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Quinbolone - Wikipedia

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Chemical compound

Pharmaceutical compound

Quinbolone Trade names Anabolicum, Anabolvis Other names MK-810; Δ1-Testosterone 17β-cyclopent-1-enyl enol ether; 1-Dehydrotestosterone 17β-cyclopent-1-enyl ether; 17β-(1-Cyclopenten-1-yloxy)androsta-1,4-dien-3-one; Androsta-1,4-dien-17β-ol-3-one 17β-(1-cyclopent-1-ene) Pregnancy
category Routes of
administration By mouth[1] ATC code Legal status Metabolism Liver Excretion Urine IUPAC name CAS Number PubChem CID ChemSpider UNII KEGG CompTox Dashboard (EPA) Formula C24H32O2 Molar mass 352.518 g·mol−1 3D model (JSmol) SMILES InChI   (verify)

Quinbolone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name), sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy.[2][3][4] It was developed by Parke-Davis[3] as a viable orally administered AAS with little or no liver toxicity.[1]

Most orally administered anabolic steroids function by having an alkylated 17α-carbon atom, which prevents first-pass metabolism by the liver.[5] This approach however results in the AAS having hepatotoxicity.[5] Quinbolone is not 17α-alkylated; instead it has increased oral bioavailability due to its cyclopentenyl ether group.[citation needed] After ingestion, the inactive quinbolone is transformed into boldenone.[1]

Quinbolone itself has very few androgenic effects, and most of what it does have are a result of its conversion to boldenone and its metabolites.[1][6][additional citation(s) needed] Because of high doses necessary for androgenic effects, cost and inconvenience meant that quinbolone never proved to be commercially successful, and its clinical applications were fulfilled by alternative, more effective, AAS.[citation needed] Its illicit usage in bodybuilding and athletics likewise proved limited, though drug tests are still used to detect its metabolites as it remains a banned substance for most competitive sports.[5]

Quinbolone, via boldenone, can be transformed into estrogens, and hence may have some estrogenic activity.[6]

Quinbolone, also known as δ1-testosterone 17β-cyclopent-1-enyl enol ether or as androsta-1,4-dien-17β-ol-3-one 17β-(1-cyclopent-1-ene) enol ether, is a synthetic androstane steroid and a derivative of testosterone.[2][3] It is the C17β cyclopentyl enol ether of boldenone (δ1-testosterone).[2][3] A related AAS is boldenone undecylenate (δ1-testosterone 17β-undec-10-enoate).[2][3]

Quinbolone can be prepared from testosterone. Dehydrogenation using DDQ forms boldenone. Reaction with 1,1-dimethoxycyclopentane followed by heating to eliminate methanol gives quinbolone.

Quinbolone synthesis:[7]

Quinbolone was described as early as 1962.[7] It was marketed in Italy by Parke-Davis.[3]

  1. ^ a b c d Galletti F, Gardi R (July 1971). "Metabolism of 1-dehydroandrostanes in man. I. Metabolism of 17 -hydroxyandrosta-1,4-dien-3-one, 17 -cyclopent-1'-enyloxyandrosta-1,4-dien-3-one (quinbolone) and androsta-1,4-diene-3,17-dione (1)". Steroids. 18 (1): 39–50. doi:10.1016/s0039-128x(71)80169-1. PMID 5098537.
  2. ^ a b c d Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1056–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 904–. ISBN 978-3-88763-075-1.
  4. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 243–. ISBN 978-94-011-4439-1.
  5. ^ a b c Mullen C, Whalley BJ, Schifano F, Baker JS (May 2020). "Anabolic androgenic steroid abuse in the United Kingdom: An update". British Journal of Pharmacology. 177 (10): 2180–2198. doi:10.1111/bph.14995. PMC 7174889. PMID 31989581.
  6. ^ a b Finkelstein M, Klopper A, Conti C (22 October 2013). Research on Steroids: Proceedings of the Fourth Meeting of the International Study Group for Steroid Hormones. Elsevier Science. pp. 121–. ISBN 978-1-4831-5403-9.
  7. ^ a b Ercoli A, Gardi R, Vitali R (1962). "Steroid-17β-yl acetals and enol ethers. New classes of orally and parenterally active hormonal derivatives". Chemistry & Industry. 28: 1284–1285.
Androgens

and

antiandrogens Androgens
(incl. AASTooltip anabolic–androgenic steroid) ARTooltip Androgen receptor agonists Progonadotropins Antiandrogens ARTooltip Androgen receptor antagonists Steroidogenesis
inhibitors 5α-Reductase Others Antigonadotropins Others
See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids
Androgen receptor modulators ARTooltip Androgen receptor Agonists SARMsTooltip Selective androgen receptor modulator Antagonists GPRC6A Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
Estrogen receptor modulators ERTooltip Estrogen receptor Agonists Mixed
(SERMsTooltip Selective estrogen receptor modulators) Antagonists GPERTooltip G protein-coupled estrogen receptor Agonists Antagonists Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens

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