ChemFOnt: Showing chemical card for Sulfisoxazole (CFc000008799)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:43 UTC

Chemfont ID

CFc000008799

Molecule Identification

Common Name

Sulfisoxazole

Definition

Sulfisoxazole is only found in individuals that have used or taken this drug. It is a short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem]Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dimethyl-5-sulfanilamidoisoxazole	ChEBI
3,4-Dimethyl-5-sulfonamidoisoxazole	ChEBI
3,4-Dimethyl-5-sulphanilamidoisoxazole	ChEBI
3,4-Dimethyl-5-sulphonamidoisoxazole	ChEBI
3,4-Dimethylisoxazole-5-sulfanilamide	ChEBI
3,4-Dimethylisoxazole-5-sulphanilamide	ChEBI
4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide	ChEBI
4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulphonamide	ChEBI
5-(4-Aminophenylsulfonamido)-3,4-dimethylisoxazole	ChEBI
5-(p-Aminobenzenesulfonamido)-3,4-dimethylisoxazole	ChEBI
5-(p-Aminobenzenesulphonamido)-3,4-dimethylisoxazole	ChEBI
5-Sulfanilamido-3,4-dimethylisoxazole	ChEBI
5-Sulphanilamido-3,4-dimethyl-isoxazole	ChEBI
N'-(3,4)dimethylisoxazol-5-yl-sulphanilamide	ChEBI
N(1)-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide	ChEBI
N(1)-(3,4-Dimethyl-5-isoxazolyl)sulphanilamide	ChEBI
Sulfadimethylisoxazole	ChEBI
Sulfafurazol	ChEBI
Sulfafurazole	ChEBI
Sulfafurazolum	ChEBI
Sulfaisoxazole	ChEBI
Sulfasoxazole	ChEBI
Sulfisonazole	ChEBI
Sulfisoxasole	ChEBI
Sulfisoxazol	ChEBI
Sulfofurazole	ChEBI
Sulphadimethylisoxazole	ChEBI
Sulphafurazol	ChEBI
Sulphafurazole	ChEBI
Sulphaisoxazole	ChEBI
Sulphisoxazol	ChEBI
Sulphofurazole	ChEBI
Gantrisin	Kegg
5-(4-Aminophenylsulphonamido)-3,4-dimethylisoxazole	Generator
5-Sulphanilamido-3,4-dimethylisoxazole	Generator
5-Sulfanilamido-3,4-dimethyl-isoxazole	Generator
N'-(3,4)dimethylisoxazol-5-yl-sulfanilamide	Generator
Sulphafurazolum	Generator
Sulphasoxazole	Generator
Sulphisonazole	Generator
Sulphisoxasole	Generator
Sulphisoxazole	Generator
Sulfisoxazole dialamine	HMDB
Sulfisoxazole diolamine	HMDB
Ammonium salt sulfisoxazole	HMDB
Diolamine, sulfisoxazole	HMDB
Roche brand OF sulfisoxazole	HMDB
Sulfasoxizole	HMDB
Sulfisoxazole roche brand	HMDB
Sulfisoxazole, monosodium salt	HMDB
TL-Azole	HMDB
V-Sul	HMDB
Pediatric, gantrisin	HMDB
Sulfisoxazole, ammonium salt	HMDB
Sulfisoxazole, monolithium salt	HMDB
TL Azole	HMDB
V Sul	HMDB
Gantrisin pediatric	HMDB
Monolithium salt sulfisoxazole	HMDB
Sulfisoxazole, monosodium, monomesylate salt	HMDB
Vangard brand OF sulfisoxazole	HMDB
FNA brand OF sulfisoxazole	HMDB
Monosodium salt sulfisoxazole	HMDB
Neoxazoi	HMDB
Roche brand OF sulfisoxazole acetate	HMDB
Roche brand OF sulfisoxazole diolamine	HMDB
Sulfadimethyloxazole	HMDB
Sulfafurazol fna	HMDB
Sulfisoxazole, triammonium salt	HMDB
Triammonium salt sulfisoxazole	HMDB
Zenith brand OF sulfisoxazole	HMDB

Chemical Formula

C₁₁H₁₃N₃O₃S

Average Molecular Weight

267.304

Monoisotopic Molecular Weight

267.067761987

IUPAC Name

4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide

Traditional Name

ganda

CAS Registry Number

127-69-5

SMILES

CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C

InChI Identifier

InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3

InChI Key

NHUHCSRWZMLRLA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Organosulfonic acid amide
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Primary amine
Organosulfur compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:102484 )
isoxazoles (CHEBI:102484 )
sulfonamide antibiotic (CHEBI:102484 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014408)

Source

Exogenous

Exogenous (HMDB: HMDB0014408)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.14	ALOGPS
logP	0.73	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	5.8	ChemAxon
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.92 m³·mol⁻¹	ChemAxon
Polarizability	26.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon