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Chemical Compound Review

Estrofan     (Z)-7-[(1R,2S,3R,5S)-2- [(E,3S)-4-(3...

Synonyms: Estrumat, Estrophan, Estrumate, Planate, Ciosin, ...
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Disease relevance of cloprostenol


High impact information on cloprostenol


Chemical compound and disease context of cloprostenol


Biological context of cloprostenol

  • However, doubling the cloprostenol dose (1.6 micrograms) caused a rapid decrease in mean urinary PdG (p < 0.05) within 2 days, and synchronous ovulation was demonstrated by an increase (p < 0.01) in mean urinary PdG 10 days after cloprostenol administration [14].
  • This study examines differences in intracellular responses to cloprostenol, a prostaglandin (PG)F(2alpha) analog, in porcine corpora lutea (CL) before (Day 9 of estrous cycle) and after (Day 17 of pseudopregnancy) acquisition of luteolytic capacity [15].
  • Sixty primiparous beef heifers from a crossbreeding study were used to examine the effects of inducing parturition with relaxin (3,000 U/mg) combined with cloprostenol (500 micrograms, i.m., n = 30) or dexamethasone (20 mg, i.m., n = 30) at Day 273, 10 +/- 1 days before expected parturition (Day 283) [1].
  • It is concluded that pregnancies on ewes carrying 1 embryo can be terminated by a single dose of 100 micrograms cloprostenol given around Day 21 of pregnancy, but 2 injections given about 7 days apart may be needed when multiple embryos are present [16].
  • 1 Human luteal tissue slices from days 18, 21 and 25 of the menstrual cycle were superfused in vitro with Medium 199 alone or containing cloprostenol (1 microgram/ml) [17].

Anatomical context of cloprostenol

  • Corpora lutea were surgically removed from beef heifers 0, 2, 7.5, or 30 min (n = 4 animals/time period) after cloprostenol injection [9].
  • 6. Unilateral treatment of one mammary gland in goats with the PGF 2 alpha analogue, Cloprostenol, at two dose levels from 2-3 days pre-partum to 1-2 days post-partum prevented the changes in milk [Na] that occur at term in untreated glands [18].
  • However, acute cloprostenol treatment (10 min) decreased progesterone production and increased PGF(2alpha) production only from Day 17 luteal cells [15].
  • Corpora lutea were also studied at 1, 3, 12, 24, and 48 hours after administration of a synthetic luteolytic substance (cloprostenol), and after temporary occlusion of the ovarian blood vessels for 15, 30, 60, or 120 minutes [19].
  • AL-8810 has weak agonist potency (EC(50)) of 261 +/- 44 nM (n = 3) and E(max) = 19% (relative to the full FP receptor agonist cloprostenol) in A7r5 cells and EC(50) of 186 +/- 63 nM (n = 3) and E(max) = 23% in 3T3 fibroblasts [20].

Associations of cloprostenol with other chemical compounds

  • However, PGD2 (EC50 = 155 +/- 29.9 nM; Emax = 49% of cloprostenol), PGE2 (EC50 = 2570 +/- 566 nM; Emax = 59%) and U46619 (EC50 = 1060 +/- 310 nM; Emax = 63%) were less potent and were partial agonists, and iloprost and BW245C were inactive [21].
  • In transient transfection assays, Cox-2 promoter was rapidly induced (4 h) by phorbol didecanoate (a protein kinase [PK] C activator), ionomycin, and cloprostenol (PGF(2 alpha) analogue), with a peak induction at 12 h [22].
  • Four groups of five mature Scottish Blackface ewes were injected with normal sheep plasma (control), antiserum to the 1-26 alpha peptide fragment of porcine inhibin, antiserum to oestradiol-17 beta, or a combination of the two antisera, 24 h following cloprostenol-induced luteal regression [23].
  • This was achieved by injection of 10 mg FSH-P in propylene glycol at the same time as luteolysis was induced by cloprostenol on day 13 of the oestrous cycle (day 0 = oestrus) [24].
  • This hypothesis has been tested by comparing the site and mode of action of PGF2 alpha, a PGF2 alpha analogue (cloprostenol) and the PKC activator phorbol myristate acetate (4 beta PMA) in human granulosa-lutein cells [25].

Gene context of cloprostenol

  • Elevated VEGF mRNA expression in response to cloprostenol treatment was also observed at early gestation (day 9) in the forming placenta (p = 0.04) and uterus (p = 0.03) [2].
  • Expression of the ET receptors, ETA and ETB was not affected by cloprostenol [26].
  • In cell culture, cloprostenol or phorbol 12, 13-didecanoate (PDD) (protein kinase C activator), induced PGHS-2 mRNA in luteal cells from both groups [15].
  • Levels of mRNA encoding IGFBP-2 increased significantly between mid-diestrus and early (P < 0.01) and late (P < 0.001) regression, and 36 h after cloprostenol administration (P < 0.001) [27].
  • As expected, ET-1 and ETA-R mRNA levels were markedly induced in midcycle CL exposed to luteolytic dose of PGF(2 alpha) analogue (Cloprostenol) [28].

