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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

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

PubMed

TitleDatePubMed
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.
1997 Sep
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:19:34 GMT 2023
Edited
by admin
on Fri Dec 15 16:19:34 GMT 2023
Record UNII
HP16WVP23Y
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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