SC-236
Identification
- Generic Name
- SC-236
- DrugBank Accession Number
- DB14059
- Background
SC-236 is a potent, selective, orally active inhibitor of cyclooxygenase-2 (COX-2) 12 that has been studied in cancer therapy 3, lower back pain 4, and inflammation 1, 2,11, 5.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 401.79
Monoisotopic: 401.02126 - Chemical Formula
- C16H11ClF3N3O2S
- Synonyms
- Not Available
- External IDs
- SC 236
- SC-236
- SC236
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
This drug is a selective inhibitor of the COX-2 enzyme 2, 3. COX-2 is expressed in the brain, in the kidney, in bone, and likely in the female reproductive system 14. Its expression at other sites is increased during inflammation, experimentally, in response to mitogenic stimuli. Growth factors, phorbol esters, and interleukin (IL)-1 stimulate the expression of COX-2 in fibroblasts, while endotoxin serves the same function in monocytes/macrophages 14.
SC-236 works also directly through suppressing the nuclear translocation of RelA/p65, a transcription factor. SC-236 directly targets proteins that facilitate the nuclear translocation of NF-κB, an inflammatory signaling pathway 2, 8.
Target Actions Organism ACyclooxygenase 2 inhibitorCanis lupus familiaris ANuclear factor NF-kappa-B complex inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Long plasma half-life 6.
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir SC-236 may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when SC-236 is combined with Abciximab. Acebutolol SC-236 may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with SC-236. Acemetacin The risk or severity of adverse effects can be increased when Acemetacin is combined with SC-236. - Food Interactions
- Not Available
Categories
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amides
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antirheumatic Agents
- Benzene Derivatives
- Cyclooxygenase Inhibitors
- Enzyme Inhibitors
- Nephrotoxic agents
- Peripheral Nervous System Agents
- Sensory System Agents
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9HGW1H8S2M
- CAS number
- 170569-86-5
- InChI Key
- NSQNZEUFHPTJME-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H11ClF3N3O2S/c17-11-3-1-10(2-4-11)14-9-15(16(18,19)20)22-23(14)12-5-7-13(8-6-12)26(21,24)25/h1-9H,(H2,21,24,25)
- IUPAC Name
- 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
- SMILES
- NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(Cl)C=C1)C(F)(F)F
References
- General References
- Kim SJ, Jeong HJ, Moon PD, Myung NY, Kim MC, Kang TH, Lee KM, Park RK, So HS, Kim EC, An NH, Um JY, Kim HM, Hong SH: The COX-2 inhibitor SC-236 exerts anti-inflammatory effects by suppressing phosphorylation of ERK in a murine model. Life Sci. 2007 Aug 23;81(11):863-72. doi: 10.1016/j.lfs.2007.06.027. Epub 2007 Sep 5. [Article]
- Kim SJ, Jeong HJ, Choi IY, Lee KM, Park RK, Hong SH, Kim HM: Cyclooxygenase-2 inhibitor SC-236 [4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] benzenesulfonamide] suppresses nuclear factor-kappaB activation and phosphorylation of p38 mitogen-activated protein kinase, extracellular signal-regulated kinase, and c-Jun N-terminal kinase in human mast cell line cells. J Pharmacol Exp Ther. 2005 Jul;314(1):27-34. doi: 10.1124/jpet.104.082792. Epub 2005 Mar 22. [Article]
- Wong BC, Jiang XH, Lin MC, Tu SP, Cui JT, Jiang SH, Wong WM, Yuen MF, Lam SK, Kung HF: Cyclooxygenase-2 inhibitor (SC-236) suppresses activator protein-1 through c-Jun NH2-terminal kinase. Gastroenterology. 2004 Jan;126(1):136-47. [Article]
- Deleo TA, Hashizume H, Rutkowski MD, Weinstein TN: Cyclooxygenase-2 inhibitor SC-236 attenuates mechanical allodynia following nerve root injury in rats. J Orthop Res. 2000 Nov;18(6):977-82. doi: 10.1002/jor.1100180618. [Article]
- Jiang XH, Lam SK, Lin MC, Jiang SH, Kung HF, Slosberg ED, Soh JW, Weinstein IB, Wong BC: Novel target for induction of apoptosis by cyclo-oxygenase-2 inhibitor SC-236 through a protein kinase C-beta(1)-dependent pathway. Oncogene. 2002 Sep 5;21(39):6113-22. doi: 10.1038/sj.onc.1205778. [Article]
- Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, AndersonGD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC: Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem. 1997 Apr 25;40(9):1347-65. [Article]
- Dai Y, Wang WH: Non-steroidal anti-inflammatory drugs in prevention of gastric cancer. World J Gastroenterol. 2006 May 14;12(18):2884-9. [Article]
- Wong BC, Jiang Xh, Fan XM, Lin MC, Jiang SH, Lam SK, Kung HF: Suppression of RelA/p65 nuclear translocation independent of IkappaB-alpha degradation by cyclooxygenase-2 inhibitor in gastric cancer. Oncogene. 2003 Feb 27;22(8):1189-97. doi: 10.1038/sj.onc.1206234. [Article]
- Randall E. Harris (2002). COX-2 Blockade in Cancer Prevention and Therapy. Humana Press.
