Identification
- Summary
Sulfasalazine is an anti-inflammatory drug used to treat Crohn's disease and rheumatoid arthritis.
- Brand Names
- Azulfidine, Salazopyrin, Salazopyrin En-tabs
- Generic Name
- Sulfasalazine
- DrugBank Accession Number
- DB00795
- Background
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)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulfasalazine (DB00795)
- Weight
- Average: 398.393
Monoisotopic: 398.068490268 - Chemical Formula
- C18H14N4O5S
- Synonyms
- 2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid
- 2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid
- 4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene
- 5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid
- 5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid
- 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid
- Azopyrin
- Salazosulfapiridina
- Salazosulfapyridine
- Salazosulfapyridinum
- Salicylazosulfapyridine
- Sulfasalazin
- Sulfasalazina
- Sulfasalazine
- Sulfasalazinum
- External IDs
- NSC-203730
- NSC-667219
- SSZ
Pharmacology
- Indication
For the treatment of Crohn's disease and rheumatoid arthritis as a second-line agent.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Sulfasalazine is an anti-inflammatory indicated for the treatment of ulcerative colitis and rheumatoid arthritis.
- Mechanism of action
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.
Target Actions Organism AArachidonate 5-lipoxygenase inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans AProstaglandin G/H synthase 1 inhibitorHumans APeroxisome proliferator-activated receptor gamma agonistHumans UInhibitor of nuclear factor kappa-B kinase subunit alpha inhibitorHumans UInhibitor of nuclear factor kappa-B kinase subunit beta inhibitorHumans UCystine/glutamate transporter inhibitorHumans UAcetyl-CoA acetyltransferase, mitochondrial inhibitorHumans UThromboxane-A synthase antagonistHumans UPhospholipase A2 antagonistHumans - Absorption
Not Available
- Volume of distribution
- 7.5 ± 1.6 L
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
The majority of 5-ASA stays within the colonic lumen and is excreted as 5-ASA and acetyl-5-ASA with the feces.
- Half-life
5-10 hours
- Clearance
- 1 L/h [IV administration]
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Arylamine N-acetyltransferase 1 NAT1*14A Not Available G > A | T > A | C > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*14B Not Available G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*15 Not Available C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*17 Not Available C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*19A Not Available C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*19B Not Available C > T | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 1 NAT1*22 Not Available A > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5A Not Available T > C | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5B Not Available T > C | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5C Not Available T > C | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5D Not Available T > C ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5E Not Available T > C | G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5F Not Available T > C | C > T | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5G Not Available T > C | C > T | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5H Not Available T > C | C > T | A > G | S287 Frameshift ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5I Not Available T > C | C > T | A > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*5J Not Available T > C | C > T | G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*6A Not Available G > A | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*6B Not Available G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*6C Not Available G > A | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*6D Not Available G > A | C > T | T > C ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*6E Not Available G > A | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*7A Not Available G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*7B Not Available G > A | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*10 Not Available G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*12D Not Available G > A | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14A Not Available G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14B Not Available G > A | C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14C Not Available G > A | T > C | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14D Not Available G > A | C > T | G > A ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14E Not Available G > A | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14F Not Available G > A | T > C | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*14G Not Available G > A | C > T | A > G ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*17 Not Available A > C ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Arylamine N-acetyltransferase 2 NAT2*19 Not Available C > T ADR Inferred Increased risk of Sulfapyridine dose related adverse effects, including skin rash. Details Glucose-6-phosphate 1-dehydrogenase Villeurbanne Not Available 1000_1002delACC ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Torun Not Available 1006A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sunderland Not Available 105_107delCAT ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Iwatsuki Not Available 1081G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Serres Not Available 1082C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tondela Not Available 1084_1101delCTGAACGAGCGCAAGGCC ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Loma Linda Not Available 1089C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aachen Not Available 1089C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tenri Not Available 1096A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Montpellier Not Available 1132G>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Calvo Mackenna Not Available 1138A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Riley Not Available 1139T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Olomouc Not Available 1141T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tomah Not Available 1153T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lynwood Not Available 1154G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Madrid Not Available 1155C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Iowa, Walter Reed, Springfield