Sugammadex

Identification

Summary

Sugammadex is a modified gamma cyclodextrin used to reverse neuromuscular blockade induced by vecuronium bromide and rocuronium bromide which are agents used for anesthesia.

Brand Names
Bridion
Generic Name
Sugammadex
DrugBank Accession Number
DB06206
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 2002.12
Monoisotopic: 2000.408874758
Chemical Formula
C72H112O48S8
Synonyms
  • Sugammadex
External IDs
  • ORG-25969

Pharmacology

Indication

Sugammadex is indicated for the reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide in adults undergoing surgery.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Sugammadex is a modified gamma-cyclodextrin which forms very tight water soluble complexes at a 1:1 ratio with steroidal neuromuscular blocking drugs (rocuronium > vecuronium >> pancuronium). Sugammadex creates a concentration gradient which favors movement of rocurionium from the neuromuscular junction into the plasma, which quickly reverses rocuronium-induced neuromuscular blockade. The free rocuronium in the plasma are then bound tightly to sugammadex, assisting the diffusion of the remaining rocuronium molecules out of the neuromuscular junction and increasing bound and free rocuronium in the plasma.

Absorption

Sugammadex is administered intravenously.

Volume of distribution

At steady state, the volume of distribution is 11-14 L in adult patients with normal renal function.

Protein binding

Sugammadex does not bind plasma proteins.

Metabolism

No metabolites of sugammadex were observed during clinical studies.

Route of elimination

Renal excretion of unchanged product. >90 of dose is excreted within 24 hours. 0.02% is excreted in feces and air.

Half-life

About 2 hours

Clearance

88L/min

Adverse Effects
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Toxicity

Patients with severe renal impairment (with creatinine clearance below 30 mL/min) should avoid use of drug as their clearance of the drug is reduced and there is inconsistent evidence about its safety in this subset of patients.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Abciximab is combined with Sugammadex.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Acenocoumarol is combined with Sugammadex.
AlteplaseThe risk or severity of bleeding and hemorrhage can be increased when Alteplase is combined with Sugammadex.
AncrodThe risk or severity of bleeding and hemorrhage can be increased when Ancrod is combined with Sugammadex.
AnistreplaseThe risk or severity of bleeding and hemorrhage can be increased when Anistreplase is combined with Sugammadex.
Antithrombin AlfaThe risk or severity of bleeding and hemorrhage can be increased when Antithrombin Alfa is combined with Sugammadex.
Antithrombin III humanThe risk or severity of bleeding and hemorrhage can be increased when Antithrombin III human is combined with Sugammadex.
ApixabanThe risk or severity of bleeding and hemorrhage can be increased when Apixaban is combined with Sugammadex.
ArdeparinThe risk or severity of bleeding and hemorrhage can be increased when Ardeparin is combined with Sugammadex.
ArgatrobanThe risk or severity of bleeding and hemorrhage can be increased when Argatroban is combined with Sugammadex.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Sugammadex sodiumERJ6X2MXV7343306-79-6KMGKABOMYQLLDJ-UHFFFAOYSA-F
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BridionInjection, solution100 mg/mlIntravenousMerck Sharp & Dohme B.V.2020-12-16Not applicableEU flag
BridionInjection, solution100 mg/1mLIntravenousMerck Sharp & Dohme Corp.2015-12-15Not applicableUS flag
BridionInjection, solution100 mg/mlIntravenousMerck Sharp & Dohme B.V.2020-12-16Not applicableEU flag
BridionInjection, solution100 mg/1mLIntravenousMedical Purchasing Solutions, Llc2015-12-15Not applicableUS flag
BridionSolution100 mg / mLIntravenousMerck Ltd.2016-02-19Not applicableCanada flag
BridionInjection, solution100 mg/1mLIntravenousMerck Sharp & Dohme Corp.2015-12-15Not applicableUS flag

