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etoricoxib 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
selective cyclo-oxygenase inhibitors	1113	202409-33-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: etoricoxib arcoxia etobrix etocox etoxib etropain nucoxia torcoxia MK-0663	A sulfone and pyridine derivative that acts as a cyclooxygenase-2 inhibitor. It is used as a NSAID for the treatment of pain associated with RHEUMATOID ARTHRITIS and ANKYLOSING SPONDYLITIS. It is also used for the short-term treatment of moderate postoperative dental pain. Molecular weight: 358.84 Formula: C18H15ClN2O2S CLOGP: 2.35 LIPINSKI: 0 HAC: 4 HDO: 0 TPSA: 59.92 ALOGS: -5.04 ROTB: 3

Molecule

Description

Molfile Inchi Smiles

Synonyms:

etoricoxib
arcoxia
etobrix
etocox
etoxib
etropain
nucoxia
torcoxia
MK-0663

A sulfone and pyridine derivative that acts as a cyclooxygenase-2 inhibitor. It is used as a NSAID for the treatment of pain associated with RHEUMATOID ARTHRITIS and ANKYLOSING SPONDYLITIS. It is also used for the short-term treatment of moderate postoperative dental pain.

Molecular weight: 358.84
Formula: C18H15ClN2O2S
CLOGP: 2.35
LIPINSKI: 0
HAC: 4
HDO: 0
TPSA: 59.92
ALOGS: -5.04
ROTB: 3

Drug dosage:

Dose	Unit	Route
60	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.14 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.78 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	1.50 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.79 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	26 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 1, 1998	YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Labelled drug-drug interaction medication error	53.42	16.34	27	7028	11559	56273453
Fixed eruption	43.57	16.34	12	7043	931	56284081
Apraxia	40.53	16.34	13	7042	1706	56283306
Drug abuse	38.71	16.34	45	7010	67565	56217447
Disorientation	36.75	16.34	33	7022	36580	56248432
Inflammatory marker increased	36.54	16.34	17	7038	6073	56278939
Spinal pain	36.09	16.34	21	7034	11863	56273149
Perseveration	35.97	16.34	8	7047	255	56284757
Chronic gastritis	35.37	16.34	13	7042	2565	56282447
Axial spondyloarthritis	35.33	16.34	8	7047	277	56284735
Thrombocytosis	32.27	16.34	15	7040	5347	56279665
Acquired porphyria	31.31	16.34	5	7050	23	56284989
Porphyrins urine increased	31.31	16.34	5	7050	23	56284989
Lumbar vertebral fracture	30.23	16.34	14	7041	4950	56280062
Porphyrins stool increased	30.20	16.34	5	7050	30	56284982
Joint contracture	28.70	16.34	10	7045	1692	56283320
Synovial disorder	28.57	16.34	9	7046	1114	56283898
Synovectomy	27.56	16.34	6	7049	173	56284839
Meteoropathy	26.40	16.34	4	7051	12	56285000
Polymyalgia rheumatica	26.24	16.34	11	7044	3071	56281941
Drug interaction	25.97	16.34	71	6984	209684	56075328
Thoracic vertebral fracture	25.89	16.34	12	7043	4251	56280761
Postoperative delirium	25.43	16.34	5	7050	86	56284926
Porphyria non-acute	24.50	16.34	6	7049	293	56284719
Serum ferritin decreased	24.27	16.34	9	7046	1819	56283193
Ovulation disorder	24.02	16.34	4	7051	25	56284987
Spinal fracture	23.11	16.34	18	7037	16406	56268606
Aortic valve stenosis	22.73	16.34	10	7045	3137	56281875
Femur fracture	22.22	16.34	26	7029	39269	56245743
Withdrawal syndrome	21.26	16.34	18	7037	18444	56266568
Ankylosing spondylitis	21.14	16.34	14	7041	9916	56275096
Hemianopia	20.98	16.34	7	7048	1039	56283973
Abdominal pain upper	20.72	16.34	59	6996	178254	56106758
Intervertebral disc protrusion	20.68	16.34	19	7036	21675	56263337
Hyperreflexia	20.65	16.34	11	7044	5239	56279773
Subileus	20.12	16.34	9	7046	2935	56282077
Renal function test abnormal	20.04	16.34	9	7046	2962	56282050
Product prescribing error	19.60	16.34	19	7036	23167	56261845
Urticaria	18.92	16.34	50	7005	144626	56140386
Allodynia	18.72	16.34	6	7049	785	56284227
Carotid artery stenosis	18.50	16.34	10	7045	4900	56280112
Junctional ectopic tachycardia	18.45	16.34	4	7051	113	56284899
Angioedema	17.95	16.34	24	7031	41429	56243583
Sopor	17.41	16.34	17	7038	20905	56264107
Infected fistula	17.18	16.34	4	7051	157	56284855
Groin pain	17.11	16.34	12	7043	9328	56275684
Red blood cell sedimentation rate increased	17.09	16.34	22	7033	36601	56248411
Infusion related reaction	16.72	16.34	3	7052	208928	56076084
Speech disorder	16.68	16.34	22	7033	37471	56247541
Alopecia	16.63	16.34	8	7047	293450	55991562
Substance abuse	16.45	16.34	9	7046	4516	56280496