Not Available 1156A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Beverly Hills, Genova, Iwate, Niigata, Yamaguchi Not Available 1160G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hartford Not Available 1162A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Praha Not Available 1166A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Krakow Not Available 1175T>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wisconsin Not Available 1177C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nashville, Anaheim, Portici Not Available 1178G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Alhambra Not Available 1180G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bari Not Available 1187C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Puerto Limon Not Available 1192G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Covao do Lobo Not Available 1205C>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Clinic Not Available 1215G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Utrecht Not Available 1225C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Suwalki Not Available 1226C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Riverside Not Available 1228G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Japan, Shinagawa Not Available 1229G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kawasaki Not Available 1229G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Munich Not Available 1231A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Georgia Not Available 1284C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sumare Not Available 1292T->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Telti/Kobe Not Available 1318C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago de Cuba, Morioka Not Available 1339G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Harima Not Available 1358T->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Figuera da Foz Not Available 1366G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amiens Not Available 1367A>T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Noi Not Available 1376G->T, 1502T->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Fukaya Not Available 1462G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Campinas Not Available 1463G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Buenos Aires Not Available 1465C>T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Arakawa Not Available 1466C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Brighton Not Available 1488_1490delGAA ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kozukata Not Available 159G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amsterdam Not Available 180_182delTCT ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase No name Not Available 202G->A, 376A->G, 1264C>G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Swansea Not Available 224T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Urayasu Not Available 281_283delAGA ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Vancouver Not Available 317C->G544C->T592C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mt Sinai Not Available 376A->G, 1159C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Plymouth Not Available 488G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Volendam Not Available 514C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Shinshu Not Available 527A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chikugo Not Available 535A->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tsukui Not Available 561_563delCTC ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Pedoplis-Ckaro Not Available 573C>G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago Not Available 593G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Minnesota, Marion, Gastonia, LeJeune Not Available 637G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cincinnati Not Available 637G->T, 1037A->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Harilaou Not Available 648T->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase North Dallas Not Available 683_685delACA ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Asahikawa Not Available 695G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Durham Not Available 713A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Stonybrook Not Available 724_729delGGCACT ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wayne Not Available 769C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aveiro Not Available 806G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cleveland Corum Not Available 820G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lille Not Available 821A>T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Not Available 825G>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sugao Not Available 826C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase La Jolla Not Available 832T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wexham Not Available 833C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Piotrkow Not Available 851T>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase West Virginia Not Available 910G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Omiya Not Available 921G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nara Not Available 953_976delCCACCAAAGGGTACCTGGAC GACC ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Manhattan Not Available 962G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Rehevot Not Available 964T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Honiara Not Available 99A->G / 1360C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tokyo, Fukushima Not Available 1246G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chatham Not Available 1003G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Fushan Not Available 1004C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Partenope Not Available 1052G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ierapetra Not Available 1057C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Anadia Not Available 1193A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Abeno Not Available 1220A->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Surabaya Not Available 1291G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Pawnee Not Available 1316G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase S. Antioco Not Available 1342A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cassano Not Available 1347G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hermoupolis Not Available 1347G->C / 1360C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Union,Maewo, Chinese-2, Kalo