ChemFOnt: Showing chemical card for Sulfadoxine (CFc000009687)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:54 UTC

Chemfont ID

CFc000009687

Molecule Identification

Common Name

Sulfadoxine

Definition

Sulfadoxine is only found in individuals that have used or taken this drug. It is a long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Sulfanilamido-5,6-dimethoxypyrimidine	ChEBI
Sulfadoxina	ChEBI
Sulfadoxinum	ChEBI
Sulforthomidine	ChEBI
Sulphadoxine	ChEBI
Sulphormethoxine	ChEBI
4-Sulphanilamido-5,6-dimethoxypyrimidine	Generator
Sulphadoxina	Generator
Sulphadoxinum	Generator
Sulphorthomidine	Generator
Sulformethoxine	Generator
Sulfadoxine roche brand	HMDB
Roche brand OF sulfadoxine	HMDB
Sulformetoxine	HMDB
Sulphormetoxin	HMDB
Fanasil	HMDB
Sulphorthodimethoxine	HMDB

Chemical Formula

C₁₂H₁₄N₄O₄S

Average Molecular Weight

310.329

Monoisotopic Molecular Weight

310.073575646

IUPAC Name

4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

Traditional Name

sulfadoxine

CAS Registry Number

2447-57-6

SMILES

COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC

InChI Identifier

InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

InChI Key

PJSFRIWCGOHTNF-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
Alkyl aryl ether
Pyrimidine
Organosulfonic acid amide
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Ether
Azacycle
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9329 )
pyrimidines (CHEBI:9329 )

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)

Source

Exogenous

Exogenous (HMDB: HMDB0015413)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	0.72	ALOGPS
logP	0.58	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.12	ChemAxon
pKa (Strongest Basic)	2.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	116.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.81 m³·mol⁻¹	ChemAxon
Polarizability	30.01 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