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Details

Stereochemistry ACHIRAL
Molecular Formula C16H11F4N3O2S
Molecular Weight 385.336
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAVACOXIB

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N2N=C(C=C2C3=CC=C(F)C=C3)C(F)(F)F

InChI

InChIKey=TTZNQDOUNXBMJV-UHFFFAOYSA-N
InChI=1S/C16H11F4N3O2S/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)

HIDE SMILES / InChI

Molecular Formula C16H11F4N3O2S
Molecular Weight 385.336
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/mavacoxib.html | https://ec.europa.eu/health/documents/community-register/2013/20130812126285/anx_126285_en.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25433056 | https://www.ncbi.nlm.nih.gov/pubmed/21219337

Mavacoxib (trade name Trocoxil) is a veterinary drug used to treat pain and inflammation in dogs with the degenerative joint disease. Mavacoxib is a non-steroidal anti-inflammatory drug (NSAID) of the coxib class. Mavacoxib acts by preferential inhibition of COX-2-mediated prostaglandin synthesis. It, therefore, possesses analgesic and anti-inflammatory properties. The products of COX-2 metabolism are also involved in ovulation, implantation, and closure of the ductus arteriosus. Mavacoxib is well absorbed after oral administration; bioavailability was 87% in fed dogs and 46 % in fasted conditions and the recommended dose is based on administration with food. Therapeutic concentrations in fed dogs are reached rapidly and peak concentrations are obtained in less than 24 hours after administering a dose. Mavacoxib is approximately 98% bound to plasma proteins. It is extensively distributed throughout the body and almost all the mavacoxib-related residues in plasma comprise parent drug. The rate of body clearance of mavacoxib is slow and the major route of elimination is by biliary excretion of the parent drug. Adverse reactions of the digestive tract such as vomiting and diarrhea were commonly reported, loss of appetite, hemorrhagic diarrhea, and melaena have been reported in uncommon cases. Gastrointestinal ulceration was reported in rare cases. Apathy, degradation of renal biochemistry parameters and impaired renal function have been reported in uncommon cases. In rare cases, these adverse reactions may be fatal.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Trocoxil

Approved Use

For the treatment of pain and inflammation associated with degenerative joint disease in dogs in cases where continuous treatment exceeding one month is indicated
Primary
Trocoxil

Approved Use

For the treatment of pain and inflammation associated with degenerative joint disease in dogs in cases where continuous treatment exceeding one month is indicated
PubMed

PubMed

TitleDatePubMed
The pharmacokinetics of mavacoxib, a long-acting COX-2 inhibitor, in young adult laboratory dogs.
2010 Oct
Patents

Sample Use Guides

The dose is 2 mg mavacoxib per kg body weight given immediately before or with the dog’s main meal. Care should be taken to ensure that the tablet is ingested. The treatment should be repeated 14 days later, thereafter the dosing interval is ONE MONTH. A treatment cycle should not exceed 7 consecutive doses (6.5 months).
Route of Administration: Oral
To determine normal keratinocytes (CPEK); osteosarcoma (D17, KTOSA5, CSKOS); glioma (J3T); lymphoma (3132); mast cell tumour (C2-S); and haemangiosarcoma (SB) cell lines viability, CellTiter-Glo® Luminescent Cell Viability Assay kit (Promega, Madison, WI, USA) was used. 500 cells were seeded per well in a 96-well plate, in triplicate. Cells were incubated for 24 h at 37°C, 5% CO2. Mavacoxib was applied at a range of concentrations (0 μM – 5 mM) and incubated for 48 h. The plate was equilibrated at room temperature for 30 min and 100 μl of CellTiter-Glo® reagent was added to each well. Luminescence was recorded by a luminometor (Viktor3, PerkinElmer, Massachusetts, USA).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:13 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:13 GMT 2023
Record UNII
YFT7X7SR77
Record Status Validated (UNII)
Record Version
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Name Type Language
MAVACOXIB
INN   USAN  
INN   USAN  
Official Name English
MAVACOXIB [USAN]
Common Name English
MAVACOXIB [MI]
Common Name English
PHA 739,521
Code English
TROCOXIL
Brand Name English
MAVACOXIB [EMA EPAR VETERINARY]
Common Name English
mavacoxib [INN]
Common Name English
PHA-739521
Code English
4-[5-(4-Fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Systematic Name English
BENZENESULFONAMIDE, 4-(5-(4-FLUOROPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL)-
Systematic Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS TROCOXIL [ AUTHORIZED ]
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
WHO-VATC QM01AH92
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90168880
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
MERCK INDEX
m11979
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
CHEBI
76207
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL28527
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
WIKIPEDIA
Mavacoxib
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
INN
8665
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
PUBCHEM
9843089
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
USAN
QQ-69
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
FDA UNII
YFT7X7SR77
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
NCI_THESAURUS
C76639
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
CAS
170569-88-7
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
SMS_ID
300000023772
Created by admin on Fri Dec 15 15:41:13 GMT 2023 , Edited by admin on Fri Dec 15 15:41:13 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY