DERACOXIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14F3N3O3S
Molecular Weight	397.372
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(F)C=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(N)(=O)=O)C(F)F

InChI

InChIKey=WAZQAZKAZLXFMK-UHFFFAOYSA-N

InChI=1S/C17H14F3N3O3S/c1-26-16-7-2-10(8-13(16)18)15-9-14(17(19)20)22-23(15)11-3-5-12(6-4-11)27(21,24)25/h2-9,17H,1H3,(H2,21,24,25)

HIDE SMILES / InChI

Description
Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050385.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/21985349

Deracoxib (trade name Deramaxx, Novartis) is a non-steroidal anti-inflammatory drug of the coxib class, used in veterinary medicine for the control of postoperative pain and inflammation associated with orthopedic and dental surgery and for the control of pain and inflammation associated with osteoarthritis in dogs. Data indicate that deracoxib inhibits the production of PGE1 and 6-keto PGF1 by its inhibitory effects on prostaglandin biosynthesis. Deracoxib was shown to have antitumor effect against transitional cell carcinoma of the urinary bladder.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Osteosarcoma cell growth 1 Target ID: Osteosarcoma cell growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/16334957	Inhibitor 8297		150.0 µM [IC50]
Prostaglandin G/H synthase 2 48 Target ID: O19183 Gene ID: 791253.0 Gene Symbol: PTGS2 Target Organism: Equus caballus (Horse) Sources: http://www.ncbi.nlm.nih.gov/pubmed/21219338	Inhibitor 8297		0.39 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteosarcoma 22 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16334957	Primary	Basic research	Unknown Approved Use Unknown
Osteoarthritis pain and inflammation 1 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050385.pdf	Palliative	Approved 8429	DERAMAXX (deracoxib) Approved Use Osteoarthritis pain and inflammation Launch Date 2002
Postoperative orthopedic pain and inflammation 1 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050385.pdf	Palliative	Approved 8429	DERAMAXX (deracoxib) Approved Use For postoperative orthopedic pain and inflammation Launch Date 2002
Postoperative dental pain and inflammation 1 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050385.pdf	Palliative	Approved 8429	DERAMAXX (deracoxib) Approved Use For postoperative dental pain and inflammation Launch Date 2002

PubMed

Title	Date	PubMed
In vivo effects of carprofen, deracoxib, and etodolac on prostanoid production in blood, gastric mucosa, and synovial fluid in dogs with chronic osteoarthritis.	2005 May	15934608
The effects of epidural deracoxib on the ground reaction forces in an acute stifle synovitis model.	2006 Jan	16409407
Cyclooxygenase expression and prostanoid production in pyloric and duodenal mucosae in dogs after administration of nonsteroidal anti-inflammatory drugs.	2008 Apr	18380576
Evaluation of outcome associated with subcutaneous and intramuscular hemangiosarcoma treated with adjuvant doxorubicin in dogs: 21 cases (2001-2006).	2008 Jul 1	18593321
Safety and tolerability of 3-week and 6-month dosing of Deramaxx (deracoxib) chewable tablets in dogs.	2009 Aug	19614837
Effect of nonsteroidal anti-inflammatory drugs with varied cyclooxygenase-2 selectivity on cyclooxygenase protein and prostanoid concentrations in pyloric and duodenal mucosa of dogs.	2009 Oct	19795939
Use of deracoxib during intense rehabilitation exercises.	2010	21155163
Randomised controlled clinical trial for the use of deracoxib during intense rehabilitation exercises after tibial plateau levelling osteotomy.	2010	20740263
In vitro and ex vivo inhibition of canine cyclooxygenase isoforms by robenacoxib: a comparative study.	2010 Jun	20004922
Characterization and modulation of canine mast cell derived eicosanoids.	2010 May 15	20036014
Spontaneous pneumothorax in a dog secondary to Dirofilaria immitis infection.	2010 Nov	21088191

Patents

Sample Use Guides

In Vivo Use Guide

Osteoarthritis Pain and Inflammation: 0.45 – 0.91 mg/lb/day (1 to 2 mg/kg/day) as a single daily dose, as needed. Postoperative Orthopedic Pain and inflammation: 1.4 – 1.8 mg/lb/day (3 to 4 mg/kg/day) as a single daily dose, as needed, not to exceed 7 days of administration. Postoperative Dental Pain and Inflammation: 0.45 – 0.91 mg/lb/day (1 to 2 mg/kg/day) as a single daily dose, for 3 days.

Route of Administration: Oral

In Vitro Use Guide

Deracoxib was used for the treatment of Canine bone marrow derived cultured mast cells (cBMCMCs) at the concentration 1uM and incubated for 24 h to strongly inhibit PGD2 and PGE2 production.

Name

Type

Language

DERACOXIB

Official Name

English

4-(3-(DIFLUOROMETHYL)-5-(3-FLUORO-4-METHOXYPHENYL)-1H-PYRAZOL-1-YL)BENZENESULFONAMIDE

Systematic Name

English

DERACOXIB [MI]

Common Name

English

NSC-758935

Code

English

deracoxib [INN]

Common Name

English

Deracoxib [WHO-DD]

Common Name

English

DERACOXIB [GREEN BOOK]

Common Name

English

SC-59046

Code

English

DERACOXIB [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323