Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00643)
Name
Sulfasalazine
Synonyms    Click to Show/Hide the Synonyms of This API
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; 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; 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; MFCD00057363; 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; Sulfasalazine-d4; 2-HYDROXY-(5-([4-(2-PYRIDINYLAMINO)SULFONYL]PHENYL)AZO)BENZOIC ACID; NSC203730; NSC667219; NSC-203730; NSC-667219; Salicylic acid, 5-((p-(2-pyridylsulfamoyl)phenyl)azo)-; 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]; 2-hydroxy-5-[[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl]benzoic acid; Salazosulfapiridina [INN-Spanish]; 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); SMR000059146; Sulphasalazine, N-; CCRIS 4713; HSDB 3395; 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; 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; 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; AC-20497; AK163126; HY-14655; SMR004703430; SY052318; SBI-0051526.P003; AB0013330; DB-017797; FT-0603483; FT-0674746; 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; 737754-28-8
Clinical Status
Approved
Disease Indication Rheumatoid arthritis ICD-11: FA20 [1]
PubChem CID
5339
Formula
C18H14N4O5S
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5339"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 398.4 Topological Polar Surface Area 150
XlogP -0.7 Complexity 657
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Sulfasalazine 500 mg tablet Click to Show/Hide the Full List of Formulation(s):        10 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Glyceryl monostearate; Magnesium stearate; Acetone; Propylene glycol; Talc; Silicon dioxide; Alcohol; Carnauba wax; Cellulose acetate; Povidone, unspecified; White wax
                   Dosage Form Delayed Release Oral Tablet
                   Company Pharmacia and Upjohn Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium stearyl fumarate; Diethyl phthalate; Talc; Croscarmellose sodium; Povidone k30; Carnauba wax; Cellacefate; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Delayed Release Oral Tablet
                   Company Qualitest Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [5]
Diethyl phthalate DIG Info Phosphodiesterase 4D (IC50 = 8.5 uM) [6]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Magnesium stearate; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actavis Pharma; AvPAK; Bryant Ranch Prepack; RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Magnesium stearate; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Acetone; Propylene glycol; Talc; Silicon dioxide; Alcohol; Carnauba wax; Povidone, unspecified; White wax
                   Dosage Form Delayed Release Oral Tablet
                   Company Greenstone
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Povidone; Silicon dioxide
                   Dosage Form Oral Tablet
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Talc; Croscarmellose sodium; Povidone k30; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aidarex Pharmaceuticals; Blenheim Phamacal; PD-Rx Pharmaceuticals; Qualitest Pharmaceuticals; RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             Drug Formulation 8 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Silicon dioxide; Povidone, unspecified
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions; Greenstone; Pharmacia and Upjohn Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 9 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Silicon dioxide; Povidones
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions; Aphena Pharma Solutions-Tennessee; Avera McKennan Hospital; Kaiser Foundation Hospitals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 10 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Sodium stearoyl lactylate; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Preferred Pharamaceuticals; RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved sulfasalazine from the official website of the U.S. Food and Drug Administration.
2 Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J Nat Prod. 2002 Feb; 65(2):206-9.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
6 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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