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B6309

(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
NACRES:
NA.77
PubChem Substance ID:
24724423
UNSPSC Code:
12352200
MDL number:
MFCD00867055
Assay:
≥98% (HPLC)
Form:
oil
Quality level:
100
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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000124375
0000124375
0000124374
0000097873
0000059947

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Prostanoid receptor EP2 as a therapeutic target: Miniperspective
Ganesh T
Journal of Medicinal Chemistry, 57(11), 4454-4465 (2014)
Anti-scarring effects of butaprost on human subconjunctival Tenon's fibroblasts
Shin JH, et al.
International journal of ophthalmology, 10(7), 1028-1028 (2017)
Yunyun Su et al.
Cancer immunology, immunotherapy : CII, 60(1), 111-122 (2010-10-21)
Previous studies document that PGE(2) and adenosine suppress production of inflammatory cytokines. The present study demonstrates for the first time that (1) PGE(2) and 2-chloroadenosine (CADO; a stable analog of adenosine) directly inhibit the cytolytic function of human tumor-infiltrating lymphocytes
cAMP-dependent activation of the Rac guanine exchange factor P-REX1 by type I protein kinase A (PKA) regulatory subunits
Adame-Garcia SR, et al.
Test, 294(7), 2232-2246 (2019)
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).
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Global Trade Item Number

SKUGTIN
B6309-1MG04061833434598
B6309-5MG04061832784335

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