General Information of Drug (ID: DMICA9H)

Drug Name
Sulfasalazine
Synonyms
sulfasalazine; 599-79-1; Salicylazosulfapyridine; Salazosulfapyridine; Azulfidine; Asulfidine; Salazopyridin; Sulcolon; Azopyrin; Accucol; Colo-Pleon; Salazopiridazin; Salisulf; Reupirin; Benzosulfa; Azopyrine; Salazosulfapyridin; Sulfasalazina; w-t Sasp oral; Sulfasalazinum; Sulfasalazin; Azulfidine EN; Sulfazalazine; Azulfidine EN-tabs; Salazosulfapiridina; Sas-500; Salazosulfapyridinum; Azosulfidin; SASP; Salazo-sulfapyridinum; 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid; SAS-500; Sulfasalizine
Indication
Disease Entry ICD 11 Status REF
Irritable bowel syndrome DD91.0 Approved [1]
Rheumatoid arthritis FA20 Approved [2]
Ulcerative colitis DD71 Approved [3]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 398.4
Logarithm of the Partition Coefficient (xlogp) -0.7
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance
The clearance of drug is 1 L/h []
Elimination
1.5% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 10 hours [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 167.336 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.004% [5]
Vd
The volume of distribution (Vd) of drug is 7.5 +/- 1.6 L []
Water Solubility
The ability of drug to dissolve in water is measured as 0.0024 mg/mL [4]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Leukopenias NEC Not Available CYP1A2 OTLLBX48 [7]
Vasculitis Not Available MPO OTOOXLIN [7]
Chemical Identifiers
Formula
C18H14N4O5S
IUPAC Name
2-hydroxy-5-[[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl]benzoic acid
Canonical SMILES
C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O
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)
InChIKey
NCEXYHBECQHGNR-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5339
ChEBI ID
CHEBI:9334
CAS Number
599-79-1
DrugBank ID
DB00795
TTD ID
D02ZTJ
VARIDT ID
DR00201
INTEDE ID
DR1513
ACDINA ID
D00643
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
ATP-binding cassette transporter G2 (ABCG2) TTIMJ02 ABCG2_HUMAN Inhibitor [8]
Nuclear factor NF-kappa-B (NFKB) TTSXVID NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN Activator [9]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [10]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [11]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [12]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [13]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [14]
Azoreductase (azoR) DEEISQ2 AZOR_ENTFA Substrate [15], [16]
Azoreductase (azoR) DEM1BHT A0A132Z973_ENTFC Substrate [15], [16]
Azoreductase (azoR) DE5CAX1 A0A074IU04_STRSL Substrate [15]
Azoreductase (azoR) DEGTKHL T0VG26_9ENTE Substrate [17]
Azoreductase (azoR) DEI2PC5 AZOR_CLOP1 Substrate [15], [16]
Azoreductase (azoR) DEIHK8V A0A349MYB4_9LACO Substrate [15], [16]
Azoreductase (azoR) DE3UF6Z A0A0P0ETC6_BACT4 Substrate [17]
Azoreductase (azoR) DE6GHJ5 A0A0P0ETC6_BACT4 Substrate [17]
Azoreductase (azoR) DETEMAH A0A349MYB4_9LACO Substrate [17]
Azoreductase (azoR) DEIKZOU A0A0P0ETC6_BACT4 Substrate [18]
Azoreductase (azoR) DENLBG3 A0A0P0ETC6_BACT4 Substrate [15], [16]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial (CYP27B1) OTTK98BH CP27B_HUMAN Gene/Protein Processing [19]
Angiotensin-converting enzyme 2 (ACE2) OTTRZGU7 ACE2_HUMAN Gene/Protein Processing [20]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Protein Interaction/Cellular Processes [21]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Protein Interaction/Cellular Processes [21]
Arylamine N-acetyltransferase 2 (NAT2) OTBPDQOY ARY2_HUMAN Biotransformations [22]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Post-Translational Modifications [23]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [21]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Protein Interaction/Cellular Processes [24]
Cystine/glutamate transporter (SLC7A11) OTKJ6PXW XCT_HUMAN Gene/Protein Processing [25]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Drug Response [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Irritable bowel syndrome
ICD Disease Classification DD91.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Nuclear factor NF-kappa-B (NFKB) DTT NFKB1; NFKB2; RELA; RELB; REL 5.39E-01 0.16 0.27
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 1.87E-02 -1.32E-01 -2.75E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 1.20E-13 -1.20E+00 -1.06E+00
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 1.29E-14 -3.25E-01 -7.49E-01
Peptide transporter 1 (SLC15A1) DTP PEPT1 7.54E-01 -1.25E-02 -8.78E-02
