Proligestone

Proligestone
Clinical data
Trade names	Covinan, Delvosteron
Other names	14α,17α-Propylidenedioxyprogesterone; 14α,17α-Dihydroxyprogesterone cyclic acetal with propionaldehyde; 14α,17α-Dihydroxypregn-4-ene-3,20-dione cyclic acetal with propionaldehyde
Drug class	Progestogen; Progestin
ATC code	G03DA90 (WHO) ;
Identifiers
	IUPAC name 14α,17α-(propylidenebis(oxy))pregn-4-ene-3,20-dione;
CAS Number	23873-85-0;
PubChem CID	71906;
ChemSpider	64917;
UNII	55772LJ01V;
KEGG	D08429;
ChEMBL	ChEMBL2106696;
CompTox Dashboard (EPA)	DTXSID501016687 ;
ECHA InfoCard	100.041.733
Chemical and physical data
Formula	C24H34O4
Molar mass	386.532 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC1O[C@@]23CC[C@]([C@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C)(O1)C(=O)C;
	InChI InChI=1S/C24H34O4/c1-5-20-27-23(15(2)25)12-13-24(28-20)19-7-6-16-14-17(26)8-10-21(16,3)18(19)9-11-22(23,24)4/h14,18-20H,5-13H2,1-4H3/t18-,19+,20?,21-,22+,23-,24+/m0/s1; Key:MQSDUYIXZDSLSZ-QSDCUGRSSA-N;

Proligestone, sold under the brand names Covinan and Delvosteron, is a progestin medication which is used in veterinary medicine.^[1]^[2]^[3]

Uses

Veterinary

Proligestone is used to control estrus in dogs and cats and has also been used to treat hypersexuality in dogs and cats.^[4]

Pharmacology

Pharmacodynamics

Proligestone is a progestogen, or an agonist of the progesterone receptor (PR).

Chemistry

Proligestone, also known as 14α,17α-propylidenedioxyprogesterone or as 14α,17α-dihydroxyprogesterone cyclic acetal with propionaldehyde, as well as 14α,17α-propylidenedioxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.^[1]^[2] It is a C14α,17α cyclic ketal of 14α,17α-dihydroxyprogesterone.^[5]^[6]^[7]

History

Proligestone was described as early as 1968 and was introduced for veterinary use in 1975.^[1]^[8]^[9]

Society and culture

Generic names

Proligestone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.^[1]^[2]^[3]

Brand names

Proligestone is marketed under the brand names Covinan and Delvosteron.^[1]^[2]^[3]

Availability

Proligestone is or has been available for veterinary use in Argentina, Australia, Austria, Belgium, Czechoslovakia, France, Germany, Ireland, Italy, the Netherlands, New Zealand, Poland, South Africa, Switzerland, and the United Kingdom.^[2]^[3]

References

^ ^a ^b ^c ^d ^e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1025–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c ^d ^e Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 882–. ISBN 978-3-88763-075-1.
^ ^a ^b ^c ^d "List of Progestins". Drugs.com.
^ Mundt S (22 April 1981). "Indications for proligestone (Delvosteron) in dogs and cats". Praktische Tierarzt. 62 (12).
^ Marler EE (1976). Pharmacological and Chemical Synonyms: A Collection of Names of Drugs, Pesticides and Other Compounds Drawn from the Medical Literature of the World. Excerpta Medica. p. 376. ISBN 978-90-219-0298-2.
^ Negwer M, Scharnow HG (4 October 2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2569. ISBN 978-3-527-30247-5.
^ "Proligestone". Medical Subject Headings: Supplementary chemical records. U.S. National Library of Medicine.
^ Official Gazette of the United States Patent and Trademark Office: Trademarks. U.S. Department of Commerce, Patent and Trademark Office. 1984. p. 30.
^ Vanos JL, Oldenkamp EP (September 1978). "Oestrus control in bitches with proligestone, a new progestational steroid". The Journal of Small Animal Practice. 19 (9): 521–529. doi:10.1111/j.1748-5827.1978.tb05534.x. PMID 567718.

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1025–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 882–. ISBN 978-3-88763-075-1.

[Drugs.com-3] "List of Progestins". Drugs.com.

[EurekaMag-4] Mundt S (22 April 1981). "Indications for proligestone (Delvosteron) in dogs and cats". Praktische Tierarzt. 62 (12).

[Marler1976-5] Marler EE (1976). Pharmacological and Chemical Synonyms: A Collection of Names of Drugs, Pesticides and Other Compounds Drawn from the Medical Literature of the World. Excerpta Medica. p. 376. ISBN 978-90-219-0298-2.

[NegwerScharnow2001-6] Negwer M, Scharnow HG (4 October 2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2569. ISBN 978-3-527-30247-5.

[MeSH_Proligestone-7] "Proligestone". Medical Subject Headings: Supplementary chemical records. U.S. National Library of Medicine.

[DOC1984-8] Official Gazette of the United States Patent and Trademark Office: Trademarks. U.S. Department of Commerce, Patent and Trademark Office. 1984. p. 30.

[pmid567718-9] Vanos JL, Oldenkamp EP (September 1978). "Oestrus control in bitches with proligestone, a new progestational steroid". The Journal of Small Animal Practice. 19 (9): 521–529. doi:10.1111/j.1748-5827.1978.tb05534.x. PMID 567718.

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