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Details

Stereochemistry ACHIRAL
Molecular Formula C18H14N4O5S
Molecular Weight 398.393
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SULFASALAZINE

SMILES

OC(=O)C1=C(O)C=CC(=C1)\N=N\C2=CC=C(C=C2)S(=O)(=O)NC3=CC=CC=N3

InChI

InChIKey=NCEXYHBECQHGNR-QZQOTICOSA-N
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+

HIDE SMILES / InChI

Molecular Formula C18H14N4O5S
Molecular Weight 398.393
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Sulfasalazine is an anti-inflammatory indicated for the treatment of ulcerative colitis and rheumatoid arthritis. 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 vitromodels, 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. Sulfasalazine is used for the treatment of Crohn's disease and rheumatoid arthritis as a second-line agent. Sulfasalazine is marketed under the trade name Azulfidine among others.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.9 mM [IC50]
293.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AZULFIDINE
Primary
AZULFIDINE

Cmax

ValueDoseCo-administeredAnalytePopulation
12.9 μg/mL
2 g single, oral
SULFASALAZINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
98 μg × h/mL
2 g single, oral
SULFASALAZINE plasma
Homo sapiens
27.4 μM × h
6.5 mmol single, rectal
SULFASALAZINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.6 h
2 g single, oral
SULFASALAZINE plasma
Homo sapiens
7.6 h
unknown, intravenous
SULFASALAZINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Initial Therapy : Adults: 3 to 4 g daily in evenly divided doses with dosage intervals not exceeding eight hours. In some cases, it is advisable to initiate therapy with a smaller dosage, e.g., 1 to 2 g daily, to reduce possible gastrointestinal intolerance. If daily doses exceeding 4 g are required to achieve desired effects, the increased risk of toxicity should be kept in mind. Children, six years of age and older: 40 to 60 mg/kg body weight in each 24-hour period, divided into 3 to 6 doses. Maintenance Therapy : Adults: 2 g daily. Children, six years of age and older: 30 mg/kg body weight in each 24-hour period, divided into 4 doses.
Route of Administration: Oral
In Vitro Use Guide
Inhibition of arachidonate 5-lipoxygenase by sulfasalazine and its major metabolites was observed at higher concentrations (2-3 mM).
Substance Class Chemical
Record UNII
3XC8GUZ6CB
Record Status Validated (UNII)
Record Version