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Merck
CN

T4949

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
NACRES:
NA.77
PubChem Substance ID:
24724631
UNSPSC Code:
12352202
MDL number:
MFCD05664743

Key Documents

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InChI key

KPQVOJYDUCZQEQ-REHYUDDHSA-M

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

assay

≥98% (HPLC)

color

off-white

mp

173-182.5 °C (lit.)

solubility

H2O: 26 mg/mL

storage temp.

2-8°C

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
043K4707

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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
D R VanAntwerp et al.
Eicosanoids, 4(1), 15-20 (1991-01-01)
Prostacyclin (PGI2) and taprostene (CG-4203) were studied in a highly lethal model of splanchnic artery occlusion (SAO) shock in pentobarbital anesthetized rats. Total occlusion of the superior mesenteric and celiac arteries for 40 min resulted in a severe shock state
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
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
C M Arroyo et al.
Chemico-biological interactions, 91(1), 29-38 (1994-04-01)
A possible mechanism by which prostacyclin (PGI2) analogues provide beneficial effects including improved survival in shock experimentally induced by endotoxin, polytrauma or hypovolemia was studied. Since several studies have implicated oxygen free radical-mediated tissue damage, we investigated whether PGI2-analogues exert
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