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Regurgitation	74.55	19.57	21	5261	1328	31690734
Oropharyngeal discomfort	59.96	19.57	21	5261	2710	31689352
Vitamin B12 deficiency	58.38	19.57	22	5260	3497	31688565
Spinal pain	53.35	19.57	23	5259	5172	31686890
Eructation	51.27	19.57	21	5261	4158	31687904
Hepatitis E antibody positive	49.67	19.57	11	5271	256	31691806
Body mass index abnormal	49.62	19.57	10	5272	145	31691917
Hepatitis E virus test positive	48.58	19.57	11	5271	284	31691778
Oral mucosa erosion	45.51	19.57	13	5269	864	31691198
Mucosal necrosis	44.26	19.57	8	5274	62	31692000
Antiphospholipid antibodies positive	43.04	19.57	10	5272	290	31691772
Neck pain	42.08	19.57	33	5249	22877	31669185
Ligament calcification	40.57	19.57	9	5273	211	31691851
Palmoplantar pustulosis	39.76	19.57	8	5274	115	31691947
General physical health deterioration	38.19	19.57	68	5214	113367	31578695
Suspected transmission of an infectious agent via product	37.69	19.57	11	5271	789	31691273
Lip erosion	37.23	19.57	10	5272	529	31691533
Hand fracture	36.59	19.57	13	5269	1748	31690314
Coating in mouth	36.52	19.57	7	5275	77	31691985
Death	36.21	19.57	8	5274	360561	31331501
Ankylosing spondylitis	35.40	19.57	18	5264	5863	31686199
Respiratory fatigue	34.96	19.57	7	5275	98	31691964
Product prescribing error	33.30	19.57	27	5255	19615	31672447
Sacroiliitis	31.96	19.57	11	5271	1347	31690715
Craniocerebral injury	30.51	19.57	13	5269	2837	31689225
Helicobacter gastritis	29.25	19.57	10	5272	1200	31690862
Otitis media	28.23	19.57	12	5270	2604	31689458
Systemic infection	28.13	19.57	13	5269	3436	31688626
Pregnancy of partner	27.09	19.57	7	5275	318	31691744
Psoriatic arthropathy	26.88	19.57	24	5258	19859	31672203
Gastrointestinal inflammation	25.82	19.57	12	5270	3213	31688849
Chronic idiopathic pain syndrome	24.37	19.57	4	5278	16	31692046
Immune-mediated adverse reaction	24.15	19.57	7	5275	490	31691572
Poor peripheral circulation	23.95	19.57	9	5273	1418	31690644
Costovertebral angle tenderness	23.64	19.57	5	5277	93	31691969
Oral pruritus	23.15	19.57	6	5276	276	31691786
Formication	23.02	19.57	9	5273	1578	31690484
Peritoneal adhesions	22.01	19.57	5	5277	131	31691931
Prerenal failure	21.67	19.57	9	5273	1844	31690218
Axial spondyloarthritis	21.66	19.57	6	5276	356	31691706
Personality change	21.32	19.57	12	5270	4783	31687279
Hypercholesterolaemia	20.22	19.57	14	5268	8016	31684046
Polyneuropathy	20.19	19.57	17	5265	13005	31679057
Mucosal ulceration	19.77	19.57	7	5275	931	31691131
Intensive care unit acquired weakness	19.60	19.57	7	5275	955	31691107
Toxic epidermal necrolysis	19.60	19.57	20	5262	19504	31672558

