Quinbolone (, ), sold under the brand names Anabolicum and Anabolvis, is an

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...

and anabolic steroid (AAS) which was previously marketed in

Italy Italy ( it, Italia ), officially the Italian Republic, ) or the Republic of Italy, is a country in Southern Europe. It is located in the middle of the Mediterranean Sea, and its territory largely coincides with the homonymous geographical ...

. It was developed by

Parke-Davis Parke-Davis is a subsidiary of the pharmaceutical company Pfizer. Although Parke, Davis & Co. is no longer an independent corporation, it was once America's oldest and largest drug maker, and played an important role in medical history. In 1970 ...

as a viable orally-administered AAS with little or no liver toxicity.

Pharmacology

Most orally administered anabolic steroids function by having an alkylated 17α-

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

atom, which prevents first-pass metabolism by the liver. This approach however results in the AAS having

hepatotoxicity Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn fr ...

. Quinbolone is not 17α-alkylated; instead it has increased oral

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. Ho ...

due to its cyclopentenyl ether group. After ingestion, the inactive quinbolone is transformed into

boldenone Boldenone (developmental code name RU-18761), is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)- dehydrogenated analogue of testosterone. Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as ...

. 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. 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. Its illicit usage in

bodybuilding Bodybuilding is the use of progressive resistance exercise to control and develop one's muscles (muscle building) by muscle hypertrophy for aesthetic purposes. It is distinct from similar activities such as powerlifting because it focuses ...

and

athletics Athletics may refer to: Sports * Sport of athletics, a collection of sporting events that involve competitive running, jumping, throwing, and walking ** Track and field, a sub-category of the above sport * Athletics (physical culture), competi ...

likewise proved limited, though

drug tests A drug test is a technical analysis of a biological specimen, for example urine, hair, blood, breath, sweat, or oral fluid/saliva—to determine the presence or absence of specified parent drugs or their metabolites. Major applications of drug ...

are still used to detect its metabolites as it remains a banned substance for most competitive sports. Quinbolone, via boldenone, can be transformed into

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...

s, and hence may have some

ic activity.

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 Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology ...

steroid and a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...

. It is the C17β

cyclopentyl Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occu ...

enol ether In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers includ ...

(δ¹-testosterone). A related AAS is

boldenone undecylenate Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used i ...

(δ¹-testosterone 17β-undec-10-enoate).

Synthesis

Quinbolone can be prepared from

. Dehydrogenation using DDQ forms

. Reaction with 1,1-dimethoxycyclopentane followed by heating to eliminate methanol gives quinbolone. Quinbolone synthesis

History

Quinbolone was described as early as 1962.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. https://scholar.google.com/scholar?cluster=7055026650056976887 It was marketed in

References

{{Estrogen receptor modulators Abandoned drugs Androgen ethers Androgens and anabolic steroids Androstanes Cyclopentyl ethers Dienes Ketones Prodrugs Synthetic estrogens World Anti-Doping Agency prohibited substances