firocoxib
Description
firocoxib: a COX-2 inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
firocoxib : An enol ether that is the cyclopropylmethyl ether of 3-hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2-one. A selective cyclooxygenase 2 inhibitor, it is used in veterinary medicine for the control of pain and inflammation associated with osteoarthritis in horses and 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]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 208910 |
CHEMBL ID | 69998 |
CHEBI ID | 76136 |
SCHEMBL ID | 1383179 |
MeSH ID | M0468235 |
Synonyms (75)
Synonym |
---|
firocoxib (usan/inn) |
D03712 |
equioxx (tn) [veterinary] |
189954-96-9 |
firocoxib |
bdbm50080082 |
3-cyclopropylmethoxy-4-(4-methanesulfonyl-phenyl)-5,5-dimethyl-5h-furan-2-one |
firocoxib (ema epar: veterinary) |
nsc-758895 |
ml-1,785,713 |
CHEMBL69998 , |
chebi:76136 , |
ml-1785713 |
previcox |
librens |
FT-0668544 |
3-(cyclopropylmethoxy)-5,5-dimethyl-4-(4-methylsulfonylphenyl)furan-2-one |
HMS3264G15 |
3-(cyclopropylmethoxy)-4-(4-methylsulfonyl)phenyl)-5,5-dimethylfuranone |
equioxx |
firocoxib [usan:inn] |
unii-y6v2w4s4wt |
y6v2w4s4wt , |
2(5h)-furanone, 3-(cyclopropylmethoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)- |
3-(cyclopropylmethoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)furan-2(5h)-one |
nsc 758895 |
C18363 |
nsc758895 |
pharmakon1600-01504526 |
firocoxib [mi] |
firocoxib [mart.] |
firocoxib [inn] |
firocoxib [green book] |
firocoxib [usan] |
ml 1785713 |
equixx |
3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5h)-furanone |
CCG-213396 |
firocoxibum |
3-(cyclopropylmethoxy)-4-(4-methylsulfonylphenyl)-5,5-dimethylfuranone |
3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2(5h)-one |
SCHEMBL1383179 |
CS-3419 |
AC-33540 |
HY-14670 |
AB01563063_01 |
DB09217 |
2(5h)-furanone, 3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]- |
AKOS027326072 |
sr-01000872758 |
SR-01000872758-1 |
3-(cyclopropylmethoxy)-4-(4-methanesulfonylphenyl)-5,5-dimethyl-2,5-dihydrofuran-2-one |
firocoxib, vetranal(tm), analytical standard |
AS-73802 |
J-012265 |
SBI-0206717.P001 |
NCGC00389572-02 |
A918990 |
BCP07253 |
3-(cyclopropylmethoxy)-4-[4-(methanesulfonyl)phenyl]-5,5-dimethylfuran-2(5h)-one |
DTXSID40870188 |
Q2034390 |
AMY378 |
NCGC00389572-01 |
C73637 |
equioxx injection |
osticoxib |
firox |
equioxx oral paste |
firocoxib chewable tablets for dogs |
flexira |
firocoxib for horses |
previcox chewable tablets |
firocoxib (mart.) |
firocoxib tablets for horses |
Research Excerpts
Overview
Firocoxib is a specific cyclooxygenase-2 (COX-2) inhibitor and has the ability to act in the uterus of mares. It is a non-steroidal anti-inflammatory drug with more than 350-fold selectivity in dogs.
Treatment
Firocoxib treatment prior to induction of arthritis in dogs resulted in a high level of analgesia from the first post-treatment assessment at 1.5 h through 24 H post-treated. Firo Coxib treatment was discontinued, and immunosuppressive therapy including cyclosporine was initiated.
Toxicity
This study evaluated the adverse effects of oral firocoxib in dogs. There was no adverse event during the study that was considered to be related to the administration of firo Coxib. This study demonstrated that firooxib is absorbed in neonatal foals with no demonstrable adverse effects.
Pharmacokinetics
The objective of the study was to conduct a review of the pharmacological regulation and pharmacokinetic parameters of firocoxib when administered orally or intravenously in horses. The pharmacodynamic results do not demonstrate a significant difference in levels of cyclooxygenase-2 inhibition, which indirectly reflects the anti-inflammatory effects.
Bioavailability
Oral firocoxib was well absorbed with an average bioavailability (absolute) of 79%. The aim of this study was to describe pharmacokinetics and bioavailability of firo Coxib in adult goats.
Dosage Studied
The goal of this study was to determine the safety of a 10-day dosage regimen of phenylbutazone and firocoxib, both at their standard dosages, in horses. In addition, practitioners will benefit from understanding the nuances of firo Coxib administration.
Roles (4)
Role | Description |
---|---|
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. |
cyclooxygenase 2 inhibitor | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. |
antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
non-narcotic analgesic | A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. |
[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] |
Drug Classes (4)
Class | Description |
---|---|
butenolide | A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives. |
sulfone | An organosulfur compound having the structure RS(=O)2R (R =/= H). |
enol ether | Ethers ROR' where R has a double bond adjacent to the oxygen of the ether linkage. |
cyclopropanes | Cyclopropane and its derivatives formed by substitution. |
[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 Targets (8)
Potency Measurements
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
cytochrome P450 family 3 subfamily A polypeptide 4 | Homo sapiens (human) | Potency | 21.3174 | 0.0123 | 7.9835 | 43.2770 | AID1645841 |
G | Vesicular stomatitis virus | Potency | 13.4504 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
Interferon beta | Homo sapiens (human) | Potency | 13.4504 | 0.0033 | 9.1582 | 39.8107 | AID1645842 |
HLA class I histocompatibility antigen, B alpha chain | Homo sapiens (human) | Potency | 13.4504 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus | Potency | 10.0000 | 0.0096 | 10.5250 | 35.4813 | AID1479145 |
Inositol hexakisphosphate kinase 1 | Homo sapiens (human) | Potency | 13.4504 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
cytochrome P450 2C9, partial | Homo sapiens (human) | Potency | 13.4504 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Inhibition Measurements
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Prostaglandin G/H synthase 1 | Homo sapiens (human) | IC50 (µMol) | 25.0000 | 0.0002 | 1.5574 | 10.0000 | AID161652 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Biological Processes (51)
Molecular Functions (23)
Ceullar Components (27)
Bioassays (8)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID161652 | Inhibitory activity against Human Prostaglandin G/H synthase 1 in U937 Microsome COX-1 assay | 1999 | Bioorganic & medicinal chemistry letters, Aug-02, Volume: 9, Issue:15 | SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor. |
AID161656 | Inhibitory activity against Prostaglandin G/H synthase 1 in human whole blood | 1999 | Bioorganic & medicinal chemistry letters, Aug-02, Volume: 9, Issue:15 | SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor. |
AID162646 | Inhibition of Prostaglandin G/H synthase 2 in human whole blood | 1999 | Bioorganic & medicinal chemistry letters, Aug-02, Volume: 9, Issue:15 | SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (94)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 1 (1.06) | 18.2507 |
2000's | 21 (22.34) | 29.6817 |
2010's | 54 (57.45) | 24.3611 |
2020's | 18 (19.15) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 41.80
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 (41.80) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 43 (42.16%) | 5.53% |
Reviews | 4 (3.92%) | 6.00% |
Case Studies | 5 (4.90%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 50 (49.02%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |