(R)-BUTAPROST Property

storage temp. 

-20°C

solubility 

DMSO: freely soluble

form 

oil

color 

light yellow

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

H336May cause drowsiness or dizziness

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

(R)-BUTAPROST Chemical Properties,Usage,Production

Description

Butaprost is a structural analog of prostaglandin E₂ (PGE₂) with good selectivity for the EP₂ receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells. Serious confusion as to the structure of butaprost was generated by Gardiner in 1986, when he reported that the epimer of butaprost showing this selective activity was the C-16 (R)-epimer (See reference and Note). Butaprost binds with about 1/10 the affinity of PGE₂ to the recombinant murine EP₂ receptor, and does not bind appreciably to any of the other murine EP receptors or DP, FP, IP, or TP receptors. The pharmacology of (R)-butaprost has not been carefully studied, but it is generally considered to be the less active epimer. (NOTE: In the Gardiner paper in the 1986 British Journal of Pharmacology, butaprost appears on page 46 where it is given the name TR 4979. The structure as drawn is incorrect, in that the author was using and referring to the more active C-16 epimer, which is actually 16(S). The structure on page 46 shows the structure as 16(R). It was not until the late 1990’s that careful studies both in the US and Japan correctly identified the actual configuration of C-16 in the compound called butaprost is 16(S).)

Uses

(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.

Uses

Bronchodilator.

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.