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
Temperature regulation disorder	350.72	13.76	101	16160	3259	46666542
Food allergy	282.54	13.76	102	16159	6831	46662970
Coeliac disease	279.32	13.76	102	16159	7059	46662742
Immunodeficiency	229.11	13.76	105	16156	13001	46656800
Bursitis	196.12	13.76	108	16153	19734	46650067
Rash erythematous	153.02	13.76	113	16148	34237	46635564
Acute kidney injury	127.37	13.76	264	15997	235591	46434210
Erythema	106.98	13.76	184	16077	142636	46527165
Fluid retention	97.71	13.76	104	16157	50942	46618859
Upper respiratory tract infection	91.97	13.76	112	16149	63444	46606357
Hyperhidrosis	85.89	13.76	129	16132	89179	46580622
Hepatic enzyme increased	84.22	13.76	122	16139	81665	46588136
Asthma	80.69	13.76	127	16134	91415	46578386
Constipation	74.74	13.76	178	16083	173919	46495882
Hepatocellular injury	72.74	13.76	69	16192	29453	46640348
Acute generalised exanthematous pustulosis	65.93	13.76	41	16220	9364	46660437
Hypersensitivity	51.28	13.76	141	16120	150180	46519621
Poisoning deliberate	49.20	13.76	32	16229	7894	46661907
Angioedema	48.42	13.76	64	16197	39278	46630523
Back pain	47.64	13.76	171	16090	209868	46459933
Peripheral nerve injury	46.87	13.76	13	16248	364	46669437
Lactic acidosis	44.59	13.76	57	16204	33852	46635949
Goitre	44.50	13.76	26	16235	5305	46664496
Spinal epidural haemorrhage	40.17	13.76	9	16252	101	46669700
Product dose omission issue	39.10	13.76	6	16255	168514	46501287
Hepatic adenoma	35.30	13.76	10	16251	303	46669498
Cholestasis	35.03	13.76	45	16216	26848	46642953
Rheumatoid arthritis	34.42	13.76	170	16091	240045	46429756
Completed suicide	34.30	13.76	5	16256	145915	46523886
Aspirin-exacerbated respiratory disease	34.22	13.76	12	16249	736	46669065
Death	34.17	13.76	40	16221	335508	46334293
Suicide attempt	33.60	13.76	65	16196	54971	46614830
Face oedema	33.09	13.76	37	16224	19116	46650685
Hepatic function abnormal	30.62	13.76	48	16213	34373	46635428
Epidural haemorrhage	28.50	13.76	7	16254	120	46669681
Burning mouth syndrome	28.48	13.76	9	16252	399	46669402
Gastritis erosive	27.06	13.76	19	16242	5311	46664490
Pneumoperitoneum	26.43	13.76	12	16249	1450	46668351
Sinoatrial block	25.87	13.76	10	16251	808	46668993
Drug hypersensitivity	25.81	13.76	159	16102	243666	46426135
Pneumococcal sepsis	25.62	13.76	9	16252	555	46669246
Coma	25.33	13.76	60	16201	58289	46611512
Melaena	25.07	13.76	39	16222	27733	46642068
Toxic skin eruption	25.03	13.76	26	16235	12361	46657440
Femoral artery dissection	24.96	13.76	5	16256	31	46669770
Atypical haemolytic uraemic syndrome	22.98	13.76	8	16253	480	46669321
Epidural analgesia	22.67	13.76	5	16256	52	46669749
Septic shock	22.44	13.76	57	16204	57836	46611965
Foetal heart rate abnormal	22.01	13.76	8	16253	545	46669256
Oedematous pancreatitis	21.68	13.76	7	16254	333	46669468
Miosis	21.22	13.76	18	16243	6639	46663162
Fine motor skill dysfunction	20.69	13.76	14	16247	3686	46666115
Anaphylactic shock	20.47	13.76	30	16231	20244	46649557
Pancreatitis necrotising	20.24	13.76	10	16251	1459	46668342
Gastric ulcer	20.15	13.76	31	16230	21832	46647969
Glomerulonephropathy	20.07	13.76	5	16256	91	46669710
Tubulointerstitial nephritis	19.66	13.76	25	16236	14763	46655038
Upper respiratory tract inflammation	19.12	13.76	12	16249	2783	46667018
Hypertransaminasaemia	19.03	13.76	13	16248	3475	46666326
Nasal disorder	19.01	13.76	11	16250	2203	46667598
