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MedKoo Cat#: 326673 | Name: Isopropyl cloprostenate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isopropyl cloprostenate also known as (+)-Cloprostenol isopropyl ester, is a PGF2α agonist and a synthetic analog of prostaglandin F2α (PGF2α). (+)-Cloprostenol reliably induces luteolysis in luteal phase mares without evoking clinical side effects or a stress response. Note: pure (+)-Cloprostenol isopropyl ester is an oily material.

Chemical Structure

Isopropyl cloprostenate
Isopropyl cloprostenate
CAS#157283-66-4

Theoretical Analysis

MedKoo Cat#: 326673

Name: Isopropyl cloprostenate

CAS#: 157283-66-4

Chemical Formula: C25H35ClO6

Exact Mass: 466.2122

Molecular Weight: 467.00

Elemental Analysis: C, 64.30; H, 7.55; Cl, 7.59; O, 20.56

Price and Availability

Size Price Availability Quantity
100mg USD 950.00 2 Weeks
200mg USD 1,650.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 4,650.00 2 Weeks
2g USD 8,650.00 2 Weeks
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Related CAS #
No Data
Synonym
(+)-16-m-chlorophenoxy tetranor Prostaglandin F2α isopropyl ester; (+)-Cloprostenol isopropyl ester; Isopropyl cloprostenate
IUPAC/Chemical Name
isopropyl (Z)-7-((1R,2R,3R,5S)-2-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
InChi Key
OCNSAYQJDKJOLH-AHTXBMBWSA-N
InChi Code
InChI=1S/C25H35ClO6/c1-17(2)32-25(30)11-6-4-3-5-10-21-22(24(29)15-23(21)28)13-12-19(27)16-31-20-9-7-8-18(26)14-20/h3,5,7-9,12-14,17,19,21-24,27-29H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
SMILES Code
CC(C)OC(CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)COC2=CC=CC(Cl)=C2)[C@H](O)C[C@@H]1O)=O
Appearance
Oily liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cloprostenol isopropyl ester is a FP receptor agonist with a Ki value of 28 nM.
In vitro activity:
The present study investigated the effect of FP receptor agonists cloprostenol and fluprostenol on the differentiation of newborn rat adipocyte precursors in primary culture. The results show that cloprostenol and fluprostenol are very potent inhibitors of adipose differentiation. Reference: Biochem Biophys Res Commun. 1997 Apr 7;233(1):200-2. https://pubmed.ncbi.nlm.nih.gov/9144422/
In vivo activity:
The prostanoid analogs this study used, Cloprostenol and CIPG isopropyl ester, have similar actions on male gonad in mice. These analogs induced significant changes in the evolution of the spermatogenesis and spermiogenesis. Reference: Rom J Morphol Embryol. 2015;56(2 Suppl):771-5. https://pubmed.ncbi.nlm.nih.gov/26429171/
Solvent mg/mL mM
Solubility
DMF 100.0 214.13
DMSO 100.0 214.13
Ethanol 100.0 214.13
PBS (pH 7.2) 10.0 21.41
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 467.00 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Serrero G, Lepak NM. Prostaglandin F2alpha receptor (FP receptor) agonists are potent adipose differentiation inhibitors for primary culture of adipocyte precursors in defined medium. Biochem Biophys Res Commun. 1997 Apr 7;233(1):200-2. doi: 10.1006/bbrc.1997.6433. PMID: 9144422. 2. Sava A, Motoc AG, Stan CI. Electron microscopic aspects of the effects of certain prostaglandin analogs on mouse testes. Rom J Morphol Embryol. 2015;56(2 Suppl):771-5. PMID: 26429171.
In vitro protocol:
1. Serrero G, Lepak NM. Prostaglandin F2alpha receptor (FP receptor) agonists are potent adipose differentiation inhibitors for primary culture of adipocyte precursors in defined medium. Biochem Biophys Res Commun. 1997 Apr 7;233(1):200-2. doi: 10.1006/bbrc.1997.6433. PMID: 9144422.