Not Available 1360C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Andalus Not Available 1361G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cosenza Not Available 1376G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Canton, Taiwan- Hakka, Gifu-like, Agrigento-like Not Available 1376G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Flores Not Available 1387C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kaiping, Anant, Dhon, Sapporo-like, Wosera Not Available 1388G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kamogawa Not Available 169C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Costanzo Not Available 179T>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amazonia Not Available 185C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Songklanagarind Not Available 196T->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hechi Not Available 202G->A / 871G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Namouru Not Available 208T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bao Loc Not Available 352T>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Crispim Not Available 375G->T, 379G->T383T->C384C>T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Acrokorinthos Not Available 376A->G / 463C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santa Maria Not Available 376A->G / 542A->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ananindeua Not Available 376A->G / 871G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Vanua Lava Not Available 383T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Valladolid Not Available 406C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Belem Not Available 409C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Liuzhou Not Available 442G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Shenzen Not Available 473G>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Taipei ‚ÄúChinese- 3‚Äù Not Available 493A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Toledo Not Available 496C>T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Naone Not Available 497G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nankang Not Available 517T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Miaoli Not Available 519C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham Not Available 563C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Coimbra Shunde Not Available 592C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nilgiri Not Available 593G>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Radlowo Not Available 679C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Roubaix Not Available 811G>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Haikou Not Available 835A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-1 Not Available 835A->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mizushima Not Available 848A>G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Osaka Not Available 853C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Viangchan, Jammu Not Available 871G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Seoul Not Available 916G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ludhiana Not Available 929G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Farroupilha Not Available 977C->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-5 Not Available 1024C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Rignano Not Available 130G>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Orissa Not Available 131C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase G6PDNice Not Available 1380G>C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kamiube, Keelung Not Available 1387C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Neapolis Not Available 1400C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aures Not Available 143T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Split Not Available 1442C->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kambos Not Available 148C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Palestrina Not Available 170G>A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Metaponto Not Available 172G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Musashino Not Available 185C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Asahi Not Available 202G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (202), Ferrara I Not Available 202G->A / 376A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Murcia Oristano Not Available 209A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ube Konan Not Available 241C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lagosanto Not Available 242G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Guangzhou Not Available 274C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hammersmith Not Available 323T->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sinnai Not Available 34G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (680) Not Available 376A->G / 680G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (968), Betica,Selma, Guantanamo Not Available 376A->G / 968T->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Salerno Pyrgos Not Available 383T>G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Quing Yan Not Available 392G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lages Not Available 40G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ilesha Not Available 466G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mahidol Not Available 487G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Malaga Not Available 542A->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sibari Not Available 634A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mexico City Not Available 680G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nanning Not Available 703C->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Seattle, Lodi, Modena, Ferrara II, Athens-like Not Available 844G->C ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bajo Maumere Not Available 844G->T ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Montalbano Not Available 854G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kalyan-Kerala, Jamnaga, Rohini Not Available 949G->A ADR Inferred Increased risk of dose-related hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Gaohe Not Available 95A->G ADR Inferred Increased risk of dose-related hemolytic anemia. