Normethandrone

Normethandrone
Clinical data
Trade names	Metalutin, others
Other names	Normetandrone; 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	G03DC31 (WHO) ;
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	514-61-4;
PubChem CID	5284597;
ChemSpider	4447645;
UNII	743F1Z557A;
KEGG	C14491;
ChEMBL	ChEMBL269549;
CompTox Dashboard (EPA)	DTXSID4023383 ;
ECHA InfoCard	100.007.440
Chemical and physical data
Formula	C19H28O2
Molar mass	288.431 g·mol−1
3D model (JSmol)	Interactive image;
	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]

^ ^a ^b ^c "Digital Medicines Information Suite | MedicinesComplete".
^ ^a ^b "Gynomin".
^ ^a ^b Cite error: The named reference pmid1964199 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Krüskemper2013 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference pmid13354223 was invoked but never defined (see the help page).
^ 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.
^ Cite error: The named reference pmid14315662 was invoked but never defined (see the help page).
^ Cite error: The named reference Brueggemeier2006 was invoked but never defined (see the help page).
^ 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.
^ Cite error: The named reference Office1957 was invoked but never defined (see the help page).