- Luka Milas, K. K Ang, C. Nieder (2003). Modification of Radiation Response: Cytokines, Growth Factors, and Other Biological Targets (Medical Radiology). Springer.
- Comparative Protection against Liver Inflammation and Fibrosis by a Selective Cyclooxygenase-2 Inhibitor and a Nonredox-Type 5-Lipoxygenase Inhibitor [Link]
- SC-236 [Link]
- Enhancement of Tumor Response to -Radiation by an Inhibitor of Cyclooxygenase-2 Enzyme [Link]
- Overview of selective COX-2 inhibitors [Link]
- External Links
- ChemSpider
- 8041499
- BindingDB
- 50057527
- ChEMBL
- CHEMBL282093
- ZINC
- ZINC000000600558
- MSDS
- Download (72.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.004 mg/mL ALOGPS logP 4.51 ALOGPS logP 4.1 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 10.6 Chemaxon pKa (Strongest Basic) -0.44 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 77.98 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 92 m3·mol-1 Chemaxon Polarizability 35.2 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-bc0b3ecc07476da16bfa Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-eff4dcc980556f22265c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000400000-14f0fb71bfe47a48abf1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0001900000-8d1f734a33675cee47fb Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-0325ebaf0b61b7f5c12d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0229000000-47b7059bc736b28e33ed Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Canis lupus familiaris
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- Q8SPQ9
- Uniprot Name
- Cyclooxygenase 2
- Molecular Weight
- 68974.625 Da
References
- Nonsteroidal Antiinflammatory Drugs and a Selective Cyclooxygenase 2 Inhibitor Uncouple Mitochondria in Intact Cells [Link]
- The COX-2 inhibitor SC-236 exerts anti-inflammatory effects by suppressing phosphorylation of ERK in a murine model [Link]
- A cyclooxygenase-2 (COX-2) inhibitor compared with dexamethasone in a survival study of rats with intracerebral 9L gliosarcomas [File]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
- Specific Function
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Components:
Name | UniProt ID |
---|---|
Nuclear factor NF-kappa-B p100 subunit | Q00653 |
Nuclear factor NF-kappa-B p105 subunit | P19838 |
Transcription factor p65 | Q04206 |
References
- Wong BC, Jiang Xh, Fan XM, Lin MC, Jiang SH, Lam SK, Kung HF: Suppression of RelA/p65 nuclear translocation independent of IkappaB-alpha degradation by cyclooxygenase-2 inhibitor in gastric cancer. Oncogene. 2003 Feb 27;22(8):1189-97. doi: 10.1038/sj.onc.1206234. [Article]
- Kim SJ, Jeong HJ, Choi IY, Lee KM, Park RK, Hong SH, Kim HM: Cyclooxygenase-2 inhibitor SC-236 [4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] benzenesulfonamide] suppresses nuclear factor-kappaB activation and phosphorylation of p38 mitogen-activated protein kinase, extracellular signal-regulated kinase, and c-Jun N-terminal kinase in human mast cell line cells. J Pharmacol Exp Ther. 2005 Jul;314(1):27-34. doi: 10.1124/jpet.104.082792. Epub 2005 Mar 22. [Article]
- Cyclooxygenase-2 Inhibitor SC-236 [4-[5-(4-Chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] Benzenesulfonamide] Suppresses Nuclear Factor-κB Activation and Phosphorylation of p38 Mitogen-Activated Protein Kinase, Extracellular Signal-Regulated Kinase, and c-Jun N-Terminal Kinase in Human Mast Cell Line Cells [Link]
Drug created at June 14, 2018 19:34 / Updated at June 12, 2020 16:53