NAV

Sulthiame

Identification

Summary

Sulthiame is a carbonic anhydrase inhibitor used primarily in benign focal epilepsies of childhood that may be useful as an adjunct therapy in a variety of other refractory epilepsies.

Generic Name
Sulthiame
DrugBank Accession Number
DB08329
Background

Not Available

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 290.359
Monoisotopic: 290.039498326
Chemical Formula
C10H14N2O4S2
Synonyms
  • Sulthiame
  • Sultiame
  • Sultiamo
  • Sultiamum
External IDs
  • Bayer A-168
  • R-594
  • RIKER 594
  • RIKER-594
  • RP 10284
  • RP-10284
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofEpilepsy, rolandic••••••••••••••••••• •••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCarbonic anhydrase 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Sulthiame is combined with 1,2-Benzodiazepine.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulthiame.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Sulthiame.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulthiame.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Sulthiame.
Food Interactions
  • Take with food. Taking sulthiame with food, may reduce gastrointestinal upset.

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International/Other Brands
Conadil / Contravul / Elisal / Ospolot

Categories

ATC Codes
N03AX03 — SultiameG01AE10 — Combinations of sulfonamides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Sulfanilides
Direct Parent
Sulfanilides
Alternative Parents
Benzenesulfonamides / Benzenesulfonyl compounds / Delta sultams / Organosulfonamides / Organic sulfonamides / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
1,2-thiazinane / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Delta-sultam / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
I00Q766CZ2
CAS number
61-56-3
InChI Key
HMHVCUVYZFYAJI-UHFFFAOYSA-N
InChI
InChI=1S/C10H14N2O4S2/c11-18(15,16)10-5-3-9(4-6-10)12-7-1-2-8-17(12,13)14/h3-6H,1-2,7-8H2,(H2,11,15,16)
IUPAC Name
4-(1,1-dioxo-1lambda6,2-thiazinan-2-yl)benzene-1-sulfonamide
SMILES
NS(=O)(=O)C1=CC=C(C=C1)N1CCCCS1(=O)=O

References

General References
Not Available
PubChem Compound
5356
PubChem Substance
99444800
ChemSpider
5163
BindingDB
26999
RxNav
10240
ChEBI
32171
ChEMBL
CHEMBL328560
ZINC
ZINC000000002119
PDBe Ligand
OSP
Wikipedia
Sultiame
PDB Entries
2q1q

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentBenign rolandic epilepsy1
2CompletedTreatmentObstructive Sleep Apnea (OSA)1
1CompletedOtherEpilepsy1
Not AvailableRecruitingNot AvailableEpilepsy1
Not AvailableRecruitingNot AvailableImportance of Interictal Epileptiform Activity on Sleep EEG / Pediatric Epilepsy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral200 mg
Tablet, film coatedOral50 mg
Tablet, film coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.96 mg/mLALOGPS
logP0.37ALOGPS
logP-0.27Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.55Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area97.54 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity67.46 m3·mol-1Chemaxon
Polarizability27.86 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9633
Blood Brain Barrier+0.9382
Caco-2 permeable-0.6039
P-glycoprotein substrateNon-substrate0.6429
P-glycoprotein inhibitor INon-inhibitor0.7975
P-glycoprotein inhibitor IINon-inhibitor0.9393
Renal organic cation transporterNon-inhibitor0.7331
CYP450 2C9 substrateNon-substrate0.7677
CYP450 2D6 substrateNon-substrate0.8014
CYP450 3A4 substrateNon-substrate0.5196
CYP450 1A2 substrateNon-inhibitor0.8171
CYP450 2C9 inhibitorNon-inhibitor0.5435
CYP450 2D6 inhibitorNon-inhibitor0.9277
CYP450 2C19 inhibitorInhibitor0.6191
CYP450 3A4 inhibitorNon-inhibitor0.6993
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5444
Ames testNon AMES toxic0.6894
CarcinogenicityNon-carcinogens0.8414
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity1.7952 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8038
hERG inhibition (predictor II)Non-inhibitor0.6671
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-cce36a59af5292d14983
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01vx-0290000000-ea6c277ddff5e0b0d899
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-02f7bc141e03c8c66063
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fi0-2970000000-ee12d94062b2e99f8bff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0079-2980000000-cf1317c5c6f33e7712de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9210000000-5b1ec0783a89cdc36c9b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-171.6380567
predicted
DarkChem Lite v0.1.0
[M-H]-156.0116
predicted
DeepCCS 1.0 (2019)
[M+H]+158.36961
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.46278
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 19, 2021 00:27