Quinbolone

Quinbolone
Clinical data
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	X;
Routes of; administration	By mouth
ATC code	A14AA06 (WHO) ;
Legal status
Legal status	CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Metabolism	Liver
Excretion	Urine
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-(1-Cyclopentenyloxy)-10,13-dimethyl- 6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	2487-63-0 ;
PubChem CID	10360683;
ChemSpider	8536132 ;
UNII	W59598KWLX;
KEGG	D05674 ;
CompTox Dashboard (EPA)	DTXSID20179580 ;
Chemical and physical data
Formula	C24H32O2
Molar mass	352.518 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\1\C=C/[C@]5(/C(=C/1)CC[C@@H]3[C@@H]5CC[C@@]4([C@@H](O/C2=C/CCC2)CC[C@@H]34)C)C;
	InChI InChI=1S/C24H32O2/c1-23-13-11-17(25)15-16(23)7-8-19-20-9-10-22(26-18-5-3-4-6-18)24(20,2)14-12-21(19)23/h5,11,13,15,19-22H,3-4,6-10,12,14H2,1-2H3/t19-,20-,21-,22-,23-,24-/m0/s1 ; Key:IUVKMZGDUIUOCP-BTNSXGMBSA-N ;
	(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]

Pharmacology

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]

Side effects

Chemistry

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]

Synthesis

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]

History

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

References

^ ^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.
^ ^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.
^ ^a ^b ^c ^d ^e ^f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 904–. ISBN 978-3-88763-075-1.
^ 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.
^ ^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.
^ ^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.
^ ^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.

[pmid5098537-1] 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.

[Elks2014-2] 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.

[IndexNominum2000-3] ^ ^a ^b ^c ^d ^e ^f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 904–. ISBN 978-3-88763-075-1.

[MortonHall2012-4] 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.

[Mullen_2020-5] 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.

[FinkelsteinKlopper2013-6] 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.

[Ercoli1962-7] 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.

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