Drug Details

General Information of the Drug (ID: DR2918)
Name
Salazosulfapyridine
Synonyms
sulfasalazine; 599-79-1; Azulfidine; Salicylazosulfapyridine; Salazosulfapyridine; Sulphasalazine; Salazopyrin; Asulfidine; Salazopyridin; Accucol; Azopyrin; Sulcolon; Colo-Pleon; Salazopiridazin; Azopyrine; Benzosulfa; Reupirin; Salisulf; Salazosulfapyridin; w-t Sasp oral; Sulfasalazin; Azulfidine EN; Sulfasalazina; Sulfasalazinum; Sulfazalazine; Azulfidine EN-tabs; Salazosulfapiridina; Salazosulfapyridinum; Sas-500; SASP; 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid; S.A.S.-500; 5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid; 4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene; 5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid; 2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid; NSC 667219; CHEBI:9334; NSC 203730; S.A.S. 500; C18H14N4O5S; UNII-3XC8GUZ6CB; 5-[4-(2-Pyridylsulfamoyl)phenylazo]salicylic Acid; MFCD00057363; Benzoic acid, 2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]-; (E)-2-hydroxy-5-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)benzoic acid; 3XC8GUZ6CB; Sulfasalazine (Azulfidine); CHEMBL421; Benzoic acid, 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)-; S.A.S.; Azosulfidin; 2-hydroxy-5-{[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid; 5-[p-(2-Pyridylsulfamoyl)phenylazo]salicylic acid; 2-HYDROXY-(5-([4-(2-PYRIDINYLAMINO)SULFONYL]PHENYL)AZO)BENZOIC ACID; NSC203730; NSC667219; NSC-203730; NSC-667219; (3Z)-6-Oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid; Salicylic acid, 5-((p-(2-pyridylsulfamoyl)phenyl)azo)-; SSZ; NCGC00090903-01; Salazo-sulfapyridinum; CAS-599-79-1; 2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic acid; DSSTox_CID_1256; 2-hydroxy-5-[(E)-{4-[(pyridin-2-ylamino)sulfonyl]phenyl}diazenyl]benzoic acid; DSSTox_RID_76043; 5-[p-(2-Pyridylsulfamyl)phenylazo]salicylic acid; DSSTox_GSID_21256; Q63398427; Sulfasalazinum [INN-Latin]; Sulfasalazina [INN-Spanish]; Salicylic acid, 5-[[p-(2-pyridylsulfamoyl)phenyl]azo]-; 2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid; Salazosulfapyridinum [INN-Latin]; Salazosulfapiridina [INN-Spanish]; SI-88; 2-Hydroxy-5-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)benzoic acid; 2-hydroxy-5-(2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl)benzoic acid; Azulfidine (TN); 6-oxo-3-[[4-(2-pyridinylsulfamoyl)phenyl]hydrazinylidene]-1-cyclohexa-1,4-dienecarboxylic acid; 737754-28-8; SMR000059146; Sulphasalazine, N-; CCRIS 4713; HSDB 3395; 13gs; 5-(p-(2-Pyridylsulfamoyl)phenylazo)salicylic acid; SR-05000001721; EINECS 209-974-3; 5-[[p-(2-Pyridylsulfamoyl)phenyl]azo]salicylic acid; Sulfasalazine (USP/INN); BRN 0356241; Iwata; 2-hydroxy-5-({4-[(2-pyridylamino)sulfonyl]phenyl}diazenyl)benzoic acid; Prestwick_848; Sulfasalazine [USAN:USP:INN:BAN]; Spectrum_000998; Prestwick0_000520; Prestwick1_000520; Prestwick2_000520; Prestwick3_000520; Spectrum2_001216; Spectrum3_001364; Spectrum4_000347; Spectrum5_001443; Epitope ID:122672; SCHEMBL4514; SCHEMBL4515; Salazosulfapyridine (JP17); SCHEMBL18490; BSPBio_000479; BSPBio_002888; KBioGR_000753; KBioGR_002314; KBioSS_001478; KBioSS_002316; 5-22-08-00433 (Beilstein Handbook Reference); MLS000759399; MLS001424109; MLS006011702; BIDD:GT0161; DivK1c_000860; SPECTRUM1500552; SPBio_001032; SPBio_002400; BPBio1_000527; CHEMBL100848; CHEMBL242373; GTPL4840; SCHEMBL1079598; SCHEMBL1229516; CHEMBL1206016; DTXSID0021256; SCHEMBL10289061; CHEBI:94500; HMS502K22; KBio1_000860; KBio2_001478; KBio2_002314; KBio2_004046; KBio2_004882; KBio2_006614; KBio2_007450; KBio3_002108; KBio3_002794; cMAP_000018; NINDS_000860; HMS1569H21; HMS1921C05; HMS2051J21; HMS2090P13; HMS2092K07; HMS2096H21; HMS2232H07; HMS3370D16; HMS3393J21; HMS3655G07; HMS3713H21; HMS3871J13; HMS3884E21; Pharmakon1600-01500552; ALBB-033361; BCP13311; ZINC3831490; Tox21_111037; Tox21_201239; Tox21_300541; ANW-43676; BDBM50097125; BDBM50103596; CCG-39145; DL-510; KM0360; NSC757330; s1576; SBB058178; ZINC14768602; ZINC85550135; AKOS002311709; AKOS025116975; AKOS026749974; Tox21_111037_1; WLN: T6NJ BSWMR DNUNR DQ CVQ; ZINC100030102; ZINC100031653; CCG-100987; DB00795; HS-0062; MCULE-7533021815; NC00237; NSC-757330; VA11798; IDI1_000860; SMP2_000059; NCGC00016518-01; NCGC00090903-02; NCGC00090903-03; NCGC00090903-04; NCGC00090903-05; NCGC00090903-06; NCGC00090903-07; NCGC00090903-08; NCGC00090903-09; NCGC00090903-11; NCGC00186644-01; NCGC00254313-01; NCGC00258791-01; (3E)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid; 6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid; AC-20497; AK163126; H881; HY-14655; SMR004703430; SY052318; SBI-0051526.P003; AB0013330; DB-017797; FT-0603483; FT-0674746; S0580; ST50767935; SW196979-4; C07316; D00448; J10488; AB00052101-04; AB00052101-06; AB00052101_07; AB00052101_08; 599S791; Q420035; Q-201769; SR-05000001721-1; SR-05000001721-2; SR-05000001721-3; Sulfasalazine, analytical