis of Metabolites of three Anabolic Androgenic Steroids, by Human Liver Microsomes (Master's thesis thesis). Institutt for Bioteknologi. Archived fromthe original on 2018-03-26. Retrieved2018-03-25.
  27. ^abDie Gestagene. Springer-Verlag. 27 November 2013. pp. 12–13, 282.ISBN 978-3-642-99941-3.
  28. ^abcdElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 888–.ISBN 978-1-4757-2085-3.
  29. ^abcMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 202–.ISBN 978-94-011-4439-1.
  30. ^Negwer M, Scharnow HG (2001).Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1831.ISBN 978-3-527-30247-5.
Progestogens
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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