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Compound Detail

CHEMBL421

SULFASALAZINE
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1cc(/N=N/c2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1O

Basic Information

ChEMBL ID CHEMBL421
Name SULFASALAZINE
Phase Approved
Structure Type MOL
InChI Key NCEXYHBECQHGNR-QZQOTICOSA-N
Therapeutic ✓ Yes

Known Names

Azulfidine Azulfidine en-tabs Benzosulfa Colizine NSC-203730 NSC-667219 S.a.s.-500 Salazopyrin Salazopyrin e.c. Salazopyrin-en Salazosulfapyridine Salicylazosulfapyridine +7 more
22
Targets
42
Activities
4
Assay Types
30
PK Parameters
20
Publications
19
Known Names
15
Indications
2
Mechanisms

Molecular Properties

398.4
MW (Da)
3.70
ALogP
7
HBA
3
HBD
141.3
PSA (Ų)
0.54
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -lazine; -sal-; sulfa-
USAN Year 1975

Extended Properties

Molecular Formula C18H14N4O5S
MW 398.40
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.07

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Arachidonate 5-lipoxygenase inhibitor INHIBITOR Polyunsaturated fatty acid 5-lipoxygenase
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase

Indications

Arthritis, Juvenile Arthritis, Rheumatoid Colitis, Ulcerative Arthritis, Psoriatic Cholangitis, Sclerosing Peripheral Nervous System Diseases Premature Birth Spondylitis, Ankylosing Glioblastoma Hypertension, Pulmonary Intestinal Obstruction Leukemia, Myeloid, Acute Nausea Paraganglioma Osteomyelitis

