cimicoxib: a COX-2 inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
cimicoxib : An imidazole substituted at positions 1, 4 and 5 by 4-aminosulfonylphenyl, chloro and 3-fluoro-4-methyoxyphenyl groups respectively. A selective cyclooxygenase 2 inhibitor, it is used in veterinary medicine for the control of pain and inflammation associated with osteoarthritis in dogs. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 213053 |
| CHEMBL ID | 435381 |
| CHEBI ID | 76127 |
| SCHEMBL ID | 3123310 |
| MeSH ID | M0476741 |
| Synonym |
|---|
| 265114-23-6 |
| ur-8880 |
| cimicoxib |
| 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)-imidazol-1-yl]-benzenesulfonamide |
| bdbm50131593 |
| chebi:76127 , |
| cimalgex |
| cimicoxib (ema epar: veterinary) |
| CHEMBL435381 , |
| 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide |
| unii-w7fhj107mc |
| cimicoxib [inn] |
| w7fhj107mc , |
| 4-(4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl)benzenesulfonamide |
| 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl]benzenesulfonamide |
| DB05095 |
| cimicoxib [mi] |
| KYXDNECMRLFQMZ-UHFFFAOYSA-N |
| SCHEMBL3123310 |
| DTXSID30181093 |
| AKOS030586367 |
| BCP24933 |
| cimicoxib;4-(4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl)benzene sulfonamide |
| Q5120133 |
| ur 8880;ur-8880;ur8880 |
| NCGC00531794-01 |
| benzenesulfonamide, 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl]- |
| HY-100516 |
| CS-0019655 |
Cimicoxib (CX) is a novel imidazole derivative that is a cyclo-oxygenase (COX)-2 selective non-steroidal anti-inflammatory drug and the latest COX-2 selective inhibitor to be released for veterinary use.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Cimicoxib has noninferior postoperative analgesic efficacy compared to buprenorphine, and both drugs have comparable analgesic effects for the control of postoperative pain in bitches undergoing ovariohysterectomy." | ( Comparison of the postoperative analgesic effects of cimicoxib, buprenorphine and their combination in healthy dogs undergoing ovariohysterectomy. Bustamante, R; Canfrán, S; Daza, MA; García, P; Gómez de Segura, IA; Suárez, M; Trobo, I, 2018) | 2.17 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Currently there is limited information available on the pharmacokinetic (PK) properties of CX." | ( Pharmacokinetic profiles of the novel COX-2 selective inhibitor cimicoxib in dogs. Giorgi, M; Kim, TW; Kowalski, CJ; Lebkowska-Wieruszewska, B; Owen, H; Yun, HI, 2014) | 0.64 |
| " After administration, blood samples were collected for up to 24 hours and plasma used for pharmacokinetic analysis." | ( Evaluation of pharmacokinetic and pharmacodynamic properties of cimicoxib in fasted and fed horses. Della Rocca, G; Di Salvo, A; Giorgi, M; Kim, TW; Ryschanova, R; Sgorbini, M, 2015) | 0.66 |
Cimicoxib was an efficacious anti-inflammatory, antipyretic and analgesic drug. A dosage regimen of 2 mg/kg daily was determined for confirmatory clinical trials. To determine a preclinical dosage regimen for cimic Oxib in dog, a reversible model of kaolin-induced paw inflammation was used.