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Spinal pain	58.91	14.87	33	11187	13737	70903487
Regurgitation	56.89	14.87	19	11201	2237	70914987
Oral mucosa erosion	53.15	14.87	17	11203	1748	70915476
Product prescribing error	52.71	14.87	46	11174	38906	70878318
Hepatitis E antibody positive	50.19	14.87	11	11209	257	70916967
Hepatitis E virus test positive	49.29	14.87	11	11209	280	70916944
Body mass index abnormal	45.78	14.87	10	11210	230	70916994
Ankylosing spondylitis	42.06	14.87	25	11195	11621	70905603
Perseveration	41.15	14.87	10	11210	372	70916852
Ligament calcification	41.00	14.87	9	11211	212	70917012
Lip erosion	40.43	14.87	13	11207	1359	70915865
Mucosal necrosis	40.17	14.87	8	11212	115	70917109
Inflammatory marker increased	39.06	14.87	22	11198	9252	70907972
Vitamin B12 deficiency	38.99	14.87	19	11201	5953	70911271
Oropharyngeal discomfort	38.66	14.87	19	11201	6060	70911164
Immune-mediated adverse reaction	37.89	14.87	11	11209	816	70916408
General physical health deterioration	37.03	14.87	101	11119	235930	70681294
Fixed eruption	36.36	14.87	14	11206	2482	70914742
Suspected transmission of an infectious agent via product	34.70	14.87	11	11209	1098	70916126
Coating in mouth	34.46	14.87	8	11212	244	70916980
Thrombocytosis	34.24	14.87	19	11201	7765	70909459
Labelled drug-drug interaction medication error	33.66	14.87	29	11191	24098	70893126
Polymyalgia rheumatica	33.54	14.87	15	11205	3871	70913353
Lumbar vertebral fracture	33.05	14.87	17	11203	5970	70911254
Antiphospholipid antibodies positive	30.68	14.87	9	11211	692	70916532
Thoracic vertebral fracture	30.48	14.87	15	11205	4799	70912425
Eructation	30.25	14.87	19	11201	9741	70907483
Synovectomy	29.74	14.87	7	11213	227	70916997
Drug interaction	29.57	14.87	129	11091	381312	70535912
Sacroiliitis	29.43	14.87	13	11207	3260	70913964
Porphyrins urine increased	29.18	14.87	5	11215	29	70917195
Respiratory fatigue	29.00	14.87	7	11213	253	70916971
Death	28.97	14.87	23	11197	510038	70407186
Apraxia	28.53	14.87	12	11208	2671	70914553
Skin hyperpigmentation	28.47	14.87	16	11204	6699	70910525
Chronic gastritis	28.20	14.87	13	11207	3600	70913624
Palmoplantar pustulosis	28.13	14.87	8	11212	551	70916673
Acquired porphyria	28.13	14.87	5	11215	37	70917187
Haemophilic arthropathy	27.76	14.87	6	11214	131	70917093
Porphyrins stool increased	27.36	14.87	5	11215	44	70917180
Synovial disorder	26.67	14.87	9	11211	1094	70916130
Helicobacter gastritis	26.54	14.87	11	11209	2360	70914864
Meteoropathy	25.47	14.87	4	11216	12	70917212
Craniocerebral injury	25.24	14.87	13	11207	4578	70912646
Toxic epidermal necrolysis	24.89	14.87	31	11189	39526	70877698
Pregnancy of partner	24.08	14.87	6	11214	248	70916976
Chronic idiopathic pain syndrome	23.84	14.87	4	11216	20	70917204
Femur fracture	23.84	14.87	29	11191	36103	70881121
Joint contracture	23.37	14.87	10	11210	2322	70914902
Neck pain	22.59	14.87	39	11181	66618	70850606
Poor peripheral circulation	22.48	14.87	11	11209	3474	70913750
Tongue oedema	21.47	14.87	13	11207	6246	70910978
Completed suicide	21.11	14.87	5	11215	227130	70690094
Systemic infection	20.73	14.87	13	11207	6644	70910580
Toxicity to various agents	20.73	14.87	18	11202	382154	70535070
Renal function test abnormal	20.61	14.87	11	11209	4163	70913061
Hand fracture	20.51	14.87	12	11208	5415	70911809
Axial spondyloarthritis	20.20	14.87	6	11214	482	70916742
Drug abuse	20.12	14.87	60	11160	147196	70770028
Urticaria	20.02	14.87	64	11156	162985	70754239
Otitis media	19.89	14.87	12	11208	5727	70911497
Disorientation	19.77	14.87	34	11186	57889	70859335
Spinal fracture	19.69	14.87	18	11202	16149	70901075
Hemianopia	19.58	14.87	8	11212	1657	70915567
Postoperative delirium	19.50	14.87	5	11215	232	70916992
Hyperreflexia	19.41	14.87	13	11207	7429	70909795
Costovertebral angle tenderness	19.40	14.87	5	11215	237	70916987
pH body fluid increased	18.94	14.87	4	11216	78	70917146
Sopor	18.87	14.87	24	11196	31243	70885981
Intervertebral disc protrusion	18.84	14.87	20	11200	21483	70895741
Spondylolisthesis	18.17	14.87	9	11211	2917	70914307
Gastrointestinal inflammation	18.15	14.87	12	11208	6711	70910513
Porphyria non-acute	17.71	14.87	6	11214	738	70916486
Cardiac valve sclerosis	17.63	14.87	4	11216	110	70917114
Peritoneal adhesions	17.60	14.87	5	11215	343	70916881
Gastrointestinal submucosal tumour	17.17	14.87	4	11216	124	70917100
Infusion related reaction	17.12	14.87	5	11215	197529	70719695
Prerenal failure	16.93	14.87	9	11211	3377	70913847
Withdrawal syndrome	16.45	14.87	20	11200	24884	70892340
Aortic valve stenosis	16.24	14.87	10	11210	4949	70912275
Face oedema	15.98	14.87	20	11200	25619	70891605
Gastrointestinal ulcer perforation	15.89	14.87	3	11217	32	70917192
Urethral stenosis	15.82	14.87	6	11214	1021	70916203
Intensive care unit acquired weakness	15.81	14.87	7	11213	1764	70915460
Subileus	15.76	14.87	10	11210	5217	70912007
Mucosal ulceration	15.70	14.87	7	11213	1794	70915430
Psychotic behaviour	15.51	14.87	6	11214	1076	70916148
Angioedema	15.23	14.87	33	11187	66577	70850647
Gamma-glutamyltransferase increased	15.05	14.87	28	11192	50657	70866567
Weight increased	14.93	14.87	10	11210	242321	70674903