Contraindicated product administered	18.85	13.76	66	16195	79881	46589920
Intentional overdose	18.34	13.76	57	16204	64887	46604914
Linear IgA disease	17.97	13.76	9	16252	1352	46668449
Upper gastrointestinal haemorrhage	17.24	13.76	25	16236	16713	46653088
Vanishing bile duct syndrome	17.00	13.76	7	16254	667	46669134
Drug interaction	17.00	13.76	125	16136	202969	46466832
Enteritis infectious	16.98	13.76	10	16251	2069	46667732
Gastroenteropancreatic neuroendocrine tumour disease	16.97	13.76	4	16257	57	46669744
Social anxiety disorder	16.88	13.76	6	16255	383	46669418
Drug level increased	16.79	13.76	26	16235	18415	46651386
Azotaemia	16.46	13.76	13	16248	4338	46665463
Enterocolitis	16.30	13.76	15	16246	6153	46663648
Arthritis bacterial	15.26	13.76	14	16247	5722	46664079
Lip pruritus	15.23	13.76	6	16255	510	46669291
Intervertebral discitis	15.14	13.76	10	16251	2529	46667272
Pyelonephritis acute	14.89	13.76	12	16249	4122	46665679
Renal cortical necrosis	14.85	13.76	4	16257	100	46669701
Metabolic acidosis	14.83	13.76	38	16223	38742	46631059
Drug abuse	14.64	13.76	52	16209	63356	46606445
Overdose	14.43	13.76	72	16189	101907	46567894
Hepatitis acute	14.41	13.76	16	16245	8198	46661603
Spinal compression fracture	14.36	13.76	20	16241	12883	46656918
Posterior capsule opacification	14.13	13.76	4	16257	121	46669680
Inflammation	13.94	13.76	43	16218	48738	46621063
Mixed anxiety and depressive disorder	13.85	13.76	4	16257	130	46669671

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	95.46	14.75	243	9239	273599	29669397
Angioedema	86.73	14.75	78	9404	34306	29908690
Lactic acidosis	56.44	14.75	59	9423	31154	29911842
Anaphylactic shock	54.74	14.75	41	9441	13952	29929044
Erythema	44.14	14.75	84	9398	77367	29865629
Poisoning deliberate	41.73	14.75	25	9457	5879	29937117
Death	41.05	14.75	32	9450	357251	29585745
Hepatocellular injury	40.51	14.75	45	9437	25426	29917570
Hepatitis cholestatic	37.49	14.75	26	9456	7846	29935150
Eyelid oedema	34.72	14.75	21	9461	5024	29937972
Gastric ulcer	33.62	14.75	32	9450	15089	29927907
Vascular purpura	33.01	14.75	14	9468	1583	29941413
Pancreatitis acute	31.90	14.75	40	9442	25655	29917341
Myoclonic epilepsy	30.40	14.75	11	9471	815	29942181
Suicide attempt	30.37	14.75	47	9435	36650	29906346
Acute generalised exanthematous pustulosis	28.71	14.75	20	9462	6078	29936918
Coma	28.30	14.75	48	9434	40401	29902595
Laryngeal discomfort	27.91	14.75	7	9475	145	29942851
Fusobacterium infection	27.55	14.75	6	9476	65	29942931
Palatal oedema	27.39	14.75	10	9472	760	29942236
Drug interaction	25.78	14.75	128	9354	199440	29743556
Polyneuropathy in malignant disease	24.41	14.75	6	9476	114	29942882
Dermatitis bullous	24.12	14.75	18	9464	6086	29936910
Mixed liver injury	23.98	14.75	12	9470	1981	29941015
Pruritus	23.95	14.75	87	9395	118117	29824879
Intentional overdose	23.61	14.75	45	9437	41436	29901560
Cholestasis	23.56	14.75	34	9448	24916	29918080
Melaena	23.36	14.75	39	9443	32398	29910598
Vomiting	22.95	14.75	133	9349	219685	29723311
Tongue oedema	22.89	14.75	13	9469	2767	29940229
Liver injury	21.61	14.75	23	9459	12377	29930619
Blood lactic acid	21.57	14.75	7	9475	373	29942623
Anaemia	21.16	14.75	125	9357	207867	29735129
Dyschezia	20.16	14.75	9	9473	1151	29941845
Vitello-intestinal duct remnant	19.61	14.75	5	9477	111	29942885
Meningoencephalitis bacterial	19.24	14.75	5	9477	120	29942876
Drug level increased	18.79	14.75	26	9456	18328	29924668
