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(+)-Cloprostenol

Names

[ CAS No. ]:
54276-21-0

[ Name ]:
(+)-Cloprostenol

[Synonym ]:
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

Biological Activity

[Description]:

(+)-Cloprostenol is a prostaglandin F2α (PGF2α) analogue, and shows selective agonistic activity at the prostaglandin receptor.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor
Research Areas >> Others

[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.


[Related Small Molecules]

Dinoprostone | Prostaglandin E1 | E7046 | ONO-AE3-208 | PF 04418948 | Fevipiprant | grapiprant | TG6-10-1 | Taprenepag | GW 627368 | MRE-269 | Ramatroban | AH 6809 | Laropiprant | AZD1981

Chemical & Physical Properties

[ 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

Precursor & DownStream

Precursor

DownStream

Related Compounds