ChemFOnt: Showing chemical card for Sulfadiazine (CFc000008879)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:50 UTC

Chemfont ID

CFc000008879

Molecule Identification

Common Name

Sulfadiazine

Definition

Sulfadiazine is only found in individuals that have used or taken this drug. It is one of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. [PubChem]Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Sulfanilamidopyrimidine	ChEBI
2-Sulfanilylaminopyrimidine	ChEBI
4-Amino-N-2-pyrimidinylbenzenesulfonamide	ChEBI
N(1)-2-Pyrimidinylsulfanilamide	ChEBI
N(1)-2-Pyrimidylsulfanilamide	ChEBI
Sulfadiazin	ChEBI
Sulfadiazina	ChEBI
Sulfadiazinum	ChEBI
Sulfapyrimidine	ChEBI
Sulphadiazine	ChEBI
2-Sulphanilamidopyrimidine	Generator
2-Sulphanilylaminopyrimidine	Generator
4-Amino-N-2-pyrimidinylbenzenesulphonamide	Generator
N(1)-2-Pyrimidinylsulphanilamide	Generator
N(1)-2-Pyrimidylsulphanilamide	Generator
Sulphadiazin	Generator
Sulphadiazina	Generator
Sulphadiazinum	Generator
Sulphapyrimidine	Generator
SDA	HMDB
Sulfadiazene	HMDB
Sulfanilamidopyrimidine	HMDB
Sulfapirimidin	HMDB
Sulfapyrimidin	HMDB
Sulfazin	HMDB
Zinc sulfadiazine	HMDB
Sulfadiazine, zinc	HMDB
Sulfazine	HMDB

Chemical Formula

C₁₀H₁₀N₄O₂S

Average Molecular Weight

250.277

Monoisotopic Molecular Weight

250.052446274

IUPAC Name

4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide

Traditional Name

sulfadiazine

CAS Registry Number

68-35-9

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1

InChI Identifier

InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

InChI Key

SEEPANYCNGTZFQ-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

substituted aniline (CHEBI:9328 )
sulfonamide (CHEBI:9328 )
pyrimidines (CHEBI:9328 )
sulfonamide antibiotic (CHEBI:9328 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014503)
Cell membrane (HMDB: HMDB0014503)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0014503)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiprotozoal (HMDB: HMDB0014503)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	0.25	ALOGPS
logP	0.39	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.01	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	64.2 m³·mol⁻¹	ChemAxon
Polarizability	24.39 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