Norethandrolone

Overview

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.[1][2][3] WP

Side effects of norethandrolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and liver damage. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong anabolic effects relative to its androgenic effects. The drug also has strong progestogenic effects.[2][4] WP

Norethandrolone was discovered in 1953 and was introduced for medical use in 1956. It was the first AAS with a favorable separation of anabolic and androgenic effect to be marketed. The drug was mostly withdrawn in the 1980s due to concerns of liver damage. In addition to its medical use, norethandrolone has been used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.[2][5–8] WP

Uses, dosage and effects

Medical uses

Norethandrolone has been used in the treatment of muscle wasting, patients with severe burns, after severe trauma, and for certain forms of aplastic anemia among other indications.[2][8] WP

Risks and side effects

Side effects

Side effects of norethandrolone include virilization among others. It has estrogenic effects and can cause gynecomastia and fluid retention. As with all 17α-alkylated AAS, long-term use of norethandrolone in high doses may result in hepatotoxicity including elevated liver enzymes and cirrhosis.[2][9] WP

Pharmacology

Pharmacodynamics

Norethandrolone is an androgen and anabolic steroid and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone. It has a high ratio of anabolic to androgenic activity. Analogously to the case of nandrolone and 5α-dihydronandrolone, 5α-dihydronorethandrolone, the 5α-reduced metabolite of norethandrolone, shows diminished affinity for the androgen receptor relative to norethandrolone. This is likely related to the high ratio of anabolic to androgenic activity observed with norethandrolone. Norethandrolone has relatively high estrogenic activity via transformation by aromatase into the potent estrogen ethylestradiol. It also has strong progestogenic activity. The progestogenic potency of norethandrolone is similar to that of norethisterone in terms of endometrial changes in women. In addition, norethandrolone is hepatotoxic.[2][10][11] WP

Pharmacokinetics

The pharmacokinetics of norethandrolone have been reviewed.[12] WP

Research

Research

Norethandrolone has been studied for use in male hormonal contraception.[13][14][15] WP

History

History

Norethandrolone was synthesized at G. D. Searle & Company in 1953 and was originally studied as a progestin, along with norethisterone and noretynodrel, but ultimately was not marketed as such. 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. Norethandrolone was introduced for medical use as an AAS in 1956 and was the first so-called "anabolic steroid", or AAS with a favorable separation of anabolic and androgenic effect, to be marketed. It was followed by normethandrone as a progestin in 1957 and by the more well-known AAS nandrolone phenylpropionate in 1959. Norethandrolone was introduced in the United States in the late 1950s under the brand name Nilevar but was discontinued in this country in the 1960s due to limited sales. Although it was also introduced into Europe and certain other markets, it was withdrawn in many countries in the 1980s due to concerns of cholestatic jaundice. Today, the drug remains available only in France.[2][3][5–8][16] WP

Legal status

Generic names

Norethandrolone is the generic name of the drug and its INN (International Nonproprietary Name) and BAN (British Approved Name). It has also been referred to as noretandrolone, ethylnandrolone, and ethylnortestosterone, as well as by its developmental code name CB-8022.[1][3] WP

Brand names

Norethandrolone is marketed under the brand names Nilevar and Pronabol.[1][2][3] WP

Availability

Norethandrolone is available today only in France.[3][17] WP

Chemistry

Formula

C20H30O2 PC

CAS number

52-78-8 PC

Molar mass (g/mol)

302.5 PC

IUPAC name (computed by PubChem)

(8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one PC

SMILES

CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O PC

InChIKey

ZDHCJEIGTNNEMY-XGXHKTLJSA-N PC

PubChem CID

5858

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
2. Other William Llewellyn. Anabolics. 2011
3. Other List of Androgens and anabolic steroids
4. Journal / agency Kicman AT. Pharmacology of anabolic steroids. Br. J. Pharmacol. 2008. doi:10.1038/bjp.2008.165 · PMID 18500378 · PMC2439524
5. Other Charles D. Kochakian. Anabolic-Androgenic Steroids. 6 December 2012
6. Other Camille Georges Wermuth. The Practice of Medicinal Chemistry. 2 May 2011
7. Other James Edward Wright. Altered States: The Use and Abuse of Anabolic Steroids. 1994
8. Other Walter Sneader. Drug Discovery: A History. 23 June 2005
9. Other Daniel Lednicer. Steroid Chemistry at a Glance. 20 June 2011
10. Journal / agency Bergink EW, Geelen JA, Turpijn EW. Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions. Acta Endocrinol Suppl (Copenh). 1985. doi:10.1530/acta.0.109S0031 · PMID 3865479
11. Journal / agency Boschann HW. Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications. Ann. N. Y. Acad. Sci. July 1958. doi:10.1111/j.1749-6632.1958.tb46803.x · PMID 13583829
12. Other Die Gestagene. 27 November 2013
13. Journal / agency Schearer SB, Alvarez-Sanchez F, Anselmo J, Brenner P, Coutinho E, Latham-Faundes A, Frick J, Heinild B, Johansson ED. Hormonal Contraception for Men. International Journal of Andrology. 1978. doi:10.1111/j.1365-2605.1978.tb00517.x
14. Journal / agency Neumann F, Diallo FA, Hasan SH, Schenck B, Traore I. The influence of pharmaceutical compounds on male fertility. Andrologia. 1976. doi:10.1111/j.1439-0272.1976.tb02137.x · PMID 793446
15. Journal / agency Brenner PF, Bernstein GS, Roy S, Jecht EW, Mishell DR. Administration of norethandrolone and testosterone as a contraceptive agent for men. Contraception. February 1975. doi:10.1016/0010-7824(75)90030-x · PMID 1112088
16. Other United States. Patent Office. Official Gazette of the United States Patent Office. 1957
17. Other IBM Watson Health Products

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.