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. 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
Structure for Sugammadex (DB06206)
- 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 or vecuronium bromide in adults and pediatric patients ≥2 years old who are undergoing surgery.4
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- Contraindications & Blackbox Warnings
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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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of bleeding and hemorrhage can be increased when Abciximab is combined with Sugammadex. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Acenocoumarol is combined with Sugammadex. Alteplase The risk or severity of bleeding and hemorrhage can be increased when Alteplase is combined with Sugammadex. Ancrod The risk or severity of bleeding and hemorrhage can be increased when Ancrod is combined with Sugammadex. Anistreplase The risk or severity of bleeding and hemorrhage can be increased when Anistreplase is combined with Sugammadex. Antithrombin Alfa The risk or severity of bleeding and hemorrhage can be increased when Antithrombin Alfa is combined with Sugammadex. Antithrombin III human The risk or severity of bleeding and hemorrhage can be increased when Antithrombin III human is combined with Sugammadex. Apixaban The risk or severity of bleeding and hemorrhage can be increased when Apixaban is combined with Sugammadex. Ardeparin The risk or severity of bleeding and hemorrhage can be increased when Ardeparin is combined with Sugammadex. Argatroban The risk or severity of bleeding and hemorrhage can be increased when Argatroban is combined with Sugammadex. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sugammadex sodium ERJ6X2MXV7 343306-79-6 KMGKABOMYQLLDJ-UHFFFAOYSA-F - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bridion Solution 100 mg / mL Intravenous Merck Ltd. 2016-02-19 Not applicable Canada 
Bridion Injection, solution 100 mg/1mL Intravenous Medical Purchasing Solutions, Llc 2015-12-15 Not applicable US 
Bridion Injection, solution 100 mg/ml Intravenous Merck Sharp & Dohme B.V. 2020-12-16 Not applicable EU 
Bridion Injection, solution 100 mg/1mL Intravenous Merck Sharp & Dohme Llc 2015-12-15 Not applicable US Bridion Injection, solution 100 mg/ml Intravenous Merck Sharp & Dohme B.V. 2020-12-16 Not applicable EU Bridion Injection, solution 100 mg/1mL Intravenous Merck Sharp & Dohme Llc 2015-12-15 Not applicable US Sugammadex Amomed 100 mg/ml Intravenous Aop Orphan Pharmaceuticals Gmb H 2023-02-08 Not applicable EU Sugammadex Fresenius Kabi Injection, solution 100 mg/ml Intravenous Fresenius Kabi Deutschland Gmb H 2022-07-25 Not applicable EU Sugammadex Fresenius Kabi Injection, solution 100 mg/ml Intravenous Fresenius Kabi Deutschland Gmb H 2022-07-25 Not applicable EU Sugammadex Fresenius Kabi Injection, solution 100 mg/ml Intravenous Fresenius Kabi Deutschland Gmb H 2022-07-25 Not applicable EU
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
- Naguib M: Sugammadex: another milestone in clinical neuromuscular pharmacology. Anesth Analg. 2007 Mar;104(3):575-81. [Article]
- 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]
- 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]
- FDA Approved Products: Bridion (sugammadex) for intravenous injection [Link]
- External Links
- KEGG Drug
- D05940
- PubChem Compound
- 6918585
- PubChem Substance
- 347827763
- ChemSpider
- 32689915
- 1726988
- ChEBI
- 90953
- ChEMBL
- CHEMBL2111107
- Wikipedia
- Sugammadex
- FDA label
- Download (354 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Coronary Artery Disease (CAD) / Surgery 1 4 Completed Not Available Laparoscopy / Neuromuscular Blockade / Pneumoperitoneum / Rating Scales / Surgical Conditions 1 4 Completed Basic Science Electromyography / Respiratory Muscles 1 4 Completed Diagnostic Intraocular Pressure Changes During Tracheal Extubation 1 4 Completed Other Laparoscopic Cholecystectomy / Neostigmine / Neuromuscular Blockade Reversal Agent / Quality of Recovery / Sugammadex 1 4 Completed Other Neuromuscular Blockade 3 4 Completed Prevention Emergence Delirium 1 4 Completed Prevention Incidence of Postoperative Nausea and Vomiting 1 4 Completed Prevention Laparoscopic Sleeve Gastrectomy / Post Operative Nausea and Vomiting (PONV) 1 4 Completed Prevention Neuromuscular Blockade / Postoperative Complications 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 100 mg/ml Injection, solution Intravenous 100 mg/1mL Injection, solution Intravenous; Parenteral 100 MG/ML Solution Intravenous 100 mg / mL Injection, solution Intravenous 100 mg/mL Solution Intravenous 100 MG/ML Injection, solution Intravenous 200 mg/2ml Injection, solution Intravenous 500 mg/5ml Injection, solution Intravenous 100 mg Solution Intravenous 200 mg Solution Intravenous 500 mg Injection Not applicable 200 mg/2mL Injection Not applicable 500 mg/5mL Injection, solution Parenteral Injection, solution 100 MG/ML Solution Intravenous 100 mg/1ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7265009 No 2007-09-04 2020-08-07 US US7265099 No 2007-09-04 2020-08-07 US US6949527 No 2005-09-27 2021-01-27 US USRE44733 No 2014-01-28 2021-01-27 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 26.6 mg/mL ALOGPS logP -0.69 ALOGPS logP -5.4 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 2.82 Chemaxon Physiological Charge -8 Chemaxon Hydrogen Acceptor Count 48 Chemaxon Hydrogen Donor Count 24 Chemaxon Polar Surface Area 769.76 Å2 Chemaxon Rotatable Bond Count 40 Chemaxon Refractivity 432.64 m3·mol-1 Chemaxon Polarizability 189.62 Å3 Chemaxon Number of Rings 9 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at March 19, 2008 16:17 / Updated at March 22, 2023 23:54