Taprostene
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MedKoo CAT#: 574421

CAS#: 108945-35-3 (free base)

Description: Taprostene is a stable prostacyclin (PGI2) analog and agonist of the prostacyclin receptor, IP. It does not activate the PGE2 receptor EP4 which, like IP, promotes vascular smooth muscle relaxation when stimulated. Taprostene has been used extensively to study the role of the IP receptor in tissue preparations and in vivo. It has also been used in the screening and evaluation of potential IP antagonists.

Chemical Structure

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Taprostene
CAS# 108945-35-3 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 574421
Name: Taprostene
CAS#: 108945-35-3 (free base)
Chemical Formula: C24H30O5
Exact Mass: 398.21
Molecular Weight: 398.490
Elemental Analysis: C, 72.34; H, 7.59; O, 20.07

Price and Availability

Size Price Availability Quantity
1mg USD 325 2 Weeks
5mg USD 1045 2 Weeks
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Related CAS #: 87440-45-7 (Na)   108945-35-3 (free base)  

Synonym: CG 4203, Rheocyclan, Taprostene

IUPAC/Chemical Name: 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]-benzoic acid

InChi Key: ZLJOKYGJNOQXDP-UHKCRUDESA-N

InChi Code: InChI=1S/C24H30O5/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)/b10-9+,18-12-/t19-,20-,21+,22-,23+/m1/s1

SMILES Code: O[C@@H]([C@@H]1/C=C/[C@H](O)C2CCCCC2)C[C@]([C@]1([H])C/3)([H])OC3=C/C4=CC=CC(C(O)=O)=C4

Appearance: Solid powder

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 398.49 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1. Jones, R.L., and Chan, K.m. Distinction between relaxations induced via prostanoid EP4 and IP1 receptors in pig and rabbit blood vessels. British Journal of Pharmacology 134, 313-324 (2001).

2. Tam, F.S.F., Chan, K.m., Bourreau, J.P., et al. The mechanisms of enhancement and inhibition of field stimulation responses of guinea-pig vas deferens by prostacyclin analogues. British Journal of Pharmacology 121, 1413-1421 (1997).

3. Virgolini, I., Fitscha, P., Sinzinger, H., et al. Effects of taprostene, a stable prostacyclin analogue, on haemodynamics, platelet function and arachidonate metabolism in healthy volunteers. European Journal of Clinical Pharmacology 38, 347-350 (1990).

4. Johnson, G., III, Furlan, L.E., Aoki, N., et al. Endothelium and myocardial protecting actions of taprostene, a stable prostacyclin analogue, after acute myocardial ischemia and reperfusion in cats. Circulation Research 66, 1362-1370 (1990).

5. Ayer, L.M., Wilson, S.M., Traves, S.L., et al. 4,5-dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxy-benzyl)-phenyl]-amine (RO1138452) is a selective, pseudo-irreversible orthosteric antagonist at the prostacyclin (IP)-receptor expressed by human airway epithelial cells: IP-receptor-mediated inhibition of CXCL9 and CXCL10 release. Journal of Pharmacology and Experimental Therapeutics 324(2), 815-826 (2008).