52212-02-9

Basic information

• Product Name: 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide
• Synonyms: pipecuronium bromide;4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide;4,4'-[(2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetoxy)androstane-2,16-diyl]bis[1,1-dimethylpiperazinium] dibromide;PIPECURIUM BROMIDE;Pipecuronium;PIPECURINIUM BROMIDE;4，4’-[(2β，3α，5α，16β，17β)-3，17-Bis(acetoxy)andrc~tane-2，16-diyl]bis(1，1-dimethylpiperazinium)dibromide;Ardtm
• CAS NO: 52212-02-9
• Molecular Formula: 2Br*C₃₅H₆₂N₄O₄
• Molecular Weight: 762.69918
• EINECS: 257-740-4
• Mol File: 52212-02-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 262-264° (dec)
• Appearance: powder
• Density: 1.329
• CAS DataBase Reference: 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide(52212-02-9)
• EPA Substance Registry System: 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide(52212-02-9)

Safety Data

• Hazardous Substances Data: 52212-02-9(Hazardous Substances Data)

Usage

Uses

Pipecuronium Bromide is a muscle relaxant and an anaesthesia used in patients undergoing coronary artery bypass graft surgery.

Brand name

Arduan (Organon).

General Description

Pipecurium bromide, 4,4 -(3 ,17 -dihydroxy-5 -androstan-2 ,16 -ylene)bis(1,1-dimeth-ylpiperazinium)dibromide diacetate (Arduan), is anondepolarizing muscle relaxant similar, both chemicallyand clinically, to pancuronium bromide. It is a long-actingdrug indicated as an adjunct to anesthesia and in patients undergoingmechanical ventilation.

Pharmacology

Pipecuronium bromide, an analogue of pancuronium, was developed in Hungary in 1980 and is marketed in Eastern Europe and the United S tates. The intubating dose is 0.07 mg kg–1. The onset time and time to recovery from block are similar to those of pancuronium, and excretion of the drug through the kidneys is significant (66%). In contrast to pancuronium, pipecuronium produces marked cardiovascular stability, having no vagolytic or sympathomimetic effects. It may therefore be useful during major surgery in patients with cardiac disease.

InChI:InChI=1/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26?,27-,28?,29?,30+,31+,32?,33+,34+,35+;;/m1../s1

Upstream product

• 74-83-9 methyl bromide 
• 52211-99-1 2β,16β-bis-(4'-methyl-1'-piperazino)-3α,17β-diacetoxy-5α-androstane 
• 74395-83-8 2β,16β-bis-(4'-methyl-1'-piperazino)-3α,17α-diacetoxy-5α-androstane 

Relevant articles and documents

ENVIRONMENT-FRIEND PROCESS FOR THE SYNTHESIS OF QUATERNARY AMMONIO-STEROΙDS

The invention relates to a new, environment-friend process for the synthesis of the known 4,4'-[3α,17β-bis(acetoxy)-5α-androstane-2β,l6β-diyl]-bis(l,l-dimethyl-ρiρerazinium) dibromide of formula (I) (from now on pipecuronium bromide) and l-[3α,17β-bis(acetoxy)-2β-(l-piperidinyl)-5α-androstane-16β-yl]-l-methyl-piperidinium bromide of formula (II) (from now on vecuronium bromide). Furthermore the invention relates to the new intermediates of formula (III) and formula (IV) of the process, wherein the meaning of X is benzenesulfonate - in given case para-substituted with a methyl or a nitro group or a bromine atom - methanesulfonate, ethanesulfonate or trifluoromethanesulfonate ion.