A stable analog of PGI2 that weakly inhibits platelet aggregation
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5-cis Carbaprostacyclin

Item No. 18211

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-5-[(3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octenyl]-2(1H)-pentalenylidene]-pentanoic acid
CAS Number
69609-77-4
Synonyms
  • (5Z)-6a-Carbaprostaglandin I2
Molecular Formula
C21H34O4
Formula Weight
350.5
Purity
≥99%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 5 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 80 µg/ml
SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(C2)=C\CCCC(O)=O
InChi Code
InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7-/t16-,17-,18+,19-,20+/m0/s1
InChi Key
XZFRIPGNUQRGPI-WLPVIMDJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $121

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    1 mg

    $229

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    Product Description

    5-cis Carbaprostacyclin is a stable analog of PGI2 and an isomer of carbaprostacyclin. It is a weak inhibitor of human platelet aggregation with an IC50 of 2.8 µM compared to 0.3 µM for carbaprostacyclin.1,2 5-cis Carbaprostacyclin is a much weaker effector of rabbit mesenteric artery relaxation with an EC50 of 104 µM compared to 5.9 µM for carbaprostacyclin. It even antagonizes the adenylate cyclase activation induced by carbaprostacyclin.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Whittle, B.J.R., Moncada, S., Whiting, F., et al. Carbacyclin — a potent stable prostacyclin analogue for the inhibition of platelet aggregation. Prostaglandins 19(4), 605-627 (1980).

    2. Corsini, A., Folco, G.C., Fumagalli, R., et al. (5Z)-carbacyclin discriminates between prostacyclin-receptors coupled to adenylate cyclase in vascular smooth muscle and platelets. Br. J. Pharmacol. 90(1), 255-261 (1987).