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 1.69E-01 2.37E-02 2.14E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Sulfasalazine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Salsalate DM13P4C Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Salsalate. Rheumatoid arthritis [FA20] [26]
Meloxicam DM2AR7L Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Meloxicam. Rheumatoid arthritis [FA20] [26]
Oxaprozin DM9UB0P Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Oxaprozin. Rheumatoid arthritis [FA20] [26]
Coadministration of a Drug Treating the Disease Different from Sulfasalazine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [27]
Repaglinide DM5SXUV Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Repaglinide. Acute diabete complication [5A2Y] [28]
Glibenclamide DM8JXPZ Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Glibenclamide. Acute diabete complication [5A2Y] [28]
Tolazamide DMIHRNA Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Tolazamide. Acute diabete complication [5A2Y] [28]
Insulin-glulisine DMQI0FU Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Insulin-glulisine. Acute diabete complication [5A2Y] [28]
Insulin-aspart DMX7V28 Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Insulin-aspart. Acute diabete complication [5A2Y] [29]
Glipizide DMZA5PQ Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Glipizide. Acute diabete complication [5A2Y] [28]
Midostaurin DMI6E0R Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Midostaurin. Acute myeloid leukaemia [2A60] [30]
Gilteritinib DMTI0ZO Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Gilteritinib. Acute myeloid leukaemia [2A60] [27]
Framycetin DMF8DNE Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Framycetin. Alcoholic liver disease [DB94] [26]
Inotersen DMJ93CT Major Increased risk of nephrotoxicity by the combination of Sulfasalazine and Inotersen. Amyloidosis [5D00] [30]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [31]
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Kanamycin. Bacterial infection [1A00-1C4Z] [26]
Streptomycin DME1LQN Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Streptomycin. Bacterial infection [1A00-1C4Z] [26]
Gentamicin DMKINJO Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Gentamicin. Bacterial infection [1A00-1C4Z] [26]
Netilmicin DMRD1QK Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Netilmicin. Bacterial infection [1A00-1C4Z] [26]
Ag-221 DMS0ZBI Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Ag-221. BCR-ABL1-negative chronic myeloid leukaemia [2A41] [27]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Sulfasalazine and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [32]
Iodipamide DMXIQYS Major Increased risk of nephrotoxicity by the combination of Sulfasalazine and Iodipamide. Cholelithiasis [DC11] [33]
PF-04449913 DMSB068 Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by PF-04449913. Chronic myelomonocytic leukaemia [2A40] [30]
Phenylbutazone DMAYL0T Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Phenylbutazone. Chronic pain [MG30] [26]
Ketoprofen DMRKXPT Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Ketoprofen. Chronic pain [MG30] [26]
Anisindione DM2C48U Major Decreased metabolism of Sulfasalazine caused by Anisindione mediated inhibition of CYP450 enzyme. Coagulation defect [3B10] [34]
Methoxyflurane DML0RAE Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Methoxyflurane. Corneal disease [9A76-9A78] [26]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Sulfasalazine due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [35]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Cannabidiol. Epileptic encephalopathy [8A62] [30]
177Lu-DOTATATE DMT8GVU Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and 177Lu-DOTATATE. Hepatitis virus infection [1E50-1E51] [26]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Brentuximab vedotin. Hodgkin lymphoma [2B30] [36]
Fostemsavir DM50ILT Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Fostemsavir. Human immunodeficiency virus disease [1C60-1C62] [37]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Sulfasalazine and Mipomersen. Hyper-lipoproteinaemia [5C80] [38]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Sulfasalazine and BMS-201038. Hyper-lipoproteinaemia [5C80] [39]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [26]
Meclofenamic acid DM05FXR Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Meclofenamic acid. Inflammatory spondyloarthritis [FA92] [40]
