SULFASALAZINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC A07EC01
UNII 3XC8GUZ6CB
EPA CompTox DTXSID0021256

Structure

InChI Key NCEXYHBECQHGNR-QZQOTICOSA-N
Smiles O=C(O)c1cc(/N=N/c2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1O
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+

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H14N4O5S
Molecular Weight 398.4
AlogP 3.7
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 141.31
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
Arachidonate 5-lipoxygenase inhibitor INHIBITOR PubMed PubMed PubMed
Protein: Arachidonate 5-lipoxygenase
Description: Polyunsaturated fatty acid 5-lipoxygenase
Organism : Homo sapiens
P09917 ENSG00000012779
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 1
Organism : Homo sapiens
P23219 ENSG00000095303
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 2
Organism : Homo sapiens
P35354 ENSG00000073756
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 38
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase SGK family
- - - - 70
Enzyme Lyase
- 3040 - 6870 -
Enzyme Oxidoreductase
- - - - 60
Enzyme Transferase
- - 7600 - 0
Enzyme
- 3040 7600 22000 0
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC03 and SLC07 families of heteromeric amino acid transporters (HATs) SLC07 Cationic amino acid transporter/glycoprotein-associated family
- 160-30000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC10 family of sodium-bile acid co-transporters
- 9600 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 12000 - 11000 72-73
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
916 - - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 14600 - - -
Assay Description Organism Bioactivity Reference
Tested in vivo for the ability to inhibit myeloperoxidase (MPO) activity in the colon of the TNB/ethanol-induced chronic colitis rats at the dosage of 500 mg/kg/day Rattus norvegicus 60.0 %
Tested for the ability to decrease lesion area in the colon of the TNB/ethanol-induced chronic colitis rats at the dosage of 500 mg/kg/day Rattus norvegicus 16.0 %
Antiarthritic activity in Freund's adjuvant-induced arthritis Wistar rat model after 13 days Rattus norvegicus 18.0 %
Antiarthritic activity in Freund's adjuvant-induced arthritis Wistar rat model after 21 days Rattus norvegicus 73.0 %
Inhibition of SGK1 at 33 uM None 70.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -3.7 %
Inhibition of human H-PGDS expressed in Escherichia coli BL21 assessed as rate of glutathione-chloro-dinitro benzene conjugation at 50 uM Homo sapiens 0.0 %
Inhibition of NF-kappaB activation expressed in TNFalpha-stimulated human HepG2 cells co-transfected with PPRE-Luc plasmid pretreated for 1 hr before TNFalpha challenge measured after 24 hrs by luciferase reporter gene assay None 900.0 nM
Inhibition of TNF-alpha-induced NFkappaB activation in human HepG2 cells after 1 hr by luciferase reporter assay Homo sapiens 900.0 nM
Inhibition of TNFalpha-induced NFkappaB transcriptional activity in human HepG2 cells pretreated for 1 hr before TNFalpha challenge by luciferase reporter gene analysis Homo sapiens 900.0 nM
Inhibition of NF-kappaB expressed in human HepG2 cells assessed as inhibition of TNFalpha-induced luciferase activity preincubated for 1 hr followed by TNFalpha challenge measured after 1 hr by reporter gene assay Homo sapiens 900.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 92.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 72.1 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 92.3 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake by scintillation counting Homo sapiens 530.0 nM Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake by scintillation counting Homo sapiens 560.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 126.2 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 72.91 %
Inhibition of TNF-alpha-induced NF-kappaB transcriptional activation in human HepG2 cells preincubated for 1 hr followed by TNF-alpha challenge measured after 1 hr by luciferase reporter gene assay Homo sapiens 900.0 nM
Anti-ulcerative colitis activity in DSS-induced acute C57Bl/6J mouse ulcerative colitis model assessed as inhibition rate of disease activity index at 300 mg/kg, po qd measured on day 8 relative to control Mus musculus 30.59 %
Antiinflammatory activity in TNBS-induced Sprague-Dawley rat colitis model assessed as inhibition of myeloperoxidase level in colon at 300 mg/kg/day, po administered for 5 days post 1 day of TNBS-challenge by colorimetric method relative to control Rattus norvegicus 58.6 %
Inhibition of Trypanosoma cruzi trans-sialidase at 1 mM using N-acetyllactosamine as substrate in presence of 3'-sialyllactose measured after 15 mins by HPAEC-PAD relative to control Trypanosoma cruzi 37.6 %
Inhibition of DSS-induced acute ulcerative colitis C57BL/6J mouse model at 500 mg/kg, po qd administered for 7 days relative to control Mus musculus 55.17 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 17.6 %
Inhibition of xCT-mediated cystein/glutamate transporter (unknown origin) assessed as reduction in L-[14C]cyctein uptake Homo sapiens 160.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 27.45 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.12 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 %
Activation of ABCB1 ATPase activity (unknown origin) expressed in baculovirus infected Sf9 insect cells using ATP as substrate measured after 1 hr by colorimetric assay Homo sapiens 916.0 nM
Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as dissociation constant by isothermal titration calorimetry Homo sapiens 440.0 nM Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as dissociation constant by isothermal titration calorimetry Homo sapiens 436.52 nM

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Hungary
Romania
Slovenia

Cross References

Resources Reference
ChEBI 9334
ChEMBL CHEMBL421
DrugBank DB00795
DrugCentral 2525
FDA SRS 3XC8GUZ6CB
Human Metabolome Database HMDB0014933
Guide to Pharmacology 4840
KEGG C07316
PDB SAS
SureChEMBL SCHEMBL4515
ZINC ZINC000003831490
CONTENTS