Scroll

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	61.49	16.39	31	7825	13368	63467798
Fixed eruption	41.23	16.39	12	7844	1152	63480014
Apraxia	39.95	16.39	13	7843	1808	63479358
Perseveration	35.72	16.39	8	7848	267	63480899
Disorientation	35.00	16.39	33	7823	39419	63441747
Inflammatory marker increased	34.87	16.39	17	7839	6822	63474344
Spinal pain	34.38	16.39	21	7835	13118	63468048
Chronic gastritis	34.30	16.39	13	7843	2828	63478338
Acquired porphyria	31.38	16.39	5	7851	23	63481143
Porphyrins urine increased	31.38	16.39	5	7851	23	63481143
Thrombocytosis	31.28	16.39	15	7841	5803	63475363
Porphyrins stool increased	30.26	16.39	5	7851	30	63481136
Drug abuse	28.82	16.39	40	7816	72478	63408688
Joint contracture	28.70	16.39	10	7846	1714	63479452
Lumbar vertebral fracture	28.30	16.39	14	7842	5796	63475370
Axial spondyloarthritis	28.00	16.39	7	7849	377	63480789
Synovectomy	27.28	16.39	6	7850	184	63480982
Meteoropathy	26.45	16.39	4	7852	12	63481154
Spinal osteoarthritis	25.77	16.39	19	7837	16167	63464999
Thoracic vertebral fracture	25.18	16.39	12	7844	4580	63476586
Postoperative delirium	25.17	16.39	5	7851	92	63481074
Porphyria non-acute	24.61	16.39	6	7850	291	63480875
Drug interaction	24.52	16.39	73	7783	229058	63252108
Polymyalgia rheumatica	24.18	16.39	11	7845	3780	63477386
Ovulation disorder	23.55	16.39	4	7852	29	63481137
Synovial disorder	23.40	16.39	9	7847	2036	63479130
Serum ferritin decreased	23.29	16.39	9	7847	2061	63479105
Ankylosing spondylitis	23.04	16.39	15	7841	10459	63470707
Sopor	22.50	16.39	20	7836	22144	63459022
Aortic valve stenosis	22.40	16.39	10	7846	3289	63477877
Spinal fracture	21.62	16.39	18	7838	18253	63462913
Femur fracture	21.21	16.39	26	7830	41730	63439436
Hemianopia	20.68	16.39	7	7849	1100	63480066
Infusion related reaction	20.48	16.39	3	7853	245518	63235648
Withdrawal syndrome	20.21	16.39	18	7838	19979	63461187
Hepatitis A antibody abnormal	20.02	16.39	4	7852	76	63481090
Interspinous osteoarthritis	20.02	16.39	4	7852	76	63481090
Pyelocaliectasis	19.95	16.39	6	7850	645	63480521
Urticaria	19.83	16.39	55	7801	165747	63315419
Product prescribing error	19.59	16.39	20	7836	26269	63454897
Subileus	19.57	16.39	9	7847	3170	63477996
Hyperreflexia	19.52	16.39	11	7845	5923	63475243
Hallucination, visual	18.77	16.39	17	7839	19281	63461885
Allodynia	18.59	16.39	6	7850	813	63480353
Toxic epidermal necrolysis	18.39	16.39	19	7837	25315	63455851
Renal function test abnormal	18.38	16.39	9	7847	3644	63477522
Junctional ectopic tachycardia	18.37	16.39	4	7852	117	63481049
Sudden death	18.31	16.39	13	7843	10436	63470730
Drug eruption	18.14	16.39	20	7836	28674	63452492
Carotid artery stenosis	18.14	16.39	10	7846	5160	63476006
Lactic acidosis	18.10	16.39	23	7833	38264	63442902
Alopecia	17.54	16.39	10	7846	337526	63143640
Osteoarthritis	17.13	16.39	37	7819	95306	63385860
Ulnar nerve injury	17.11	16.39	4	7852	162	63481004
Speech disorder	17.02	16.39	23	7833	40606	63440560
Angioedema	16.91	16.39	25	7831	47940	63433226
Spondylitis	16.89	16.39	9	7847	4345	63476821

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	78.41	17.84	23	5818	1676	34949414
General physical health deterioration	65.37	17.84	93	5748	128176	34822914
Oropharyngeal discomfort	64.12	17.84	23	5818	3173	34947917
Vitamin B12 deficiency	62.48	17.84	24	5817	4007	34947083
Eructation	55.36	17.84	23	5818	4708	34946382
Spinal pain	53.69	17.84	24	5817	5865	34945225
Systemic infection	49.95	17.84	22	5819	5190	34945900
Hepatitis E antibody positive	49.64	17.84	11	5830	256	34950834
Body mass index abnormal	49.09	17.84	10	5831	153	34950937
Hepatitis E virus test positive	48.40	17.84	11	5830	288	34950802
Oral mucosa erosion	44.15	17.84	13	5828	959	34950131
Mucosal necrosis	43.58	17.84	8	5833	68	34951022
Neck pain	43.23	17.84	35	5806	25314	34925776
Antiphospholipid antibodies positive	42.37	17.84	10	5831	310	34950780
