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Details

Stereochemistry ACHIRAL
Molecular Formula C10H14N2O4S2
Molecular Weight 290.359
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULTHIAME

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N2CCCCS2(=O)=O

InChI

InChIKey=HMHVCUVYZFYAJI-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C10H14N2O4S2
Molecular Weight 290.359
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.cochrane.org/CD009472/EPILEPSY_sulthiame-add-therapy-epilepsy

Sulthiame is a potent inhibitor of carbonic anhydrase II, VII, IX, and XII. Sulthiame is an antiepileptic drug that is used widely in some European countries and in Israel. Sometimes it is used as an additional (add-on) antiepileptic medicine in non responders, alongside an existing antiepileptic medicine.

CNS Activity

Originator

Schenley Industries
1
Curator's Comment: reference retrieved from http://www.druglead.com/cds/Sulthiame.html

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 7.0 nM [Ki]
Inhibitor
8297
 6.0 nM [Ki]
Inhibitor
8297
 43.0 nM [Ki]
Inhibitor
8297
 56.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
OSPOLOT

Approved Use

Epileptic seizures of focal origin with or without secondary generalisation, especially benign partial epilepsies in childhood, such as rolandic epilepsy, pseudo-Lennox syndrome, bioelectric status epilepticus in non-REM sleep (ESES), Landau-Kleffner syndrome.

Launch Date

1969
PubMed

PubMed

TitleDatePubMed
Phenytoin (Dilantin) intoxication.
1967
[Treatment of partial epilepsies with a sultiamum containing combination].
1969 Dec
[Permanent cerebellar damage through temporary overdase of hydantoin].
1969 Jun 20
Delayed phenytoin idiosyncrasy.
1969 Nov 22
Carbamazepine-induced choreoathetoid dyskinesias.
1982 Jun
Sulthiame in adults with refractory epilepsy and learning disability: an open trial.
2002 Aug
Carbamazepine versus sulthiame in treating benign childhood epilepsy with centrotemporal spikes.
2002 Dec
Serum concentrations of topiramate in patients with epilepsy: influence of dose, age, and comedication.
2002 Jun
Carbonic anhydrase inhibitor sulthiame reduces intracellular pH and epileptiform activity of hippocampal CA3 neurons.
2002 May
New antiepileptic drug therapies.
2002 Nov
Add-on treatment with pyridoxine and sulthiame in 12 infants with West syndrome: an open clinical study.
2002 Sep
[Electroclinical characteristics of Landau-Kleffner syndrome].
2003
Treatment with Sulthiame (Ospolot) in benign partial epilepsy of childhood and related syndromes: an open clinical and EEG study.
2003 Apr
The influence of sulthiame on EEG in children with benign childhood epilepsy with centrotemporal spikes (BECTS).
2003 Feb
Effect of antiepileptic drug monotherapy on crystalluria in children and young adults.
2003 Oct
Visually self-induced seizures sensitive to round objects.
2005 May
The spectrum from BCECTS to LKS: The Rolandic EEG trait-impact on cognition.
2006
Sulthiame therapy for continuous spike and wave in slow-wave sleep.
2006 Sep
Treatment of epilepsy in Rett syndrome.
2007 Jan
Tiagabine: efficacy and safety in partial seizures - current status.
2008 Aug
Deterioration in cognitive function in children with benign epilepsy of childhood with central temporal spikes treated with sulthiame.
2008 Jan
Current trends in the treatment of infantile spasms.
2009
Rational treatment options with AEDs and ketogenic diet in Landau-Kleffner syndrome: still waiting after all these years.
2009 Aug
Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings.
2009 Feb 15
Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates?
2009 Sep
Correspondence on ''deterioration in cognitive function in children with benign epilepsy of childhood with central temporal spikes treated with sulthiame''.
2010 Jan
2-Chloro-N-(4-sulfamoylphen-yl)acetamide.
2010 Jun 5
Chronic antiepileptic monotherapy, bone metabolism, and body composition in non-institutionalized children.
2010 Mar
Respiratory alkalosis and metabolic acidosis in a child treated with sulthiame.
2010 Oct
Patents

Patents

US20030056896
1
WO1995029665A1
2

Sample Use Guides

In Vivo Use Guide
The dosage must be established and monitored by the doctor on an individual basis. The maintenance dose is about 5 to 10 mg/kg body weight per day. It should be build up step-wise (tapered in) over a one-week period. Ospolot film-coated tablets have a dose notch. Due to the short half-life of sulthiame, the daily dose should as far as possible be spread over three single doses. If the daily dose is spread over the day in this way, constant plasma levels are to be expected after five to six days. Therapeutic plasma concentrations of sulthiame have not yet been determined.
Route of Administration: Oral
In Vitro Use Guide
In the majority of hippocampal CA3 neurons sulthiame (1.0-1.5 mM) reversibly decreased pHi. Sulthiame (1.0-2.5 mM) reversibly reduced the frequency of action potentials and epileptiform bursts.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:41 GMT 2023
Record UNII
I00Q766CZ2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULTHIAME
MI   USAN  
USAN  
Official Name English
SULTIAME [JAN]
Common Name English
SULTIAME
INN   MART.   WHO-DD  
INN  
Official Name English
sultiame [INN]
Common Name English
SULTIAME [MART.]
Common Name English
SULTHIAME [MI]
Common Name English
Sultiame [WHO-DD]
Common Name English
TROLONE
Brand Name English
OSPOLOT
Brand Name English
P-(TETRAHYDRO-2H-1,2-THIAZIN-2-YL)BENZENESULFONAMIDE, S,S-DIOXIDE
Common Name English
SULTHIAME [USAN]
Common Name English
4-(Tetrahydro-2H-1,2-thiazin-2-yl)benzenesulfonamide, S,S-dioxide
Common Name English
RIKER-594
Code English
RIKER 594
Code English
BENZENESULFONAMIDE, 4-(TETRAHYDRO-2H-1,2-THIAZIN-2-YL)-, S,S-DIOXIDE
Common Name English
CONADIL
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 401213
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
NCI_THESAURUS C264
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WHO-ATC N03AX03
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WHO-VATC QN03AX03
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Code System Code Type Description
ChEMBL
CHEMBL328560
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PRIMARY
EPA CompTox
DTXSID4023626
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PRIMARY
SMS_ID
100000088819
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PRIMARY
NCI_THESAURUS
C152469
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PRIMARY
FDA UNII
I00Q766CZ2
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PRIMARY
MESH
C084593
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PRIMARY
INN
1434
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PRIMARY
DRUG BANK
DB08329
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PRIMARY
EVMPD
SUB10762MIG
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PRIMARY
ECHA (EC/EINECS)
200-511-0
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PRIMARY
MERCK INDEX
m10392
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PRIMARY Merck Index
DRUG CENTRAL
2540
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PRIMARY
RXCUI
10240
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PRIMARY RxNorm
PUBCHEM
5356
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PRIMARY
WIKIPEDIA
Sultiame
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
CAS
61-56-3
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
Related Record Type Details
Structure of SULTHIAME
ACTIVE MOIETY
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