SULTHIAME

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17588751
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17588751	Inhibitor 8504	7.0 nM [Ki]
Carbonic anhydrase VI 17 Target ID: CHEMBL3025 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17588751	Inhibitor 8504	6.0 nM [Ki]
Carbonic anhydrase IX 36 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17588751	Inhibitor 8504	43.0 nM [Ki]
Carbonic anhydrase XII 30 Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17588751	Inhibitor 8504	56.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Rishum_1_250060716.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Analyte	Population
0.02 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.18 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.88 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1.24 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.57 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
24.04 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
50.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
90.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31990440/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SULTHIAME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
71% OTHER GOV'T https://www.pharmadoor.com.br/images/medicamentos/bulas/bula_ospolot.pdf	single, oral		SULTHIAME plasma	Homo sapiens population: age: UNKNOWN sex: UNKNOWN food status:

Doses

Dose	Population	Adverse events
400 mg 1 times / day steady, oral Highest studied dose\|Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/	Disc. AE: Parasthesia, Headache... AEs leading to discontinuation/dose reduction: Parasthesia (79%) Headache (24%) Dizziness (6%) Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/
6 mg/kg 1 times / day multiple, Studied dose Dose: 6 mg/kg, 1 times / day Route: multiple Dose: 6 mg/kg, 1 times / day Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext	Disc. AE: Seizures, Behavior abnormal... AEs leading to discontinuation/dose reduction: Seizures (2 patients) Behavior abnormal (1 patient) Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext

AEs

AE	Significance	Dose	Population
Headache	24% Disc. AE	400 mg 1 times / day steady, oral Highest studied dose\|Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/
Dizziness	6% Disc. AE	400 mg 1 times / day steady, oral Highest studied dose\|Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/
Parasthesia	79% Disc. AE	400 mg 1 times / day steady, oral Highest studied dose\|Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/35202553/
Behavior abnormal	1 patient Disc. AE	6 mg/kg 1 times / day multiple, Studied dose Dose: 6 mg/kg, 1 times / day Route: multiple Dose: 6 mg/kg, 1 times / day Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext
Seizures	2 patients Disc. AE	6 mg/kg 1 times / day multiple, Studied dose Dose: 6 mg/kg, 1 times / day Route: multiple Dose: 6 mg/kg, 1 times / day Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://www.seizure-journal.com/article/S1059-1311(17)30107-3/fulltext

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 123.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 124.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 118.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 124.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 114.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5356#section=Biological-Test-Results Page: 122.0

