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B6309 Sigma-Aldrich

(R)-Butaprost

≥98% (HPLC)

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

  • CAS Number 69648-38-0

  • Empirical Formula (Hill Notation) C24H40O5

  • Molecular Weight 408.57

  •  MDL number MFCD00867055

  •  PubChem Substance ID 24724423

  •  NACRES NA.77

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, B, Bayer, Bioactive Small Molecule Alphabetical Index,
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

Description

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.

Packaging

1, 5 mg in glass bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Within mammalian cells, a multitude of lipid compounds are found with a variety of cellular functions, including structural components of cell membranes and as second messengers in cell signaling pat...
Keywords: Absorption, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell signaling, Diabetes, Digestions, Diseases, Growth factors, Hormones, Inflammation, Lipid Metabolism, Lipid signaling, Metabolism

Peer-Reviewed Papers
15

References

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