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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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J J Belch et al.
International angiology : a journal of the International Union of Angiology, 14(4), 353-356 (1995-12-01)
Critical limb ischaemia (CLI) is a serious clinical condition that often immediately precedes limb loss. The Consensus Documents of 1989 and 1991 attempted to define CLI and give direction to its investigation and management. Whilst the need for such a
Sylvia M Wilson et al.
Molecular pharmacology, 79(3), 586-595 (2010-12-22)
Herein we provide evidence for the coexpression of two distinct prostacyclin (PGI(2)) receptors (IP) on BEAS-2B human airway epithelial cells. IP receptor heterogeneity initially was suggested by the finding that the rank orders of potency of PGI(2) and three structurally
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
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
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