Celecoxib

Base Information

• Chemical Name: Celecoxib
• CAS No.: 169590-42-5
• Deprecated CAS: 184007-95-2,194044-54-7
• Molecular Formula: C17H14F3N3O2S
• Molecular Weight: 381.378
• Hs Code.: 29350090
• European Community (EC) Number: 685-962-5
• NSC Number: 758624,719627
• UNII: JCX84Q7J1L
• DSSTox Substance ID: DTXSID0022777
• Nikkaji Number: J833.239H
• Wikipedia: Celecoxib
• Wikidata: Q408801
• NCI Thesaurus Code: C1728
• RXCUI: 140587
• Pharos Ligand ID: DYM83CYSZL6G
• Metabolomics Workbench ID: 38701
• ChEMBL ID: CHEMBL118
• Mol file: 169590-42-5.mol

Synonyms:4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide;Celebrex;celecoxib;SC 58635;SC-58635;SC58635

Chemical Property of Celecoxib

Chemical Property:

• Appearance/Colour: white to pale yellow solid
• Vapor Pressure: 2.81E-11mmHg at 25°C
• Melting Point: 157-159 °C
• Refractive Index: 1.605
• Boiling Point: 529 °C at 760 mmHg
• PKA: 9.68±0.10(Predicted)
• Flash Point: 273.7 °C
• PSA: 86.36000
• Density: 1.43 g/cm³
• LogP: 5.29500
• Storage Temp.: Store at RT
• Solubility.: DMSO: >20mg/mL
• Water Solubility.: 7mg/L(25 oC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 381.07588236
• Heavy Atom Count: 26
• Complexity: 577

Purity/Quality:

99.5% ^*data from raw suppliers

Celecoxib ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-52-61-60
• Safety Statements: 22-24/25-28-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: Precision psychiatry: Anti-inflammatory medication in Immuno-metabolic depression
• Recent NIPH Clinical Trials: Efficacy of Mirogabalin and pain after total hip arthroplasty: a randomized controlled trial
• Anti-inflammatory, Analgesic, and Antipyretic Medication: Celecoxib is a selective non鈥恠teroidal anti鈥恑nflammatory drug (NSAID) used for its anti-inflammatory, analgesic, and antipyretic properties. It is marketed as being as effective as traditional anti-inflammatory drugs (tNSAIDs) such as naproxen and diclofenac but with fewer gastrointestinal and other associated problems.
• COX-2 Selective Inhibition: Celecoxib is a paradigmatic selective inhibitor of cyclooxygenase-2 (COX-2), which is an enzyme involved in the inflammatory response. Its selective inhibition of COX-2 makes it effective in reducing inflammation and pain while minimizing gastrointestinal side effects associated with non-selective NSAIDs.
• Anti-tumor Activity: Celecoxib exhibits potent anti-tumor activity in various human epithelial tumor types, including colorectal, breast, non-small cell lung, and prostate cancers. It has been utilized in cancer prevention, particularly in patients with familial adenomatous polyposis. Celecoxib is being tested for its potential in preventing and treating pancreatic, breast, ovarian, non-small cell lung cancer, and other advanced human epithelial cancers.
• Induction of Apoptosis: Celecoxib induces apoptosis (programmed cell death) independently from its COX-2 inhibitory action. It activates a mitochondrial apoptosis pathway, which is not inhibited by overexpression of certain anti-apoptotic proteins such as Bcl-2. Celecoxib exerts antagonistic effects on anti-apoptotic proteins Mcl-1 and survivin, suggesting its potential in treating apoptosis-resistant tumors.
• Chemopreventive Activity Against Breast Cancer (BC): Preclinical evidence suggests that celecoxib may provide strong chemopreventive activity against breast cancer. Celecoxib treatment has been shown to decrease the incidence, multiplicity, and tumor volume in several animal models of breast cancer.
• Market Availability and Formulation: Celecoxib is available in oral capsule form and was initially approved by the US Food and Drug Administration (FDA) in 1999. It is marketed by Pfizer, Inc. as a selective COX-2 inhibitor for the management of pain, inflammation, and fever.

Technology Process of Celecoxib

There total 88 articles about Celecoxib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N,N-dibenzyl-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (853793-24-5) → 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide (169590-42-5,194044-54-7)

Guidance literature:

With sulfuric acid; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2015.09.007

Reference yield: 99.0%

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione (720-94-5) + 4-hydrazinobenzene-1-sulfonamide hydrochloride (17852-52-7,27918-19-0) → 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide (169590-42-5,194044-54-7)

Guidance literature:

at 90 ℃; Temperature;

Reference yield: 98.8%

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione (720-94-5) + 4-hydrazinobenzene-1-sulfonamide hydrochloride → 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide (169590-42-5,194044-54-7)

Guidance literature:

In ethanol; for 24h; Solvent; Inert atmosphere; Reflux;

upstream raw materials:

4-[5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonyl chloride

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-hydrazinobenzene-1-sulfonamide hydrochloride

methyl iodide

Downstream raw materials:

3,5-bis[(triisopropylsilyloxy)-methyl]-phenyl {4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenyl}-sulfonylcarbamate

4-[(nitrooxy)-methyl]-phenyl {4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenyl}-sulfonylcarbamate

4-bromobutyl {4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenyl}-sulfonylcarbamate

C₃₇H₃₄F₃N₅O₆S

Refernces

• 1、 Oh, Lynette M.. "Synthesis of celecoxib via 1,3-dipolar cycloaddition". . p. 7943 - 7946. Retrieved 2006.
• 2、 Sommer, Heiko,Braun, Max,Schr?der, Benjamin,Kirschning, Andreas. "4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes - A Short Synthesis of Celebrex (Celecoxib)". . p. 121 - 125. Retrieved 2018.
• 3、 Reddy, Anumula Raghupathi,Sampath, Alla,Goverdhan, Gilla,Yakambaram, Bojja,Mukkanti, Kagga,Reddy, Padi Pratap. "An improved and scalable process for celecoxib: A selective cyclooxygenase-2 inhibitor". . p. 98 - 101. Retrieved 2009.
• 4、 Liu, Yongan,Pan, Qijun,Hu, Xiaojun,Guo, Yong,Chen, Qing-Yun,Liu, Chao. "Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides". . p. 3975 - 3980. Retrieved 2021/05/26.
• 5、 Lo, Pui Kin Tony,Willis, Michael C.. "Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides". . p. 15576 - 15581. Retrieved 2021/10/02.