| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-10-16 06:25:20 -0600 |
| Update Date |
2013-03-26 14:20:55 -0600 |
| HMDB ID |
HMDB05006 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Atorvastatin |
| Description |
Atorvastatin is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; Atorvastatin is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; As with other statins, atorvastatin is a competitive inhibitor of HMG-CoA reductase. Unlike most others, however, it is a completely synthetic compound. HMG-CoA reductase catalyzes the reduction of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) to mevalonate, which is the rate-limiting step in hepatic cholesterol biosynthesis. Inhibition of the enzyme decreases de novo cholesterol synthesis, increasing expression of low-density lipoprotein receptors (LDL receptors) on hepatocytes. This increases the LDL uptake by the hepatocytes, decreasing the amount of LDL in the blood. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Atorvastatin acid
- Atorvastatin calcium
- Cardyl
- Lipitor
|
| Chemical Formula |
C33H35FN2O5 |
| Average Molecular Weight |
558.6398 |
| Monoisotopic Molecular Weight |
558.253000445 |
| IUPAC Name |
(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid |
| Traditional IUPAC Name |
atorvastatin |
| CAS Registry Number |
134523-00-5 |
| SMILES |
CC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CC[C@@H](O)C[C@@H](O)CC(O)=O)C1=CC=C(F)C=C1)C1=CC=CC=C1 |
| InChI Identifier |
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 |
| InChI Key |
XUKUURHRXDUEBC-KAYWLYCHSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Anilides |
| Sub Class |
N/A |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- Branched Fatty Acids
- Halogenated Fatty Acids
- Heterocyclic Fatty Acids
- Organic Compounds
- dihydroxy monocarboxylic acid(ChEBI)
- pyrroles(ChEBI)
|
| Substituents |
- Aryl Fluoride
- Beta Hydroxy Acid
- Carboxamide Group
- Carboxylic Acid
- Fluorobenzene
- Organofluoride
- Pyrrole
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
|
| Direct Parent |
Anilides |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available
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| Application |
Not Available
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| Cellular locations |
Not Available
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
159.1 - 190.6 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
Not Available
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.010 +/- 0.0044 uM |
Adult (>18 years old) |
Both |
Normal
|
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| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.22 +/- 0.16 uM |
Adult (>18 years old) |
Both |
Sepsis patients dosed with 20 mg of Atorvastatin
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| Associated Disorders and Diseases |
|---|
| Disease References |
| Sepsis |
|---|
- Kruger PS, Freir NM, Venkatesh B, Robertson TA, Roberts MS, Jones M: A preliminary study of atorvastatin plasma concentrations in critically ill patients with sepsis. Intensive Care Med. 2008 Nov 26.
Pubmed: 19034423
|
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| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023579 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
54810 |
| KEGG Compound ID |
C06834 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Atorvastatin |
| NuGOwiki Link |
HMDB05006 |
| Metagene Link |
HMDB05006 |
| METLIN ID |
1136 |
| PubChem Compound |
60823 |
| PDB ID |
117 |
| ChEBI ID |
2910 |
| References |
|---|
| Synthesis Reference |
Roth, Bruce David. Preparation of anticholesteremic (R-(R*R*))-2-(4-fluorophenyl)-b, d-dihydroxy-5-(1-methylethyl-3-phenyl-4((phenylamino)carbonyl)-1H-pyrrolyl-1-heptanoic acid, its lactone form and salts thereof. Eur. Pat. Appl. (1991), 18 pp. CODEN: EPXXDW EP 409281 A1 19910123 CAN 115:29107 AN 1991:429107 |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Taylor PJ, Kubler PA, Lynch SV, Allen J, Butler M, Pillans PI: Effect of atorvastatin on cyclosporine pharmacokinetics in liver transplant recipients. Ann Pharmacother. 2004 Feb;38(2):205-8. Epub 2003 Dec 19.
Pubmed: 14742751
- Funatsu T, Suzuki K, Goto M, Arai Y, Kakuta H, Tanaka H, Yasuda S, Ida M, Nishijima S, Miyata K: Prolonged inhibition of cholesterol synthesis by atorvastatin inhibits apo B-100 and triglyceride secretion from HepG2 cells. Atherosclerosis. 2001 Jul;157(1):107-15.
Pubmed: 11427209
- Tannous M, Cheung R, Vignini A, Mutus B: Atorvastatin increases ecNOS levels in human platelets of hyperlipidemic subjects. Thromb Haemost. 1999 Nov;82(5):1390-4.
Pubmed: 10595624
- Naoumova RP, Dunn S, Rallidis L, Abu-Muhana O, Neuwirth C, Rendell NB, Taylor GW, Thompson GR: Prolonged inhibition of cholesterol synthesis explains the efficacy of atorvastatin. J Lipid Res. 1997 Jul;38(7):1496-500.
Pubmed: 9254075
- Izar MC: [Hypolipidemic treatment under special conditions: posttransplant and/or immunosuppressive therapy] Arq Bras Cardiol. 2005 Oct;85 Suppl 5:50-7. Epub 2006 Jan 2.
Pubmed: 16400400
- Hwang YS, Tsai WC, Lu YH, Lin CC, Chen YF: Effect of atorvastatin on the expression of CD40 ligand and P-selectin on platelets in patients with hypercholesterolemia. Am J Cardiol. 2004 Aug 1;94(3):364-6.
Pubmed: 15276107
- Bruni F, Pasqui AL, Pastorelli M, Bova G, Cercignani M, Palazzuoli A, Sawamura T, Auteri A, Puccetti L: Different effect of statins on platelet oxidized-LDL receptor (CD36 and LOX-1) expression in hypercholesterolemic subjects. Clin Appl Thromb Hemost. 2005 Oct;11(4):417-28.
Pubmed: 16244767
- Fenton JW 2nd, Brezniak DV, Ofosu FA, Shen GX, Jacobson JR, Garcia JG: Statins and thrombin. Curr Drug Targets Cardiovasc Haematol Disord. 2005 Apr;5(2):115-20.
Pubmed: 15853752
- Pokrovskaia EV, Vaulin NA, Gratsianskii NA, Averkov OV, Deev AD: [Markers of inflammation and platelet aggregation in patients with non ST elevation acute coronary syndrome treated with atorvastatin or pravastatin] Kardiologiia. 2003;43(1):7-18.
Pubmed: 12891281
- Funatsu T, Kakuta H, Tanaka H, Arai Y, Suzuki K, Miyata K: [Atorvastatin (Lipitor): a review of its pharmacological and clinical profile] Nippon Yakurigaku Zasshi. 2001 Jan;117(1):65-76.
Pubmed: 11233299
- Tousoulis D, Bosinakou E, Kotsopoulou M, Antoniades C, Katsi V, Stefanadis C: Effects of early administration of atorvastatin treatment on thrombotic process in normocholesterolemic patients with unstable angina. Int J Cardiol. 2006 Jan 26;106(3):333-7.
Pubmed: 16337041
- Malinowski JM: Atorvastatin: a hydroxymethylglutaryl-coenzyme A reductase inhibitor. Am J Health Syst Pharm. 1998 Nov 1;55(21):2253-67; quiz 2302-3.
Pubmed: 9825877
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