A PGH2 analog
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U-51605

Item No. 16465

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α-azoprosta-5Z,13E-dien-1-oic acid
CAS Number
64192-56-9
Molecular Formula
C20H32N2O2
Formula Weight
332.5
Purity
≥98%
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/ml (from U-46619)DMSO: >100 mg/ml (from U-46619)Ethanol: >100 mg/ml (from U-46619)PBS pH 7.2: >2 mg/ml (from U-46619)
SMILES
CCCCCC/C=C/[C@H]1C2N=NC(C2)[C@@H]1C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32N2O2/c1-2-3-4-5-6-9-12-16-17(19-15-18(16)21-22-19)13-10-7-8-11-14-20(23)24/h7,9-10,12,16-19H,2-6,8,11,13-15H2,1H3,(H,23,24)/b10-7-,12-9+/t16-,17-,18?,19?/m1/s1
InChi Key
SRIZDZJPKIYUPZ-ACGFIOGVSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    U-51605 is a stable analog of the endoperoxide prostaglandin H2 (PGH2). It is an inhibitor of both prostacyclin (PGI) and thromboxane (TX) synthases with more selectivity towards PGI synthase. U-51605 is also a partial agonist at TP receptors.1 In human foreskin fibroblasts, U-51605 inhibits PGI synthase at a concentration of 2.8 µM, whereas, human platelet TX synthase is inhibited at a concentration of 5.6 µM.2,3 At concentrations up to 1 µM, U-51605 reduced the release of prostacyclin in SHR aorta elicited by the calcium ionophore A-23187 with no effect on TXA2 production and yet significantly increased PGE2 and PGF2α release.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Needleman, P., Bryan, B., Wyche, A., et al. Thromboxane synthetase inhibitors as pharmacological tools: Differential biochemical and biological effects on platelet suspensions. Prostaglandins 14, 897-907 (1977).

    2. Gorman, R.R., Hamilton, R.D., and Hopkins, N.K. Stimulation of human foreskin fibroblast adenosine 3':5'-cyclic monophosphate levels by prostacyclin (prostaglandin I2). The Journal of Biological Chemisty 254, 1671-1676 (1979).

    3. Gorman, R.R., Bundy, G.L., Peterson, D.C., et al. Inhibition of human platelet thromboxane synthetase by 9,11-azoprosta-5,13-dienoic acid. Proc. Natl. Acad. Sci. USA 74, 4007-4011 (1977).

    4. Gluais, P., Paysant, J., Badier-Commander, C., et al. In SHR aorta, calcium ionophore A-23187 releases prostacyclin and thromboxane A2 as endothelium-derived contracting factors. Am. J. Physiol. Heart Circ. Physiol. 291, H2255-H2264 (2006).