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

Stem definition	Drug id	CAS RN
	1285	25812-30-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: gemfibrosil gemfibrozil decrelip lopizid	A lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol. Molecular weight: 250.34 Formula: C15H22O3 CLOGP: 3.94 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 46.53 ALOGS: -3.95 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

gemfibrosil
gemfibrozil
decrelip
lopizid

A lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol.

Molecular weight: 250.34
Formula: C15H22O3
CLOGP: 3.94
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 46.53
ALOGS: -3.95
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
1.20	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.02 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)	79.89 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	98 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Dec. 21, 1981	FDA	PFIZER PHARMS

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
Rhabdomyolysis	206.71	13.66	122	9813	41787	46634340
Drug hypersensitivity	69.28	13.66	157	9778	243668	46432459
Blood triglycerides increased	54.60	13.66	33	9902	11750	46664377
Coronary artery disease	43.00	13.66	44	9891	33708	46642419
Blood creatine phosphokinase increased	42.52	13.66	40	9895	27684	46648443
Myocardial infarction	37.21	13.66	71	9864	97457	46578670
Acute interstitial pneumonitis	36.63	13.66	11	9924	679	46675448
Myopathy	33.91	13.66	22	9913	8859	46667268
Myalgia	28.13	13.66	73	9862	123015	46553112
Cardiac failure congestive	28.10	13.66	61	9874	91689	46584438
Pancreatitis	27.76	13.66	40	9895	43587	46632540
Cerebrovascular accident	26.31	13.66	63	9872	100976	46575151
Pancreatitis acute	25.65	13.66	29	9906	24843	46651284
Hypertriglyceridaemia	23.94	13.66	15	9920	5689	46670438
Drug interaction	23.18	13.66	95	9840	202999	46473128
Lip infection	23.13	13.66	5	9930	80	46676047
Diabetes mellitus	21.01	13.66	38	9897	50027	46626100
Blood glucose increased	19.93	13.66	46	9889	71967	46604160
Bursitis	18.55	13.66	22	9913	19820	46656307
Tendon rupture	17.59	13.66	14	9921	7745	46668382
Off label use	16.64	13.66	35	9900	379806	46296321
Microalbuminuria	16.37	13.66	5	9930	327	46675800
Rheumatoid arthritis	15.46	13.66	17	9918	240198	46435929
Diabetes mellitus inadequate control	14.64	13.66	16	9919	13198	46662929
Blood cholesterol increased	13.87	13.66	28	9907	39985	46636142

