BUTAPROST

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 Search

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

Description
Sources: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=4132738.PN.&OS=PN/4132738&RS=PN/4132738 | https://www.ncbi.nlm.nih.gov/pubmed/15159280 | https://www.ncbi.nlm.nih.gov/pubmed/27940058 | https://www.ncbi.nlm.nih.gov/pubmed/28730102 | https://www.ncbi.nlm.nih.gov/pubmed/16936121

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
EP2 Receptor Signaling Regulates Microglia Death.	2015-07	25715797
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.	2013-07	23526216
The prostaglandin E2 receptor, EP2, regulates survivin expression via an EGFR/STAT3 pathway in UVB-exposed mouse skin.	2011-06	21268125
Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling.	2009-03-16	19273625
Trigeminal nociceptors express prostaglandin receptors.	2008-03	18296611
PTGER1 and PTGER2 receptors mediate regulation of progesterone synthesis and type 1 11beta-hydroxysteroid dehydrogenase activity by prostaglandin E2 in human granulosa lutein cells.	2007-09	17761898
Exploration of prostanoid receptor subtype regulating estradiol and prostaglandin E2 induction of spinophilin in developing preoptic area neurons.	2007-05-25	17408863
Functional role of prostacyclin receptor in rat dorsal root ganglion neurons.	2005-11-18	16039053
Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats.	2003-09	14622681
Prostaglandin E prevents indomethacin-induced gastric and intestinal damage through different EP receptor subtypes.	2001-10-12	11595431
Cyclooxygenase-2 expression in lipopolysaccharide-stimulated human monocytes is modulated by cyclic AMP, prostaglandin E(2), and nonsteroidal anti-inflammatory drugs.	2000-11-30	11095985
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.	1997-09	9298541
Effect of NMDA receptor antagonists on prostaglandin E2-induced hyperalgesia in conscious mice.	1995-04-17	7606458

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:25:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:08 GMT 2025`
Record UNII	HP16WVP23Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTAPROST

Official Name

English

BAY Q 4218

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C78568