Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C72H112O48S8 |
| Molecular Weight | 2002.151 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 40 / 40 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
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
| Molecular Formula | C72H112O48S8 |
| Molecular Weight | 2002.151 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 40 / 40 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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 |
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 dose: 4 mg/kg route of administration: Intravenous 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 dose: 4 mg/kg route of administration: Intravenous 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 dose: 4 mg/kg route of administration: Intravenous 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 dose: 4 mg/kg route of administration: Intravenous 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 dose: 4 mg/kg route of administration: Intravenous 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 dose: 4 mg/kg route of administration: Intravenous 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Anaphylactic shock... AEs leading to discontinuation/dose reduction: Anaphylactic shock (1 patient) Sources: |
4 mg/kg single, intravenous Recommended Dose: 4 mg/kg Route: intravenous Route: single Dose: 4 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hypersensitivity reaction... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction (1 patient) Sources: |
32 mg/kg single, intravenous Dose: 32 mg/kg Route: intravenous Route: single Dose: 32 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hypersensitivity reaction... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction (1 patient) Sources: |
8 mg/kg single, intravenous Dose: 8 mg/kg Route: intravenous Route: single Dose: 8 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Tachycardia... AEs leading to discontinuation/dose reduction: Tachycardia (1 patient) Sources: |
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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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 Health Status: healthy Age Group: 18-65 years Sex: M+F 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| Hypersensitivity reaction | 1 patient Disc. AE |
32 mg/kg single, intravenous Dose: 32 mg/kg Route: intravenous Route: single Dose: 32 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Tachycardia | 1 patient Disc. AE |
8 mg/kg single, intravenous Dose: 8 mg/kg Route: intravenous Route: single Dose: 8 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sugammadex: A revolutionary drug in neuromuscular pharmacology. | 2015-04-18 |
|
| Sugammadex, a neuromuscular blockade reversal agent, causes neuronal apoptosis in primary cultures. | 2013 |
|
| Discovery, development, and clinical application of sugammadex sodium, a selective relaxant binding agent. | 2009-02-06 |
|
| Pharmacokinetic-pharmacodynamic model for the reversal of neuromuscular blockade by sugammadex. | 2009-01 |
|
| Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing. | 2008-09 |
|
| Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships. | 2002-04-25 |
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
| Substance Class |
Chemical
Created
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| Record UNII |
361LPM2T56
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Validated (UNII)
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WHO-VATC |
QV03AB35
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V03AB35
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NCI_THESAURUS |
C26170
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C80629
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1726988
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343306-71-8
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6918585
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SUGAMMADEX
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N0000168522
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PRIMARY | gamma-Cyclodextrins [Chemical/Ingredient] | ||
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C453980
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m10289
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CD-10
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Sugammadex
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LIGAND->BINDER |
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EXCRETED UNCHANGED |
On an average, more than 90% of sugammadex was recovered in urine within 24 hours. Other PK studies also showed that 65-97% of the dose was recovered in urine. The differences in urine excretion percentage may be partly due to error associated with urine sample collection.
URINE
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LIGAND->BINDER |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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