Cypionic acid

Cypionic acid
Names
	Preferred IUPAC name 3-Cyclopentylpropanoic acid
	Other names 3-Cyclopentylpropionic acid; 3-Cyclopentanepropionic acid; Cypionate; Cipionate
Identifiers
CAS Number	140-77-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	8487;
ECHA InfoCard	100.004.940
PubChem CID	8818;
UNII	931H8F0JEE ;
CompTox Dashboard (EPA)	DTXSID4059700 ;
	InChI InChI=1S/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10) Key: ZRPLANDPDWYOMZ-UHFFFAOYSA-N; InChI=1/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10) Key: ZRPLANDPDWYOMZ-UHFFFAOYAK;
	SMILES O=C(O)CCC1CCCC1;
Properties
Chemical formula	C8H14O2
Molar mass	142.198 g·mol−1
Appearance	Liquid
Density	0.996 g/mL
Melting point	12 °C (54 °F; 285 K)
Boiling point	130 to 133 @12mmHg
Hazards
Flash point	122 ± 9.8 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cypionic acid, also known as cyclopentylpropionic acid, is an aliphatic carboxylic acid with the molecular formula C₈H₁₄O₂. Its salts and esters are known as cypionates or cipionates.

The primary use of cypionic acid is in pharmaceutical formulations. Cypionic acid is used to prepare ester prodrugs which have increased half-lives relative to the parent compound. The lipophilicity of the cypionate group allows the prodrug to be sequestered in fat depots after intramuscular injection.^[2] The ester group is slowly hydrolyzed by metabolic enzymes, releasing steady doses of the active ingredient. Examples include testosterone cypionate, estradiol cypionate, hydrocortisone cypionate, oxabolone cipionate, and mesterolone cypionate.

References

^ 3-Cyclopentylpropionic acid at Sigma-Aldrich
^ VJ. Stella, W.N A. Charman and V.H. Naringrekar (1985). "Prodrugs: Do They Have Advantages in Clinical Practice?". Drugs. 29 (5): 455–473. doi:10.2165/00003495-198529050-00002. PMID 3891303.

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[Aldrich-1] 3-Cyclopentylpropionic acid at Sigma-Aldrich

[2] VJ. Stella, W.N A. Charman and V.H. Naringrekar (1985). "Prodrugs: Do They Have Advantages in Clinical Practice?". Drugs. 29 (5): 455–473. doi:10.2165/00003495-198529050-00002. PMID 3891303.

[1]

[2]