ketoprofen Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
anti-inflammatory agents, ibuprofen derivatives	1528	22071-15-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: RP 19583 RP-19583 ketoprofen ketoprofene ketoprophen	An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis. Molecular weight: 254.29 Formula: C16H14O3 CLOGP: 2.76 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 54.37 ALOGS: -4.08 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

RP 19583
RP-19583
ketoprofen
ketoprofene
ketoprophen

An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.

Molecular weight: 254.29
Formula: C16H14O3
CLOGP: 2.76
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 54.37
ALOGS: -4.08
ROTB: 4

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.15	g	O
0.15	g	P
0.15	g	R

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.18 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)	19.66 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.13 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.60 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.01 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2.10 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 9, 1986	FDA

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
Acute kidney injury	258.91	50.09	81	712	28041	2329251
Temperature regulation disorder	236.29	50.09	32	761	129	2357163
Food allergy	199.65	50.09	33	760	598	2356694
Erythema	191.96	50.09	63	730	25096	2332196
Coeliac disease	190.54	50.09	33	760	799	2356493
Immunodeficiency	182.06	50.09	33	760	1043	2356249
Bursitis	157.25	50.09	32	761	1876	2355416
Asthma	152.63	50.09	44	749	11270	2346022
Rash erythematous	140.30	50.09	36	757	5940	2351352
Hepatic enzyme increased	131.55	50.09	38	755	9764	2347528
Drug hypersensitivity	123.65	50.09	54	739	46589	2310703
Hypersensitivity	117.09	50.09	43	750	23550	2333742
Fluid retention	115.67	50.09	32	761	7014	2350278
Hyperhidrosis	114.58	50.09	38	755	15384	2341908
Hepatitis	109.64	50.09	30	763	6307	2350985
Back pain	108.25	50.09	44	749	31615	2325677
Constipation	105.70	50.09	39	754	21590	2335702
Upper respiratory tract infection	104.07	50.09	31	762	8820	2348472
Vomiting	98.74	50.09	53	740	71549	2285743
Hepatocellular injury	97.83	50.09	25	768	4030	2353262
Melaena	87.79	50.09	23	770	4083	2353209
Rheumatoid arthritis	84.23	50.09	32	761	19108	2338184
Angioedema	79.83	50.09	25	768	8371	2348921
Urticaria	73.50	50.09	31	762	24230	2333062
Poisoning deliberate	69.26	50.09	15	778	1176	2356116
Pain	69.16	50.09	40	753	61817	2295475
Suicide attempt	68.70	50.09	24	769	11258	2346034
Intentional overdose	68.62	50.09	24	769	11297	2345995
Peripheral nerve injury	67.88	50.09	10	783	80	2357212
Aspirin-exacerbated respiratory disease	67.17	50.09	11	782	185	2357107
Headache	66.98	50.09	43	750	80136	2277156
Abdominal pain upper	62.78	50.09	27	766	22073	2335219
Lactic acidosis	59.63	50.09	18	775	5312	2351980
Overdose	55.46	50.09	24	769	19883	2337409
Fatigue	55.17	50.09	39	754	84834	2272458
Intentional self-injury	55.17	50.09	16	777	4111	2353181
Nasal disorder	54.57	50.09	10	783	331	2356961
Spinal epidural haemorrhage	54.26	50.09	7	786	17	2357275
Hepatitis cholestatic	53.07	50.09	12	781	1145	2356147
Toxicity to various agents	52.64	50.09	27	766	32727	2324565
Cholestasis	52.29	50.09	15	778	3706	2353586
Somnolence	51.65	50.09	24	769	23461	2333831
Toxic epidermal necrolysis	50.17	50.09	14	779	3130	2354162

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
Acute kidney injury	187.95	52.61	75	649	34869	1711188
Angioedema	129.11	52.61	41	683	9623	1736434
Vomiting	100.54	52.61	50	674	38265	1707792
Erythema	91.49	52.61	35	689	14153	1731904
Pruritus	87.54	52.61	39	685	23183	1722874
Poisoning deliberate	85.27	52.61	18	706	824	1745233
Coma	73.32	52.61	25	699	7237	1738820
Vascular purpura	71.01	52.61	13	711	280	1745777
Melaena	64.78	52.61	21	703	5189	1740868
Eyelid oedema	61.67	52.61	15	709	1298	1744759
Hepatitis cholestatic	56.51	52.61	14	710	1307	1744750

