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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10N4O2S2
Molecular Weight 270.331
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETHIZOLE

SMILES

CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1

InChI

InChIKey=VACCAVUAMIDAGB-UHFFFAOYSA-N
InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

HIDE SMILES / InChI
Molecular Formula C9H10N4O2S2
Molecular Weight 270.331
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sulfamethizole is an oral antiobiotic, which was used against urinary tract infections under the name Thiosulfil. Sulfamethizole blocks bacterial growth by inhibiting folic acid synthesis via enzyme called dihydropteroate synthase. The drug is no longer marketed in the USA.

Approval Year

1953
193

Targets

Primary TargetPharmacologyConditionPotency
Bacterial dihydropteroate synthase
44
Inhibitor
8,297
 7.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Urinary tract infections
205
 Curative
Approved
8,429
THIOSULFIL

Cmax

ValueDoseCo-administeredAnalytePopulation
62.88 μg/mL
1 g single, oral
 SULFAMETHIZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
144 μg × h/mL
1 g single, oral
 SULFAMETHIZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.4 h
1 g single, oral
 SULFAMETHIZOLE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1,767

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Patents

JP2010528172A
6
JP2011528275A
455

Sample Use Guides

In Vivo Use Guide
Sulfamethizole is given orally at a dose of 1 gram twice daily for three days.
Route of Administration: Oral
In Vitro Use Guide
MIC values for Sulfamethizole were: 64 ug/ml (KMA-4845 and KMA-21476 E.coli strains), 128 ug/ml (KMA-26883 strain), 512 ug/ml (21804403-132 and UVI-203 strains), 1024 ug/ml (UVI-202 and 21398355-97 strains).
Substance Class Chemical
Record UNII
25W8454H16
Record Status Validated (UNII)
Record Version
NIH
NCATS
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