Drug Details

General Information of the Drug (ID: DR2742)
Name
Celecoxib
Synonyms
CEL; Celebra; Celebrex; Celecox; Celecoxi; Celocoxib; Eurocox; Medicoxib; Onsenal; Solexa; Xilebao; Celecoxib [Old RN]; Celecoxib [USAN]; Pfizer brand of celecoxib; SC 58635; SC58635; YM 177; YM177; AI-525; CEP-33222; Celebra (TN); Celebrex (TN); SC-58635; TPI-336; YM-177; Celebrex, Celebra, Celecoxib; Celecoxib (SC-58635); Celecoxib (JAN/USAN/INN); SC-58553, SC-58635; P-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide; Benzenesulfonamide,4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl); 4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide; 4-[5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE; 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl] benzenesulfonamide; 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
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Molecular Type
Small molecule
Disease Rheumatoid arthritis [ICD-11: FA20] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Elimination
2% of drug is excreted from urine in the unchanged form
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 17.48915 micromolar/kg/day
Water Solubility
The ability of drug to dissolve in water is measured as 0.005 mg/mL
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Formula
C17H14F3N3O2S
PubChem CID
2662
Canonical SMILES
CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
InChI
1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChIKey
RZEKVGVHFLEQIL-UHFFFAOYSA-N
CAS Number
CAS 169590-42-5
ChEBI ID
CHEBI:41423
TTD Drug ID
D03RTS
DrugBank ID
DB00482
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Allyl isothiocyanate      Armoracia rusticana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression PTGER2  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model AY-27 CVCL_S825 Rat urinary system neoplasms Rattus norvegicus
                    In-vivo Model Female F344 rats (Harlan) at 9-10 weeks of age were anesthetized with ketamine and xylazine.
                    Experimental
                    Result(s)		 The combination regime was more effective than each single agent in inhibiting microvessel formation and stimulating microvessel maturation in the tumor tissues.
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Aberrant crypt foci (ACF) animal model was induced by subcutaneously injecting 0.2 ml DMH (30 mg/kg b.w.) in male, 6-week-old, F344 rats.
                    Experimental
                    Result(s)		 Celecoxib and curcumin additively inhibit the growth of colorectal cancer in a rat model.
          Epigallocatechin gallate      Hamamelis virginiana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-2  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model COLO 357 CVCL_0221 Pancreatic adenosquamous carcinoma Homo sapiens
                    Experimental
                    Result(s)		 EGCG synergistically boosts celecoxib-mediated effects and reduces the levels of celecoxib required to elicit beneficial effects on tumorigenic mediators by a factor of ten.
          Gamma tocotrienol      Bixa orellana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
                    In-vitro Model +SA mammary epithelial cells' Healthy Homo sapiens
                    Experimental
                    Result(s)		 Combined low dose treatment of Gamma-tocotrienol and celecoxibthe showed synergistic antiproliferative effects of against +SA mammary tumor cells in culture.
          Levodopa      Mucuna pruriens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Parkinsonian rats were used as animal model in this study.
                    Experimental
                    Result(s)		 L-DOPA + celecoxib combination produces an antiallodynic and antihyperalgesic synergistic interaction at the systemic level, and these effects are mediated, at the central level, through activation of the NO-cGMP-ATP-sensitive K+ channel pathway.
          Luteolin      Abrus precatorius     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAD  Molecule Info 
Pathway MAP
Up-regulation Expression BAK  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
SK-BR-3 CVCL_0033 Breast adenocarcinoma Homo sapiens
                    In-vivo Model MDA-MB-231 cells (2*107) were inoculated subcutaneously into the right flanks of female BALB/c nude mice (6-7 weeks old).
                    Experimental
                    Result(s)		 Synergistic effect between celecoxib and luteolin is dependent on estrogen receptor in human breast cancer cells.
          Piperine      Piper nigrum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP7  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation GSK-3B  Molecule Info 
Pathway MAP
Down-regulation Expression MYC  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Expression WNT3A  Molecule Info 
Pathway MAP
Down-regulation Expression WNT5A  Molecule Info 
Pathway MAP
                    In-vitro Model HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    In-vivo Model CT26.WT (5*106) cells were inoculated subcutaneously in female Balb/c mice.
                    Experimental
                    Result(s)		 Piperine and Celecoxib synergistically inhibit colon cancer cell proliferation via modulating Wnt/beta-catenin signaling pathway.
          Plumbagin      Plumbago europaea     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [10]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model UACC-903 CVCL_4052 Cutaneous melanoma Homo sapiens
Mel JuSo CVCL_1403 Cutaneous melanoma Homo sapiens
A375-M CVCL_B222 Amelanotic melanoma Homo sapiens
1205Lu CVCL_5239 Melanoma Homo sapiens
FF2441 Healthy Homo sapiens
                    In-vivo Model Subcutaneous injection of 1.0 * 106 UACC 903 or 1205 Lu melanoma cells were injected above both the left and right rib cages of 4-5 week-old female Athymic-Foxn1nu nude mice.
