An isomer of PGI2
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15(R)-Prostaglandin I2 (sodium salt)

Item No. 21586

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,9α,11α,13E,15R)-6,9-epoxy-11,15-dihydroxy-prosta-5,13-dien-1-oic acid, monosodium salt
Synonyms
  • 15(R)-PGI2
Molecular Formula
C20H31O5 • Na
Formula Weight
374.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlPBS (pH 9.0): > 11 mg/ml
SMILES
CCCCC[C@@H](O)/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(O2)=C/CCCC([O-])=O.[Na+]
InChi Code
InChI=1S/C20H32O5.Na/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22;/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24);/q;+1/p-1/b11-10+,15-8-;/t14-,16-,17-,18-,19+;/m1./s1
InChi Key
LMHIPJMTZHDKEW-MYQOGOCISA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

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    10 mg

    $546

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    25 mg

    $1,286

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    Product Description

    15(R)-Prostaglandin I2 (15(R)-PGI2) is an isomer of the natural 15(S) prostanoid, PGI2 (Item No. 18220). PGI2 is an unstable cyclooxygenase metabolite detected first in vascular endothelial cells.1,2,3 It elevates platelet cAMP and is a potent vasodilator and inhibitor of human platelet aggregation with an IC50 value of 5 nM.4 While the physiological properties of 15(R)-PGI2 are not well known, 15(R) isomers of PGs typically have reduced receptor agonist activity compared to their 15(S) forms.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Moncada, S., Gryglewski, R., Bunting, S., et al. An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation. Nature 263(5579), 663-665 (1976).

    2. Johnson, R.A., Morton, D.R., Kinner, J.H., et al. The chemical structure of prostaglandin X (prostacyclin). Prostaglandins 12(6), 915-928 (1976).

    3. Stehle, R.G. Physical chemistry, stability, and handling of prostaglandins E2, F2α, D2 and I2: A critical summary. Methods Enzymol. 86, 436-459 (1982).

    4. Aristoff, P.A., Johnson, P.D., and Harrison, A.W. Synthesis of 9-substituted carbacyclin analogues. The Journal of Organic Chemistry 48(26), 5341-5348 (1983).