ChemFOnt: Showing chemical card for Sulfasalazine (CFc000009257)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:20 UTC

Chemfont ID

CFc000009257

Molecule Identification

Common Name

Sulfasalazine

Definition

Sulfasalazine is only found in individuals that have used or taken this drug. It is a drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see mesalamine) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907)The mode of action of Sulfasalazine or its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), is still under investigation, but may be related to the anti-inflammatory and/or immunomodulatory properties that have been observed in animal and in vitro models, to its affinity for connective tissue, and/or to the relatively high concentration it reaches in serous fluids, the liver and intestinal walls, as demonstrated in autoradiographic studies in animals. In ulcerative colitis, clinical studies utilizing rectal administration of Sulfasalazine, SP and 5-ASA have indicated that the major therapeutic action may reside in the 5-ASA moiety. The relative contribution of the parent drug and the major metabolites in rheumatoid arthritis is unknown.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid	ChEBI
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid	ChEBI
4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene	ChEBI
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid	ChEBI
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid	ChEBI
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid	ChEBI
Azulfidine	ChEBI
Salazosulfapiridina	ChEBI
Salazosulfapyridine	ChEBI
Salazosulfapyridinum	ChEBI
Salicylazosulfapyridine	ChEBI
Sulfasalazina	ChEBI
Sulfasalazinum	ChEBI
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoic acid	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoic acid	Generator
4-(Pyridyl-2-amidosulphonyl)-3'-carboxy-4'-hydroxyazobenzene	Generator
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylic acid	Generator
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoic acid	Generator
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylic acid	Generator
Salazosulphapiridina	Generator
Salazosulphapyridine	Generator
Salazosulphapyridinum	Generator
Salicylazosulphapyridine	Generator
Sulphasalazina	Generator
Sulphasalazinum	Generator
Sulphasalazine	Generator
Sulfasalazin	HMDB

Chemical Formula

C₁₈H₁₄N₄O₅S

Average Molecular Weight

398.393

Monoisotopic Molecular Weight

398.068490268

IUPAC Name

2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

Traditional Name

sulfasalazine

CAS Registry Number

599-79-1

SMILES

OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1

InChI Identifier

InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+

InChI Key

NCEXYHBECQHGNR-QZQOTICOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

Alternative Parents

Substituents

Azobenzene
Benzenesulfonamide
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Benzenesulfonyl group
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyridine
Imidolactam
Benzenoid
Organosulfonic acid amide
Heteroaromatic compound
Vinylogous acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Azo compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9334 )
azobenzenes (CHEBI:9334 )
pyridines (CHEBI:9334 )

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

Cytoplasm (HMDB: HMDB0014933)
Membrane (HMDB: HMDB0014933)

Source

Exogenous

Exogenous (HMDB: HMDB0014933)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Non-steroidal anti-inflammatory drug (HMDB: HMDB0014933)
Gastrointestinal drug (HMDB: HMDB0014933)

Antiinfective agent (HMDB: HMDB0014933)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.94	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	2.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	141.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.6 m³·mol⁻¹	ChemAxon
Polarizability	39.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014933

DrugBank ID

DB00795

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10605946

KEGG Compound ID

C07316

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfasalazine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9334

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Sulfasalazine (CFc000009257)

MOL for CFc000009257 (Sulfasalazine)

3D MOL for CFc000009257 (Sulfasalazine)

3D SDF for CFc000009257 (Sulfasalazine)

3D-SDF for CFc000009257 (Sulfasalazine)

PDB for CFc000009257 (Sulfasalazine)

3D PDB for CFc000009257 (Sulfasalazine)

SMILES for CFc000009257 (Sulfasalazine)

INCHI for CFc000009257 (Sulfasalazine)

Structure for CFc000009257 (Sulfasalazine)

3D Structure for CFc000009257 (Sulfasalazine)