Death	41.86	17.84	8	5833	398041	34553049
Ligament calcification	40.55	17.84	9	5832	211	34950879
Product prescribing error	39.82	17.84	32	5809	22895	34928195
Palmoplantar pustulosis	39.61	17.84	8	5833	117	34950973
Suspected transmission of an infectious agent via product	37.02	17.84	11	5830	837	34950253
Coating in mouth	35.94	17.84	7	5834	84	34951006
Lip erosion	35.56	17.84	10	5831	626	34950464
Respiratory fatigue	34.88	17.84	7	5834	99	34950991
Hand fracture	33.78	17.84	13	5828	2179	34948911
Pregnancy of partner	31.50	17.84	8	5833	338	34950752
Sacroiliitis	30.87	17.84	11	5830	1487	34949603
Helicobacter gastritis	29.01	17.84	10	5831	1226	34949864
Craniocerebral injury	28.79	17.84	13	5828	3250	34947840
Adjustment disorder with disturbance of conduct	28.08	17.84	6	5835	117	34950973
Fluid intake reduced	27.22	17.84	13	5828	3688	34947402
Otitis media	27.12	17.84	12	5829	2860	34948230
Ankylosing spondylitis	24.82	17.84	14	5827	5590	34945500
Gastrointestinal inflammation	24.82	17.84	12	5829	3499	34947591
Costovertebral angle tenderness	23.48	17.84	5	5836	96	34950994
Poor peripheral circulation	23.45	17.84	9	5832	1498	34949592
Chronic idiopathic pain syndrome	23.31	17.84	4	5837	22	34951068
Immune-mediated adverse reaction	23.06	17.84	7	5834	573	34950517
Oral pruritus	22.42	17.84	6	5835	312	34950778
Formication	22.30	17.84	9	5832	1710	34949380
Peritoneal adhesions	21.89	17.84	5	5836	134	34950956
Axial spondyloarthritis	21.81	17.84	6	5835	346	34950744
Prerenal failure	20.62	17.84	9	5832	2075	34949015
Personality change	20.52	17.84	12	5829	5127	34945963
Mucosal ulceration	19.35	17.84	7	5834	988	34950102
Intensive care unit acquired weakness	19.14	17.84	7	5834	1020	34950070
Hypercholesterolaemia	19.09	17.84	14	5827	8748	34942342
Arthralgia	19.02	17.84	67	5774	169974	34781116
pH body fluid increased	18.97	17.84	4	5837	73	34951017
Sialadenosis	18.94	17.84	3	5838	9	34951081
Cardiac valve sclerosis	18.63	17.84	4	5837	80	34951010
Polyneuropathy	18.17	17.84	17	5824	14879	34936211
Endocarditis	17.91	17.84	12	5829	6499	34944591
Toxic epidermal necrolysis	17.84	17.84	20	5821	21626	34929464

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
Regurgitation	64.81	14.79	22	12404	2765	79729197
General physical health deterioration	60.74	14.79	133	12293	275105	79456857
Product prescribing error	59.47	14.79	52	12374	44761	79687201
Spinal pain	58.59	14.79	34	12392	15358	79716604
Oral mucosa erosion	51.76	14.79	17	12409	1930	79730032
Hepatitis E antibody positive	50.36	14.79	11	12415	257	79731705
Hepatitis E virus test positive	49.23	14.79	11	12415	286	79731676
Labelled drug-drug interaction medication error	46.91	14.79	37	12389	27613	79704349
Body mass index abnormal	45.52	14.79	10	12416	240	79731722
Oropharyngeal discomfort	44.71	14.79	22	12404	7144	79724818
Vitamin B12 deficiency	44.49	14.79	22	12404	7219	79724743
Ligament calcification	41.13	14.79	9	12417	212	79731750
Perseveration	40.92	14.79	10	12416	387	79731575
Mucosal necrosis	39.79	14.79	8	12418	123	79731839
Lip erosion	38.98	14.79	13	12413	1547	79730415
Ankylosing spondylitis	38.77	14.79	24	12402	12181	79719781
Systemic infection	38.33	14.79	22	12404	9730	79722232
Fixed eruption	37.73	14.79	15	12411	2939	79729023
Immune-mediated adverse reaction	37.20	14.79	11	12415	883	79731079
Axial spondyloarthritis	37.06	14.79	10	12416	576	79731386
Inflammatory marker increased	36.36	14.79	22	12404	10718	79721244
Eructation	36.05	14.79	22	12404	10887	79721075
Toxic epidermal necrolysis	35.27	14.79	39	12387	44542	79687420
Suspected transmission of an infectious agent via product	34.14	14.79	11	12415	1175	79730787
Coating in mouth	33.80	14.79	8	12418	270	79731692
Thrombocytosis	32.89	14.79	19	12407	8507	79723455
Death	31.90	14.79	25	12401	566489	79165473
Polymyalgia rheumatica	31.54	14.79	15	12411	4522	79727440
Femur fracture	30.90	14.79	34	12392	38618	79693344
Lumbar vertebral fracture	30.74	14.79	17	12409	7005	79724957