Categories

ATC Codes
V03AB35 — Sugammadex
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Oligosaccharides
Alternative Parents
Oxanes / Secondary alcohols / Sulfenyl compounds / Polyols / Oxacyclic compounds / Dialkylthioethers / Carboxylic acids / Acetals / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Acetal / Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkylthioether / Hydrocarbon derivative / Oligosaccharide / Organic oxide
show 8 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
361LPM2T56
CAS number
343306-71-8
InChI Key
WHRODDIHRRDWEW-VTHZAVIASA-N
InChI
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
IUPAC Name
3-({[(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36S,38S,40S,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis({[(2-carboxyethyl)sulfanyl]methyl})-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2³,⁶.2⁸,¹¹.2¹³,¹⁶.2¹⁸,²¹.2²³,²⁶.2²⁸,³¹.2³³,³⁶]hexapentacontan-5-yl]methyl}sulfanyl)propanoic acid
SMILES
O[C@@H]1[C@@H](O)[C@@H]2O[C@H]3O[C@H](CSCCC(O)=O)[C@@H](O[C@H]4O[C@H](CSCCC(O)=O)[C@@H](O[C@H]5O[C@H](CSCCC(O)=O)[C@@H](O[C@H]6O[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](O[C@H]1O[C@@H]2CSCCC(O)=O)[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

References

General References
  1. Naguib M: Sugammadex: another milestone in clinical neuromuscular pharmacology. Anesth Analg. 2007 Mar;104(3):575-81. [Article]
  2. Schaller SJ, Fink H: Sugammadex as a reversal agent for neuromuscular block: an evidence-based review. Core Evid. 2013;8:57-67. doi: 10.2147/CE.S35675. Epub 2013 Sep 25. [Article]
  3. Nag K, Singh DR, Shetti AN, Kumar H, Sivashanmugam T, Parthasarathy S: Sugammadex: A revolutionary drug in neuromuscular pharmacology. Anesth Essays Res. 2013 Sep-Dec;7(3):302-6. doi: 10.4103/0259-1162.123211. [Article]
KEGG Drug
D05940
PubChem Compound
6918585
PubChem Substance
347827763
ChemSpider
32689915
RxNav
1726988
ChEBI
90953
ChEMBL
CHEMBL2111107
Wikipedia
Sugammadex
FDA label
Download (354 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionResidual Paralysis, Post Anesthesia1
4Active Not RecruitingTreatmentPharmacodynamics / Pharmacokinetics1
4CompletedNot AvailableLaparoscopy / Neuromuscular Blockade / Pneumoperitoneum / Rating Scales / Surgical Conditions1
4CompletedBasic ScienceElectromyography / Respiratory Muscles1
4CompletedDiagnosticIntraocular Pressure Changes During Tracheal Extubation1
4CompletedOtherLaparoscopic Cholecystectomy / Neostigmine / Neuromuscular Blockade Reversal Agent / Quality of Recovery / Sugammadex1
4CompletedOtherNeuromuscular Blockade3
4CompletedPreventionEmergence Delirium1
4CompletedPreventionIncidence of Postoperative Nausea and Vomiting1
4CompletedPreventionNeuromuscular Blockade / Postoperative Complications1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
InjectionIntravenous
Injection, solutionIntravenous100 mg/1mL
Injection, solutionIntravenous100 mg/ml
Injection, solutionIntravenous; Parenteral
SolutionIntravenous100 mg / mL
Injection, solutionIntravenous
SolutionIntravenous100 MG/ML
SolutionIntravenous500 mg
SolutionIntravenous200 mg
InjectionNot applicable200 mg/2mL
InjectionNot applicable500 mg/5mL
Injection, solutionParenteral
SolutionIntravenous100 mg/1ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7265009No2007-09-042020-08-07US flag
US7265099No2007-09-042020-08-07US flag
US6949527No2005-09-272021-01-27US flag
USRE44733No2014-01-282021-01-27US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility26.6 mg/mLALOGPS
logP-0.69ALOGPS
logP-5.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count48ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area769.76 Å2ChemAxon
Rotatable Bond Count40ChemAxon
Refractivity432.64 m3·mol-1ChemAxon
Polarizability189.62 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on March 19, 2008 16:17 / Updated on July 29, 2021 06:27