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T4949

Sigma-Aldrich

Taprostene sodium salt

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C24H29NaO5
CAS Number:
87440-45-7
Molecular Weight:
420.47
MDL number:
MFCD05664743
UNSPSC Code:
12352200
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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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M Spiecker et al.
Haemostasis, 27(4), 184-192 (1997-07-01)
We investigated the in vitro thrombolytic effects of streptokinase, urokinase, alteplase and saruplase, alone or in combination, with the prostacyclin analogues, iloprost and taprostene. Human platelet-rich plasma was stimulated with collagen (1 microgram/ml) to generate thrombi containing platelets and fibrin.
A M Lefer et al.
Methods and findings in experimental and clinical pharmacology, 16(9), 623-631 (1994-11-01)
We examined the effects of taprostene (2.5 x 10(-8) M to 1 x 10(-7) M), a stable prostacyclin analog, on PMN-endothelial interaction (i.e., adherence) and subsequent vasocontraction and endothelial dysfunction. Taprostene effectively inhibited the adherence of leukotriene B4-stimulated autologous cat
O Michel et al.
ORL; journal for oto-rhino-laryngology and its related specialties, 56(6), 305-309 (1994-11-01)
A probable relation between prostaglandin formation and the pathophysiology of hearing loss led to the application of the potent vasodilator prostacyclin in the treatment of inner ear disorders. Two drugs may be administered to humans: (1) unstable natural prostacyclin (epoprostenol)
M Heinz et al.
VASA. Zeitschrift fur Gefasskrankheiten, 25(1), 65-72 (1996-01-01)
In a double blind pilot study, we examined the effects of the stable prostacyclin derivate taprostene compared to a combination of aspirin and dipyridamole on platelet uptake and clinical outcome after peripheral percutaneous angioplasty. Taprostene was administered to 19 patients
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
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