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T4949

Sigma-Aldrich

Taprostene sodium salt

≥98% (HPLC)

Synonym(s):

Rheocyclan, Sodium 3-[(Z)-[(3aR,4R,5R,6aS)-4-[(1E,3S)-3-cyclohexyl-3-hydroxy-1-propenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-ylidene]methyl]benzoate

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About This Item

Empirical Formula (Hill Notation):
C24H29NaO5
CAS Number:
87440-45-7
Molecular Weight:
420.47
MDL number:
MFCD05664743
UNSPSC Code:
12352202
PubChem Substance ID:
24724631
NACRES:
NA.77

Assay

≥98% (HPLC)

color

off-white

mp

173-182.5 °C (lit.)

solubility

H2O: 26 mg/mL

storage temp.

2-8°C

SMILES string

[Na+].[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)C3CCCCC3)[C@@]1([H])C\C(O2)=C\c4cccc(c4)C([O-])=O

InChI

1S/C24H30O5.Na/c25-21(16-6-2-1-3-7-16)10-9-19-20-13-18(29-23(20)14-22(19)26)12-15-5-4-8-17(11-15)24(27)28;/h4-5,8-12,16,19-23,25-26H,1-3,6-7,13-14H2,(H,27,28);/q;+1/p-1/b10-9+,18-12-;/t19-,20-,21-,22-,23+;/m1./s1

InChI key

KPQVOJYDUCZQEQ-REHYUDDHSA-M

Application

Taprostene has been used as an IP receptor agonist and was found to increase cAMP expression in human bronchial epithelial cells1.

Biochem/physiol Actions

Highly selective IP1 prostanoid receptor agonist.

Preparation Note

Taprostene is soluble in water at 26 mg/ml.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
043K4707

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R L Jones et al.
Prostaglandins, leukotrienes, and essential fatty acids, 72(4), 289-299 (2005-03-15)
The possibility that the prostacyclin analogues AFP-07 and cicaprost relax saphenous vein preparations of pig, guinea-pig and rabbit by simultaneously activating prostanoid EP4 and IP (prostacyclin) receptors was investigated using the high-affinity EP4 antagonist GW 627368. The IP receptor system
Jakob Labus et al.
The Laryngoscope, 120(9), 1863-1871 (2010-08-31)
To estimate the effect of recovery of idiopathic sudden hearing loss under placebo (first aim) and under medical therapy (second aim). Systematic review and meta-analysis. A total of 1,674 studies published between January 1974 and April 2009 were found following
X L Ma et al.
Journal of the American College of Cardiology, 19(1), 197-204 (1992-01-01)
The effects of low dose human superoxide dismutase and low dose taprostene, a stable analogue of prostacyclin, were investigated separately and together in a model of myocardial ischemia (1.5 h) with reperfusion (4.5 h) in open chest, anesthetized cats. Taprostene
T Wöhrmann et al.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, 46(1), 71-73 (1994-03-01)
Beagle dogs were exposed orally to the prostacyclin analogue taprostene for four weeks. Dose levels of 200-3000 micrograms/kg body weight/day were used. Specific activity of taprostene on the digestive system compared to other species is reported. It is characterized by
J J F Belch et al.
International angiology : a journal of the International Union of Angiology, 30(2), 150-155 (2011-03-24)
Atherosclerotic peripheral arterial disease is a major health problem in the western world, often manifested as intermittent claudication, affecting 10-20% males above 60 years. Ischemic complications can lead to rest pain, ulceration and gangrene. The treatment of choice for critical
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