| Excerpt | Relevance | Reference |
|---|---|---|
| " To determine a preclinical dosage regimen for cimicoxib in dog, a reversible model of kaolin-induced paw inflammation was used." | ( Pharmacokinetic/pharmacodynamic modeling for the determination of a cimicoxib dosing regimen in the dog. Faucher, M; Jeunesse, EC; Lefebvre, HP; Schneider, M; Toutain, PL; Woehrle, F, 2013) | 0.88 |
| " Thus pharmacokinetic and pharmacodynamic parameters obtained from the EM beagle dogs were selected to simulate the dose-effect relationship of cimicoxib after an oral administration allowing a dosage regimen to be selected for confirmation by a clinical trial." | ( Pharmacokinetic/pharmacodynamic modeling for the determination of a cimicoxib dosing regimen in the dog. Faucher, M; Jeunesse, EC; Lefebvre, HP; Schneider, M; Toutain, PL; Woehrle, F, 2013) | 0.83 |
| "Cimicoxib was an efficacious anti-inflammatory, antipyretic and analgesic drug and a dosage regimen of 2 mg/kg daily was determined for confirmatory clinical trials." | ( Pharmacokinetic/pharmacodynamic modeling for the determination of a cimicoxib dosing regimen in the dog. Faucher, M; Jeunesse, EC; Lefebvre, HP; Schneider, M; Toutain, PL; Woehrle, F, 2013) | 2.07 |
| " Further investigations are required to establish an optimal dosage regimen and safety profile before clinical trials are initiated." | ( Evaluation of pharmacokinetic and pharmacodynamic properties of cimicoxib in fasted and fed horses. Della Rocca, G; Di Salvo, A; Giorgi, M; Kim, TW; Ryschanova, R; Sgorbini, M, 2015) | 0.66 |
| Role | Description |
|---|---|
| cyclooxygenase 2 inhibitor | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. |
| non-steroidal anti-inflammatory drug | An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| sulfonamide | An amide of a sulfonic acid RS(=O)2NR'2. |
| imidazoles | A five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton. |
| organochlorine compound | An organochlorine compound is a compound containing at least one carbon-chlorine bond. |
| organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus | Potency | 8.9125 | 0.0096 | 10.5250 | 35.4813 | AID1479145 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Prostaglandin G/H synthase 1 | Homo sapiens (human) | IC50 (µMol) | 3.3000 | 0.0002 | 1.5574 | 10.0000 | AID161480 |
| Prostaglandin G/H synthase 2 | Homo sapiens (human) | IC50 (µMol) | 0.0367 | 0.0001 | 0.9950 | 10.0000 | AID1532176; AID162489; AID280834 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID162630 | In vitro percent inhibition of Prostaglandin G/H synthase 2 (COX-2) in human whole blood was determined | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID160262 | Inhibition of Prostaglandin G/H synthase 2 (COX-2) in human whole blood at 10 uM | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID182047 | In vivo inhibition of contralateral paw swelling after oral treatment for 28 days (1 mg/kg od) was determined by adjuvabt arthritis in rat | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID184044 | In vivo analgesic activity of compound was determined by inflammatory hyperalgesia model at 3 mg/kg perorally in rat | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID160400 | In vitro percent inhibition of prostaglandin G/H synthase 2 (COX-2) in human whole blood at 1 uM | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID174679 | Percentage of [51Cr]- secreted in feces was determined by fecal drug-induced bleeding method in rat at 100 mg/kg, bid for 5 days | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID1532176 | Inhibition of COX-2 in human 143982 cells | 2019 | European journal of medicinal chemistry, Jan-15, Volume: 162 | Medicinal chemistry of vicinal diaryl scaffold: A mini review. |
| AID29856 | Half life of compound was determined at 1 mg/kg intravenous administration in rat | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID162489 | In vitro inhibitory activity against human Prostaglandin G/H synthase 2 (COX-2) in 143982 cells | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID236294 | Volume of distribution after i.v. administration of 2 mg/kg to Dogs | 2004 | Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22 | New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs. |
| AID280835 | Inhibition of COX1 in human whole blood assessed as TxB2 production after 1 hr | 2007 | Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7 | NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. |
| AID280834 | Activity of COX2 in human heparinized blood assessed as inhibition of LPS-induced PGE2 production after 24 hrs | 2007 | Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7 | NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. |
| AID237580 | Area under curve after i.v. administration of 2 mg/kg to Dogs | 2004 | Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22 | New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs. |
| AID280837 | Vasodilation of phenylephrine-induced contraction in Wistar rat aorta in the presence of ODQ | 2007 | Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7 | NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. |
| AID237149 | Half life after i.v. administration of 2 mg/kg to Dogs | 2004 | Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22 | New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs. |
| AID251823 | Percentage inhibition of rat carrageenan-induced paw edema after iv administration at 3 mg/kg | 2004 | Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22 | New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs. |
| AID236232 | Clearance after i.v. administration of 2 mg/kg to Dogs | 2004 | Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22 | New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs. |
| AID161480 | In vitro inhibitory activity against human Prostaglandin G/H synthase 1 (COX-1) in U-937 cells | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID184174 | In vivo anti-inflammatory activity determined by rat carrageenan paw edema method at 10 mg/kg perorally | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID184173 | In vivo anti-inflammatory activity by air pouch model at 1 mg/kg perorally in rat. | 2003 | Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16 | Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. |
| AID493017 | Wombat Data for BeliefDocking | 2007 | Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7 | NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 3 (18.75) | 29.6817 |
| 2010's | 11 (68.75) | 24.3611 |
| 2020's | 2 (12.50) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (42.19) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 7 (43.75%) | 5.53% |
| Reviews | 1 (6.25%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (50.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||