LOVASTATIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1987)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: C10AA02
UNII: 9LHU78OQFD

Structure
InChI Key PCZOHLXUXFIOCF-BXMDZJJMSA-N
Smile CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]21
InChI
InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H36O5
Molecular Weight 404.55
AlogP 4.2
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 72.83
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR HMG-CoA reductase inhibitor DailyMed
Primary Target
hydroxymethylglutaryl-CoA reductase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Adhesion
- 2400 12900 - 38-61
Enzyme Hydrolase
- - - 1100-5012 -
Enzyme Oxidoreductase
- 3-530 - 1 -90-84
Enzyme
- 3-530 - 1100-5012 -90-84
Epigenetic regulator Eraser Histone deacetylase HDAC class I
- 11911 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- 16285 - - -
Membrane receptor
- 2400 12900 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 21-101
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 19300-19300 - - -

Metabolites

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Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypercholesterolemia 4 D006937 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Intermittent Claudication 3 D007383 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Carotid Stenosis 2 D016893 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Intracranial Arteriosclerosis 2 D002537 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Neurofibromatosis 1 2 D009456 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Rett Syndrome 2 D015518 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Fragile X Syndrome 2 D005600 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Xanthomatosis, Cerebrotendinous 2 D019294 ClinicalTrials
Learning Disabilities 2 D007859 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Intracranial Arteriovenous Malformations 2 D002538 ClinicalTrials
Stroke 1 D020521 ClinicalTrials
Porokeratosis 1 D017499 ClinicalTrials
Asthma 1 D001249 ClinicalTrials
Metabolic Diseases 1 D008659 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Inflammation 0 D007249 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Flatulence 4.5
Gastrointestinal disorders Flatulence 4.3
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 3.9
Gastrointestinal disorders Flatulence 3.7
Gastrointestinal disorders Constipation 3.5
Gastrointestinal disorders Constipation 3.2
Nervous system disorders Headache 3.2
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Nervous system disorders Headache 2.8
Nervous system disorders Headache
Gastrointestinal disorders Diarrhoea 2.6
Nervous system disorders Headache 2.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.6
Musculoskeletal and connective tissue disorders Myalgia 2.6
Gastrointestinal disorders Abdominal pain 2.5
Gastrointestinal disorders Gastrointestinal pain 2.5
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 2.5
Gastrointestinal disorders Diarrhoea 2.4
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Abdominal pain 2.2
Gastrointestinal disorders Diarrhoea 2.2
Gastrointestinal disorders Gastrointestinal pain 2.2
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.2
Musculoskeletal and connective tissue disorders Myalgia 2.2
Gastrointestinal disorders Nausea 2.2
Nervous system disorders Headache 2.1
Gastrointestinal disorders Abdominal pain 2.0
Gastrointestinal disorders Constipation 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Nausea 1.9
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.8
Musculoskeletal and connective tissue disorders Myalgia 1.8
General disorders and administration site conditions Asthenia 1.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Dyspepsia 1.6
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Asthenia 1.5
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.3
Gastrointestinal disorders Dyspepsia 1.3
Skin and subcutaneous tissue disorders Rash 1.3
General disorders and administration site conditions Asthenia 1.2
Skin and subcutaneous tissue disorders Dermatitis 1.2
Cardiac disorders Dizziness 1.2
Skin and subcutaneous tissue disorders Rash 1.2
Eye disorders Vision blurred 1.2
Musculoskeletal and connective tissue disorders Muscle spasms 1.1
Eye disorders Vision blurred 1.1
Skin and subcutaneous tissue disorders Dermatitis 1.0
Gastrointestinal disorders Dyspepsia 1.0
Musculoskeletal and connective tissue disorders Muscle spasms 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Eye disorders Vision blurred 0.9
Skin and subcutaneous tissue disorders Dermatitis 0.8
Musculoskeletal and connective tissue disorders Muscle spasms 0.8
Skin and subcutaneous tissue disorders Rash 0.8
Eye disorders Vision blurred
Skin and subcutaneous tissue disorders Dermatitis
Cardiac disorders Dizziness
Cardiac disorders Dizziness 0.7
Skin and subcutaneous tissue disorders Rash
Musculoskeletal and connective tissue disorders Muscle spasms 0.6
Cardiac disorders Dizziness 0.5
Musculoskeletal and connective tissue disorders Muscle spasms

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Musculoskeletal and connective tissue disorders
23.43
General disorders and administration site conditions
12.37
Nervous system disorders
11.87
Psychiatric disorders
8.65
Immune system disorders
6.27
Gastrointestinal disorders
6.18
Injury, poisoning and procedural complications
3.92
Respiratory, thoracic and mediastinal disorders
3.74
Cardiac disorders
3.66
Investigations
3.48
Vascular disorders
3.4
Skin and subcutaneous tissue disorders
2.96
Hepatobiliary disorders
2.29

Cross References

Resources Reference
CAS NUMBER 75330-75-5
ChEBI 40303
ChEMBL CHEMBL503
DrugBank DB00227
DrugCentral 1612
EPA CompTox DTXSID5020784
FDA SRS 9LHU78OQFD
Human Metabolome Database HMDB0014372
Guide to Pharmacology 2739
KEGG C07074
PDB 803
PharmGKB PA450272
PubChem 53232
SureChEMBL SCHEMBL3136
ZINC ZINC000003812841
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