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Details

Stereochemistry ACHIRAL
Molecular Formula C18H14N4O5S
Molecular Weight 398.393
Optical Activity UNSPECIFIED
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=NC=CC=C3

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
Stereochemistry ACHIRAL
Additional Stereochemistry
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

Approval Year

PubMed

PubMed

TitleDatePubMed
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Patents

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
Created
by admin
on Mon Oct 21 20:42:30 UTC 2019
Edited
by admin
on Mon Oct 21 20:42:30 UTC 2019
Record UNII
3XC8GUZ6CB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFASALAZINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
SULFASALAZINE [USAN]
Common Name English
SULFASALAZINE [INN]
Common Name English
SULFASALAZINE [ORANGE BOOK]
Common Name English
SULFASALAZINE [EP]
Common Name English
SALAZOSULFAPYRIDINE [JAN]
Common Name English
SULFASALAZINE [WHO-DD]
Common Name English
SALAZOPYRIN
Brand Name English
SULFASALAZINE [MART.]
Common Name English
SULFASALAZINE [MI]
Common Name English
SULFASALAZINE [USP-RS]
Common Name English
SULFASALAZINE [VANDF]
Common Name English
SULFASALAZINUM [WHO-IP LATIN]
Common Name English
SULFASALAZINE [USP]
Common Name English
AZULFIDINE
Brand Name English
SALICYLAZOSULFAPYRIDINE
Common Name English
NSC-203730
Code English
NSC-667219
Code English
BENZOSULFA
Common Name English
SULFASALAZINE [IARC]
Common Name English
SULFASALAZOPYRIDINE
Common Name English
SULFASALAZINE [WHO-IP]
Common Name English
2-HYDROXY-5-((4-((2-PYRIDINYLAMINO)SULFONYL)PHENYL)AZO)BENZOIC ACID [WHO-IP]
Common Name English
BENZOIC ACID, 2-HYDROXY-5-(2-(4-((2-PYRIDINYLAMINO)SULFONYL)PHENYL)DIAZENYL)-
Systematic Name English
SULFASALAZINE [HSDB]
Common Name English
SULPHASALAZINE
Common Name English
Classification Tree Code System Code
NDF-RT N0000005760
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
NDF-RT N0000005760
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
WHO-VATC QA07EC01
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
NCI_THESAURUS C257
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
LIVERTOX 912
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
NDF-RT N0000005760
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
NDF-RT N0000175781
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
WHO-ATC A07EC01
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 17.3
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
NDF-RT N0000005760
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
Code System Code Type Description
MESH
D012460
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
EPA CompTox
599-79-1
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
NCI_THESAURUS
C29469
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
INN
2210
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
CAS
599-79-1
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
EVMPD
SUB20720
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
RXCUI
9524
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY RxNorm
EVMPD
SUB10727MIG
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFASALAZINE
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY Description: A bright yellow to brownish yellow powder; odourless. Solubility: Practically insoluble in water and ether R; very slightly soluble in ethanol (~750 g/l) TS; soluble in alkali hydroxides. Category: Antibacterial drug. Storage: Sulfasalazine should be kept in a tightly closed container, protected from light. Additional information: Sulfasalazine melts at about 255?C with decomposition. Definition: Sulfasalazine contains not less than 93.0% and not more than 103.0% of C18H14N4O5S, calculated with reference to the dried substance.
DRUG BANK
DB00795
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
HSDB
599-79-1
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
ECHA (EC/EINECS)
209-974-3
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
MERCK INDEX
M10343
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL421
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
IUPHAR
4840
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
WIKIPEDIA
Sulfasalazine
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
LactMed
599-79-1
Created by admin on Mon Oct 21 20:42:30 UTC 2019 , Edited by admin on Mon Oct 21 20:42:30 UTC 2019
PRIMARY
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