(+)-Fluprostenol | CAS# 54276-17-4 | PGF2α Analog

MedKoo Cat#: 573636 | Name: (+)-Fluprostenol

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Description:

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

Fluprostenol, (+)-, is an analog of Prostaglandin F2α with potent FP receptor agonist activity. Fluprostenol is the optically active enantiomer of fluprostenol and would be expected to have twice the potency as the racemic mixture. Fluprostenol inhibits PGF2α binding to human and rat FP receptors with IC50 values of 3.5 and 7.5 nM, respectively. This product is being supplied as a solution in ethanol.

Chemical Structure

(+)-Fluprostenol

CAS#54276-17-4 (rotation positive)

Theoretical Analysis

MedKoo Cat#: 573636

Name: (+)-Fluprostenol

CAS#: 54276-17-4 (rotation positive)

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

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 250.00	2 Weeks
5mg	USD 650.00	2 Weeks

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Related CAS #

40666-16-8 (free acid) 55028-71-2 (sodium) 54276-17-4 (rotation positive)

Synonym

(+)-Fluprostenol; Fluprostenol, (+)-; Travoprost acid; ICI80008; ICI 80008; ICI-80008

IUPAC/Chemical Name

5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3R)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-buten-1-yl)cyclopentyl)-, (5Z)-

InChi Key

WWSWYXNVCBLWNZ-QIZQQNKQSA-N

InChi Code

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

c1cc(cc(c1)OC[C@@H](/C=C/[C@H]2[C@@H](C[C@@H]([C@@H]2C/C=C\CCCC(=O)O)O)O)O)C(F)(F)F

Appearance

Solution in ethanol

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

Shelf Life

>3 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

Instruction

View handling instruction

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.

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

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J Clin Endocrinol Metab. 1996 Jun;81(6):2104-10. doi: 10.1210/jcem.81.6.8964835. PMID: 8964835. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: Dodson KS, Watson J. Effects of cloprostenol (ICI 80996) and fluprostenol (ICI 81008) on progesterone production by human luteal tissue superfused in vitro. Prostaglandins Med. 1979 Mar;2(3):239-40. doi: 10.1016/0161-4630(79)90041-7. PMID: 550147. 17: Rossdale PD, Pashen RL, Jeffcott LB. The use of synthetic prostaglandin analogue (fluprostenol) to induce foaling. J Reprod Fertil Suppl. 1979;(27):521-9. PMID: 289831. 18: Klug E, Merkt H, Günzel A. Klinische Erfahrungen mit Prostaglandin F2 alpha. Uber den Einsatz von ICI 81008 Fluprostenol (Equimate) zur Zyklussteuerung beim Pferd [Clinical findings with prostaglandin F2 alpha. Use of ICI 81008 fluprostenol (equimate) for estrous cycle regulation in the mare]. Tierarztl Prax. 1977;5(4):475-80. German. PMID: 563631. 19: Rossdale Pd, Jeffcott LB, Allen WR. Foaling induced by a synthetic prostaglandin analogue (fluprostenol). 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