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343306-71-8

343306-71-8 Structure

343306-71-8 Structure
IdentificationBack Directory
[Name]

SUGAMMADEX
[CAS]

343306-71-8
[Synonyms]

Bridion
Org 25969
SUGAMMADEX
Sugammagex
Shu Glucose
Unii-361lpm2T56
Sugammadex [inn]
Suggmadex Sodium
SugaMMadex SodiuM
Sodium sulcoglucan
Sugammadex Impurity 58
6A,6B,6C,6D,6E,6F,6G,6H-octakis-S-(2-carboxyethyl)-6A,6B,6C,6D,6E,6F,6G,6H-octathio-γ-Cyclodextrin
γ-Cyclodextrin, 6A,6B,6C,6D,6E,6F,6G,6H-octakis-S-(2-carboxyethyl)-6A,6B,6C,6D,6E,6F,6G,6H-octathio-
[EINECS(EC#)]

253-874-2
[Molecular Formula]

C72H112O48S8
[MOL File]

343306-71-8.mol
[Molecular Weight]

2002.12
Chemical PropertiesBack Directory
[density ]

1.559±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[pka]

3.42±0.10(Predicted)
Hazard InformationBack Directory
[Description]

Sugammadex is a selective relaxant binding agent indicated for reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide during surgery in adults. Rocuronium bromide and vecuronium bromide are neuromuscular blocking medications that cause temporary paralysis and are especially useful for general anesthesia, ventilation, or tracheal intubation that patients may require for surgery. Sugammadex provides a new treatment option to reverse the effects of those medications and possibly help patients recover sooner post-surgery. Sugammadex (brand name Bridion) is marketed by Merck Sharp and Dohme, and was approved by the United States FDA on December 15, 2015.
[Uses]

Reversal agent for neuromuscular blocking drugs.
[Definition]

ChEBI: An octasaccharide derivative that is gamma-cyclodextrin in which all eight primary hydroxy groups are replaced by 2-(carboxyethyl)sulfanyl groups. Used (as the octasodium salt) for reversal of neuromuscular blockade induced by rocuronium and vecuronium in adults undergoing surgery.
[Chemical Synthesis]

Bromination of γ-cyclodexdrin 127 with the Vilsmeier-Haack reagent prepared by reaction of bromine with triphenylphospine in DMF gave the per-6-bromo-γ-cyclodextrin 128 in 95-98% yield. Nucleophilic displacement of the bromines of 128 with methyl 3-mercaptopropionate (129) and cesium carbon-ate at 50°C in DMF gave 6-perdeoxy-6-per(2-methoxycarbonylethyl) thio-γ-cyclodextrin 130 as a white powder. Saponification of the esters of 130 was accomplished by reaction with aqueous sodium hydroxide solution to provide sugammadex (XVII) as a glassy solid in 52% yield for the 2 steps.

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