Analytical, diagnostic and therapeutic context of cloprostenol

  • Pigs on Day 9 or Day 17 were treated with saline or 500 microgram cloprostenol, and CL were collected 10 h (experiment I) or 0.5 h (experiment III) after treatment [15].
  • At laparotomy, timed samples of ovarian blood were collected and ovaries were removed from 39 Scottish Blackface ewes (ovulation rate 1.3 +/- 0.1) on Day 10 of the luteal phase or 24, 48, 60, 72, or 84 h after injection of cloprostenol (PG; 100 micrograms) on Days 10-12 [29].
  • Cows in the midluteal phase (Days 8-12) were injected with the PGF(2alpha) analogue cloprostenol, and CL were collected by transvaginal ovariectomy before and 2, 4, 12, 48, and 64 h after PGF(2alpha) injection [30].
  • The aim of this study was to investigate real-time changes of these factors in luteal tissue of cows (n = 4-5 per group) in the mid-luteal phase (day 8-12) after intramuscular injection of the PGF2alpha-analog Cloprostenol [31].
  • Ovulation was induced in 18 heifers and 5 cows by injection of cloprostenol at days 8-14 (day 0 = day of ovulation), and follicular development was monitored by ultrasonography [32].


  1. Induction of parturition, progesterone secretion, and delivery of placenta in beef heifers given relaxin with cloprostenol or dexamethasone. Musah, A.I., Schwabe, C., Willham, R.L., Anderson, L.L. Biol. Reprod. (1987) [Pubmed]
  2. Cloprostenol, a prostaglandin F(2alpha) analog, induces hypoxia in rat placenta: BOLD contrast MRI. Girsh, E., Plaks, V., Gilad, A.A., Nevo, N., Schechtman, E., Neeman, M., Dekel, N. NMR in biomedicine (2007) [Pubmed]
  3. Treatment of chronic post partum endometritis in cattle with cloprostenol. Jackson, P.S. Vet. Rec. (1977) [Pubmed]
  4. Reproductive performance of dairy cows with ovarian cysts after different GnRH and cloprostenol treatments. López-Gatius, F., López-Béjar, M. Theriogenology (2002) [Pubmed]
  5. Study of combined injections of 1 alpha-hydroxy-cholecaldiferol and cloprostenol in the prevention of parturient paresis. Manston, R., Mallinson, C.B., Vagg, M.J., Sansom, B.F. Vet. Rec. (1981) [Pubmed]
  6. A prostaglandin f(2alpha) analog induces suppressors of cytokine signaling-3 expression in the corpus luteum of the pregnant rat: a potential new mechanism in luteolysis. Curlewis, J.D., Tam, S.P., Lau, P., Kusters, D.H., Barclay, J.L., Anderson, S.T., Waters, M.J. Endocrinology (2002) [Pubmed]
  7. Synthesis and biological activity of a novel 11a-homo (cyclohexyl) prostaglandin. Klimko, P.G., Davis, T.L., Griffin, B.W., Sharif, N.A. J. Med. Chem. (2000) [Pubmed]
  8. Distinct expression of gelatinase A [matrix metalloproteinase (MMP)-2], collagenase-3 (MMP-13), membrane type MMP 1 (MMP-14), and tissue inhibitor of MMPs type 1 mediated by physiological signals during formation and regression of the rat corpus luteum. Liu, K., Olofsson, J.I., Wahlberg, P., Ny, T. Endocrinology (1999) [Pubmed]
  9. Involvement of protein kinase-C, calpains, and calpastatin in prostaglandin F2 alpha-induced oxytocin secretion from the bovine corpus luteum. Orwig, K.E., Bertrand, J.E., Ou, B.R., Forsberg, N.E., Stormshak, F. Endocrinology (1994) [Pubmed]
  10. The effect of a single administration of cephapirin or cloprostenol on the reproductive performance of dairy cows with subclinical endometritis. Kasimanickam, R., Duffield, T.F., Foster, R.A., Gartley, C.J., Leslie, K.E., Walton, J.S., Johnson, W.H. Theriogenology (2005) [Pubmed]
  11. Morphology of canine placental sites after induced embryonic or fetal death. Steiger, K., Politt, E., Hoeftmann, T., Meyer-Lindenberg, A., Schoon, H.A., Günzel-Apel, A.R. Theriogenology (2006) [Pubmed]
  12. The effect of treatment of clinical endometritis on reproductive performance in dairy cows. LeBlanc, S.J., Duffield, T.F., Leslie, K.E., Bateman, K.G., Keefe, G.P., Walton, J.S., Johnson, W.H. J. Dairy Sci. (2002) [Pubmed]
  13. Reduced incidence of retained placenta with induction of parturition in the cow. Bo, G.A., Fernandez, M., Barth, A.D., Mapletoft, R.J. Theriogenology (1992) [Pubmed]