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Sulfasalazine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The risk or severity of adverse effects can be increased when Sulfasalazine is combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Sulfasalazine is combined with Abciximab. Abemaciclib Sulfasalazine may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Acarbose Sulfasalazine may increase the hypoglycemic activities of Acarbose. Acebutolol Sulfasalazine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Sulfasalazine can be decreased when used in combination with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Sulfasalazine is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Sulfasalazine is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Sulfasalazine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Drink plenty of fluids. Inadequate fluid intake is associated with crystalluria and stone formation.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Asasurfan (Choseido Pharmaceutical) / Azulfdidina (Pfizer) / Azulfin (Apsen) / Bomecon (Fu Seng) / Colo-Pleon (Sanofi-Aventis) / Disalazin (AC Farma) / Eminapyrin (Taiyo Pharmaceutical) / Flogostop (Ivax) / Iwata (Cadila) / Lanofen (Taisho Yakuhin) / Lazafin (Novell) / Pleon (Sanofi-Aventis) / Pyralin EN (Pfizer) / Reumazin (Aristopharma) / Saaz (Ipca) / Saaz-DS (Ipca) / Salasopyrine (Upjohn) / Salazar (Cadila) / Salazidin (Helcor) / Salazine (Opsonin) / Salazopirina (Jaba Recordati) / Salazoprin (Cazi) / Salazopyrin (Pfizer) / Salazopyrin EN (Pfizer) / Salazopyrin EN-Tabs (Pharmacia) / Sulcolon (Bernofarm) / Sulfacol (Drug International) / Weiliufen (Sunve) / Zopyrin (Han Lim)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Azulfidine Tablet 500 mg/1 Oral Physicians Total Care, Inc. 1995-11-06 2011-06-30 US 
Azulfidine Tablet 500 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1950-06-20 Not applicable US Azulfidine EN-tabs Tablet, delayed release 500 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1950-06-20 Not applicable US S.A.S. Enteric 500mg Tablet, delayed release 500 mg Oral Icn Pharmaceuticals 1979-12-31 2005-04-26 Canada 
Salazopyrin En-tabs 500 mg Tablet, delayed release 500 mg Oral Pfizer Canada Ulc 1995-12-31 Not applicable Canada Salazopyrin Enema 3.0gm/100ml Suspension 3 g / 100 mL Rectal Kabi Pharmacia Canada Inc. 1994-12-31 1996-09-10 Canada Salazopyrin Enema 3gm/100ml Enema 3 g / 100 mL Rectal Pfizer Canada Ulc 1996-12-31 2006-08-02 Canada Salazopyrin Tab 500mg Tablet 500 mg Oral Pfizer Canada Ulc 1995-12-31 Not applicable Canada Sas Enema 3gm/100ml Enema 3 g / 100 mL Rectal Icn Pharmaceuticals 1984-12-31 2005-04-26 Canada Sas Tab 500mg Tablet 500 mg Oral Icn Pharmaceuticals 1973-12-31 2005-04-26 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo Sulfasalazine Tab 500mg Tablet 500 mg Oral Apotex Corporation 1978-12-31 Not applicable Canada Orb-sulfasalazine EC Tablet, delayed release 500 mg Oral Orbus Pharma Inc Not applicable Not applicable Canada PMS-sulfasalazine 500mg/tab USP Tablet 500 mg Oral Pharmascience Inc 1984-12-31 Not applicable Canada PMS-sulfasalazine-E.C. Tab 500mg Tablet, delayed release 500 mg Oral Pharmascience Inc 1984-12-31 Not applicable Canada Ratio-sulfasalazine En Tablet, delayed release 500 mg Oral Ratiopharm Inc Division Of Teva Canada Limited 1986-12-31 2008-08-01 Canada Ratio-sulfasalazine Tab 500mg Tablet 500 mg Oral Ratiopharm Inc Division Of Teva Canada Limited 1986-12-31 2008-08-01 Canada Sulfasalazine Tablet 500 mg/1 Oral Aidarex Pharmaceuticals LLC 2002-01-11 Not applicable US 
Sulfasalazine Tablet 500 mg/1 Oral AvPAK 2014-01-14 Not applicable US 
Sulfasalazine Tablet 500 mg/1 Oral REMEDYREPACK INC. 2013-01-08 2017-12-22 US Sulfasalazine Tablet 500 mg/1 Oral Greenstone LLC 2003-07-01 Not applicable US
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Amides
- Aminosalicylate
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Infective Agents
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antirheumatic Agents
- BCRP/ABCG2 Inhibitors
- BCRP/ABCG2 Substrates
- Gastrointestinal Agents
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Immunosuppressive Agents
- Intestinal Antiinflammatory Agents
- Methemoglobinemia Associated Agents
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Peripheral Nervous System Agents
- Salicylates
- Sensory System Agents
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Salicylic acids / Benzenesulfonamides / Benzenesulfonyl compounds / Benzoic acids / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / Pyridines and derivatives / Organosulfonamides / Imidolactams / Vinylogous acids show 11 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Azacycle / Azo compound / Azobenzene / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Benzoic acid show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfonamide, azobenzenes, pyridines (CHEBI:9334)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3XC8GUZ6CB
- CAS number
- 599-79-1
- InChI Key
- NCEXYHBECQHGNR-QZQOTICOSA-N
- InChI
- 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+
- IUPAC Name
- 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
- SMILES
- OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1
References
- General References
- FDA Approved Drug Products: Azulfidine (sulfasalazine) tablets for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0014933
- KEGG Drug
- D00448
- KEGG Compound
- C07316
- PubChem Compound
- 5359476
- PubChem Substance
- 46505451
- ChemSpider
- 10605946
- BindingDB
- 50103596
- 9524
- ChEBI
- 9334
- ChEMBL
- CHEMBL421
- ZINC
- ZINC000003831490
- Therapeutic Targets Database
- DAP000153
- PharmGKB
- PA451547
- PDBe Ligand
- SAS
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulfasalazine
- PDB Entries
- 13gs / 4j7x / 5acl / 6g0g / 6r7s / 7er8
- MSDS
- Download (72.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Rheumatoid Arthritis 1 4 Completed Treatment Ankylosing Spondylitis (AS) 1 4 Completed Treatment Psoriatic Arthritis 1 4 Completed Treatment Rheumatoid Arthritis 7 4 Not Yet Recruiting Treatment Ankylosing Spondylitis (AS) / Spondyloarthritis (SpA) 1 4 Not Yet Recruiting Treatment Rheumatoid Arthritis 1 4 Recruiting Treatment Cardiovascular Risk / Endothelial Dysfunction / Rheumatoid Arthritis / Stiffness, Aortic 1 4 Recruiting Treatment Insufficient Response to Methotrexate or Leflunomide / Rheumatoid Arthritis 1 4 Recruiting Treatment Psoriatic Arthritis 1 4 Terminated Treatment Rheumatoid Arthritis 1
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Vintage pharmaceuticals inc
- Watson laboratories inc
- Solvay pharmaceuticals
- Heritage pharmaceuticals inc
- Mutual pharmaceutical co inc
- Sandoz inc
- Superpharm corp
- Packagers
- Amerisource Health Services Corp.
- A-S Medication Solutions LLC
- Carlisle Laboratories Inc.
