Sugammadex

Identification

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Name
Sugammadex
Accession Number
DB06206
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Sugammadex
External IDs
ORG-25969
Product Ingredients
IngredientUNIICASInChI Key
Sugammadex sodiumERJ6X2MXV7343306-79-6KMGKABOMYQLLDJ-UHFFFAOYSA-F
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BridionInjection, solution100 mg/1mLIntravenousMerck Sharp & Dohme Corp.2015-12-15Not applicableUs
BridionInjection, solution100 mg/1mLIntravenousMerck Sharp & Dohme Corp.2015-12-15Not applicableUs
BridionSolution100 mgIntravenousMerck Ltd.2016-02-19Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
361LPM2T56
CAS number
343306-71-8
Weight
Average: 2002.12
Monoisotopic: 2000.408874758
Chemical Formula
C72H112O48S8
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

Pharmacology

Indication

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

Associated Conditions
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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

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.

Affected organisms
  • Humans and other mammals
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
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when (R)-warfarin is combined with Sugammadex.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when (S)-Warfarin is combined with Sugammadex.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when 4-hydroxycoumarin is combined with Sugammadex.
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.
Acetylsalicylic acidThe risk or severity of bleeding and hemorrhage can be increased when Acetylsalicylic acid is combined with Sugammadex.
AlteplaseThe risk or severity of bleeding and hemorrhage can be increased when Alteplase is combined with Sugammadex.
AmediplaseThe risk or severity of bleeding and hemorrhage can be increased when Amediplase is combined with Sugammadex.
AnagrelideThe risk or severity of bleeding and hemorrhage can be increased when Anagrelide is combined with Sugammadex.
AncrodThe risk or severity of bleeding and hemorrhage can be increased when Ancrod is combined with Sugammadex.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
No interactions found.