standard, >=98% (HPLC); 5-[[4-(2-Pyridylsulfamoyl)phenyl]azo]salicylic acid; BRD-K10670311-001-06-4; BRD-K10670311-001-08-0; Q27166356; Sulphasalazine, Antibiotic for Culture Media Use Only; F2173-1125; Z2030502809; 4-(Pyridyl-2-amidosulfonyl)-3''-carboxy-4''-hydroxyazobenzene; Sulfasalazine, European Pharmacopoeia (EP) Reference Standard; 2-hydroxy-5-[(E)-[4-(2-pyridylsulfamoyl)phenyl]azo]benzoic acid; 5-{4-[(2-pyridylideneamino)sulfonyl]phenyldiazenyl}salicylic acid; Sulfasalazine, United States Pharmacopeia (USP) Reference Standard; (E)-2-hydroxy-5-((4-(N-pyridin-2-ylsulfamoyl)phenyl)diazenyl)benzoic acid; 2-hydroxy-5-((4-(N-pyridin-2-ylsulfamoyl)phenyl)diazenyl)benzoic acid; 2-Hydroxy-5-((4-[(2-pyridinylamino)sulfonyl]phenyl)diazenyl)benzoic acid #; 2-hydroxy-5-{(E)-[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid; 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid; 6-oxo-3-(2-[4-(n-pyridin-2-ylsulfamoyl)phenyl]hydrazono)cyclohexa-1,4-dienecarboxylic acid; 6-oxo-3-((4-(pyridin-2-ylsulfamoyl)phenyl) hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid
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Molecular Type
Small molecule
Disease Rheumatoid arthritis [ICD-11: FA20] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Clearance
The clearance of drug is 1 L/h
Elimination
1.5% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 10 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 167.336 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.004%
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
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C18H14N4O5S
PubChem CID
5339
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
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
CAS Number
CAS 599-79-1
ChEBI ID
CHEBI:9334
TTD Drug ID
D02ZTJ
DrugBank ID
DB00795
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Bucillamine      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 The triple DMARD combination therapy provided a new treatment option for those patients for whom treatment with biologics is difficult.
          Manuka honey      Apis mellifera     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model In vivo experiment was carried out with rats.
                    Experimental
                    Result(s)		 Combination therapy showed additive effect of the MH which restored lipid peroxidation and improvement of antioxidant parameters.
Target and Pathway
Target(s) ATP-binding cassette G2 (ABCG2)  Molecule Info  [4]
Nuclear factor NF-kappa-B (NFKB)  Molecule Info  [5]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 NF-kappa B signaling pathway
3 Osteoclast differentiation
4 Legionellosis
5 HTLV-I infection
6 Epstein-Barr virus infection
7 Pathways in cancer
8 Viral carcinogenesis
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 B cell activation
3 Inflammation mediated by chemokine and cytokine signaling pathway
4 T cell activation
5 Toll receptor signaling pathway
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Pathway Interaction Database IL12-mediated signaling events Click to Show/Hide
2 Alternative NF-kappaB pathway
Reactome RIP-mediated NFkB activation via ZBP1 Click to Show/Hide
2 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
3 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
4 Interleukin-1 processing
5 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
6 IkBA variant leads to EDA-ID
7 Dectin-1 mediated noncanonical NF-kB signaling
8 NIK-->noncanonical NF-kB signaling
9 TRAF6 mediated NF-kB activation
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 DNA Damage Response (only ATM dependent)
3 SIDS Susceptibility Pathways
4 Nuclear Receptors Meta-Pathway
5 Cytosolic sensors of pathogen-associated DNA
6 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
7 EBV LMP1 signaling
8 TNF alpha Signaling Pathway
9 TSLP Signaling Pathway
10 Neural Crest Differentiation
11 TWEAK Signaling Pathway
12 RANKL/RANK Signaling Pathway
13 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
14 Interleukin-1 processing
15 Folate Metabolism
16 Vitamin B12 Metabolism
17 Selenium Micronutrient Network
18 Regulation of toll-like receptor signaling pathway
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4840).
Reference 2 The usefulness of a new triple combination treatment utilizing methotrexate, salazosulfapyridine, and bucillamine in rheumatoid arthritis. Mod Rheumatol. 2016;26(1):51-6.
Reference 3 Effect of Manuka honey and sulfasalazine in combination to promote antioxidant defense system in experimentally induced ulcerative colitis model in rats. Indian J Exp Biol. 2008 Aug;46(8):583-90.
Reference 4 The anti-inflammatory mechanism of sulfasalazine is related to adenosine release at inflamed sites. J Immunol. 1996 Mar 1;156(5):1937-41.
Reference 5 Emerging drugs for rheumatoid arthritis. Expert Opin Emerg Drugs. 2008 Mar;13(1):175-96.
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