In vivo protocol:
1. Sava A, Motoc AG, Stan CI. Electron microscopic aspects of the effects of certain prostaglandin analogs on mouse testes. Rom J Morphol Embryol. 2015;56(2 Suppl):771-5. PMID: 26429171.
1: Taktaz T, Kafi M, Mokhtari A, Heidari M. Reproductive responses of dairy cows with ovarian cysts to simultaneous human chorionic gonadotropin or gonadotropin-releasing hormone and cloprostenol compared to gonadotropin-releasing hormone alone treatment. Vet World. 2015 May;8(5):640-4. doi: 10.14202/vetworld.2015.640-644. Epub 2015 May 22. PubMed PMID: 27047149; PubMed Central PMCID: PMC4774727. 2: Kuhl J, Nagel C, Ille N, Aurich JE, Aurich C. The PGF2α agonists luprostiol and d-cloprostenol reliably induce luteolysis in luteal phase mares without evoking clinical side effects or a stress response. Anim Reprod Sci. 2016 May;168:92-9. doi: 10.1016/j.anireprosci.2016.02.031. Epub 2016 Mar 2. PubMed PMID: 26963045. 3: Wei S, Gong Z, An L, Zhang T, Dai H, Chen S. Cloprostenol and pregnant mare serum gonadotropin promote estrus synchronization, uterine development, and follicle-stimulating hormone receptor expression in mice. Genet Mol Res. 2015 Jun 29;14(2):7184-95. doi: 10.4238/2015.June.29.12. PubMed PMID: 26125929. 4: Chen Y, Yan H, Chen HX, Weng J, Lu G. An Improved and Efficient Process for the Preparation of (+)-cloprostenol. Chirality. 2015 Jun;27(6):392-6. doi: 10.1002/chir.22457. Epub 2015 May 12. PubMed PMID: 25965955. 5: Trevisol E, Ferreira JC, Ackermann CL, Destro FC, Marques Filho WC, Carmagos AS, Biehl MV, do Amaral JB, de Figueiredo Pantoja JC, Sartori R, Ferreira JC. Luteal changes after treatment with sub-luteolytic doses of prostaglandin (cloprostenol sodium) in cattle. Anim Reprod Sci. 2015 Feb;153:8-12. doi: 10.1016/j.anireprosci.2014.12.005. Epub 2014 Dec 26. PubMed PMID: 25578505. 6: de Moraes CN, Maia L, de Lima PF, Dias MC, Raposo-Ferreira TM, Sudano MJ, Junior JB, Oba E. Temporal analysis of prostaglandin F2α receptor, caspase 3, and cyclooxygenase 2 messenger RNA expression and prostaglandin F2α receptor and cyclooxygenase 2 protein expression in endometrial tissue from multiparous Nelore (Bos taurus indicus) cows treated with cloprostenol sodium during puerperium. Theriogenology. 2015 Jan 15;83(2):276-84. doi: 10.1016/j.theriogenology.2014.09.022. Epub 2014 Sep 23. PubMed PMID: 25442016. 7: Pérez-Marín CC, Sánchez JM, Vizuete G, Quintela LA, Molina L. Oestrus synchronisation in postpartum dairy cows using repetitive prostaglandin doses: Comparison between D-cloprostenol and dinoprost. Acta Vet Hung. 2015 Mar;63(1):79-88. doi: 10.1556/AVet.2014.028. PubMed PMID: 25374258. 8: Alavez Ramírez A, Arroyo Ledezma J, Montes Pérez R, Zamora Bustillos R, Navarrete Sierra LF, Magaña Sevilla H. Short communication: estrus synchronization using progestogens or cloprostenol in tropical hair sheep. Trop Anim Health Prod. 2014 Dec;46(8):1515-8. doi: 10.1007/s11250-014-0660-z. Epub 2014 Sep 4. PubMed PMID: 25187025. 9: Kaya D, Küçükaslan I, Ağaoğlu AR, Ay SS, Schäfer-Somi S, Emre B, Bal Y, Einspanier A, Gürcan IS, Gültiken N, Aslan S. The effects of aglepristone alone and in combination with cloprostenol on hormonal values during termination of mid-term pregnancy in bitches. Anim Reprod Sci. 2014 May;146(3-4):210-7. doi: 10.1016/j.anireprosci.2014.03.002. Epub 2014 Mar 22. PubMed PMID: 24703776. 