Flugestone acetate

Flugestone acetate

Clinical data
Trade names	Cronolone, others
Other names	Flurogestone acetate; Fluorogestone acetate; FGA; NSC-65411; SC-9880; 17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone
Routes of administration	Intravaginal
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
IUPAC name [(8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11-hydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number	2529-45-5
PubChem CID	10476437
ChemSpider	8651847
UNII	X60881643X
KEGG	D04235
ChEMBL	ChEMBL2106773
CompTox Dashboard (EPA)	DTXSID6046210
ECHA InfoCard	100.017.979
Chemical and physical data
Formula	C23H31FO5
Molar mass	406.494 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)O[C@@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(C)=O
InChI InChI=1S/C23H31FO5/c1-13(25)22(29-14(2)26)10-8-17-18-6-5-15-11-16(27)7-9-20(15,3)23(18,24)19(28)12-21(17,22)4/h11,17-19,28H,5-10,12H2,1-4H3/t17-,18-,19-,20-,21-,22-,23-/m0/s1 Key:JKQQZJHNUVDHKP-FQJIPJFPSA-N

Flugestone acetate (FGA), sold under the brand name Cronolone among others, is a progestin medication which is used in veterinary medicine.^{[1][2][3][4][5][6]}

Uses

Veterinary

FGA is used as an intravaginal sponge preparation to synchronize estrus in ewes and goats.^[2][4][5][6]

Chemistry

See also: List of progestogens, Progestogen ester, and List of progestogen esters

FGA, also known as 17α-acetoxy-9α-fluoro-11β-hydroxyprogesterone or as 17α-acetoxy-9α-fluoro-11β-hydroxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.^[1][3] It is the C17α acetate ester of flugestone.^[1][3][2]

History

FGA was developed and marketed by G.D. Searle & Company in the 1960s.^[7][8]

Society and culture

Generic names

Flugestone acetate is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANMTooltip British Approved Name, while flurogestone acetate is its USANTooltip United States Adopted Name.^[1][3][2][9] Flugestone is the BANTooltip British Approved Name and DCITTooltip Denominazione Comune Italiana of the unesterified free alcohol form.^[1][3][2][9] FGA is also known by its developmental code names NSC-65411 and SC-9880.^[1][3][2][9]

Brand names

FGA is or has been marketed under the brand names Chronogest, Chrono-Gest, Crono-Gest, Cronolone, Gyncro-Mate, Ova-Gest, Ovakron, Synchro-Mate, Syncro Part, and Syncropart.^[1][3][2][9]

Availability

FGA is marketed for veterinary use in Australia, France, Ireland, Israel, Italy, the Netherlands, South Africa, and the United Kingdom.^[3][9]

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 559. ISBN 978-1-4757-2085-3.
2. Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 122–. ISBN 978-0-7514-0499-9.
3. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 451–. ISBN 978-3-88763-075-1.
4. Office of the Federal Register (US) (29 May 2012). Code of Federal Regulations Title 21: Food and Drug Administration: Parts 500-599, Revised April 1, 2012. Government Printing Office. pp. 359–. ISBN 978-0-16-090718-0.
5. Youngquist RS, Threlfall WR (23 November 2006). Current Therapy in Large Animal Theriogenology. Elsevier Health Sciences. pp. 2640–. ISBN 1-4377-1340-8.
6. Studdert VP, Gay CC, Blood DC (9 December 2011). Saunders Comprehensive Veterinary Dictionary. Elsevier Health Sciences. pp. 2673–. ISBN 978-0-7020-4744-2.
7. Animal Husbandry Research: Reports on Agricultural Industry. 1967. p. 60.
8. Dairy Science Handbook. Agriservices Foundation. 1971. p. 10.
9. "Flugestone". Drugs.com.