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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
Structure of BUTAPROST

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

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
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
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
The prostaglandin E2 receptor, EP2, regulates survivin expression via an EGFR/STAT3 pathway in UVB-exposed mouse skin.
2011 Jun
EP2 Receptor Signaling Regulates Microglia Death.
2015 Jul
Patents

Patents

Name Type Language
BUTAPROST
INN   USAN  
USAN   INN  
Official Name English
BUTAPROST [USAN]
Common Name English
METHYL (13E,16R)-11.ALPHA.,16-DIHYDROXY-9-OXO-17,17-TRIMETHYLENEPROST-13-EN-1-OATE
Systematic Name English
Methyl (1R,2R,3R)-3-hydroxy-2-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxocyclopentaneheptanoate
Systematic Name English
BAY-Q-4218
Code English
BAYQ-4218
Code English
butaprost [INN]
Common Name English
TR-4979
Code English
CYCLOPENTANEHEPTANOIC ACID, 3-HYDROXY-2-(4-HYDROXY-4-(1-PROPYLCYCLOBUTYL)-1-BUTENYL)-5-OXO-, METHYL ESTER, (1R-(1.ALPHA.,2.BETA.(1E,4R*),3.ALPHA.))-
Systematic Name English
BAY Q 4218
Code English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID8048993
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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INN
5927
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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CAS
69648-38-0
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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NCI_THESAURUS
C74369
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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PUBCHEM
5311035
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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ChEMBL
CHEMBL271896
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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USAN
X-64
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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FDA UNII
HP16WVP23Y
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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SMS_ID
100000088480
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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EVMPD
SUB06008MIG
Created by admin on Fri Dec 15 16:19:34 GMT 2023 , Edited by admin on Fri Dec 15 16:19:34 GMT 2023
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