U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C72H112O48S8
Molecular Weight 2002.1625
Optical Activity UNSPECIFIED
Defined Stereocenters 40 / 40
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUGAMMADEX

SMILES

C(CSC[C@]1([H])[C@]2([H])[C@@]([H])([C@]([H])([C@]([H])(O1)O[C@]3([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]3([H])O)O)O[C@]4([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]4([H])O)O)O[C@]5([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]5([H])O)O)O[C@]6([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]6([H])O)O)O[C@]7([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]7([H])O)O)O[C@]8([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]8([H])O)O)O[C@]9([H])[C@@]([H])(CSCCC(=O)O)O[C@@]([H])([C@@]([H])([C@@]9([H])O)O)O2)O)O)C(=O)O

InChI

InChIKey=WHRODDIHRRDWEW-VTHZAVIASA-N
InChI=1S/C72H112O48S8/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)/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

Description
Curator's Comment:: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022225lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25885973

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

Curator's Comment:: Sugammadex passes across blood brain barrier in a very low ratio (< 3% in rats) and intracerebroventricular Sugammadex administration did not result in any changes in behavioral status, locomotor activity or posture in animals. However sugammadex had a neuroprotective effect in a transient global cerebral ischemia/reperfusion rat model.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL1201219: VECURONIUM
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
BRIDION

Approved Use

BRIDION (sugammadex) is indicated for the reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide in adults undergoing surgery

Launch Date

1.45013762E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
66.1 ug/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: healthy
age:
sex:
food status:
60.6 ug/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
62.2 ug/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
61.1 ug*h/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: healthy
age:
sex:
food status:
148 ug*h/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
335 ug*h/mL
4 mg/kg single, intravenous bolus
dose: 4 mg/kg
route of administration: intravenous bolus
experiment type: single
co-administered:
SUGAMMADEX plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
Doses

Doses

DosePopulationAdverse events​
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Other AEs: Dysgeusia, Headache...
Other AEs:
Dysgeusia (66.7%)
Headache (16.7%)
Fatigue (16.7%)
Nausea (16.7%)
Dizziness postural (8.3%)
Abdominal pain (8.3%)
Pharyngolaryngeal pain (16.7%)
Micturition urgency (8.3%)
Sources:
16 mg/kg single, intravenous
Recommended
Dose: 16 mg/kg
Route: intravenous
Route: single
Dose: 16 mg/kg
Sources: Page: p. 66
unhealthy
n = 496
Health Status: unhealthy
Population Size: 496
Sources: Page: p. 66
Disc. AE: Anaphylactic shock...
AEs leading to
discontinuation/dose reduction:
Anaphylactic shock (1 patient)
Sources: Page: p. 66
4 mg/kg single, intravenous
Recommended
Dose: 4 mg/kg
Route: intravenous
Route: single
Dose: 4 mg/kg
Sources: Page: p. 66
unhealthy
n = 1505
Health Status: unhealthy
Population Size: 1505
Sources: Page: p. 66
Disc. AE: Hypersensitivity reaction...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity reaction (1 patient)
Sources: Page: p. 66
32 mg/kg single, intravenous
Dose: 32 mg/kg
Route: intravenous
Route: single
Dose: 32 mg/kg
Sources: Page: p. 66
unhealthy
n = 165
Health Status: unhealthy
Population Size: 165
Sources: Page: p. 66
Disc. AE: Hypersensitivity reaction...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity reaction (1 patient)
Sources: Page: p. 66
8 mg/kg single, intravenous
Dose: 8 mg/kg
Route: intravenous
Route: single
Dose: 8 mg/kg
Sources: Page: p. 66
unhealthy
n = 156
Health Status: unhealthy
Population Size: 156
Sources: Page: p. 66
Disc. AE: Tachycardia...
AEs leading to
discontinuation/dose reduction:
Tachycardia (1 patient)
Sources: Page: p. 66
AEs

