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
SMILES
C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C
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
| Molecular Formula | C19H28O2 |
| Molecular Weight | 288.4244 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
| Title | Date | PubMed |
|---|---|---|
| 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. | 2009-11 |
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| 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. | 2008-06 |
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| 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. | 2006-03-01 |
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| Steroids LIV. Synthesis of 19-nor-17alpha-ethynyltestosterone and 19-nor-17alpha-methyltestosterone. 1954. | 2006-01 |
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| Bone and muscle protective potential of the prostate-sparing synthetic androgen 7alpha-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model. | 2005-04 |
|
| New tissue-selective androgens: perspectives in the treatment of androgen deficits. | 2003-04 |
|
| Inhibition of recovery of spermatogenesis in irradiated rats by different androgens. | 2002-09 |
Patents
| Substance Class |
Chemical
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| Record UNII |
743F1Z557A
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Validated (UNII)
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QG03FA05
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QG03DC31
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DEA NO. |
4000
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NCI_THESAURUS |
C776
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WHO-ATC |
G03DC31
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WHO-ATC |
G03FA05
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5284597
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100000080022
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DTXSID4023383
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CHEMBL2106801
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METHYLESTRENOLONE
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C073330
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m8069
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514-61-4
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743F1Z557A
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C95970
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DB13533
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208-183-0
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