SUGAMMADEX SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C72H104O48S8.8Na
Molecular Weight	2178.006
Optical Activity	UNSPECIFIED
Defined Stereocenters	40 / 40
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[H][C@@]12O[C@H](CSCCC([O-])=O)[C@@H](O[C@@]3([H])O[C@H](CSCCC([O-])=O)[C@@H](O[C@@]4([H])O[C@H](CSCCC([O-])=O)[C@@H](O[C@@]5([H])O[C@H](CSCCC([O-])=O)[C@@H](O[C@@]6([H])O[C@H](CSCCC([O-])=O)[C@@]([H])(O[C@H]7O[C@H](CSCCC([O-])=O)[C@@]([H])(O[C@H]8O[C@H](CSCCC([O-])=O)[C@@]([H])(O[C@H]9O[C@H](CSCCC([O-])=O)[C@@H](O1)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O

InChI

InChIKey=KMGKABOMYQLLDJ-VKHHSAQNSA-F

InChI=1S/C72H112O48S8.8Na/c73-33(74)1-9-121-17-25-57-41(89)49(97)65(105-25)114-58-26(18-122-10-2-34(75)76)107-67(51(99)43(58)91)116-60-28(20-124-12-4-36(79)80)109-69(53(101)45(60)93)118-62-30(22-126-14-6-38(83)84)111-71(55(103)47(62)95)120-64-32(24-128-16-8-40(87)88)112-72(56(104)48(64)96)119-63-31(23-127-15-7-39(85)86)110-70(54(102)46(63)94)117-61-29(21-125-13-5-37(81)82)108-68(52(100)44(61)92)115-59-27(19-123-11-3-35(77)78)106-66(113-57)50(98)42(59)90;;;;;;;;/h25-32,41-72,89-104H,1-24H2,(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,83,84)(H,85,86)(H,87,88);;;;;;;;/q;8*+1/p-8/t25-,26-,27-,28-,29-,30-,31-,32-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-;;;;;;;;/m1......../s1

HIDE SMILES / InChI

Molecular Formula	C72H104O48S8
Molecular Weight	1994.087
Charge	-8
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	40 / 40
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count	MOL RATIO 8 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Sugammadex (ORG 25969) is a cyclodextrin derivative was synthesized as synthetic receptor (or host molecule) for neuromuscular blockers (rocuronium and vecuronium). It forms a complex with the neuromuscular blocking agents rocuronium and vecuronium, and it reduces the amount of neuromuscular blocking agent available to bind to nicotinic cholinergic receptors in the neuromuscular junction. This results in the reversal of neuromuscular blockade induced by rocuronium and vecuronium. The clinical use of sugammadex promises to eliminate many of the shortcomings in current anesthetic practice with regard to antagonism of rocuronium and other aminosteroid muscle relaxants. Sugammadex is indicated for the reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide in adults undergoing surgery.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CHEMBL1201244: ROCURONIUM 2	Binding Agent 1,064
CHEMBL1201219: VECURONIUM 2	Binding Agent 1,064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neuromuscular blockade 5	Preventing		Approved 8,429	BRIDION

C_max

Value	Dose	Analyte	Population
66.1 ug/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens
60.6 ug/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens
62.2 ug/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
61.1 ug*h/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens
148 ug*h/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens
335 ug*h/mL	4 mg/kg single, intravenous	SUGAMMADEX plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years	Other AEs: Dysgeusia, Headache...
16 mg/kg single, intravenous Recommended	unhealthy	Disc. AE: Anaphylactic shock...
4 mg/kg single, intravenous Recommended	unhealthy	Disc. AE: Hypersensitivity reaction...
32 mg/kg single, intravenous	unhealthy	Disc. AE: Hypersensitivity reaction...
8 mg/kg single, intravenous	unhealthy	Disc. AE: Tachycardia...

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AEs

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AE	Significance	Dose	Population
Fatigue	16.7%	96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years
Headache	16.7%	96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years
Nausea	16.7%	96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years
Pharyngolaryngeal pain	16.7%	96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years
Dysgeusia	66.7%	96 mg/kg single, intravenous Highest studied dose	healthy, 18-65 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:90953	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:90953
ChemicalBook	CB71011756	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB71011756
MolPort	MolPort-046-424-800	https://www.molport.com/shop/molecule-link/MolPort-046-424-800

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PubMed

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Title	Date	PubMed
Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.	2002 Apr 25	11960492
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.	2008 Sep	18559352
Discovery, development, and clinical application of sugammadex sodium, a selective relaxant binding agent.	2009 Feb 6	19920893
Pharmacokinetic-pharmacodynamic model for the reversal of neuromuscular blockade by sugammadex.	2009 Jan	19104176
Sugammadex, a neuromuscular blockade reversal agent, causes neuronal apoptosis in primary cultures.	2013	23983586

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Patents

Sample Use Guides

In Vivo Use Guide

BRIDION (sugammadex) can be used to reverse different levels of rocuronium- or vecuronium-induced neuromuscular blockade. For rocuronium and vecuronium: • A dose of 4 mg/kg BRIDION is recommended if spontaneous recovery of the twitch response has reached 1 to 2 post-tetanic counts (PTC) and there are no twitch responses to train-of-four (TOF) stimulation following rocuronium- or vecuronium-induced neuromuscular blockade. • A dose of 2 mg/kg BRIDION is recommended if spontaneous recovery has reached the reappearance of the second twitch (T2) in response to TOF stimulation following rocuronium- or vecuronium-induced neuromuscular blockade. For rocuronium only: • A dose of 16 mg/kg BRIDION is recommended if there is a clinical need to reverse neuromuscular blockade soon (approximately 3 minutes) after administration of a single dose of 1.2 mg/kg of rocuronium. The efficacy of the 16 mg/kg dose of BRIDION following administration of vecuronium has not been studied.

Route of Administration: Intravenous

In Vitro Use Guide

75 ug/ml sugammadex causes apoptotic/necrosis neuron death in primary cultures.

Substance Class	Chemical
Record UNII	ERJ6X2MXV7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUGAMMADEX SODIUM

Official Name

English

Sugammadex sodium [WHO-DD]

Common Name

English

ORG-25969

Code

English

SUGAMMADEX OCTASODIUM SALT

Common Name

English

ORG 25969

Code

English

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Classification Tree

Code System

Code

Pharmacologic Substance

NCI_THESAURUS

C26170

ANESTHESIA AND ANALGESIA

EMA ASSESSMENT REPORTS

BRIDION (AUTHORIZED: NEUROMUSCULAR BLOCKADE)

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Code System

Code

Type

Description

EVMPD

SUB32205

PRIMARY

JAPANESE REVIEW

BRIDION

PRIMARY

APPROVED JANUARY 2010

SMS_ID

100000124531

PRIMARY

CHEBI

90952

PRIMARY

CAS

343306-79-6

PRIMARY

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Related Record

Type

Details


					361LPM2T56

SUGAMMADEX

PARENT -> SALT/SOLVATE

Amount:

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Related Record

Type

Details


					361LPM2T56

SUGAMMADEX

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

Doses

AEs

Overview

OverviewOther

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max