10: Hatvani C, Balogh OG, Endrődi T, Abonyi-Tóth Z, Holló I, Kastelic JP, Gábor G. Estrus response and fertility after a single cloprostenol treatment in dairy cows with various ovarian structures. Can J Vet Res. 2013 Jul;77(3):218-20. PubMed PMID: 24101799; PubMed Central PMCID: PMC3700448. 11: García Mitacek MC, Stornelli MC, Tittarelli CM, Nuñez Favre R, de la Sota RL, Stornelli MA. Cloprostenol treatment of feline open-cervix pyometra. J Feline Med Surg. 2014 Feb;16(2):177-9. doi: 10.1177/1098612X13498248. Epub 2013 Jul 24. PubMed PMID: 23884637. 12: El-Sherry TM, Senosy W, Mahmoud GB, Wasfy SI. Effect of dinoprost and cloprostenol on serum nitric oxide and corpus luteum blood flow during luteolysis in ewes. Theriogenology. 2013 Sep 15;80(5):513-8. doi: 10.1016/j.theriogenology.2013.05.007. Epub 2013 Jun 10. PubMed PMID: 23764011. 13: Valldecabres-Torres X, Larrosa-Morales P, Cuervo-Arango J. The effect of dose and type of cloprostenol on the luteolytic response of dairy cattle during the Ovsynch protocol under different oestrous cycle and physiological characteristics. Reprod Domest Anim. 2013 Oct;48(5):874-80. doi: 10.1111/rda.12178. Epub 2013 May 21. PubMed PMID: 23691976. 14: Kumaresan A, Chand S, Suresh S, Mohanty TK, Prasad S, Layek SS, Behera K. Effect of estradiol and cloprostenol combination therapy on expulsion of mummified fetus and subsequent fertility in four crossbred cows. Vet Res Forum. 2013 Spring;4(2):85-9. PubMed PMID: 25653777; PubMed Central PMCID: PMC4313007. 15: García Mitacek MC, Stornelli MC, Praderio R, Stornelli MA, de la Sota RL. Efficacy of cloprostenol or aglepristone at 21-22 and 35-38 days of gestation for pregnancy termination in queens. Reprod Domest Anim. 2012 Dec;47 Suppl 6:200-3. doi: 10.1111/rda.12023. PubMed PMID: 23279499. 16: Valldecabres-Torres X, García-Roselló E, García-Muñoz A, Cuervo-Arango J. Effects of d-cloprostenol dose and corpus luteum age on ovulation, luteal function, and morphology in nonlactating dairy cows with early corpora lutea. J Dairy Sci. 2012 Aug;95(8):4389-95. doi: 10.3168/jds.2011-5284. PubMed PMID: 22818452. 17: Pursley JR, Martins JP, Wright C, Stewart ND. Compared to dinoprost tromethamine, cloprostenol sodium increased rates of estrus detection, conception and pregnancy in lactating dairy cows on a large commercial dairy. Theriogenology. 2012 Sep 1;78(4):823-9. doi: 10.1016/j.theriogenology.2012.03.032. Epub 2012 May 22. PubMed PMID: 22626771. 18: Duque-Bonisoli C, Salvador A, Díaz T, Contreras-Solis I. Ovarian response to oestrous synchronization protocol based on use of reduced doses of cloprostenol in cyclic goats. Reprod Domest Anim. 2012 Dec;47(6):e79-82. doi: 10.1111/j.1439-0531.2011.01974.x. Epub 2011 Dec 29. PubMed PMID: 22211362. 19: Cuervo-Arango J, Newcombe JR. Relationship between dose of cloprostenol and age of corpus luteum on the luteolytic response of early dioestrous mares: a field study. Reprod Domest Anim. 2012 Aug;47(4):660-5. doi: 10.1111/j.1439-0531.2011.01940.x. Epub 2011 Nov 4. PubMed PMID: 22050446. 20: Martins JP, Policelli RK, Neuder LM, Raphael W, Pursley JR. Effects of cloprostenol sodium at final prostaglandin F2α of Ovsynch on complete luteolysis and pregnancy per artificial insemination in lactating dairy cows. J Dairy Sci. 2011 Jun;94(6):2815-24. doi: 10.3168/jds.2010-3652. PubMed PMID: 21605751.

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