ATORVASTATIN

Search structure
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C10AA05
UNII: A0JWA85V8F

Structure
InChI Key XUKUURHRXDUEBC-KAYWLYCHSA-N
Smile CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O
InChI
InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H35FN2O5
Molecular Weight 558.65
AlogP 6.31
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 12.0
Polar Surface Area 111.79
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 41.0

Pharmacology

Primary Target
hydroxymethylglutaryl-CoA reductase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 5100 - - -
Enzyme Hydrolase
- - - -
Enzyme Oxidoreductase
- 0.227-12.9 - 6.2 20-83
Enzyme Protease Serine protease Serine protease SC clan Serine protease S9B subfamily
- 175100 - - 66
Epigenetic regulator Eraser Histone deacetylase HDAC class I
- 11148-11619 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- 14151-14466 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 600-1600 - - 74.4
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 271000-307000 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 4300 - - -
Unclassified protein
- 5000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Metabolic Syndrome 3 D024821 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
Bicuspid Aortic Valve Disease 3 D000082882 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Hyperlipoproteinemia Type II 3 D006938 ClinicalTrials
Hyperlipidemia, Familial Combined 3 D006950 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Diabetes Mellitus 3 D003920 ClinicalTrials
Hypertriglyceridemia 3 D015228 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Hyperlipoproteinemia Type IV 3 D006953 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Hyperlipoproteinemia Type III 3 D006952 ClinicalTrials
Hyperlipidemias 3 D006949 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Cardiomyopathy, Hypertrophic 3 D002312 ClinicalTrials
Pre-Eclampsia 3 D011225 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Psoriasis 3 D011565 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Kidney Diseases 3 D007674 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Acute Coronary Syndrome 3 D054058 ClinicalTrials
Acute Chest Syndrome 3 D056586 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Necrosis 3 D009336 ClinicalTrials
Graves Ophthalmopathy 3 D049970 ClinicalTrials
Edema, Cardiac 3 D004489 ClinicalTrials
Hematoma, Subdural, Intracranial 3 D046648 ClinicalTrials
Renal Insufficiency 3 D051437 ClinicalTrials
Ischemic Stroke 3 D000083242 ClinicalTrials
Cognitive Dysfunction 3 D060825 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Lupus Erythematosus, Systemic 3 D008180 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Coronary Artery Disease 3 D003324 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Nasopharyngeal Carcinoma 2 D000077274 ClinicalTrials
Sepsis 2 D018805 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Myocardial Infarction 2 D009203 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Chagas Disease 2 D014355 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Stroke 2 D020521 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Liver Cirrhosis 2 D008103 ClinicalTrials
Acute Kidney Injury 2 D058186 ClinicalTrials
Diabetes Insipidus 2 D003919 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Inflammatory Bowel Diseases 2 D015212 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Intracranial Aneurysm 2 D002532 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Sleep Apnea, Obstructive 2 D020181 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 2 D020529 ClinicalTrials
Vitiligo 2 D014820 ClinicalTrials
Glomerulosclerosis, Focal Segmental 2 D005923 ClinicalTrials
Nephrotic Syndrome 2 D009404 ClinicalTrials
Vascular Diseases 2 D014652 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 2 D016553 ClinicalTrials
Hepatitis C 2 D006526 ClinicalTrials
Influenza, Human 2 D007251 ClinicalTrials
Paraplegia 2 D010264 ClinicalTrials
Migraine Disorders 2 D008881 ClinicalTrials
Multiple Sclerosis 2 D009103 ClinicalTrials
Carotid Artery Diseases 2 D002340 ClinicalTrials
Inflammatory Breast Neoplasms 2 D058922 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Osteonecrosis 2 D010020 ClinicalTrials
Sarcoidosis 2 D012507 ClinicalTrials
Scleroderma, Localized 2 D012594 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Periodontitis 2 D010518 ClinicalTrials
Cardiomyopathies 2 D009202 ClinicalTrials
Crohn Disease 2 D003424 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Mucocutaneous Lymph Node Syndrome 1 D009080 ClinicalTrials
Hemorrhagic Fever, Ebola 1 D019142 ClinicalTrials
Epilepsy 1 D004827 ClinicalTrials
Venous Thromboembolism 1 D054556 ClinicalTrials
Colorectal Neoplasms 1 D015179 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Essential Hypertension 1 D000075222 ClinicalTrials
Constriction, Pathologic 1 D003251 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Colorectal Neoplasms, Hereditary Nonpolyposis 1 D003123 ClinicalTrials
Endometrial Neoplasms 1 D016889 ClinicalTrials
Sleep Wake Disorders 1 D012893 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 134523-00-5
ChEBI 39548
ChEMBL CHEMBL1487
DrugBank DB01076
DrugCentral 257
EPA CompTox DTXSID60274003
FDA SRS A0JWA85V8F
Human Metabolome Database HMDB0005006
Guide to Pharmacology 2949
KEGG C06834
PDB 117
PharmGKB PA448500
PubChem 60823
SureChEMBL SCHEMBL3831
ZINC ZINC000003920719
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