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	M01AH05	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Coxibs
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
MeSH PA	D000893	Anti-Inflammatory Agents
MeSH PA	D000894	Anti-Inflammatory Agents, Non-Steroidal
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D052246	Cyclooxygenase 2 Inhibitors
MeSH PA	D016861	Cyclooxygenase Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:50629	COX-2 inhibitor

Drug Use | Suggest Off label Use Form| |View source of the data|

None

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.6	Basic
pKa2	1.75	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	6.10	WOMBAT-PK	IUPHAR
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN		IC50	4.92	CHEMBL
Prostaglandin E2 receptor EP2 subtype	GPCR	P43116	PE2R2_HUMAN		Ki	7.10	PDSP
Mitogen-activated protein kinase 14	Kinase	Q16539	MK14_HUMAN		IC50	6.28	CHEMBL
Prostaglandin G/H synthase 2	Enzyme		PGH2_SHEEP		IC50	6.64	CHEMBL

External reference:

ID	Source
D03710	KEGG_DRUG
C0972314	UMLSCUI
CHEBI:6339	CHEBI
5CH	PDB_CHEM_ID
CHEMBL416146	ChEMBL_ID
DB01628	DRUGBANK_ID
D000077613	MESH_DESCRIPTOR_UI
123619	PUBCHEM_CID
2896	IUPHAR_LIGAND_ID
8082	INN_ID
WRX4NFY03R	UNII
307296	RXNORM
009633	NDDF
395292007	SNOMEDCT_US
409134009	SNOMEDCT_US

Pharmaceutical products:

None