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
Rhabdomyolysis	526.11	12.88	344	13904	63236	29874994
Acute kidney injury	106.55	12.88	328	13920	273514	29664716
Blood triglycerides increased	103.76	12.88	71	14177	13946	29924284
Blood creatine phosphokinase increased	102.50	12.88	115	14133	43733	29894497
Myalgia	85.17	12.88	140	14108	76527	29861703
Coronary artery disease	66.60	12.88	99	14149	49613	29888617
Blood cholesterol increased	56.78	12.88	54	14194	16916	29921314
Drug hypersensitivity	52.98	12.88	107	14141	68412	29869818
Myocardial infarction	49.96	12.88	152	14096	125473	29812757
Polymyositis	48.23	12.88	20	14228	1416	29936814
Cardiac failure congestive	41.18	12.88	110	14138	84297	29853933
Pancreatitis	34.36	12.88	62	14186	36428	29901802
Off label use	32.17	12.88	43	14205	249247	29688983
Drug interaction	31	12.88	181	14067	199387	29738843
Myopathy	30.40	12.88	31	14217	10555	29927675
International normalised ratio increased	27.19	12.88	66	14182	47673	29890557
Hyperglycaemia	26.02	12.88	54	14194	35146	29903084
Thunderclap headache	25.03	12.88	6	14242	66	29938164
Death	24.94	12.88	87	14161	357196	29581034
Drug abuse	23.81	12.88	5	14243	82067	29856163
Hypertriglyceridaemia	23.77	12.88	24	14224	8074	29930156
Chromaturia	23.59	12.88	31	14217	13834	29924396
Chronic kidney disease	23.37	12.88	54	14194	37784	29900446
Granulocytopenia	23.11	12.88	21	14227	6205	29932025
Haemodialysis	22.41	12.88	27	14221	11046	29927184
Blood glucose increased	22.14	12.88	72	14176	61458	29876772
Type 2 diabetes mellitus	20.96	12.88	29	14219	13593	29924637
Myositis	20.51	12.88	25	14223	10352	29927878
Drug ineffective	20.45	12.88	88	14160	340299	29597931
Reversible cerebral vasoconstriction syndrome	17.72	12.88	6	14242	241	29937989
Erosive duodenitis	17.67	12.88	10	14238	1403	29936827
Blood glucose decreased	17.46	12.88	26	14222	13027	29925203
Angina unstable	17.16	12.88	25	14223	12285	29925945
Angioedema	16.93	12.88	45	14203	34339	29903891
Lacrimation decreased	16.66	12.88	3	14245	6	29938224
Treatment noncompliance	16.66	12.88	37	14211	25216	29913014
Pyrexia	16.55	12.88	78	14170	294411	29643819
Muscular weakness	16.55	12.88	67	14181	63578	29874652
General physical health deterioration	16.47	12.88	14	14234	99930	29838300
Hyperlipidaemia	16.22	12.88	26	14222	13881	29924349
Pneumonia haemophilus	16.14	12.88	6	14242	317	29937913
Fanconi syndrome	15.57	12.88	10	14238	1765	29936465
Metabolic acidosis	15.47	12.88	46	14202	37415	29900815
Product use in unapproved indication	15.26	12.88	8	14240	73685	29864545
Interstitial lung disease	14.93	12.88	5	14243	60192	29878038
Otitis externa	14.78	12.88	8	14240	1029	29937201
Asthenia	14.55	12.88	165	14083	221125	29717105
Breast neoplasm	14.42	12.88	3	14245	16	29938214
Hyperlactacidaemia	14.26	12.88	11	14237	2595	29935635
Tricuspid valve incompetence	14.24	12.88	19	14229	8604	29929626
Blood creatinine increased	14.21	12.88	83	14165	91292	29846938
Iron deficiency anaemia	13.56	12.88	19	14229	9005	29929225
Coronary artery stenosis	13.49	12.88	19	14229	9051	29929179
Renal tubular necrosis	13.20	12.88	25	14223	15226	29923004
Arteriosclerosis coronary artery	13.17	12.88	21	14227	11155	29927075
Supraventricular tachycardia	13.08	12.88	20	14228	10252	29927978
Paralysis	12.95	12.88	15	14233	5886	29932344

Pharmacologic Action:

Source	Code	Description
ATC	C10AB04	CARDIOVASCULAR SYSTEM LIPID MODIFYING AGENTS LIPID MODIFYING AGENTS, PLAIN Fibrates
FDA CS	M0199111	PPAR alpha
FDA MoA	N0000175375	Peroxisome Proliferator-activated Receptor alpha Agonists
FDA EPC	N0000175596	Peroxisome Proliferator Receptor alpha Agonist
CHEBI has role	CHEBI:35679	hypolipidemic agent
MeSH PA	D000963	Antimetabolites
MeSH PA	D065687	Cytochrome P-450 CYP2C8 Inhibitors
MeSH PA	D065607	Cytochrome P-450 Enzyme Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D000960	Hypolipidemic Agents
MeSH PA	D057847	Lipid Regulating Agents
MeSH PA	D065606	Metabolic Side Effects of Drugs and Substances