  14. Natural and induced ovarian synchrony in golden lion tamarins (Leontopithecus rosalia). Monfort, S.L., Bush, M., Wildt, D.E. Biol. Reprod. (1996) [Pubmed]
  15. Prostaglandin f(2alpha) induces distinct physiological responses in porcine corpora lutea after acquisition of luteolytic capacity. Diaz, F.J., Crenshaw, T.D., Wiltbank, M.C. Biol. Reprod. (2000) [Pubmed]
  16. Effect of embryos on luteolysis and termination of early pregnancy in sheep with cloprostenol. Nancarrow, C.D., Evison, B.M., Connell, P.J. Biol. Reprod. (1982) [Pubmed]
  17. The effect of cloprostenol on human luteal steroid and prostaglandin secretion in vitro. McDougall, A.N., Walker, F.M., Watson, J. Br. J. Pharmacol. (1977) [Pubmed]
  18. Local production of prostaglandins in relation to mammary function at the onset of lactation in the goat. Maule Walker, F.M., Peaker, M. J. Physiol. (Lond.) (1980) [Pubmed]
  19. Mechanism of deletion of endothelial cells during regression of the corpus luteum. Azmi, T.I., O'Shea, J.D. Lab. Invest. (1984) [Pubmed]
  20. AL-8810: a novel prostaglandin F2 alpha analog with selective antagonist effects at the prostaglandin F2 alpha (FP) receptor. Griffin, B.W., Klimko, P., Crider, J.Y., Sharif, N.A. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  21. FP prostaglandin receptors mediating inositol phosphates generation and calcium mobilization in Swiss 3T3 cells: a pharmacological study. Griffin, B.W., Williams, G.W., Crider, J.Y., Sharif, N.A. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  22. Transcriptional regulation of cyclooxygenase-2 gene in ovine large luteal cells. Wu, Y.L., Wiltbank, M.C. Biol. Reprod. (2001) [Pubmed]
  23. Effects of passively immunizing ewes against inhibin and oestradiol during the follicular phase of the oestrous cycle. Mann, G.E., Campbell, B.K., McNeilly, A.S., Baird, D.T. J. Endocrinol. (1990) [Pubmed]
  24. Modification by propylene glycol of ovulation rate in ewes in response to a single injection of FSH. Lopez-Sebastian, A., Gomez-Brunet, A., Lishman, A.W., Johnson, S.K., Inskeep, E.K. J. Reprod. Fertil. (1993) [Pubmed]
  25. Mode of action of prostaglandin F2 alpha in human luteinized granulosa cells: role of protein kinase C. Abayasekara, D.R., Michael, A.E., Webley, G.E., Flint, A.P. Mol. Cell. Endocrinol. (1993) [Pubmed]
  26. Involvement of endothelin-1 and its receptors in PGF2alpha-induced luteolysis in the rat. Girsh, E., Dekel, N. Mol. Reprod. Dev. (2002) [Pubmed]
  27. Expression of mRNA encoding insulin-like growth factor binding protein-2 (IGFBP-2) during induced and natural regression of equine corpora lutea. Watson, E.D., Bae, S.E., Al-Zi'abi, M.O., Hogg, C.O., Armstrong, D.G. Theriogenology (2005) [Pubmed]
  28. Administration of prostaglandin f(2 alpha) during the early bovine luteal phase does not alter the expression of ET-1 and of its type A receptor: a possible cause for corpus luteum refractoriness. Levy, N., Kobayashi, S., Roth, Z., Wolfenson, D., Miyamoto, A., Meidan, R. Biol. Reprod. (2000) [Pubmed]
  29. Expression of messenger ribonucleic acid for inhibin subunits and ovarian secretion of inhibin and estradiol at various stages of the sheep estrous cycle. Engelhardt, H., Smith, K.B., McNeilly, A.S., Baird, D.T. Biol. Reprod. (1993) [Pubmed]
  30. Involvement of pro-inflammatory cytokines, mediators of inflammation, and basic fibroblast growth factor in prostaglandin F2alpha-induced luteolysis in bovine corpus luteum. Neuvians, T.P., Schams, D., Berisha, B., Pfaffl, M.W. Biol. Reprod. (2004) [Pubmed]
  31. Vascular endothelial growth factor (VEGF) and fibroblast growth factor (FGF) expression during induced luteolysis in the bovine corpus luteum. Neuvians, T.P., Berisha, B., Schams, D. Mol. Reprod. Dev. (2004) [Pubmed]
  32. Oocyte morphology in dominant and subordinate follicles. Assey, R.J., Hyttel, P., Greve, T., Purwantara, B. Mol. Reprod. Dev. (1994) [Pubmed]
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