An IP and EP1 receptor agonist
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Labeled Version(s)
9000366Iloprost-d4
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Iloprost

Item No. 18215

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5E)-5-[(3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2(1H)-pentalenylidene]-pentanoic acid
CAS Number
78919-13-8
Synonyms
  • Ciloprost
  • ZK 36374
Molecular Formula
C22H32O4
Formula Weight
360.5
Purity
≥97%
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
O[C@@H]1C[C@H](C/2)[C@H](CC2=C\CCCC(O)=O)[C@H]1/C=C/[C@@H](O)C(C)CC#CC
InChi Code
InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1
InChi Key
HIFJCPQKFCZDDL-ACWOEMLNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

    $32

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    500 µg

    $88

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    1 mg

    $128

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    5 mg

    $483

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    Product Description

    Iloprost is an agonist of the IP receptor and the prostaglandin E2 (PGE2) receptor subtype EP1 and a derivative of PGI2.1,2 It selectively binds to IP and EP1 receptors (Ki = 11 nM for both) over EP2, EP4, DP, FP, and TP receptors (Kis = 1,870, 284, 1,035, 619, and 6,487 nM, respectively) but also binds to the EP3 receptor (Ki = 56 nM).1 Iloprost increases cAMP levels in HEK293 cells expressing IP or EP3 receptors (EC50s = 0.37 and 27.5 nM, respectively) and increases calcium levels in HEK293 cells expressing the EP1 receptor (EC50 = 0.3 nM).2 It inhibits ADP-, thrombin-, and collagen-induced platelet aggregation in isolated human platelet-rich plasma (IC50s = 1.07, 0.71, and 0.24 nM, respectively).3 Iloprost (100 ng/kg per minute) increases the time to occlusive coronary artery thrombosis in a porcine model of electrically induced coronary artery thrombosis.4 Aerosolized administration of iloprost (130-1,300 ng/kg per minute) reduces right ventricular systolic pressure and reverses vascular remodeling in rats in a model of chronic pulmonary hypertension induced by the alkaloid monocrotaline (Item No. 16666).5 Formulations containing iloprost have been used in the treatment of pulmonary arterial hypertension and severe frostbite.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim. Biophys. Acta 1483(2), 285-293 (2000).

    2. Whittle, B.J., Silverstein, A.M., Mottola, D.M., et al. Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP1 and EP2 agonist. Biochem. Pharmacol. 84(1), 68-75 (2012).

    3. Schrör, K., Darius, H., Matzky, R., et al. The antiplatelet and cardiovascular actions of a new carbacyclin derivative (ZK36374) — equipotent to PGI2 in vitro. Naunyn Schmiedebergs Arch. Pharmacol. 316(3), 252-255 (1981).

    4. van der Giessen, W.J., Mooi, W.J., Rutteman, A.M., et al. The effect of the stable prostacyclin analogue ZK 36374 on experimental coronary thrombosis in the pig. Thromb. Res. 36(1), 45-51 (1984).

    5. Schermuly, R.T., Yilmaz, H., Ghofrani, H.A., et al. Inhaled iloprost reverses vascular remodeling in chronic experimental pulmonary hypertension. Am. J. Respir. Crit. Care Med. 172(3), 358-363 (2005).

    Product Citations

    Meurer, M., Ebert, K., Schweda, K., et al. The renal vasodilatory effect of prostaglandins is ameliorated in isolated-perfused kidneys of endotoxemic mice. Pflugers Arch. 470(11), 1691-1703 (2018).

    Fuchikami, C., Murakami, K., Tajima, K., et al. A comparison of vasodilation mode among selexipag (NS-304; [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide]), its active metabolite MRE-269 and various prostacyclin receptor agonists in rat, porcine and human pulmonary arteries. Eur. J. Pharmacol. 795, 75-83 (2017).

    Whittle, B.J., Silverstein, A.M., Mottola, D.M., et al. Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP1 and EP2 agonist. Biochem. Pharmacol. 84(1), 68-75 (2012).