- Darby Dental Supply Co. Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Greenstone LLC
- Kaiser Foundation Hospital
- Kemwell AB
- Major Pharmaceuticals
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Nucare Pharmaceuticals Inc.
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Pharmacia Inc.
- Pharmedix
- Physicians Total Care Inc.
- Prepak Systems Inc.
- Qualitest
- Remedy Repack
- Tya Pharmaceuticals
- United Research Laboratories Inc.
- Vintage Pharmaceuticals Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet, coated Oral 500 mg Tablet, film coated Oral 500 mg Tablet, delayed release Oral 500 mg Suspension Rectal 3 g / 100 mL Enema Rectal 3 g / 100 mL Tablet Oral 500 mg Tablet Oral Tablet, delayed release Oral Powder Not applicable 1 g/1g Tablet Oral 500 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, delayed release Oral 500 mg/1 - Prices
Unit description Cost Unit Sulfasalazine powder 2.14USD g Azulfidine EN-tabs 500 mg Enteric Coated Tabs 0.73USD tab Azulfidine entab 500 mg 0.69USD tablet Azulfidine 500 mg tablet 0.59USD tablet Salazopyrin En-Tabs 500 mg Enteric-Coated Tablet 0.45USD tablet Sulfasalazine 500 mg Enteric Coated Tabs 0.4USD tab Pms-Sulfasalazine 500 mg Enteric-Coated Tablet 0.34USD tablet Salazopyrin 500 mg Tablet 0.28USD tablet Sulfasalazine 500 mg tablet 0.25USD tablet Sulfazine 500 mg tablet 0.25USD tablet Pms-Sulfasalazine 500 mg Tablet 0.22USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 220 dec °C PhysProp logP 2.5 Not Available Caco2 permeability -6.33 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0464 mg/mL ALOGPS logP 2.92 ALOGPS logP 4.25 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 3.23 ChemAxon pKa (Strongest Basic) 0.55 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 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier - 0.7294 Caco-2 permeable - 0.6893 P-glycoprotein substrate Non-substrate 0.8405 P-glycoprotein inhibitor I Non-inhibitor 0.9096 P-glycoprotein inhibitor II Non-inhibitor 0.853 Renal organic cation transporter Non-inhibitor 0.8956 CYP450 2C9 substrate Non-substrate 0.6445 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7557 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.923 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8895 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.6468 Biodegradation Not ready biodegradable 0.9472 Rat acute toxicity 1.4383 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.939 hERG inhibition (predictor II) Non-inhibitor 0.821
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0002-0239100000-5bf223e6e250eb77105a
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Iron ion binding
- Specific Function
- Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
- Gene Name
- ALOX5
- Uniprot ID
- P09917
- Uniprot Name
- Arachidonate 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
References
- Nielsen OH, Bukhave K, Elmgreen J, Ahnfelt-Ronne I: Inhibition of 5-lipoxygenase pathway of arachidonic acid metabolism in human neutrophils by sulfasalazine and 5-aminosalicylic acid. Dig Dis Sci. 1987 Jun;32(6):577-82. [Article]
- Allgayer H, Eisenburg J, Paumgartner G: Soybean lipoxygenase inhibition: studies with the sulphasalazine metabolites N-acetylaminosalicylic acid, 5-aminosalicylic acid and sulphapyridine. Eur J Clin Pharmacol. 1984;26(4):449-51. [Article]
- Sircar JC, Schwender CF, Carethers ME: Inhibition of soybean lipoxygenase by sulfasalazine and 5-aminosalicylic acid: a possible mode of action in ulcerative colitis. Biochem Pharmacol. 1983 Jan 1;32(1):170-2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Mifflin RC, Saada JI, Di Mari JF, Valentich JD, Adegboyega PA, Powell DW: Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8. [Article]
- Generini S, Fiori G, Matucci Cerinic M: Therapy of spondylarthropathy in inflammatory bowel disease. Clin Exp Rheumatol. 2002 Nov-Dec;20(6 Suppl 28):S88-94. [Article]
- Distrutti E, Sediari L, Mencarelli A, Renga B, Orlandi S, Russo G, Caliendo G, Santagada V, Cirino G, Wallace JL, Fiorucci S: 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3yl)-phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol Exp Ther. 2006 Oct;319(1):447-58. Epub 2006 Jul 19. [Article]
- Cipolla G, Crema F, Sacco S, Moro E, de Ponti F, Frigo G: Nonsteroidal anti-inflammatory drugs and inflammatory bowel disease: current perspectives. Pharmacol Res. 2002 Jul;46(1):1-6. [Article]
- Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, Chavatte P, Farce A, Bulois P, Cortot A, Colombel JF, Desreumaux P: Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 2005 Apr 18;201(8):1205-15. Epub 2005 Apr 11. [Article]
- Schwab M, Reynders V, Loitsch S, Shastri YM, Steinhilber D, Schroder O, Stein J: PPARgamma is involved in mesalazine-mediated induction of apoptosis and inhibition of cell growth in colon cancer cells. Carcinogenesis. 2008 Jul;29(7):1407-14. doi: 10.1093/carcin/bgn118. Epub 2008 Jun 9. [Article]
- Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [Article]
- Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Scaffold protein binding
- Specific Function
- Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
- Gene Name
- CHUK
- Uniprot ID
- O15111
- Uniprot Name
- Inhibitor of nuclear factor kappa-B kinase subunit alpha
- Molecular Weight
- 84638.88 Da
References
- Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [Article]
- Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Scaffold protein binding
- Specific Function
- Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
- Gene Name
- IKBKB
- Uniprot ID
- O14920
- Uniprot Name
- Inhibitor of nuclear factor kappa-B kinase subunit beta
- Molecular Weight
- 86563.245 Da
References
- Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [Article]
- Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Cystine:glutamate antiporter activity
- Specific Function
- Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
- Gene Name
- SLC7A11
- Uniprot ID
- Q9UPY5
- Uniprot Name
- Cystine/glutamate transporter
- Molecular Weight
- 55422.44 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Gout PW, Buckley AR, Simms CR, Bruchovsky N: Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug. Leukemia. 2001 Oct;15(10):1633-40. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Plays a major role in ketone body metabolism.
- Gene Name
- ACAT1
- Uniprot ID
- P24752
- Uniprot Name
- Acetyl-CoA acetyltransferase, mitochondrial
- Molecular Weight
- 45199.2 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Faison LD, White HL: Sulfasalazine inhibits lyso-PAF: acetyl-COA acetyltransferase. Prostaglandins. 1992 Sep;44(3):245-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Thromboxane-a synthase activity
- Specific Function
- Not Available
- Gene Name
- TBXAS1
- Uniprot ID
- P24557
- Uniprot Name
- Thromboxane-A synthase
- Molecular Weight
- 60517.69 Da
References
- Stenson WF, Lobos E: Inhibition of platelet thromboxane synthetase by sulfasalazine. Biochem Pharmacol. 1983 Jul 15;32(14):2205-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Receptor binding
- Specific Function
- PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
- Gene Name
- PLA2G1B
- Uniprot ID
- P04054
- Uniprot Name
- Phospholipase A2
- Molecular Weight
- 16359.535 Da
References
- Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Karlsson JE, Heddle C, Rozkov A, Rotticci-Mulder J, Tuvesson O, Hilgendorf C, Andersson TB: High-activity p-glycoprotein, multidrug resistance protein 2, and breast cancer resistance protein membrane vesicles prepared from transiently transfected human embryonic kidney 293-epstein-barr virus nuclear antigen cells. Drug Metab Dispos. 2010 Apr;38(4):705-14. doi: 10.1124/dmd.109.028886. Epub 2010 Jan 13. [Article]
- Shukla S, Zaher H, Hartz A, Bauer B, Ware JA, Ambudkar SV: Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7. doi: 10.1007/s11095-008-9735-8. Epub 2008 Oct 9. [Article]
- Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- Canalicular multispecific organic anion transporter 1
- Molecular Weight
- 174205.64 Da
References
- Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Methotrexate transporter activity
- Specific Function
- Has been shown to act both as an intestinal proton-coupled high-affinity folate transporter and as an intestinal heme transporter which mediates heme uptake from the gut lumen into duodenal epithel...
- Gene Name
- SLC46A1
- Uniprot ID
- Q96NT5
- Uniprot Name
- Proton-coupled folate transporter
- Molecular Weight
- 49770.04 Da
References
- Nakai Y, Inoue K, Abe N, Hatakeyama M, Ohta KY, Otagiri M, Hayashi Y, Yuasa H: Functional characterization of human proton-coupled folate transporter/heme carrier protein 1 heterologously expressed in mammalian cells as a folate transporter. J Pharmacol Exp Ther. 2007 Aug;322(2):469-76. Epub 2007 May 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 06, 2022 03:22