Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H40O5 |
Molecular Weight | 408.5714 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1(CCC1)[C@H](O)C\C=C\[C@H]2[C@H](O)CC(=O)[C@@H]2CCCCCCC(=O)OC
InChI
InChIKey=XRISENIKJUKIHD-LHQZMKCDSA-N
InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21-,22-/m1/s1
Butaprost, a structural analog of PGE2, is a selective agonist for the EP2 receptor subtype. EP2 receptors are expressed on human neutrophils and on respiratory, vascular, and uterine smooth muscle. Butaprost binds with about 1/10 the affinity of PGE2 to the recombinant murine EP2 receptor and does not bind appreciably to the other murine EP receptors or the DP, TP, FP, and IP receptors. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells. Butaprost effectively reduces the subconjunctival scarring response. Given the significance of wound healing modulation in blebs, butaprost's inhibitory effect on subconjunctival Tenon's fibroblasts may be beneficial in managing postoperative scarring in glaucoma surgery.
Approval Year
PubMed
Title | Date | PubMed |
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Effect of NMDA receptor antagonists on prostaglandin E2-induced hyperalgesia in conscious mice. | 1995 Apr 17 |
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Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats. | 2003 Sep |
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Trigeminal nociceptors express prostaglandin receptors. | 2008 Mar |
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The prostaglandin E2 receptor, EP2, regulates survivin expression via an EGFR/STAT3 pathway in UVB-exposed mouse skin. | 2011 Jun |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C78568
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DTXSID8048993
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5927
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69648-38-0
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C74369
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5311035
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CHEMBL271896
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X-64
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HP16WVP23Y
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100000088480
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SUB06008MIG
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ACTIVE MOIETY
METABOLITE ACTIVE (PRODRUG)