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
Thumb
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

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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Toxicity

Not Available

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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Sulthiame is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Sulthiame.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Sulthiame.
AclidiniumSulthiame may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Sulthiame.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Sulthiame.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Sulthiame.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Sulthiame.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Sulthiame.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Sulthiame.
Interactions
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Food Interactions
  • Take with food. Taking sulthiame with food, may reduce gastrointestinal upset.

Products

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International/Other Brands
Conadil / Contravul / Elisal / Ospolot

Categories

ATC Codes
N03AX03 — Sultiame
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
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentEpilepsy, Rolandic1
1CompletedOtherEpilepsies1
Not AvailableRecruitingNot AvailableEpilepsies1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
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/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

Targets

Drugtargets2
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Details
1. 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 on September 15, 2010 21:30 / Updated on June 19, 2021 00:27