Cypionic acid, also known as cyclopentylpropionic acid, is an

aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

with the molecular formula C₈H₁₄O₂. Its

salts In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions ( cations) and negatively charged ions (anions), which results in a compound with no net electric charge (electrically neutral). ...

and

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s are known as cypionates or cipionates. The primary use of cypionic acid is in

pharmaceutical formulation Pharmaceutical formulation, in pharmaceutics, is the process in which different chemical substances, including the active drug, are combined to produce a final medicinal product. The word ''formulation'' is often used in a way that includes dos ...

s. Cypionic acid is used to prepare ester

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

s which have increased

half-lives Half-life is a mathematical and scientific description of exponential or gradual decay. Half-life, half life or halflife may also refer to: Film * ''Half-Life'' (film), a 2008 independent film by Jennifer Phang * '' Half Life: A Parable for t ...

relative to the parent compound. The

lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are called lipophilic (translated ...

of the cypionate group allows the prodrug to be sequestered in fat depots after intramuscular injection. The ester group is slowly

hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...

by metabolic enzymes, releasing steady doses of the active ingredient. Examples include

testosterone cypionate Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men, including hormone therapy for transg ...

estradiol cypionate Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in horm ...

hydrocortisone cypionate Hydrocortisone cypionate, sold under the brand name Cortef, is a synthetic glucocorticoid corticosteroid and a corticosteroid ester Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well ...

oxabolone cipionate Oxabolone cipionate (, ) (brand names Steranabol Depo, Steranabol Ritardo; former developmental code name FI-5852), or oxabolone cypionate, also known as 4-hydroxy-19-nortestosterone 17β-cypionate or estr-4-en-4,17β-diol-3-one 17β-cypionate, i ...

, and

mesterolone cypionate Mesterolone cipionate is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the C17β cypionate ester of mesterolone – which was never marketed. It is administered via intramuscular injection once every two weeks ...

References

Carboxylic acids Cyclopentyl compounds {{alkanederivative-stub