Norethandrolone
Norethandrolone
|
Systematic (IUPAC) name |
---|
(17β)-17-ethyl-17-hydroxyester-4-en-3-one |
Clinical data |
---|
AHFS/Drugs.com |
International Drug Names |
---|
Legal status |
|
---|
Identifiers |
---|
CAS Number |
52-78-8 |
---|
ATC code |
A14AA09 (WHO) |
---|
PubChem |
CID 5858 |
---|
ChemSpider |
5649 Y |
---|
UNII |
P7W01638W6 Y |
---|
KEGG |
D07127 Y |
---|
Synonyms |
Noretandrolone; CB-8022 |
---|
Chemical data |
---|
Formula |
C20H30O2 |
---|
Molar mass |
302.451 g/mol |
---|
O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)C)CC4
|
InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 YKey:ZDHCJEIGTNNEMY-XGXHKTLJSA-N Y
|
(verify) |
---|
Norethandrolone (INN, BAN) (brand names Nilevar, Pronabol), also known as 17α-ethyl-19-nortestosterone, is an anabolic steroid.[1] It was synthesized at G. D. Searle & Company in 1953 and was originally studied as a progestin, along with norethisterone and noretynodrel, but was ultimately not marketed as such.[2][3] In 1955, it was re-examined for testosterone-like activity and was found to have similar anabolic activity to testosterone but only one-sixteenth the androgenic potency.[3][4] The drug was introduced in the United States as an anabolic steroid in 1965 under the trade name Nilevar[5] but was withdrawn from the market in the 1980s due to concerns of cholestatic jaundice.[4] Norethandrolone is now only marketed in Australia, France, and Switzerland, and as with all 17α-alkylated oral steroids, long-term use in high doses may result in elevated liver enzymes and consequently cirrhosis.[6] It is used in the treatment of muscle wasting,[4] patients with severe burns, after severe trauma, and for certain forms of aplastic anemia.
See also
References
|
---|
| Receptor (ligands) | |
---|
| Enzyme | |
---|
| Others | Precursors/prohormones | |
---|
| Indirect |
- Antigonadotropins (e.g., estrogens, progestogens, prolactin)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
|
---|
|
---|
| See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics |
|
|
---|
| Receptor (ligands) | | Agonists | |
---|
| | |
---|
| Antagonists |
- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Aglepristone
- Lilopristone
- Lonaprisan
- Onapristone
- Toripristone
- Valproic acid
- Vilaprisan
- ZM-150,271
- ZM-172,406
|
---|
|
---|
|
---|
| Enzyme | |
---|
| Others | Precursors/prohormones | |
---|
| Indirect |
- Antigonadotropins (e.g., estrogens, progestogens, prolactin)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
|
---|
|
---|
| See also: Androgenics • Estrogenics • Glucocorticoids • Mineralocorticoids |
|