Normethandrone

Not to be confused with Normethadone or Norethandrolone.
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
IUPAC name
  • (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 InfoCard100.007.440
Chemical and physical data
FormulaC19H28O2
Molar mass288.431 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CCC4=CC(=O)CC[C@H]34
InChI
  • 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]

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]

  1. ^ a b c "Digital Medicines Information Suite | MedicinesComplete".
  2. ^ a b "Gynomin".
  3. ^ a b Cite error: The named reference pmid1964199 was invoked but never defined (see the help page).
  4. ^ a b Cite error: The named reference Krüskemper2013 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference pmid13354223 was invoked but never defined (see the help page).
  6. ^ Lundberg 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. ^ Cite error: The named reference pmid14315662 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Brueggemeier2006 was invoked but never defined (see the help page).
  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. ^ Cite error: The named reference Office1957 was invoked but never defined (see the help page).
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.