ATC Classification

A07EC01
sulfasalazine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

Activity Summary

IC50 30 meas. best 6.8
Ki 7 meas. best 6.28
Kd 4 meas. best 6.36
EC50 1 meas. best 6.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cystine/glutamate transporter
CHEMBL1075149
IC50 6.8 5.32 160.0 4
Flavin reductase (NADPH)
CHEMBL5019
Kd 6.36 6.36 436.5 2
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 6.34 6.34 460.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
Ki 6.28 6.28 530.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 6.25 6.25 560.0 1
Unchecked
CHEMBL612545
IC50 6.05 6.05 900.0 5
ATP-dependent translocase ABCB1
CHEMBL4302
EC50 6.04 6.04 916.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 5.82 5.82 1500.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
Ki 5.52 5.52 3000.0 1
Carbonic anhydrase 1
CHEMBL261
IC50 5.52 5.52 3040.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
IC50 5.52 5.52 3000.0 1
Carbonic anhydrase 2
CHEMBL205
IC50 5.35 5.35 4490.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
IC50 5.2 5.2 6332.0 1
Carbonic anhydrase 1
CHEMBL261
Ki 5.16 5.16 6870.0 1
Replicase polyprotein 1ab
CHEMBL4295557
Kd 5.12 5.12 7600.0 1
Carbonic anhydrase 2
CHEMBL205
Ki 5.06 5.06 8720.0 1
Hepatic sodium/bile acid cotransporter
CHEMBL5287
IC50 5.02 5.02 9600.0 2
Nuclear factor NF-kappa-B complex
CHEMBL2094258
IC50 5.0 5.0 10000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
Ki 4.96 4.96 11000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 4.92 4.92 12000.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 4.84 4.84 14600.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
IC50 4.77 4.77 17042.0 1
Thromboxane-A synthase
CHEMBL1835
IC50 4.71 4.71 19639.0 1
Bifunctional purine biosynthesis protein ATIC
CHEMBL2518
Ki 4.66 4.66 22000.0 1
Interstitial collagenase
CHEMBL332
IC50 4.63 4.63 23549.0 1
Caspase-1
CHEMBL4801
IC50 4.54 4.54 28812.0 1
Androgen receptor
CHEMBL3072
Ki 4.53 4.53 29301.0 1
Androgen receptor
CHEMBL3072
IC50 4.36 4.36 43951.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 462.0 ng.hr.mL-1 Rattus norvegicus
AUC 1810.0 ng.hr.mL-1 Rattus norvegicus
AUC 7730.0 ng.hr.mL-1 Rattus norvegicus
AUC 12300.0 ng.hr.mL-1 Rattus norvegicus
AUC 635.0 ng.hr.mL-1 Rattus norvegicus
AUC 13104.0 ng.hr.mL-1 Rattus norvegicus
AUC 711.0 ng.hr.mL-1 Rattus norvegicus
AUC 562.0 ng.hr.mL-1 Rattus norvegicus
AUC 4320.0 ng.hr.mL-1 Rattus norvegicus
AUC 10727.0 ng.hr.mL-1 Rattus norvegicus
AUC 6260.0 ng.hr.mL-1 Rattus norvegicus
AUC 8401.0 ng.hr.mL-1 Rattus norvegicus
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.24 mL.min-1.kg-1 Homo sapiens
CL 10.9 mL.min-1.kg-1 Rattus norvegicus
CL 6.8 mL.min-1.kg-1 Rattus norvegicus
CL 22.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.8 mL.min-1.kg-1 Rattus norvegicus
CL 13.5 mL.min-1.kg-1 Rattus norvegicus
CL 10.4 mL.min-1.kg-1 Rattus norvegicus
Cmax 0.144 ug.mL-1 Rattus norvegicus
Cmax 0.49 ug.mL-1 Rattus norvegicus
Cmax 0.32 ug.mL-1 Rattus norvegicus
Cmax 3.872 ug.mL-1 Rattus norvegicus
Cmax 0.213 ug.mL-1 Rattus norvegicus
Cmax 0.185 ug.mL-1 Rattus norvegicus
F 37.0 % Mus musculus
F 1.5 % Rattus norvegicus
F 3.8 % Rattus norvegicus
F 4.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cystine/glutamate transporter IC50 = 160.0 nM 6.8 Inhibition of xCT-mediated cystein/glutamate transporter (unknown origin) assess... 30522056
Flavin reductase (NADPH) Kd = 440.0 nM 6.36 Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLV... 34957824
Flavin reductase (NADPH) Kd = 436.52 nM 6.36 Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLV... 34957824
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 460.0 nM 6.34 Inhibition of ABCG2 (unknown origin) expressed in human HEK cells membrane vesic... 35483322
Solute carrier organic anion transporter family member 1B1 Ki = 530.0 nM 6.28 Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
Solute carrier organic anion transporter family member 1B1 IC50 = 560.0 nM 6.25 Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
Unchecked IC50 = 900.0 nM 6.05 Inhibition of NF-kappaB activation expressed in TNFalpha-stimulated human HepG2 ... 21889336
Unchecked IC50 = 900.0 nM 6.05 Inhibition of TNF-alpha-induced NF-kappaB transcriptional activation in human He... 24314396
Unchecked IC50 = 900.0 nM 6.05 Inhibition of NF-kappaB expressed in human HepG2 cells assessed as inhibition of... 23031596
Unchecked IC50 = 900.0 nM 6.05 Inhibition of TNFalpha-induced NFkappaB transcriptional activity in human HepG2 ... 22381047
Unchecked IC50 = 900.0 nM 6.05 Inhibition of TNF-alpha-induced NFkappaB activation in human HepG2 cells after 1... 21870831
ATP-dependent translocase ABCB1 EC50 = 916.0 nM 6.04 Activation of ABCB1 ATPase activity (unknown origin) expressed in baculovirus in... 32105979
ATP-binding cassette sub-family C member 4 IC50 = 1500.0 nM 5.82 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Carbonic anhydrase 1 IC50 = 3040.0 nM 5.52 Inhibition of human carbonic anhydrase 1 esterase activity by spectrophotometry 18819808
Solute carrier organic anion transporter family member 2B1 IC50 = 3000.0 nM 5.52 Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
Solute carrier organic anion transporter family member 2B1 Ki = 3000.0 nM 5.52 Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
Carbonic anhydrase 2 IC50 = 4490.0 nM 5.35 Inhibition of human carbonic anhydrase 2 esterase activity by spectrophotometry 18819808
Mitogen-activated protein kinase 1 IC50 = 6332.0 nM 5.2 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Carbonic anhydrase 1 Ki = 6870.0 nM 5.16 Inhibition of human carbonic anhydrase 1 esterase activity by noncompetitive Lin... 18819808
Replicase polyprotein 1ab Kd = 7600.0 nM 5.12 Binding affinity to MERS-CoV papain-like protease by SPR analysis 30940566

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1426
31158845 10.1038/s41586-019-1291-3 ADMET 126
- 10.5281/zenodo.13943903 ADMET 88
22711747 10.1124/dmd.112.046508 Rattus norvegicus 54
21051535 10.1124/dmd.110.034629 ADMET 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
6136612 10.1021/jm00363a015 Rattus norvegicus 16
34842428 10.1021/acs.jmedchem.1c01276 Mus musculus 16
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
30151084 10.1039/C8MD00156A Rattus norvegicus 8
28364659 10.1016/j.ejmech.2017.03.063 Trypanosoma cruzi 7
20070106 10.1021/jm901371v Homo sapiens 7
- 10.1039/C6MD00235H Solute carrier organic anion transporter family member 2B1 7
26321079 10.1021/acs.jmedchem.5b00964 Mus musculus 6
33895277 10.1016/j.bmcl.2021.128059 Rattus norvegicus 6
21149540 10.1124/dmd.110.035998 Brain 6
18070971 10.1128/aac.00678-07 Mycobacterium avium subsp. paratuberculosis 5

Data from ChEMBL 36 via Core Engine