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, like hexane, or ...

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

with the molecular formula C₈H₁₄O₂. Its

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

and

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

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 dosage ...

s. Cypionic acid is used to prepare ester

prodrug A prodrug is a 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 used to improve how the drug ...

s which have increased

half-lives Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable at ...

relative to the parent compound. The

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

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 hydrolysis ...

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. It is also used in hormone therapy fo ...

estradiol cypionate Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen (medication), estrogen medication which is used in Hormone replacement therapy, hormone therapy for menopausal symptoms and hypoestrogenism, low estrog ...

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 wel ...

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, is ...

, 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.Herrmann, W. M., Horowski, R., Itil, T. M., Kehr, W., Palenschat, D ...

References

{{Organic-compound-stub Carboxylic acids Cyclopentyl compounds