Capmatinib DMYCXKL Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Capmatinib. Lung cancer [2C25] [41]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [42]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Idelalisib. Mature B-cell leukaemia [2A82] [43]
Moxetumomab pasudotox DMN63DZ Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Moxetumomab pasudotox. Mature B-cell leukaemia [2A82] [26]
Mercaptopurine DMTM2IK Moderate Decreased metabolism of Sulfasalazine caused by Mercaptopurine mediated inhibition of non-CYP450 enzyme. Mature B-cell lymphoma [2A85] [44]
Rimegepant DMHOAUG Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Rimegepant. Migraine [8A80] [45]
Lasmiditan DMXLVDT Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Lasmiditan. Migraine [8A80] [46]
Exjade DMHPRWG Major Increased risk of nephrotoxicity by the combination of Sulfasalazine and Exjade. Mineral absorption/transport disorder [5C64] [47]
Gallium nitrate DMF9O6B Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Gallium nitrate. Mineral excesses [5B91] [26]
Rolapitant DM8XP26 Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Rolapitant. Nausea/vomiting [MD90] [48]
Olaparib DM8QB1D Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Olaparib. Ovarian cancer [2C73] [27]
Rucaparib DM9PVX8 Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Rucaparib. Ovarian cancer [2C73] [49]
Diflunisal DM7EN8I Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Diflunisal. Pain [MG30-MG3Z] [26]
Ibuprofen DM8VCBE Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Ibuprofen. Pain [MG30-MG3Z] [26]
Bromfenac DMKB79O Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Bromfenac. Postoperative inflammation [1A00-CA43] [26]
Darolutamide DMV7YFT Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Darolutamide. Prostate cancer [2C82] [50]
Temsirolimus DMS104F Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Temsirolimus. Renal cell carcinoma [2C90] [26]
Colistimethate DMZ9BMU Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Colistimethate. Respiratory infection [CA07-CA4Z] [26]
Tedizolid DMG2SKR Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Tedizolid. Skin and skin-structure infection [1F28-1G0Z] [30]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Sulfasalazine and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [30]
Telavancin DM58VQX Moderate Increased risk of nephrotoxicity by the combination of Sulfasalazine and Telavancin. Staphylococcal/streptococcal disease [1B5Y] [26]
Eltrombopag DMOGFIX Moderate Decreased clearance of Sulfasalazine due to the transporter inhibition by Eltrombopag. Thrombocytopenia [3B64] [51]
Sirolimus DMGW1ID Major Increased risk of nephrotoxicity by the combination of Sulfasalazine and Sirolimus. Transplant rejection [NE84] [52]
Azathioprine DMMZSXQ Moderate Decreased metabolism of Sulfasalazine caused by Azathioprine mediated inhibition of non-CYP450 enzyme. Transplant rejection [NE84] [44]
Tacrolimus DMZ7XNQ Major Increased risk of nephrotoxicity by the combination of Sulfasalazine and Tacrolimus. Transplant rejection [NE84] [52]
Tolbutamide DM02AWV Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Tolbutamide. Type 2 diabetes mellitus [5A11] [28]
Insulin-detemir DMOA4VW Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Insulin-detemir. Type-1/2 diabete [5A10-5A11] [28]
Insulin degludec DMPL395 Moderate Increased risk of hypoglycemia by the combination of Sulfasalazine and Insulin degludec. Type-1/2 diabete [5A10-5A11] [28]
⏷ Show the Full List of 61 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Diethyl phthalate E00135 6781 Plasticizing agent; Solvent
Glyceryl monostearate E00310 24699 Emollient; Emulsifying agent; Emulsion stabilizing agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Sodium stearyl fumarate E00545 23665634 lubricant
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Acetone E00004 180 Solvent
Carmellose sodium E00625 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium stearoyl lactylate E00558 23671849 Emulsifying agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
⏷ Show the Full List of 13 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Sulfasalazine 500 mg tablet 500 mg Delayed Release Oral Tablet Oral
Sulfasalazine 500 mg tablet 500 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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49 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
50 Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
51 Allred AJ, Bowen CJ, Park JW, et al. "Eltrombopag increases plasma rosuvastatin exposure in healthy volunteers." Br J Clin Pharmacol 72 (2011): 321-9. [PMID: 21434975]
52 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.