ChemFOnt: Showing chemical card for Sulfamethazine (CFc000009786)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:02 UTC

Chemfont ID

CFc000009786

Molecule Identification

Common Name

Sulfamethazine

Definition

Sulfamethazine is only found in individuals that have used or taken this drug. It is a sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]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
(p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin	ChEBI
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine	ChEBI
2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine	ChEBI
2-Sulfanilamido-4,6-dimethylpyrimidine	ChEBI
4,6-Dimethyl-2-sulfanilamidopyrimidine	ChEBI
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide	ChEBI
4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide	ChEBI
4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide	ChEBI
6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin	ChEBI
N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide	ChEBI
N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide	ChEBI
N(1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide	ChEBI
SMZ	ChEBI
Sulfadimethyldiazine	ChEBI
Sulfadimethylpyrimidine	ChEBI
Sulfadimidina	ChEBI
Sulfadimidine	ChEBI
Sulfadimidinum	ChEBI
Sulfametazina	ChEBI
Sulfametazyny	ChEBI
Sulfamethazone	ChEBI
Sulfamezathine	ChEBI
Sulphadimethylpyrimidine	ChEBI
Sulphamethazine	ChEBI
(p-Aminobenzolsulphonyl)-2-amino-4,6-dimethylpyrimidin	Generator
2-(4-Aminobenzenesulphonamido)-4,6-dimethylpyrimidine	Generator
2-(p-Aminobenzenesulphonamido)-4,6-dimethylpyrimidine	Generator
2-Sulphanilamido-4,6-dimethylpyrimidine	Generator
4,6-Dimethyl-2-sulphanilamidopyrimidine	Generator
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulphonamide	Generator
4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulphonamide	Generator
4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulphonamide	Generator
6-(4'-Aminobenzol-sulphonamido)-2,4-dimethylpyrimidin	Generator
N-(4,6-Dimethyl-2-pyrimidyl)sulphanilamide	Generator
N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulphanilamide	Generator
N(1)-(4,6-Dimethyl-2-pyrimidyl)sulphanilamide	Generator
Sulphadimethyldiazine	Generator
Sulphadimidina	Generator
Sulphadimidine	Generator
Sulphadimidinum	Generator
Sulphametazina	Generator
Sulphametazyny	Generator
Sulphamethazone	Generator
Sulphamezathine	Generator
Sulfadimezine	MeSH, HMDB

Chemical Formula

C₁₂H₁₄N₄O₂S

Average Molecular Weight

278.33

Monoisotopic Molecular Weight

278.083746402

IUPAC Name

4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide

Traditional Name

sulfamethazine

CAS Registry Number

57-68-1

SMILES

CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1

InChI Identifier

InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)

InChI Key

ASWVTGNCAZCNNR-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
Pyrimidine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:102265 )
pyrimidines (CHEBI:102265 )
sulfonamide antibiotic (CHEBI:102265 )

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

Extracellular (HMDB: HMDB0015522)

Source

Exogenous

Exogenous (HMDB: HMDB0015522)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Anti-infective (HMDB: HMDB0015522)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	0.43	ALOGPS
logP	0.65	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.38 m³·mol⁻¹	ChemAxon
Polarizability	28.8 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