References

General References
  1. Naguib M: Sugammadex: another milestone in clinical neuromuscular pharmacology. Anesth Analg. 2007 Mar;104(3):575-81. [PubMed:17312211]
  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. [PubMed:24098155]
  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. [PubMed:25885973]
External Links
KEGG Drug
D05940
PubChem Compound
6918585
PubChem Substance
347827763
ChemSpider
32689915
ChEBI
90953
ChEMBL
CHEMBL2111107
Wikipedia
Sugammadex
ATC Codes
V03AB35 — Sugammadex
AHFS Codes
  • 92:12.00 — Antidotes
FDA label
Download (354 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionIncidence of Postoperative Residual Curarization1
1Active Not RecruitingTreatmentNeuromuscular Blockade1
1CompletedTreatmentAnaphylaxis / Hypersensitivity1
1CompletedTreatmentHypersensitivity1
1CompletedTreatmentImpaired kidney function1
1RecruitingTreatmentHigh-Frequency Jet Ventilation / Vocal Cord Resection1
2CompletedNot AvailableObesity, Morbid1
2CompletedTreatmentMorbidly Obese Patients1
2CompletedTreatmentNeuromuscular Blockade2
2CompletedTreatmentAdjunct to general anesthesia therapy6
2Not Yet RecruitingPreventionCurarization, Postoperative Residual2
2Not Yet RecruitingTreatmentNeuromuscular Blockade1
2RecruitingSupportive CareAdjunct to general anesthesia therapy / Neuromuscular Blockade1
2RecruitingTreatmentImpaired kidney function / Neuromuscular Blockade1
2, 3CompletedTreatmentOrganophosphate Poisoning1
2, 3Not Yet RecruitingTreatmentAnaesthesia therapy / Beta-Thalassemia / Hepatic Metastases / Pediatric Cancer / Pediatric Hepatoblastoma / Pediatric Tumor1
2, 3RecruitingSupportive CareGeneral Surgery, Above 18 Years of Age / Non-operative Time1
2, 3Unknown StatusTreatmentNeuromuscular Blockade / Obesity, Morbid1
3CompletedHealth Services ResearchBariatric Patients1
3CompletedPreventionPost Operative Nausea and Vomiting (PONV)1
3CompletedTreatmentAnaesthesia therapy4
3CompletedTreatmentAnaesthesia therapy / Neuromuscular Blockade1
3CompletedTreatmentAntithrombotic Agents / Arthroplasty, Replacement, Hip / Arthroplasty, Replacement, Knee / Coagulation, Blood / Neuromuscular Blockade1
3CompletedTreatmentDiaphragmatic Dysfunction / Muscle Fatigue / Muscle Weakness1
3CompletedTreatmentNeuromuscular Blockade6
3CompletedTreatmentAdjunct to general anesthesia therapy / Neuromuscular Blockade2
3CompletedTreatmentPostoperative Neuromuscular Block1
3CompletedTreatmentSurgical Procedures, Elective1
3CompletedTreatmentAdjunct to general anesthesia therapy10
3RecruitingTreatmentGeneral Surgery1
3RecruitingTreatmentMinor burns1
3Unknown StatusNot AvailableNeuromuscular Blockade1
4Active Not RecruitingPreventionNeuromuscular Blockade / Postoperative Complications1
4Active Not RecruitingSupportive CareBladder Cancers / Malignant Neoplasms of Urinary Tract1
4Active Not RecruitingSupportive CareMuscle Relaxation1
4Active Not RecruitingTreatmentCoronary Artery Disease / General Surgery1
4Active Not RecruitingTreatmentGeneral Surgery1
4Active Not RecruitingTreatmentMalignant Neoplasms of Digestive Organs / Malignant Neoplasms of Female Genital Organs / Malignant Neoplasms of Male Genital Organs / Malignant Neoplasms of Urinary Tract1
4Active Not RecruitingTreatmentPharmacodynamics / Pharmacokinetics1
4CompletedNot AvailableInjury to Nerve During Surgery1
4CompletedNot AvailableLaparoscopy / Neuromuscular Blockade / Pneumoperitoneum / Rating Scales / Surgical Conditions1
4CompletedBasic ScienceElectromyography / Respiratory Muscles1
4CompletedDiagnosticIntraocular Pressure Changes During Tracheal Extubation1
4CompletedOtherNeuromuscular Blockade3
4CompletedPreventionIncidence of Postoperative Nausea and Vomiting1
4CompletedScreeningAnesthesia; Functional1
4CompletedScreeningSpinal Curvatures1
4CompletedSupportive CareAnaesthesia therapy / General Surgery / Neuromuscular Blockade / Spinal Diseases1
4CompletedSupportive CareBMI >30 kg/m2 / Cerebral Tissue Oxygenation / Laparoscopic Gastric Bypass Surgery / Respiratory Function / Surgical Conditions1
4CompletedTreatmentAnaesthesia1
4CompletedTreatmentAnaesthesia therapy2
4CompletedTreatmentAnesthesia Recovery1
4CompletedTreatmentAnesthesia Recovery Period / Laparoscopy1
4CompletedTreatmentBrain Cancer1
4CompletedTreatmentCaesarean Sections / Pregnancy1
4CompletedTreatmentChronic Renal Failure (CRF) / Neuromuscular Blockade1
4CompletedTreatmentCirrhosis and Chronic Liver Disease1
4CompletedTreatmentComplication of Ventilation Therapy / Observation of Neuromuscular Block / Postoperative Recovery1
4CompletedTreatmentGallbladder disorders1
4CompletedTreatmentIncomplete Reversal of Neuromuscular Block2
4CompletedTreatmentIntubation, Endotracheal1
4CompletedTreatmentLaparoscopic Herniotomy1
4CompletedTreatmentMajor Abdominal Surgery1
4CompletedTreatmentNeuromuscular Block2
4CompletedTreatmentNeuromuscular Blockade5
4CompletedTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
4CompletedTreatmentPostoperative Respiratory Condition1
4CompletedTreatmentPre-eclampsia Aggravated1
4CompletedTreatmentRespiratory Insufficiency1
4CompletedTreatmentRespiratory-Gated Imaging Techniques1
4CompletedTreatmentReversal of Neuromuscular Blockade1
4CompletedTreatmentReversal of Skeletal Muscle Relaxant / Underdosing of Skeletal Muscle Relaxants for Laparotomy1
4CompletedTreatmentSpine Surgery1
4CompletedTreatmentTime of a TOF Ratio >0,91
