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
| Molecular Formula | C24H40O5 |
| Molecular Weight | 408.5714 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Effect of NMDA receptor antagonists on prostaglandin E2-induced hyperalgesia in conscious mice. | 1995 Apr 17 |
|
| Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation. | 1997 Sep |
|
| Cyclooxygenase-2 expression in lipopolysaccharide-stimulated human monocytes is modulated by cyclic AMP, prostaglandin E(2), and nonsteroidal anti-inflammatory drugs. | 2000 Nov 30 |
|
| Prostaglandin E prevents indomethacin-induced gastric and intestinal damage through different EP receptor subtypes. | 2001 Jan-Dec |
|
| Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats. | 2003 Sep |
|
| Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. | 2005 Nov 18 |
|
| Exploration of prostanoid receptor subtype regulating estradiol and prostaglandin E2 induction of spinophilin in developing preoptic area neurons. | 2007 May 25 |
|
| PTGER1 and PTGER2 receptors mediate regulation of progesterone synthesis and type 1 11beta-hydroxysteroid dehydrogenase activity by prostaglandin E2 in human granulosa lutein cells. | 2007 Sep |
|
| Trigeminal nociceptors express prostaglandin receptors. | 2008 Mar |
|
| Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling. | 2009 Mar 16 |
|
| The prostaglandin E2 receptor, EP2, regulates survivin expression via an EGFR/STAT3 pathway in UVB-exposed mouse skin. | 2011 Jun |
|
| Role of hypoxia-inducible factor 1, α subunit and cAMP-response element binding protein 1 in synergistic release of interleukin 8 by prostaglandin E2 and nickel in lung fibroblasts. | 2013 Jul |
|
| EP2 Receptor Signaling Regulates Microglia Death. | 2015 Jul |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:19:34 GMT 2023
by
admin
on
Fri Dec 15 16:19:34 GMT 2023
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| Record UNII |
HP16WVP23Y
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| Record Status |
Validated (UNII)
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| Record Version |
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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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| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
