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Merck

B6309

Sigma-Aldrich

(R)-Butaprost

≥98% (HPLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C24H40O5
Número de CAS:
Peso molecular:
408.57
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)


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Visite la Librería de documentos

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
Mudit Vaid et al.
American journal of cancer research, 5(11), 3325-3338 (2016-01-26)
Melanoma is a highly aggressive form of skin cancer and a leading cause of death from skin diseases mainly due to its propensity to metastasis. Due to metastatic tendency, melanoma is often associated with activation of Wnt/β-catenin signaling mechanism. Blocking
Prostanoid receptor EP2 as a therapeutic target: Miniperspective
Ganesh T
Journal of Medicinal Chemistry, 57(11), 4454-4465 (2014)
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)

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