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Hypertriglyceridemia	indication	302870006
Primary Prevention of Coronary Heart Disease	indication
Hypoalphalipoproteinemia	off-label use	190785000
Primary biliary cirrhosis	contraindication	31712002	DOID:12236
Disorder of gallbladder	contraindication	39621005	DOID:0060262
Acute nephropathy	contraindication	58574008
Leukopenia	contraindication	84828003	DOID:615
Impaired renal function disorder	contraindication	197663003
Disease of liver	contraindication	235856003	DOID:409
Calculus in biliary tract	contraindication	266474003
Anemia	contraindication	271737000	DOID:2355
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Breastfeeding (mother)	contraindication	413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	5.13	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
Peroxisome proliferator-activated receptor alpha	Nuclear hormone receptor	Q07869	PPARA_HUMAN	AGONIST	EC50	4.23	IUPHAR	CHEMBL
Cytochrome P450 2C8	Enzyme	P10632	CP2C8_HUMAN		Ki	5.74	WOMBAT-PK
Lipoprotein lipase	Enzyme	P06858	LIPL_HUMAN				WOMBAT-PK
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		Ki	4.52	WOMBAT-PK
Transthyretin	Secreted	P02766	TTHY_HUMAN		Kd	7	CHEMBL
Fatty acid-binding protein, liver	Unclassified		FABPL_RAT		Ki	5.73	CHEMBL

External reference:

ID	Source
4018639	VUID
N0000146952	NUI
D00334	KEGG_DRUG
4018639	VANDF
C1567527	UMLSCUI
CHEBI:5296	CHEBI
4TX	PDB_CHEM_ID
CHEMBL457	ChEMBL_ID
DB01241	DRUGBANK_ID
D015248	MESH_DESCRIPTOR_UI
3463	PUBCHEM_CID
3439	IUPHAR_LIGAND_ID
3899	INN_ID
Q8X02027X3	UNII
4719	RXNORM
4778	MMSL
523	MMSL
d00245	MMSL
002050	NDDF
35282000	SNOMEDCT_US
387189002	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Lopid	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0737	TABLET, FILM COATED	600 mg	ORAL	NDA	18 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9130	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9707	TABLET, FILM COATED	600 mg	ORAL	ANDA	18 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8354	TABLET, FILM COATED	600 mg	ORAL	ANDA	15 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	10544-569	TABLET, FILM COATED	600 mg	ORAL	ANDA	18 sections
Gemfibrozil	Human Prescription Drug Label	1	16571-784	TABLET, FILM COATED	600 mg	ORAL	ANDA	15 sections
Gemfibrozil	Human Prescription Drug Label	1	16714-101	TABLET	600 mg	ORAL	ANDA	18 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	21695-732	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	24658-260	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
GEMFIBROZIL	HUMAN PRESCRIPTION DRUG LABEL	1	31722-128	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	31722-225	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	33261-146	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
GEMFIBROZIL	HUMAN PRESCRIPTION DRUG LABEL	1	42806-260	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	43063-745	TABLET	600 mg	ORAL	ANDA	11 sections
GEMFIBROZIL	HUMAN PRESCRIPTION DRUG LABEL	1	43063-921	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	43353-090	TABLET, FILM COATED	600 mg	ORAL	ANDA	18 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	43353-772	TABLET, FILM COATED	600 mg	ORAL	ANDA	21 sections
GEMFIBROZIL	HUMAN PRESCRIPTION DRUG LABEL	1	43602-452	TABLET	600 mg	ORAL	ANDA	10 sections
Gemfibrozil	Human Prescription Drug Label	1	50090-2450	TABLET, FILM COATED	600 mg	ORAL	ANDA	15 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2902	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	50268-350	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	51138-588	TABLET, FILM COATED	600 mg	ORAL	ANDA	18 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	51655-142	TABLET	600 mg	ORAL	ANDA	9 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	51655-143	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	53002-1068	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	Human Prescription Drug Label	1	53002-2068	TABLET, FILM COATED	600 mg	ORAL	ANDA	15 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	53217-251	TABLET	600 mg	ORAL	ANDA	11 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0251	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0368	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections
Gemfibrozil	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0673	TABLET, FILM COATED	600 mg	ORAL	ANDA	17 sections