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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O2
Molecular Weight 288.4244
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORMETHANDRONE

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=ZXSWTMLNIIZPET-ZOFHRBRSSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H28O2
Molecular Weight 288.4244
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Normethandrone (Orgasteron; Metalutin; Methalutin) is a progestin and androgen/anabolic steroid agent which is used in combination with an estrogen in the treatment of menstruation disorders in women. Normethandrone is a modified form of nandrolone. It differs by the addition of a methyl group at carbon 17-alpha to protect the hormone during oral administration. Normethandrone is aromatized by the body, and converts to a synthetic estrogen with a high level of biological activity (17alpha-methyl-estradiol). Orgasteron has been used as progestational agent and as an androgen. Normethandrone is available in combination with methylestradiol or estradiol valerate in a few countries, including Brazil, Indonesia, and Venezuela. This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01. Normethandrone was first described in 1954. Shortly after, it was developed into a medicine by Organon (now Merck/MSD), which introduced it under the Orgasterone brand name in Belgium and Switzerland, and as Orgasteron in the Netherlands. This steroid had also been sold by other manufacturers in various parts of Europe as Methalutin, Lutenin, and Matdonal. Although a simple oral methylated nandrolone, with strong properties as an anabolic steroid, Normethandrone exhibits such strong progestational activity that it was marketed as an oral progestin. Its anabolic effects were more looked at as secondary applications for the drug, and accounted for very little medical interest.

Originator

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
743F1Z557A
Record Status Validated (UNII)
Record Version