Pharmacologic Action:

Source	Code	Description
ATC	M01AE03	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
ATC	M01AE53	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
ATC	M02AA10	MUSCULO-SKELETAL SYSTEM TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN Antiinflammatory preparations, non-steroids for topical use
FDA Chemical/Ingredient	N0000175721	Nonsteroidal Anti-inflammatory Compounds
FDA EPC	N0000175722	Nonsteroidal Anti-inflammatory Drug
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
CHEBI has role	CHEBI:88188	drug allergen
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory drug
CHEBI has role	CHEBI:35493	antipyretic
MeSH PA	D000893	Anti-Inflammatory Agents
MeSH PA	D000894	Anti-Inflammatory Agents, Non-Steroidal
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D016861	Cyclooxygenase Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Pain	indication	22253000
Rheumatoid arthritis	indication	69896004	DOID:7148
Dysmenorrhea	indication	266599000
Osteoarthritis	indication	396275006
Ankylosing spondylitis	off-label use	9631008	DOID:7147
Gout	off-label use	90560007	DOID:13189
Vascular headache	off-label use	128187005
Peptic ulcer	contraindication	13200003	DOID:750
Myocardial infarction	contraindication	22298006	DOID:5844
Hypertensive disorder	contraindication	38341003	DOID:10763
Gastrointestinal ulcer	contraindication	40845000
Chronic heart failure	contraindication	48447003
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Hepatic failure	contraindication	59927004
Blood coagulation disorder	contraindication	64779008	DOID:1247
Gastrointestinal hemorrhage	contraindication	74474003
Kidney disease	contraindication	90708001	DOID:557
Hypoalbuminemia	contraindication	119247004
Coronary artery bypass graft	contraindication	232717009
Pregnancy, function	contraindication	289908002
Cardiovascular event risk	contraindication	395112001
Smokes tobacco daily	contraindication	449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.28	acidic

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 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	7.33	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	6.62	WOMBAT-PK	CHEMBL
Cyclooxygenase	Enzyme		PGH1_BOVIN PGH2_BOVIN		IC50	5.47	CHEMBL
Prostaglandin G/H synthase 1	Enzyme		PGH1_SHEEP		IC50	6.10	CHEMBL

External reference:

ID	Source
4018064	VUID
N0000146405	NUI
C0022635	UMLSCUI
D00132	KEGG_DRUG
10099000	SNOMEDCT_US
3365	MMSL
6142	RXNORM
386832008	SNOMEDCT_US
4946	MMSL
d00028	MMSL
4018064	VANDF
002394	NDDF
90Y4QC304K	UNII
3284	INN_ID
CHEBI:6128	CHEBI
CHEMBL571	ChEMBL_ID
DB01009	DRUGBANK_ID
3825	PUBCHEM_CID
D007660	MESH_DESCRIPTOR_UI
4795	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	0378-8200	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	13 sections
KETOPROFEN	HUMAN PRESCRIPTION DRUG LABEL	1	16590-136	CAPSULE	50 mg	ORAL	ANDA	13 sections
KETOPROFEN	HUMAN PRESCRIPTION DRUG LABEL	1	16590-137	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	21695-340	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	21695-341	CAPSULE	75 mg	ORAL	ANDA	13 sections
ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	23155-020	CAPSULE	25 mg	ORAL	ANDA	13 sections
ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	23155-021	CAPSULE	50 mg	ORAL	ANDA	13 sections
ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	23155-022	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	33261-064	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	42254-037	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	45865-379	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	45865-485	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0453	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2729	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	52959-245	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	53217-221	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2414	CAPSULE	50 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2415	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4826	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	63187-018	CAPSULE	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	67296-0369	TABLET	75 mg	ORAL	ANDA	13 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	69336-127	CAPSULE	25 mg	ORAL	ANDA	13 sections
KETOPHENE	HUMAN PRESCRIPTION DRUG LABEL	1	70332-101	KIT	33.50 g	None	unapproved drug other	2 sections