GEMFIBROZIL

Search structure
Trade Names:
Synonyms:
Status: Approved (1981)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C10AB04
UNII: Q8X02027X3

Structure
InChI Key HEMJJKBWTPKOJG-UHFFFAOYSA-N
Smile Cc1ccc(C)c(OCCCC(C)(C)C(=O)O)c1
InChI
InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H22O3
Molecular Weight 250.34
AlogP 3.57
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 46.53
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 18.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 4.770 - EST
Atmospheric OH Rate Constant 8.24E-11 cm3/molecule-sec EST
Melting Point 62 deg C EXP

Pharmacology

Action Mechanism of Action Reference
AGONIST Peroxisome proliferator-activated receptor alpha agonist
Primary Target
Peroxisome proliferator-activated receptor-α
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 1860-179000 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 4100-95000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 9600 - - -
Enzyme Hydrolase
- - - - 2.802
Enzyme Lyase Guanylate cyclase Soluble guanylate cyclase
624000 - - - -
Enzyme Oxidoreductase
- - - - 14
Enzyme Transferase
- - - - 7.55-31.76
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 4.07-7.2
Secreted protein
- 180000 100 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 1
11800-15190000 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
68400-147800 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 4073.8-130000 - - 14.4-71.16
Unclassified protein
- 170600 - 7291 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Coronary Disease 4 D003327 ClinicalTrials
Myocardial Ischemia 2 D017202 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Smoking Cessation 2 D016540 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Multiple Sclerosis 1 D009103 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Hypertriglyceridemia 1 D015228 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Gastrointestinal disorder 34.2
Gastrointestinal disorders Gastrointestinal disorder
Gastrointestinal disorders Dyspepsia 19.6
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Abdominal pain 9.8
Gastrointestinal disorders Gastrointestinal pain 9.8
Gastrointestinal disorders Diarrhoea 7.2
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Abdominal pain 6.4
Gastrointestinal disorders Gastrointestinal pain 6.4
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Flatulence 5.3
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 5.1
Gastrointestinal disorders Diarrhoea 4.9
Gastrointestinal disorders Nausea 4.3
Gastrointestinal disorders Abdominal pain
Cardiac disorders Dizziness
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Headache
General disorders and administration site conditions Asthenia 3.8
General disorders and administration site conditions Fatigue 3.8
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 3.8
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Abdominal pain upper 3.4
Cardiac disorders Dizziness 2.8
Skin and subcutaneous tissue disorders Dermatitis 2.5
Gastrointestinal disorders Nausea 2.5
Skin and subcutaneous tissue disorders Rash 2.5
Gastrointestinal disorders Vomiting 2.5
Nervous system disorders Headache 2.3
Gastrointestinal disorders Vomiting 2.3
Cardiac disorders Chest pain 2.1
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 2.1
Gastrointestinal disorders Nausea
Gastrointestinal disorders Vomiting
Skin and subcutaneous tissue disorders Eczema 1.9
Gastrointestinal disorders Abdominal pain upper
Gastrointestinal disorders Abdominal pain upper 1.7
Cardiac disorders Chest pain
Skin and subcutaneous tissue disorders Dermatitis 1.7
Musculoskeletal and connective tissue disorders Musculoskeletal pain
General disorders and administration site conditions Pain
Skin and subcutaneous tissue disorders Rash 1.7
Gastrointestinal disorders Flatulence 1.5
Musculoskeletal and connective tissue disorders Musculoskeletal pain 1.5
General disorders and administration site conditions Pain 1.5
Ear and labyrinth disorders Vertigo 1.5
Gastrointestinal disorders Constipation 1.4
Gastrointestinal disorders Constipation
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 1.3
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 1.3
Ear and labyrinth disorders Vertigo
Gastrointestinal disorders Appendicitis 1.2
Skin and subcutaneous tissue disorders Eczema
Nervous system disorders Headache 1.2
Nervous system disorders Headache
Eye disorders Vision blurred 1.1
General disorders and administration site conditions Asthenia 0.9
General disorders and administration site conditions Fatigue 0.9
Metabolism and nutrition disorders Gout 0.9
Nervous system disorders Paraesthesia 0.9
Metabolism and nutrition disorders Gout
Skin and subcutaneous tissue disorders Pruritus 0.8
Eye disorders Vision blurred
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 0.8
Cardiac disorders Atrial fibrillation 0.7
Gastrointestinal disorders Appendicitis
Skin and subcutaneous tissue disorders Dermatitis 0.6
General disorders and administration site conditions Asthenia
Skin and subcutaneous tissue disorders Dermatitis
General disorders and administration site conditions Fatigue
Nervous system disorders Paraesthesia
Nervous system disorders Paraesthesia 0.4
Immune system disorders Urticaria 0.2
Cardiac disorders Atrial fibrillation

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Immune system disorders
18.49
General disorders and administration site conditions
11.53
Musculoskeletal and connective tissue disorders
9.8
Nervous system disorders
9.31
Gastrointestinal disorders
7.21
Psychiatric disorders
5.84
Injury, poisoning and procedural complications
4.41
Skin and subcutaneous tissue disorders
4.19
Investigations
3.98
Vascular disorders
3.96
Cardiac disorders
3.9
Respiratory, thoracic and mediastinal disorders
3.8
Renal and urinary disorders
3.07
Metabolism and nutrition disorders
2.86

Cross References

Resources Reference
CAS NUMBER 25812-30-0
ChEBI 5296
ChEMBL CHEMBL457
DrugBank DB01241
DrugCentral 1285
EPA CompTox DTXSID0020652
FDA SRS Q8X02027X3
Human Metabolome Database HMDB15371
Guide to Pharmacology 3439
KEGG C07020
PDB 4TX
PharmGKB PA449750
PubChem 3463
SureChEMBL SCHEMBL4813
ZINC ZINC000001530641
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