Antiphospholipid antibodies positive	30.01	14.79	9	12417	759	79731203
Chronic gastritis	29.97	14.79	14	12412	4054	79727908
Thoracic vertebral fracture	29.45	14.79	15	12411	5238	79726724
Synovectomy	29.41	14.79	7	12419	242	79731720
Porphyrins urine increased	29.26	14.79	5	12421	29	79731933
Pregnancy of partner	28.97	14.79	7	12419	258	79731704
Respiratory fatigue	28.84	14.79	7	12419	263	79731699
Drug interaction	28.46	14.79	134	12292	415049	79316913
Acquired porphyria	28.20	14.79	5	12421	37	79731925
Apraxia	27.94	14.79	12	12414	2855	79729107
Palmoplantar pustulosis	27.92	14.79	8	12418	575	79731387
Sacroiliitis	27.91	14.79	13	12413	3741	79728221
Skin hyperpigmentation	27.44	14.79	16	12410	7287	79724675
Porphyrins stool increased	27.43	14.79	5	12421	44	79731918
Helicobacter gastritis	26.36	14.79	11	12415	2438	79729524
Neck pain	25.88	14.79	44	12382	75373	79656589
Meteoropathy	25.53	14.79	4	12422	12	79731950
Sopor	24.61	14.79	28	12398	32982	79698980
Craniocerebral injury	23.91	14.79	13	12413	5183	79726779
Disorientation	23.38	14.79	38	12388	62738	79669224
Completed suicide	23.16	14.79	5	12421	245762	79486200
Joint contracture	22.76	14.79	10	12416	2514	79729448
Poor peripheral circulation	22.06	14.79	11	12415	3672	79728290
Toxicity to various agents	21.99	14.79	20	12406	421520	79310442
Haemophilic arthropathy	21.99	14.79	5	12421	141	79731821
Chronic idiopathic pain syndrome	21.86	14.79	4	12422	36	79731926
Synovial disorder	21.66	14.79	9	12417	1974	79729988
Fluid intake reduced	21.60	14.79	13	12413	6275	79725687
Infusion related reaction	21.06	14.79	5	12421	230232	79501730
Tongue oedema	20.11	14.79	13	12413	7104	79724858
Urticaria	20.07	14.79	69	12357	185132	79546830
Musculoskeletal pain	19.78	14.79	47	12379	102307	79629655
Hemianopia	19.40	14.79	8	12418	1720	79730242
Otitis media	19.37	14.79	12	12414	6094	79725868
Costovertebral angle tenderness	19.33	14.79	5	12421	244	79731718
Dysuria	19.19	14.79	31	12395	50920	79681042
Hand fracture	19.16	14.79	12	12414	6213	79725749
Hepatitis A antibody abnormal	19.10	14.79	4	12422	76	79731886
Interspinous osteoarthritis	19.10	14.79	4	12422	76	79731886
pH body fluid increased	18.95	14.79	4	12422	79	79731883
Renal function test abnormal	18.91	14.79	11	12415	4987	79726975
Weight increased	18.63	14.79	10	12416	277376	79454586
Aortic valve stenosis	18.32	14.79	11	12415	5283	79726679
Spinal fracture	18.23	14.79	18	12408	18036	79713926
Hyperreflexia	18.18	14.79	13	12413	8372	79723590
Porphyria non-acute	17.76	14.79	6	12420	743	79731219
Spondylolisthesis	17.61	14.79	9	12417	3166	79728796
Cardiac valve sclerosis	17.58	14.79	4	12422	113	79731849
Peritoneal adhesions	17.58	14.79	5	12421	350	79731612
Postoperative delirium	17.47	14.79	5	12421	358	79731604
Spinal osteoarthritis	17.32	14.79	17	12409	16910	79715052
Gastrointestinal submucosal tumour	17.13	14.79	4	12422	127	79731835
Gastrointestinal inflammation	17.06	14.79	12	12414	7532	79724430
Drug eruption	16.91	14.79	27	12399	43908	79688054
Disease progression	16.87	14.79	4	12422	184358	79547604
Spondylitis	16.82	14.79	10	12416	4721	79727241
Prerenal failure	16.32	14.79	9	12417	3689	79728273
Iridocyclitis	16.30	14.79	9	12417	3695	79728267
Gamma-glutamyltransferase increased	16.30	14.79	30	12396	54650	79677312
Ulnar nerve injury	16.17	14.79	4	12422	163	79731799
Mucosal ulceration	15.54	14.79	7	12419	1866	79730096
Withdrawal syndrome	15.48	14.79	20	12406	26834	79705128
Urethral stenosis	15.47	14.79	6	12420	1100	79730862
Lactic acidosis	15.47	14.79	34	12392	70325	79661637
Off label use	15.40	14.79	81	12345	907134	78824828
Psychotic behaviour	15.35	14.79	6	12420	1123	79730839
Intensive care unit acquired weakness	15.32	14.79	7	12419	1926	79730036
Psoriatic arthropathy	15.27	14.79	36	12390	77963	79653999
Subileus	15.18	14.79	10	12416	5644	79726318

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