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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11960492Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11960492
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1201244: ROCURONIUM |
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Target ID: CHEMBL1201219: VECURONIUM Sources: https://www.ncbi.nlm.nih.gov/pubmed/19104176 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | BRIDION Approved UseBRIDION (sugammadex) is indicated for the reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide in adults undergoing surgery Launch Date2015 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
66.1 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
61.1 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02011490 |
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
Dose | Population | Adverse 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%) Sources: 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%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/022225Orig1s000PharmR.pdf#page=198 Page: 198.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing. | 2008 Sep |
|
Sugammadex, a neuromuscular blockade reversal agent, causes neuronal apoptosis in primary cultures. | 2013 |
|
Sugammadex: A revolutionary drug in neuromuscular pharmacology. | 2013 Sep-Dec |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23983586
75 ug/ml sugammadex causes apoptotic/necrosis neuron death in primary cultures.
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NCI_THESAURUS |
C26170
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EMA ASSESSMENT REPORTS |
BRIDION (AUTHORIZED: NEUROMUSCULAR BLOCKADE)
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CHEMBL2111107
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ACTIVE MOIETY
SUBSTANCE RECORD