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MedKoo Cat#: 576538 | Name: Fluprostenol

Description:

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

Fluprostenol is a synthetic prostaglandin F2 alpha analog used as an abortifacient. This product is supplied as 10 mg/mL in ethanol

Chemical Structure

Fluprostenol
Fluprostenol
CAS#40666-16-8 (free acid)

Theoretical Analysis

MedKoo Cat#: 576538

Name: Fluprostenol

CAS#: 40666-16-8 (free acid)

Chemical Formula: C23H29F3O6

Exact Mass: 458.1916

Molecular Weight: 458.47

Elemental Analysis: C, 60.25; H, 6.38; F, 12.43; O, 20.94

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Related CAS #
40666-16-8 (free acid) 55028-71-2 (sodium) 54276-17-4 (rotation positive)
Synonym
Fluprostenol; ICI81008; ICI-81008; ICI 81008
IUPAC/Chemical Name
(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoic acid
InChi Key
WWSWYXNVCBLWNZ-QIZQQNKQSA-N
InChi Code
InChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
SMILES Code
O[C@@H]1[C@@H]([C@H]([C@@H](C1)O)/C=C/[C@H](COC2=CC=CC(C(F)(F)F)=C2)O)C/C=C\CCCC(O)=O
Appearance
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 458.47 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
1: Williams LM, Hollingsworth M, Dukes M, Morris ID. Fluprostenol-induced softening of the cervix of the pregnant rat. J Endocrinol. 1983 May;97(2):283-90. doi: 10.1677/joe.0.0970283. PMID: 6304223. 2: Carrasco MP, Phaneuf S, Asbóth G, López Bernal A. Fluprostenol activates phospholipase C and Ca2+ mobilization in human myometrial cells. J Clin Endocrinol Metab. 1996 Jun;81(6):2104-10. doi: 10.1210/jcem.81.6.8964835. PMID: 8964835. 3: Fabbrocini G, Napolitano A, Masarà A, Cacciapuoti S. 15 keto fluprostenol isopropyl ester (80 µgr/mL) gel for cosmetic eyelash growth and enhancement. J Cosmet Dermatol. 2019 Apr;18(2):545-549. doi: 10.1111/jocd.12844. Epub 2019 Jan 21. PMID: 30664828. 4: Rice KM, Walker EM, Kakarla SK, Paturi S, Wu M, Narula S, Blough ER. Fluprostenol-induced MAPK signaling is independent of aging in Fischer 344/NNiaHSd x Brown Norway/BiNia rat aorta. Ann Clin Lab Sci. 2010 Winter;40(1):26-31. PMID: 20124327. 5: Fuchshofer R, Kuespert S, Junglas B, Tamm ER. The prostaglandin f2α analog fluprostenol attenuates the fibrotic effects of connective tissue growth factor on human trabecular meshwork cells. J Ocul Pharmacol Ther. 2014 Mar- Apr;30(2-3):237-45. doi: 10.1089/jop.2013.0205. Epub 2014 Feb 27. PMID: 24576038. 6: Zhu K, Jiang M, Ye B, Zhang GT, Li W, Tang P, Huang Z, Chen F. A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis. Chem Sci. 2021 Jul 1;12(30):10362-10370. doi: 10.1039/d1sc03237b. PMID: 34377422; PMCID: PMC8336452. 7: Ciro C, Luigi P. Effect of Fluprostenol Isopropyl Ester and 15-Keto Fluprostenol on Eyelash Growth: A Clinical and Pharmacologic Study. Skinmed. 2018 Jul 1;16(4):231-233. PMID: 30207524. 8: Chapman DI, Moss MS, Tomlinson PW, Harrison MP, Simmons PJ. The disposition and metabolism of the synthetic prostaglandin fluprostenol (ICI 81,008) in the horse. Xenobiotica. 