69648-38-0

Basic information

• Product Name: (R)-BUTAPROST
• Synonyms: BAY-q-4218;(1r,2r,3r)-3-hydroxy-2-[(1e,4r)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxo-cyclopentaneheptanoic acid methyl ester;(1R)-3α-Hydroxy-2β-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutan-1-yl)-1-butenyl]-5-oxocyclopentaneheptanoic acid methyl ester
• CAS NO: 69648-38-0
• Molecular Formula: C24H40O5
• Molecular Weight: 408.575
• Mol File: 69648-38-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 525.1°Cat760mmHg
• Flash Point: 168.4°C
• Appearance: light yellow/oil
• Density: 1.105g/cm³
• Vapor Pressure: 3.2E-13mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: −20°C
• Solubility: DMSO: freely soluble
• CAS DataBase Reference: (R)-BUTAPROST(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BUTAPROST(69648-38-0)
• EPA Substance Registry System: (R)-BUTAPROST(69648-38-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 69648-38-0(Hazardous Substances Data)

Usage

Description

(R)-BUTAPROST is a structural analog of prostaglandin E2 (PGE2) with good selectivity for the EP2 receptor subtype. It has been frequently used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells. (R)-BUTAPROST is generally considered to be the less active epimer compared to its C-16 (S) counterpart.

Uses

Used in Pharmaceutical Research:
(R)-BUTAPROST is used as a prostanoid receptor (EP)-specific agonist for studying its effects on protein kinase A (PKA) regulatory subunits in MCF7 cells. It is used as an EP2 agonist in Madin-Darby canine kidney and mouse cortical collecting duct (mpkCCD14) cells, as well as in human fetal lung fibroblasts (HFL-1) cells to test its effect on vascular endothelial growth factor (VEGF) production.
Used in Respiratory Applications:
(R)-BUTAPROST is used as a bronchodilator, helping to relax and widen the airways in the lungs, which can be beneficial for individuals with respiratory conditions such as asthma or chronic obstructive pulmonary disease (COPD).

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.

InChI:InChI=1/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

Upstream product

• 69647-86-5 4-(1-Propyl-cyclobutyl)-1-iodo-but-1E-en-4RS-ol 
• 69647-58-1 2,2-trimethylene-1-pentanal 
• 69647-61-6 2,2-trimethylene-1-pentanol 
• 69647-71-8 4-hydroxy-5,5-trimethylene-1-octyne 
• 58148-14-4 2,2-trimethylenepentanoic acid 
• 60934-42-1 7-{5-oxo-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopent-1-en-1-yl}heptanoic acid methyl ester 
• 69648-02-8 4-(1-Propyl-cyclobutyl)-1-iodo-4RS-(2-ethoxyethoxy)-but-1E-en 

Relevant articles and documents

Preparation of 15-deoxy-16-hydroxyprostaglandins

Analogues of PGE1 having the structural formula, STR1 in which J is R-hydroxymethylene or S-hydroxymethylene; R1 is hydrogen; R2 is hydrogen or together with R4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R3 is hydrogen or methyl, or together with R4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R4 is bicycloalkyl or bicycloalkenyl moiety having the formula: STR2 SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R4 is hydrogen or methyl or together with R2 or R3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R4 forms a cycloalkyl as defined above; and R6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge1 ester analogues of the above formula, limited to the structures wherein two of R2, R3 R4 and R5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.