SULFASALAZINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1950)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: A07EC01
UNII: 3XC8GUZ6CB

Structure
InChI Key NCEXYHBECQHGNR-QZQOTICOSA-N
Smile 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

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Arachidonate 5-lipoxygenase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 5 Cytochrome P450 family 5A Cytochrome P450 5A1
- 19639 - - -
Enzyme Hydrolase
- - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase SGK family
- - - - 70
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase ERK subfamily
- 6332 - - -
Enzyme Lyase
- 3040 - 6870 -
Enzyme Oxidoreductase
- 17042 436.52-440 - 60
Enzyme Protease Cysteine protease Cysteine protease CD clan Cysteine protease C14 family
- 28812 - - -
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M10A subfamily
- 23549 - - -
Enzyme Transferase
- - 7600 - 19.12-27.45
Enzyme
- 17042 436.52-440 22000 19.12-27.45
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -21.39-0.23
Other cytosolic protein
- 10000 - - -
Secreted protein
- - 609000 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 43951 - 29301 -
Transcription factor
- 10000 - 29301 -
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
- 160-460000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC10 family of sodium-bile acid co-transporters
- 9600-9600 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 12000 - 11000 72.1-72.91
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 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 460 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Arthritis, Psoriatic 3 D015535 ClinicalTrials
Peripheral Nervous System Diseases 2 D010523 ClinicalTrials
Cholangitis, Sclerosing 2 D015209 ClinicalTrials
Premature Birth 2 D047928 ClinicalTrials
Spondylitis, Ankylosing 2 D013167 ClinicalTrials
Paraganglioma 1 D010235 ClinicalTrials
Osteomyelitis 1 D010019 ClinicalTrials
Nausea 1 D009325 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Intestinal Obstruction 1 D007415 ClinicalTrials
Hypertension, Pulmonary 1 D006976 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
20.43
Musculoskeletal and connective tissue disorders
12.19
Immune system disorders
9.61
Gastrointestinal disorders
7.74
Skin and subcutaneous tissue disorders
7.12
Investigations
5.08
Respiratory, thoracic and mediastinal disorders
4.93
Nervous system disorders
4.71
Infections and infestations
4.51
Injury, poisoning and procedural complications
4.47
Vascular disorders
3.17
Cardiac disorders
2.27
Blood and lymphatic system disorders
2.22

Cross References

Resources Reference
CAS NUMBER 599-79-1
ChEBI 9334
ChEMBL CHEMBL421
DrugBank DB00795
DrugCentral 2525
EPA CompTox DTXSID0021256
FDA SRS 3XC8GUZ6CB
Human Metabolome Database HMDB14933
Guide to Pharmacology 4840
KEGG C07316
PDB SAS
SureChEMBL SCHEMBL4515
ZINC ZINC000003831490
CONTENTS