1980 Sep;10(9):715-23. doi: 10.3109/00498258009108378. PMID: 7445532. 9: Ousey JC, Dudan FE, Rossdale PD, Silver M. Effects of fluprostenol administration in mares during late pregnancy. Equine Vet J. 1984 Jul;16(4):264-9. doi: 10.1111/j.2042-3306.1984.tb01924.x. PMID: 6090118. 10: Thieme H, Schimmat C, Münzer G, Boxberger M, Fromm M, Pfeiffer N, Rosenthal R. Endothelin antagonism: effects of FP receptor agonists prostaglandin F2alpha and fluprostenol on trabecular meshwork contractility. Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. doi: 10.1167/iovs.05-0527. PMID: 16505027. 11: Cooper MJ. Fluprostenol in mares: clinical trials for the treatment of infertility. Vet Rec. 1976 Jun 26;98(26):523-5. doi: 10.1136/vr.98.26.523. PMID: 941381. 12: Eichhold TH, Kuhlenbeck DL, Baker TR, Stella ME, Amburgey JS, deLong MA, Hartke JR, Cruze CA, Pierce SA, Wehmeyer KR. Use of short high-performance liquid chromatography columns and tandem-mass spectrometry for the rapid analysis of a prostaglandin analog, fluprostenol, in rat plasma. J Chromatogr B Biomed Sci Appl. 2000 May 12;741(2):213-20. doi: 10.1016/s0378-4347(00)00093-1. PMID: 10872591. 13: Rossdale Pd, Jeffcott LB, Allen WR. Foaling induced by a synthetic prostaglandin analogue (fluprostenol). Vet Rec. 1976 Jul 10;99(2):26-8. doi: 10.1136/vr.99.2.26. PMID: 951924. 14: Sharif NA, Davis TL, Williams GW. [3H]AL-5848 ([3H]9beta-(+)-Fluprostenol). Carboxylic acid of travoprost (AL-6221), a novel FP prostaglandin to study the pharmacology and autoradiographic localization of the FP receptor. J Pharm Pharmacol. 1999 Jun;51(6):685-94. doi: 10.1211/0022357991772989. PMID: 10454045. 15: Caruso C, Pacente L, Troiano P, Ostacolo C, D'Andrea L, Bartollino S, Costagliola C. Intraocular pressure reduction with once-a-day application of a new prostaglandin eye drop: a pilot placebo-controlled study in 12 patients. Int Ophthalmol. 2020 Apr;40(4):823-831. doi: 10.1007/s10792-019-01243-0. Epub 2019 Dec 3. PMID: 31792856. 16: Copeland DD, Schultz RH, Canady JD. Use of fluprostenol to manage the equine estrous cycle. Vet Med Small Anim Clin. 1981 Sep;76(9):1329-31. PMID: 6916556. 17: Nervina JM, Camargo PM, Bezouglaia O, Tetradis S. Prostanoid- and interleukin-1-induced primary genes in cementoblastic cells. J Periodontol. 2006 Aug;77(8):1362-70. doi: 10.1902/jop.2006.050354. PMID: 16881805. 18: Hutchison DM, Duffens A, Yale K, Park A, Cardenas K, Mesinkovska NA. Eyelash trichomegaly: a systematic review of acquired and congenital aetiologies of lengthened lashes. J Eur Acad Dermatol Venereol. 2022 Apr;36(4):536-546. doi: 10.1111/jdv.17877. Epub 2021 Dec 31. PMID: 34919300. 19: Cunningham L, Mishra S, Matthews L, Fletcher SP. A General Catalyst Controlled Route to Prostaglandin F2α. Org Lett. 2022 Dec 9;24(48):8886-8889. doi: 10.1021/acs.orglett.2c03718. Epub 2022 Nov 29. PMID: 36446080; PMCID: PMC9745796. 20: Schultz RH, Copeland DD, Canady JD. Treatment of infertility in the mare with fluprostenol. Vet Med Small Anim Clin. 1981 Jun;76(6):885-8. PMID: 6911921.