ChemFOnt: Showing chemical card for Sulfamethoxazole (CFc000009446)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:35 UTC

Chemfont ID

CFc000009446

Molecule Identification

Common Name

Sulfamethoxazole

Definition

Sulfamethoxazole is only found in individuals that have used or taken this drug. It is a bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(p-Aminophenylsulfonamido)-5-methylisoxazole	ChEBI
3-Sulfanilamido-5-methylisoxazole	ChEBI
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide	ChEBI
Gantanol	ChEBI
SMX	ChEBI
Sulphamethoxazole	ChEBI
3-(p-Aminophenylsulphonamido)-5-methylisoxazole	Generator
3-Sulphanilamido-5-methylisoxazole	Generator
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulphonamide	Generator
3-(p-Aminobenzenesulfonamido)-5-methylisoxazole	HMDB
3-(Para-aminophenylsulphonamido)-5-methylisoxazole	HMDB
4-Amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide	HMDB
4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide	HMDB
5-Methyl-3-sulfanilamidoisoxazole	HMDB
5-Methyl-3-sulfanylamidoisoxazole	HMDB
5-Methyl-3-sulfonylamidoisoxazole	HMDB
5-Methyl-3-sulphanil-amidoisoxazole	HMDB
Azo-gantanol	HMDB
Bactrim	HMDB
Metoxal	HMDB
N'-(5-methyl-3-isoxazole)sulfanilamide	HMDB
N'-(5-methyl-3-isoxazolyl)-sulfanilamide	HMDB
N'-(5-methyl-3-isoxazolyl)sulfanilamide	HMDB
N'-(5-methylisoxazol-3-yl)sulphanilamide	HMDB
N1-(5-Methyl-3-isoxazolyl)-sulfanilamide	HMDB
N1-(5-Methyl-3-isoxazolyl)sulfanilamide	HMDB
N1-(5-Methyl-3-isoxazolyl)sulphanilamide	HMDB
Ndimethyl1-(5-methyl-3-isoxazolyl)-sulfanilamide	HMDB
N^1-(5-methyl-3-isoxazolyl)-sulfanilamide	HMDB
Radonil	HMDB
Simsinomin	HMDB
Sinomin	HMDB
Sulfamethalazole	HMDB
Sulfamethoxazol	HMDB
Sulfamethoxazole(usan)	HMDB
Sulfamethylisoxazole	HMDB
Sulfisomezole	HMDB
Sulpha-methoxizole	HMDB
Sulphamethoxazol	HMDB
Sulphamethylisoxazole	HMDB
Sulphisomezole	HMDB

Chemical Formula

C₁₀H₁₁N₃O₃S

Average Molecular Weight

253.278

Monoisotopic Molecular Weight

253.052111923

IUPAC Name

4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

Traditional Name

sulfamethoxazole

CAS Registry Number

723-46-6

SMILES

CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1

InChI Identifier

InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

InChI Key

JLKIGFTWXXRPMT-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
Imidolactam
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
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

substituted aniline (CHEBI:9332 )
sulfonamide (CHEBI:9332 )
isoxazoles (CHEBI:9332 )
sulfonamide antibiotic (CHEBI:9332 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0015150)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	0.79	ALOGPS
logP	0.79	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.16	ChemAxon
pKa (Strongest Basic)	1.97	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	64.5 m³·mol⁻¹	ChemAxon
Polarizability	24.99 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