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

Stem definition	Drug id	CAS RN
anti-inflammatory, isoxicam derivatives	2210	36322-90-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: piroxicam olamine piroxicam betadex brexicam brexidol brexin cicladol piroxicam-beta-cyclodextrin complex piroxicam beta-cyclodextrin feldene CP16171 CP-16171 piroxicam	A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. Molecular weight: 331.35 Formula: C15H13N3O4S CLOGP: 1.89 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 99.60 ALOGS: -3.37 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

piroxicam olamine
piroxicam betadex
brexicam
brexidol
brexin
cicladol
piroxicam-beta-cyclodextrin complex
piroxicam beta-cyclodextrin
feldene
CP16171
CP-16171
piroxicam

A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily.

Molecular weight: 331.35
Formula: C15H13N3O4S
CLOGP: 1.89
LIPINSKI: 0
HAC: 7
HDO: 2
TPSA: 99.60
ALOGS: -3.37
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
20	mg	O
20	mg	P
20	mg	R

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	5 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.51 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.02 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
April 6, 1982	FDA	PFIZER

FDA Adverse Event Reporting System (Female)

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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
Sciatica	657.97	15.07	306	25201	34018	63429497
Drug hypersensitivity	422.91	15.07	569	24938	310118	63153397
Psoriatic arthropathy	406.38	15.07	318	25189	91202	63372313
Sinusitis	189.69	15.07	332	25175	226321	63237194
Blood iron abnormal	182.93	15.07	66	25441	3810	63459705
Treatment failure	145.39	15.07	275	25232	198768	63264747
Deep vein thrombosis postoperative	145.18	15.07	77	25430	11292	63452223
Rheumatoid arthritis	140.88	15.07	313	25194	253506	63210009
Drug intolerance	124.82	15.07	337	25170	308324	63155191
Autoimmune disorder	118.15	15.07	78	25429	17099	63446416

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FDA Adverse Event Reporting System (Male)

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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
Drug hypersensitivity	53.59	15.94	60	4662	80469	34871740
Sacroiliitis	49.81	15.94	15	4707	1483	34950726
Mast cell activation syndrome	46.95	15.94	10	4712	240	34951969
Fixed eruption	39.72	15.94	13	4709	1687	34950522
Chest expansion decreased	39.59	15.94	8	4714	147	34952062
Osteopenia	39.04	15.94	17	4705	4832	34947377
Benign abdominal neoplasm	37.06	15.94	7	4715	89	34952120
Angioedema	34.09	15.94	33	4689	37341	34914868
Ankylosing spondylitis	33.60	15.94	16	4706	5588	34946621
Urticaria	32.41	15.94	41	4681	62336	34889873

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FDA Adverse Event Reporting System (Geriatric)

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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
Sciatica	534.56	15.56	248	26397	32974	79684769
Psoriatic arthropathy	372.09	15.56	263	26382	77736	79640007
Drug hypersensitivity	355.72	15.56	467	26178	298449	79419294
Sinusitis	189.34	15.56	277	26368	195224	79522519
Rheumatoid arthritis	168.96	15.56	272	26373	208198	79509545
Rheumatic fever	166.33	15.56	109	26536	28416	79689327
Swollen joint count increased	162.16	15.56	99	26546	22828	79694915
Treatment failure	158.45	15.56	237	26408	170249	79547494
Deep vein thrombosis postoperative	153.55	15.56	74	26571	10678	79707065
Blood iron abnormal	152.92	15.56	43	26602	1324	79716419

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	M01AC01	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Oxicams
ATC	M02AA07	MUSCULO-SKELETAL SYSTEM TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN Antiinflammatory preparations, non-steroids for topical use
ATC	S01BC06	SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFLAMMATORY AGENTS Antiinflammatory agents, non-steroids
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:35544	cyclooxygenase inhibitors
CHEBI has role	CHEBI:35842	anti-rheumatic drugs
CHEBI has role	CHEBI:50630	COX-1 inhibitor
FDA CS	M0001335	Anti-Inflammatory Agents, Non-Steroidal
FDA EPC	N0000175722	Nonsteroidal Anti-inflammatory Drug
FDA MoA	N0000000160	Cyclooxygenase Inhibitors

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

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Disease	Relation	SNOMED_ID	DOID
Rheumatoid arthritis	indication	69896004	DOID:7148
Osteoarthritis	indication	396275006
Ankylosing spondylitis	off-label use	9631008	DOID:7147
Juvenile rheumatoid arthritis	off-label use	410795001
Alcoholism	contraindication	7200002
Asthenia	contraindication	13791008
Myocardial infarction	contraindication	22298006	DOID:5844
Hypertensive disorder	contraindication	38341003	DOID:10763
Gastrointestinal ulcer	contraindication	40845000
Body fluid retention	contraindication	43498006

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.31	acidic
pKa2	8.26	acidic
pKa3	5.18	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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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	4.70	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	5.18	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 1	Enzyme		PGH1_SHEEP		IC50	4.68	CHEMBL
Cyclooxygenase	Enzyme		PGH1_BOVIN PGH2_BOVIN		IC50	4.19	CHEMBL
Cyclooxygenase	Enzyme		PGH2_RAT PGH1_RAT		IC50	7	CHEMBL

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External reference:

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ID	Source
002389	NDDF
006310	NDDF
13T4O6VMAM	UNII
1529	MMSL
1753	MMSL
197288	RXNORM
27754002	SNOMEDCT_US
3713	INN_ID
387153005	SNOMEDCT_US
4018626	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Feldene	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3220	CAPSULE	10 mg	ORAL	NDA	29 sections
Feldene	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3220	CAPSULE	10 mg	ORAL	NDA	29 sections
Feldene	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3230	CAPSULE	20 mg	ORAL	NDA	29 sections
Feldene	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3230	CAPSULE	20 mg	ORAL	NDA	29 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0756	CAPSULE	10 mg	ORAL	ANDA	28 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0756	CAPSULE	10 mg	ORAL	ANDA	28 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0757	CAPSULE	20 mg	ORAL	ANDA	28 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0757	CAPSULE	20 mg	ORAL	ANDA	28 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0143-3107	CAPSULE	10 mg	ORAL	ANDA	25 sections
Piroxicam	HUMAN PRESCRIPTION DRUG LABEL	1	0143-3108	CAPSULE	20 mg	ORAL	ANDA	25 sections

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