PubMed

Title	Date	PubMed
Respiratory alkalosis and metabolic acidosis in a child treated with sulthiame.	2010-10	20930598
2-Chloro-N-(4-sulfamoylphen-yl)acetamide.	2010-06-05	21587833
Chronic antiepileptic monotherapy, bone metabolism, and body composition in non-institutionalized children.	2010-03	19709134
Correspondence on ''deterioration in cognitive function in children with benign epilepsy of childhood with central temporal spikes treated with sulthiame''.	2010-01	20032519
Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates?	2009-09	19703035
Rational treatment options with AEDs and ketogenic diet in Landau-Kleffner syndrome: still waiting after all these years.	2009-08	19682054
Clinical spectrum and medical treatment of children with electrical status epilepticus in sleep (ESES).	2009-06	19054417
Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings.	2009-02-15	19168351
[Sulthiame treatment for patients with intractable epilepsy].	2009-01	19172811
Current trends in the treatment of infantile spasms.	2009	19557123
Treatment of Lennox-Gastaut syndrome: overview and recent findings.	2008-12	19337447
Tiagabine: efficacy and safety in partial seizures - current status.	2008-08	19043517
Deterioration in cognitive function in children with benign epilepsy of childhood with central temporal spikes treated with sulthiame.	2008-01	18184938
[Treatment of epilepsy with third-line antiepileptic drugs: felbamate, tiagabine, and sulthiame].	2007-12	17604973
Carbonic anhydrase inhibitors. Interaction of the antiepileptic drug sulthiame with twelve mammalian isoforms: kinetic and X-ray crystallographic studies.	2007-09-01	17588751
Treatment of epilepsy in Rett syndrome.	2007-01	17178248
A single dose of sulthiame induces a selective increase in resting motor threshold in human motor cortex: A transcranial magnetic stimulation study.	2006-11	16930943
Recurrent absence status epilepticus (spike-and-wave stupor) associated with lamotrigine therapy.	2006-09	16970892
Sulthiame therapy for continuous spike and wave in slow-wave sleep.	2006-09	16939861
P50 sensory gating deficit in children with centrotemporal spikes and sharp waves in the EEG.	2006-01-30	16246492
Effect of antiepileptic drug monotherapy on urinary pH in children and young adults.	2006-01	15909204
The spectrum from BCECTS to LKS: The Rolandic EEG trait-impact on cognition.	2006	17105466
Children with rolandic epilepsy have abnormalities of oromotor and dichotic listening performance.	2005-09	16138667
Sulthiame but not levetiracetam exerts neurotoxic effect in the developing rat brain.	2005-06	15869952
Perisylvian polymicrogyria in Landau-Kleffner syndrome.	2005-05-10	15883344
Visually self-induced seizures sensitive to round objects.	2005-05	15857450
Effect of antiepileptic drug polytherapy on crystalluria.	2005-02	15664771
[Antiepileptic drugs in the treatment of autistic regression syndromes].	2005-01-15	15736083
Management of Landau-Kleffner syndrome.	2005	16356025
[The risk of second seizure in children with benign childhood epilepsy with centrotemporal spikes without treatment--a prospective study].	2005	15813357
Sulthiame in childhood epilepsy.	2004-10	15491376
Sulthiame in the primary therapy of West syndrome: a randomized double-blind placebo-controlled add-on trial on baseline pyridoxine medication.	2004-02	14738417
Effect of antiepileptic drug monotherapy on crystalluria in children and young adults.	2003-10	14586614
Treatment with Sulthiame (Ospolot) in benign partial epilepsy of childhood and related syndromes: an open clinical and EEG study.	2003-04	12776234
The influence of sulthiame on EEG in children with benign childhood epilepsy with centrotemporal spikes (BECTS).	2003-02	12558577
[Electroclinical characteristics of Landau-Kleffner syndrome].	2003	14571670
Carbamazepine versus sulthiame in treating benign childhood epilepsy with centrotemporal spikes.	2002-12	12593467
New antiepileptic drug therapies.	2002-11	12616686
Add-on treatment with pyridoxine and sulthiame in 12 infants with West syndrome: an open clinical study.	2002-09	12160666
Sulthiame in adults with refractory epilepsy and learning disability: an open trial.	2002-08	12200218
Serum concentrations of topiramate in patients with epilepsy: influence of dose, age, and comedication.	2002-06	12021627
Carbonic anhydrase inhibitor sulthiame reduces intracellular pH and epileptiform activity of hippocampal CA3 neurons.	2002-05	12027906
Progressive elevation of liver enzymes in a child treated with sulthiame.	2001-06	11521216
Reduction of voltage-operated sodium currents by the anticonvulsant drug sulthiame.	2001-05-04	11325350
Carbamazepine-induced choreoathetoid dyskinesias.	1982-06	6811702
[Treatment of partial epilepsies with a sultiamum containing combination].	1969-12	4392323
Delayed phenytoin idiosyncrasy.	1969-11-22	5354845
[Permanent cerebellar damage through temporary overdase of hydantoin].	1969-06-20	5785298
Phenytoin (Dilantin) intoxication.	1967	6081207

Patents

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 `Mon Mar 31 17:45:03 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:03 GMT 2025`
Record UNII	I00Q766CZ2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULTIAME

Preferred Name

English

SULTHIAME

Official Name

English

SULTIAME [JAN]

Common 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