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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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of recovery of spermatogenesis in irradiated rats by different androgens.
2002 Sep
New tissue-selective androgens: perspectives in the treatment of androgen deficits.
2003 Apr
Bone and muscle protective potential of the prostate-sparing synthetic androgen 7alpha-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model.
2005 Apr
Steroids LIV. Synthesis of 19-nor-17alpha-ethynyltestosterone and 19-nor-17alpha-methyltestosterone. 1954.
2006 Jan
Comparison of the growth-promoting effects of testosterone and 7-alpha-methyl-19-nor-testosterone (MENT) on the prostate and levator ani muscle of LPB-tag transgenic mice.
2006 Mar 1
Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase.
2008 Jun
Lymphatic transport of Methylnortestosterone undecanoate (MU) and the bioavailability of methylnortestosterone are highly sensitive to the mass of coadministered lipid after oral administration of MU.
2009 Nov
Patents

Patents

Name Type Language
NORMETHANDRONE
MART.   MI   WHO-DD  
Common Name English
17.ALPHA.-METHYL-19-NORTESTOSTERONE
Common Name English
NORMETHANDRONE [MART.]
Common Name English
METHYLESTRENOLONE
Common Name English
NORMETHANDROLONE
Common Name English
LUTENIN
Brand Name English
NORMETHANDRONE [MI]
Common Name English
17.ALPHA.-METHYL-17.BETA.-HYDROXYESTR-4-EN-3-ONE
Systematic Name English
NSC-10039
Code English
ORGASTERON
Brand Name English
MATRONAL
Brand Name English
METHYLNORTESTOSTERONE
Common Name English
NORMETANDRONE
Common Name English
Normethandrone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QG03FA05
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
WHO-VATC QG03DC31
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
DEA NO. 4000
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
NCI_THESAURUS C776
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
WHO-ATC G03DC31
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
WHO-ATC G03FA05
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
Code System Code Type Description
PUBCHEM
5284597
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
SMS_ID
100000080022
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023383
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106801
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
WIKIPEDIA
METHYLESTRENOLONE
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
MESH
C073330
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
MERCK INDEX
m8069
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY Merck Index
CAS
514-61-4
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
FDA UNII
743F1Z557A
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
NCI_THESAURUS
C95970
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
DRUG BANK
DB13533
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
EVMPD
SUB14667MIG
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
NSC
10039
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
DRUG CENTRAL
1970
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-183-0
Created by admin on Fri Dec 15 17:24:48 UTC 2023 , Edited by admin on Fri Dec 15 17:24:48 UTC 2023
PRIMARY