4CompletedTreatmentUnderdosing of Other General Anesthetics1
4Not Yet RecruitingDiagnosticResidual Neuromuscular Blockade1
4Not Yet RecruitingPreventionKidney Transplant; Complications / Postoperative Residual Curarization / Postoperative Residual Weakness1
4Not Yet RecruitingPreventionPost-operative Residual Curarization1
4Not Yet RecruitingPreventionPulmonary Complications1
4Not Yet RecruitingTreatmentGynecology / Surgery, Laparoscopic1
4Not Yet RecruitingTreatmentLaryngoscopic Surgical Procedures1
4Not Yet RecruitingTreatmentNeuromuscular Block1
4Not Yet RecruitingTreatmentNeuromuscular Block / Postoperative Residual Curarization1
4RecruitingOtherNeuromuscular Blockade1
4RecruitingPreventionEmergence Delirium1
4RecruitingPreventionLaparoscopic Sleeve Gastrectomy / Post Operative Nausea and Vomiting (PONV)1
4RecruitingSupportive CareCoronary Artery Bypass Graft Surgery Patients / Coronary Artery Bypass Graft, Aortic Valve Replacement or Coronary Artery Bypass Graft-Aortic Valve Replacement Combination Surgery / Post CABG Extubation1
4RecruitingTreatmentAnaesthesia therapy / Neuromuscular Blockade1
4RecruitingTreatmentAnesthesiology Management1
4RecruitingTreatmentMicrolaryngoscopy / Rigid Bronchoscopy1
4RecruitingTreatmentNeuromuscular Blockade3
4RecruitingTreatmentNeuromuscular Blockade / Respiratory Insufficiency1
4RecruitingTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
4RecruitingTreatmentPost-operative Residual Curarization1
4RecruitingTreatmentPosterior Cervical Decompression and Fusion / Posterior Cervical Spine Surgery1
4TerminatedTreatmentPost Operative Nausea and Vomiting (PONV) / Respiratory Conditions Due to Other External Agents1
4Unknown StatusSupportive CareAnesthesia Recovery Period1
4Unknown StatusTreatmentAdult Subjects Undergoing Abdominal Surgery Under General Anesthesia1
4Unknown StatusTreatmentNeuromuscular Blockade1
4WithdrawnNot AvailableNeuromuscular Blockade1
4WithdrawnOtherAmbulatory Difficulty1
4WithdrawnTreatmentGeneral Surgery / Postoperative pain1
4WithdrawnTreatmentAdjunct to general anesthesia therapy / Hip Fracture / Neuromuscular Blockade / Spinal Anaesthesia1
Not AvailableActive Not RecruitingNot AvailableNeuromuscular Blockade1
Not AvailableCompletedNot AvailableAnaesthesia therapy / General Surgery1
Not AvailableCompletedNot AvailableAnesthesia Recovery Period, Neuromuscular Blockade1
Not AvailableCompletedNot AvailableNeuromuscular Blockade2
Not AvailableCompletedNot AvailableNeuromuscular Monitoring After Administration of Neuromuscular Blocking Agents in Different Types of Surgery1
Not AvailableCompletedNot AvailableOutcome, Fatal1
Not AvailableCompletedNot AvailablePostoperative Residual Paralysis1
Not AvailableCompletedNot AvailableResidual Neuromuscular Block (TOF-ratio of 0.2)1
Not AvailableCompletedNot AvailableResidual Neuromuscular Blockade1
Not AvailableCompletedHealth Services ResearchMuscle Relaxation1
Not AvailableCompletedOtherAnesthesiology Management1
Not AvailableCompletedOtherPostoperative Residual Curarization / Transplantation, Liver1
Not AvailableCompletedOtherThyroid Intra-Operative Injury1
Not AvailableCompletedPreventionElderly Patients Undergoing Trans Pars Plana Vitrectomy With General Anesthesia1
Not AvailableCompletedScreeningPost Operative Cognitive Dysfunction1
Not AvailableCompletedSupportive CareResidual Neuromuscular Block1
Not AvailableCompletedSupportive CareRobot-Assisted Laparoscopic Radical Prostatectomy1
Not AvailableCompletedTreatmentFasciculations / Intubating Conditions / Patients Satisfaction / Postoperative Myalgia / Sore Throat1
Not AvailableCompletedTreatmentNeuromuscular Blockade1
Not AvailableCompletedTreatmentAdjunct to general anesthesia therapy1
Not AvailableEnrolling by InvitationSupportive CareSupratentorial Brain Tumor Surgery1
Not AvailableNot Yet RecruitingOtherPost-gastrointestinal bypass surgery1
Not AvailableNot Yet RecruitingPreventionThyroid Surgery1
Not AvailableRecruitingNot AvailableDelirium1
Not AvailableRecruitingDiagnosticBlood Coagulation Tests ( INR, APTT)1
Not AvailableRecruitingOtherBMI >30 kg/m2 / Malignant Neoplasm of Stomach1
Not AvailableRecruitingPreventionRecurrent Laryngeal Nerve / Vocal Cord Paralysis1
Not AvailableRecruitingScreeningAdjunct to general anesthesia therapy / Anesthetics, Inhalation / Neuromuscular Blockade1
Not AvailableRecruitingSupportive CareCritical Illness1
Not AvailableUnknown StatusTreatmentObesity, Morbid1
Not AvailableUnknown StatusTreatmentSurgical Procedure, Unspecified1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionIntravenous100 mg/1mL
SolutionIntravenous100 mg
InjectionNot applicable200 mg/2mL
InjectionNot applicable500 mg/5mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7265009No2007-09-042020-08-07Us
US7265099No2007-09-042020-08-07Us
US6949527No2005-09-272021-01-27Us
USRE44733No2014-01-282021-01-27Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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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

Taxonomy

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
Oligosaccharide / Oxane / Secondary alcohol / Acetal / Carboxylic acid derivative / Carboxylic acid / Polyol / Oxacycle / Thioether / Organoheterocyclic compound
show 8 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on March 19, 2008 10:17 / Updated on December 11, 2019 03:43