54276-21-0

54276-21-0 structure
54276-21-0 structure
  • Name: (+)-Cloprostenol
  • Chemical Name: (+)-Cloprostenol
  • CAS Number: 54276-21-0
  • Molecular Formula: C22H29ClO6
  • Molecular Weight: 424.915
  • Catalog: Signaling Pathways GPCR/G Protein Prostaglandin Receptor
  • Create Date: 2018-08-14 15:59:11
  • Modify Date: 2025-08-24 02:59:51
  • (+)-Cloprostenol is a prostaglandin F2α (PGF2α) analogue, and shows selective agonistic activity at the prostaglandin receptor.

Name (+)-Cloprostenol
Synonyms 5-Heptenoic acid, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, (5Z)-rel-
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)-, monosodium salt, (5Z)-rel-
(±)-Sodium (Z)-7-((1R*,2R*,3R*,5S*)-2-((E)-(3R*)-4-(m-Chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoate
Cloprostenol
Oestrophan
Sodium (5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoate
(Z)-7-[(1S,2S,3S,5R)-2-[(E,3S)-4-(3-chloranylphenoxy)-3-oxidanyl-but-1-enyl]-3,5-bis(oxidanyl)cyclopentyl]hept-5-enoic acid
Dalmazin [veterinary] (TN)
Racemic cloprostenol
Estrophan
(Z)-7-(2-((E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid
(5Z)-rel-7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoic Acid Monosodium Salt
(5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic Acid
Sodium (5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate
Cloprostenol Sodium
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, sodium salt, (5Z)- (1:1)
(5Z)-7-{(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoic acid
Estrofan
UNII:4208238832
Cloprostenol (INN)
UNII:886SAV9675
(Z)-7-[(1S,2S,3S,5R)-2-[(E,3S)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid
Description (+)-Cloprostenol is a prostaglandin F2α (PGF2α) analogue, and shows selective agonistic activity at the prostaglandin receptor.
Related Catalog
Target

PGF2α

In Vitro D-Cloprostenol and PGF2 alpha are equipotent, about 150 times more potent than dl-cloprostenol (P < 0.05) and approximately 280 times more potent than PGE1 in inhibiting [3H]PGF2 alpha binding to corpus luteum cell membranes. However, d-cloprostenol and PGF2 alpha are about 10 times more potent than dl-cloprostenol and approximately 95 times more potent than PGE1 in myometrial cell membranes[2].
In Vivo D-cloprostenol (15 g per head) is the lowest dose that consistently achieves abortion; D-cloprostenol causes mild adverse effects including salivation, defecation and hyperventilation in bitches weighing less than 10 kg. Intra-vesicle administration of a single low dose of d-cloprostenol is a safe and successful technique to induce abortion in the bitch[1].
References

[1]. Manca R, et al. Intra-vesicle administration of D-cloprostenol for induction of abortion in mid-gestation bitches. Anim Reprod Sci. 2008 Jun;106(1-2):133-42. Epub 2007 Apr 21.

[2]. Re G, et al. Specific binding of dl-cloprostenol and d-cloprostenol to PGF2 alpha receptors in bovine corpus luteum and myometrial cell membranes. J Vet Pharmacol Ther. 1994 Dec;17(6):455-8.

Density 1.3±0.1 g/cm3
Boiling Point 628.0±55.0 °C at 760 mmHg
Molecular Formula C22H29ClO6
Molecular Weight 424.915
Flash Point 333.6±31.5 °C
Exact Mass 424.165253
PSA 110.05000
LogP 2.31
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.623
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