Cloprostenol: Difference between revisions

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{{Short description|Chemical compound}}
{{unreferenced|date=December 2016}}

{{Drugbox
{{Drugbox
| IUPAC_name = (5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoic acid
| IUPAC_name = (5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoic acid
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<!-- Identifiers -->
<!-- Identifiers -->
| CAS_number = 40665-92-7
| CAS_number = 40665-92-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4208238832
| ATCvet = yes
| ATC_prefix = G02
| ATC_suffix = AD90
| PubChem = 5311053
| PubChem = 5311053
| ChemSpiderID = 4470590
| ChemSpiderID = 4470590
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}}
}}


'''Cloprostenol''' is a synthetic analogue of [[Prostaglandin F2alpha|prostaglandin F<sub>2α</sub>]] (PGF<sub>2α</sub>).<ref name="Cooper 1981"/> It is a potent luteolytic agent; this means that, within hours of administration, it causes the [[corpus luteum]] to stop production of [[progesterone]], and to reduce in size over several days.<ref name="Cooper 1981">{{cite journal | vauthors = Cooper M | title = Prostaglandins in veterinary practice | journal = In Practice | volume = 3 | issue = 1 | pages = 30, 32-4 | date = January 1981 | pmid = 7346485 | doi = 10.1136/inpract.3.1.30 | s2cid = 6197103 }}</ref> This effect is used in animals to induce [[estrus]] and to cause abortion.<ref name="Plumb 2015">{{cite book| vauthors = Plumb DC |title=Plumb's Veterinary Drug Handbook|date=2015|publisher=Wiley|isbn=9781118911938|edition=8th|chapter=Cloprostenol Sodium}}</ref>
'''Cloprostenol''' is a synthetic prostaglandin analogue structurally related to prostaglandin F2-α (PGF2 α). It causes functional and morphological regression of the corpus luteum (luteolysis) in cattle.


==Uses==
== References ==
{{Reflist}}


[[Category:Veterinary drugs]]
[[Category:Cyclopentanes]]


{{Veterinary-med-stub}}
{{Veterinary-med-stub}}
[[Category:Veterinary medicine]]

Latest revision as of 12:24, 29 January 2023

Cloprostenol
Clinical data
Trade namesCyclomate, Estrumate
Routes of
administration
Intramuscular
ATCvet code
Pharmacokinetic data
Excretion67% renal, 25% fecal
Identifiers
  • (5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.050.009 Edit this at Wikidata
Chemical and physical data
FormulaC22H29ClO6
Molar mass424.915
3D model (JSmol)
  • c1cc(cc(c1)Cl)OC[C@@H](/C=C/[C@H]2[C@@H](C[C@@H]([C@@H]2C/C=C\CCCC(=O)O)O)O)O
  • InChI=1S/C22H29ClO6/c23-15-6-5-7-17(12-15)29-14-16(24)10-11-19-18(20(25)13-21(19)26)8-3-1-2-4-9-22(27)28/h1,3,5-7,10-12,16,18-21,24-26H,2,4,8-9,13-14H2,(H,27,28)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
  • Key:VJGGHXVGBSZVMZ-QIZQQNKQSA-N

Cloprostenol is a synthetic analogue of prostaglandin F (PGF).[1] It is a potent luteolytic agent; this means that, within hours of administration, it causes the corpus luteum to stop production of progesterone, and to reduce in size over several days.[1] This effect is used in animals to induce estrus and to cause abortion.[2]

References[edit]

  1. ^ a b Cooper M (January 1981). "Prostaglandins in veterinary practice". In Practice. 3 (1): 30, 32–4. doi:10.1136/inpract.3.1.30. PMID 7346485. S2CID 6197103.
  2. ^ Plumb DC (2015). "Cloprostenol Sodium". Plumb's Veterinary Drug Handbook (8th ed.). Wiley. ISBN 9781118911938.