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B6309

Sigma-Aldrich

(R)-Butaprost

≥98% (HPLC)

Synonym(s):

(1R,2R,3R)-3-Hydroxy-2-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxo-cyclopentaneheptanoic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C24H40O5
CAS Number:
69648-38-0
Molecular Weight:
408.57
MDL number:
MFCD00867055
UNSPSC Code:
12352200
PubChem Substance ID:
24724423
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

oil

color

light yellow

solubility

DMSO: freely soluble
ethanol: freely soluble

originator

Bayer

storage temp.

−20°C

SMILES string

CCCC1(CCC1)[C@H](O)C\C=C\[C@H]2[C@H](O)CC(=O)[C@@H]2CCCCCCC(=O)OC

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

InChI key

XRISENIKJUKIHD-LHQZMKCDSA-N

Application

(R)-Butaprost has been used as a prostanoid receptor (EP)-specific agonist to study its effects on protein kinase A (PKA) regulatory subunits in MCF7 cells. It may be used as EP2 agonist in Madin-Darby canine kidney and mouse cortical collecting duct (mpkCCD14) cells. It may also be used as EP2 agonist in human fetal lung fibroblasts (HFL-1) cells to test its effect on vascular endothelial growth factor (VEGF) production.

Biochem/physiol Actions

Butaprost comprises hydroxy-cyclopentanone ring and ω-chain. It aids protection in events of glutamate based N-methyl-D-aspartate receptor toxicity. Butaprost inhibits conjunctival fibrosis and lowers the intraocular pressure in post glaucoma filtration surgery. It also promotes wound healing by reducing the subconjunctival scarring Tenon′s fibroblasts. Butaprost plays a protective role in pulmonary fibrosis and aids protection against the aggregated amyloid β (Aβ) peptides in Alzheimer′s disease.
(R)-Butaprost is a selective EP2 prostanoid receptor agonist.

Features and Benefits

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Terence Peters et al.
The Journal of pharmacology and experimental therapeutics, 335(2), 424-433 (2010-08-07)
Protease-activated receptors (PARs) are widely expressed throughout the respiratory tract, and PAR(2) has been investigated as a potential drug target for inflammatory airway diseases. The primary focus of this study was to determine the extent to which PAR(2)-activating peptides modulate
Boris P L Lee et al.
International immunopharmacology, 9(5), 534-539 (2009-06-23)
Limited data are available on the mechanisms that constrain the function of regulatory populations of T cells. Prostaglandin E2 (PGE2) is an endogenous membrane phospholipid metabolite that has important immunomodulatory effects on T cell function. Our previous microarray data indicated
K J af Forselles et al.
British journal of pharmacology, 164(7), 1847-1856 (2011-05-21)
Studies of the role of the prostaglandin EP(2) receptor) have been limited by the availability of potent and selective antagonist tools. Here we describe the in vitro/in vivo pharmacological characterization of a novel EP(2) receptor antagonist, PF-04418948 (1-(4-fluorobenzoyl)-3-{[(6-methoxy-2-naphthyl)oxy]methyl} azetidine-3-carboxylic acid).
Structural features of subtype-selective EP receptor modulators
Markovivc T, et al.
Drug Discovery Today, 22(1), 57-71 (2017)
The vasopressin type 2 receptor and prostaglandin receptors EP2 and EP4 can increase aquaporin-2 plasma membrane targeting through a cAMP-independent pathway
Olesen ETB, et al.
American Journal of Physiology: Renal Physiology, 311(5), F935-F944 (2016)
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