AEs

AESignificanceDosePopulation
Fatigue 16.7%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Headache 16.7%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Nausea 16.7%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Pharyngolaryngeal pain 16.7%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Dysgeusia 66.7%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Abdominal pain 8.3%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Dizziness postural 8.3%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Micturition urgency 8.3%
96 mg/kg single, intravenous
Highest studied dose
Dose: 96 mg/kg
Route: intravenous
Route: single
Dose: 96 mg/kg
Sources:
healthy, 18-65 years
n = 12
Health Status: healthy
Age Group: 18-65 years
Sex: M+F
Population Size: 12
Sources:
Anaphylactic shock 1 patient
Disc. AE
16 mg/kg single, intravenous
Recommended
Dose: 16 mg/kg
Route: intravenous
Route: single
Dose: 16 mg/kg
Sources: Page: p. 66
unhealthy
n = 496
Health Status: unhealthy
Population Size: 496
Sources: Page: p. 66
Hypersensitivity reaction 1 patient
Disc. AE
4 mg/kg single, intravenous
Recommended
Dose: 4 mg/kg
Route: intravenous
Route: single
Dose: 4 mg/kg
Sources: Page: p. 66
unhealthy
n = 1505
Health Status: unhealthy
Population Size: 1505
Sources: Page: p. 66
Hypersensitivity reaction 1 patient
Disc. AE
32 mg/kg single, intravenous
Dose: 32 mg/kg
Route: intravenous
Route: single
Dose: 32 mg/kg
Sources: Page: p. 66
unhealthy
n = 165
Health Status: unhealthy
Population Size: 165
Sources: Page: p. 66
Tachycardia 1 patient
Disc. AE
8 mg/kg single, intravenous
Dose: 8 mg/kg
Route: intravenous
Route: single
Dose: 8 mg/kg
Sources: Page: p. 66
unhealthy
n = 156
Health Status: unhealthy
Population Size: 156
Sources: Page: p. 66
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.
2008 Sep
Sugammadex: A revolutionary drug in neuromuscular pharmacology.
2013 Sep-Dec
Patents

Patents

Sample Use Guides

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
75 ug/ml sugammadex causes apoptotic/necrosis neuron death in primary cultures.
Name Type Language
SUGAMMADEX
EMA EPAR   INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
.GAMMA.-CYCLODEXTRIN, 6A,6B,6C,6D,6E,7F,6G,6H-OCTAKIS-S-(2-CARBOXYETHYL)-6A,6B,6C,6D,6E,7F,6G,6H-OCTATHIO-
Common Name English
SUGAMMADEX [WHO-DD]
Common Name English
6,6',6'',6''',6'''',6''''',6'''''',6'''''''-OCTAKIS-S-(2-CARBOXYLATOETHYL)-6,6',6'',6''',6'''',6''''',6'''''',6'''''''-OCTATHIOCYCLO-.ALPHA.-(1->4)-D-OCTAGLUCOPYRANOSIDE
Common Name English
SUGAMMADEX [USAN]
Common Name English
SUGAMMADEX [EMA EPAR]
Common Name English
SUGAMMADEX [MI]
Common Name English
SUGAMMADEX [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QV03AB35
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
WHO-ATC V03AB35
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
NCI_THESAURUS C26170
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C80629
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
RXCUI
1726988
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY RxNorm
CAS
343306-71-8
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
PUBCHEM
6918585
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
WIKIPEDIA
SUGAMMADEX
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
NDF-RT
N0000168522
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY gamma-Cyclodextrins [Chemical/Ingredient]
FDA UNII
361LPM2T56
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
EVMPD
SUB26695
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
MESH
C453980
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
DRUG CENTRAL
4233
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
MERCK INDEX
M10289
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB06206
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
INN
8528
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL2111107
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY
LACTMED
Sugammadex
Created by admin on Sat Jun 26 00:54:54 UTC 2021 , Edited by admin on Sat Jun 26 00:54:54 UTC 2021
PRIMARY