Enterocolitis	18.49	14.75	16	9466	6671	29936325
Prothrombin time shortened	17.65	14.75	9	9473	1546	29941450
Anterograde amnesia	17.60	14.75	5	9477	169	29942827
Brain empyema	17.57	14.75	3	9479	7	29942989
Gastric ulcer haemorrhage	17.36	14.75	14	9468	5300	29937696
Altered state of consciousness	17.16	14.75	26	9456	19893	29923103
Hepatic function abnormal	16.33	14.75	39	9443	41906	29901090
Diarrhoea infectious	16.33	14.75	6	9476	464	29942532
Metastases to lung	16.21	14.75	16	9466	7879	29935117
Pruritus allergic	16.08	14.75	4	9478	80	29942916
Gastric cancer	16.08	14.75	13	9469	4937	29938059
Pathological fracture	15.93	14.75	12	9470	4114	29938882
Fatigue	15.54	14.75	51	9431	320622	29622374
Mediastinitis	15.50	14.75	6	9476	536	29942460
Hyperkalaemia	15.45	14.75	51	9431	65959	29877037
Allergic colitis	15.34	14.75	3	9479	18	29942978
Metastases to bone	15.23	14.75	17	9465	9641	29933355
Hyperaesthesia	15.16	14.75	11	9471	3562	29939434

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 CS	M0001335	Anti-Inflammatory Agents, Non-Steroidal
FDA MoA	N0000000160	Cyclooxygenase Inhibitors
FDA EPC	N0000175722	Nonsteroidal Anti-inflammatory Drug
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory drugs
CHEBI has role	CHEBI:35493	anti-pyretic
CHEBI has role	CHEBI:35544	cyclooxygenase inhibitors
CHEBI has role	CHEBI:35703	xenobiotic
CHEBI has role	CHEBI:78298	environmental contaminants
CHEBI has role	CHEBI:88188	allergenic drug
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	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
D00132	KEGG_DRUG
4018064	VANDF
C0022635	UMLSCUI
CHEBI:6128	CHEBI
CHEMBL571	ChEMBL_ID
D007660	MESH_DESCRIPTOR_UI
DB01009	DRUGBANK_ID
4795	IUPHAR_LIGAND_ID
3284	INN_ID
90Y4QC304K	UNII
3825	PUBCHEM_CID
6142	RXNORM
3365	MMSL
4946	MMSL
d00028	MMSL
002394	NDDF
10099000	SNOMEDCT_US
386832008	SNOMEDCT_US

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	29 sections
KETOPROFEN	HUMAN PRESCRIPTION DRUG LABEL	1	16590-136	CAPSULE	50 mg	ORAL	ANDA	28 sections
KETOPROFEN	HUMAN PRESCRIPTION DRUG LABEL	1	16590-137	CAPSULE	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	21695-340	CAPSULE	50 mg	ORAL	ANDA	30 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	21695-341	CAPSULE	75 mg	ORAL	ANDA	30 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	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	42254-037	CAPSULE	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	45865-379	CAPSULE	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	45865-485	CAPSULE	50 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0453	CAPSULE	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2729	CAPSULE	50 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	52959-245	CAPSULE	50 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	53217-221	CAPSULE	50 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2414	CAPSULE	50 mg	ORAL	ANDA	30 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2415	CAPSULE	75 mg	ORAL	ANDA	30 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4826	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	ANDA	30 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	63187-018	CAPSULE	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	67296-0369	TABLET	75 mg	ORAL	ANDA	28 sections
Ketoprofen	HUMAN PRESCRIPTION DRUG LABEL	1	69336-127	CAPSULE	25 mg	ORAL	ANDA	14 sections