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CAS 54276-21-0

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(+)-Cloprostenol

Description:
(+)-Cloprostenol is a synthetic prostaglandin analog, specifically a potent agonist of the prostaglandin F2α receptor. It is primarily used in veterinary medicine for its ability to induce luteolysis, thereby facilitating estrus synchronization and abortion in livestock. The compound is characterized by its stereochemistry, which is crucial for its biological activity, as the (+) enantiomer exhibits significant potency compared to its counterparts. (+)-Cloprostenol is typically administered via injection and is known for its rapid onset of action. In terms of chemical properties, it is a white to off-white crystalline powder, soluble in organic solvents but less so in water. Its mechanism of action involves the contraction of smooth muscle, particularly in the uterus, and it can also influence other physiological processes such as the regulation of blood pressure and bronchoconstriction. Safety and handling precautions are essential due to its biological activity, and it is classified under controlled substances in some regions due to its potential effects on reproductive processes.
Formula:C22H29ClO6
InChI: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
InChI key:InChIKey=VJGGHXVGBSZVMZ-QIZQQNKQSA-N
SMILES:C(/C=C\CCCC(O)=O)[C@@H]1[C@@H](/C=C/[C@H](COC2=CC(Cl)=CC=C2)O)[C@H](O)C[C@@H]1O
Synonyms:
  • (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid
  • 16-(m-Chlorophenoxy)-17,18,19,20-tetranorprostaglandin F<sub>2α</sub>
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, (5Z)-
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, (5Z)-
  • 5-Heptenoic acid, 7-[2-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, [1R-[1α(Z),2β(1E,3R*),3α,5α]]-
  • <span class="text-smallcaps">D</span>-cloprostenol
  • D-Cloprostenol
  • Dalmaprost D
  • Dalmazin
  • Prolise
  • See more synonyms
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