                    Experimental
                    Result(s)		 Combination of Celecoxib and Plumbagin decreased melanoma cell proliferation and retarded vascular development of tumors mediated by inhibition of COX-2 and STAT3 leading to decreased levels of key cyclins key on which melanoma cell were dependent for survival.
          Resveratrol      Gnetum parvifolium     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [11]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    In-vivo Model Mammary carcinogenesis was initiated with two intra peritoneal doses (50 mg/kg body weight each) of N-methyl-N-nitrosourea (NMU) dissolved in a physiological NaCl solution.
                    Experimental
                    Result(s)		 Resveratrol enhances the chemopreventive effect of celecoxib in chemically induced breast cancer in rats.
          Gamma tocotrienol + Vitamin E     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation p105  Molecule Info 
Pathway MAP
                    In-vitro Model +SA mammary epithelial cells' Healthy Homo sapiens
                    Experimental
                    Result(s)		 Combination therapy with these agents may provide enhanced therapeutic response in breast cancer patients, while avoiding the toxicity associated with high-dose COX-2 inhibitor monotherapy.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Honokiol      Magnolia officinalis     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [12]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression FOXM1  Molecule Info 
Pathway MAP
Down-regulation Expression FOXP3  Molecule Info 
Pathway MAP
Down-regulation Expression ITGAM  Molecule Info 
Pathway MAP
Down-regulation Expression MKI67  Molecule Info 
Pathway MAP
Down-regulation Expression NNT  Molecule Info 
Pathway MAP
Down-regulation Expression PECAM1  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model 4T1 CVCL_0125 Malignant neoplasms Mus musculus
                    Experimental
                    Result(s)		 The combined treatment with PV-CXB and PV-HNK showed synergistic effect both in vitro and in vivo.
Target and Pathway
Target(s) Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [13]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 NF-kappa B signaling pathway
4 VEGF signaling pathway
5 TNF signaling pathway
6 Retrograde endocannabinoid signaling
7 Serotonergic synapse
8 Ovarian steroidogenesis
9 Oxytocin signaling pathway
10 Regulation of lipolysis in adipocytes
11 Leishmaniasis
12 Pathways in cancer
13 Chemical carcinogenesis
14 MicroRNAs in cancer
15 Small cell lung cancer
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Aryl Hydrocarbon Receptor
4 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
5 Spinal Cord Injury
6 Integrated Pancreatic Cancer Pathway
7 Eicosanoid Synthesis
8 Selenium Micronutrient Network
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2892).
Reference 2 Enhanced inhibition of urinary bladder cancer growth and muscle invasion by allyl isothiocyanate and celecoxib in combination. Carcinogenesis. 2013 Nov;34(11):2593-9.
Reference 3 Celecoxib and curcumin additively inhibit the growth of colorectal cancer in a rat model. Digestion. 2006;74(3-4):140-4.
Reference 4 (-)-Epigallocatechin-3-gallate, a green tea-derived catechin, synergizes with celecoxib to inhibit IL-1-induced tumorigenic mediators by human pancreatic adenocarcinoma cells Colo357. Eur J Pharmacol. 2012 Jun 5;684(1-3):36-43.
Reference 5 Synergistic anticancer effects of combined gamma-tocotrienol and celecoxib treatment are associated with suppression in Akt and NFkappaB signaling. Biomed Pharmacother. 2010 May;64(5):327-32.
Reference 6 Synergistic actions of atorvastatin with gamma-tocotrienol and celecoxib against human colon cancer HT29 and HCT116 cells. Int J Cancer. 2010 Feb 15;126(4):852-63.
Reference 7 Synergistic antiallodynic and antihyperalgesic interaction between L-DOPA and celecoxib in parkinsonian rats is mediated by NO-cGMP-ATP-sensitive K + channel. Eur J Pharmacol. 2020 Dec 15;889:173537.
Reference 8 Synergistic effect between celecoxib and luteolin is dependent on estrogen receptor in human breast cancer cells. Tumour Biol. 2015 Aug;36(8):6349-59.
Reference 9 Piperine and Celecoxib synergistically inhibit colon cancer cell proliferation via modulating Wnt/beta-catenin signaling pathway. Phytomedicine. 2021 Apr;84:153484.
Reference 10 Synergistic inhibitory effects of Celecoxib and Plumbagin on melanoma tumor growth. Cancer Lett. 2017 Jan 28;385:243-250.
Reference 11 Resveratrol enhances the chemopreventive effect of celecoxib in chemically induced breast cancer in rats. Eur J Cancer Prev. 2014 Nov;23(6):506-13.
Reference 12 Tuning mPEG-PLA/vitamin E-TPGS-based mixed micelles for combined celecoxib/honokiol therapy for breast cancer. Eur J Pharm Sci. 2020 Apr 15;146:105277.
Reference 13 Pfizer. Product Development Pipeline. March 31 2009.
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