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Lovastatin information


Lovastatin
Clinical data
Trade namesMevacor, Altocor, others
Other namesMonacolin K, Mevinolin
AHFS/Drugs.comMonograph
MedlinePlusa688006
License data
  • US DailyMed: Lovastatin
Routes of
administration
By mouth
ATC code
  • C10AA02 (WHO)
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailability<5%[1]
Protein binding>98%[1]
MetabolismLiver (CYP3A and CYP2C8 substrate)[1]
Elimination half-life2–5 hours[1]
ExcretionFaeces (83%), urine (10%)[1]
Identifiers
IUPAC name
  • (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
CAS Number
  • 75330-75-5 checkY
PubChem CID
  • 53232
IUPHAR/BPS
  • 2739
DrugBank
  • DB00227 checkY
ChemSpider
  • 48085 checkY
UNII
  • 9LHU78OQFD
KEGG
  • D00359 checkY
ChEBI
  • CHEBI:40303 checkY
ChEMBL
  • ChEMBL503 checkY
CompTox Dashboard (EPA)
  • DTXSID5020784 Edit this at Wikidata
ECHA InfoCard100.115.931 Edit this at Wikidata
Chemical and physical data
FormulaC24H36O5
Molar mass404.547 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(O[C@@H]1[C@H]3C(=C/[C@H](C)C1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)[C@@H](C)CC
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 checkY
  • Key:PCZOHLXUXFIOCF-BXMDZJJMSA-N checkY
  (verify)

Lovastatin, sold under the brand name Mevacor among others, is a statin medication, to treat high blood cholesterol and reduce the risk of cardiovascular disease.[2] Its use is recommended together with lifestyle changes.[2] It is taken by mouth.[2]

Common side effects include diarrhea, constipation, headache, muscles pains, rash, and trouble sleeping.[2] Serious side effects may include liver problems, muscle breakdown, and kidney failure.[2] Use during pregnancy may harm the baby and use during breastfeeding is not recommended.[3] It works by decreasing the liver's ability to produce cholesterol by blocking the enzyme HMG-CoA reductase.[2]

Lovastatin was patented in 1979 and approved for medical use in 1987.[4] It is on the World Health Organization's List of Essential Medicines.[5] It is available as a generic medication.[2] In 2021, it was the 100th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[6][7]

  1. ^ a b c d e Neuvonen PJ, Backman JT, Niemi M (2008). "Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin". Clinical Pharmacokinetics. 47 (7): 463–474. doi:10.2165/00003088-200847070-00003. PMID 18563955. S2CID 11716425.
  2. ^ a b c d e f g "Lovastatin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ^ "Lovastatin Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 472. ISBN 9783527607495.
  5. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  6. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  7. ^ "Lovastatin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Lovastatin

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Lovastatin, sold under the brand name Mevacor among others, is a statin medication, to treat high blood cholesterol and reduce the risk of cardiovascular...

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Red yeast rice

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yeast rice. Chemical analysis soon showed that lovastatin and monacolin K were identical. Lovastatin became the patented prescription drug Mevacor. Red...

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Statin

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various forms of statins, some of which include atorvastatin, fluvastatin, lovastatin, pitavastatin, pravastatin, rosuvastatin, and simvastatin. Combination...

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Lovastatin nonaketide synthase

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In enzymology, lovastatin nonaketide synthase (EC 2.3.1.161) is an enzyme that catalyzes the chemical reaction acetyl-CoA + 8 malonyl-CoA + 11 NADPH +...

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Aspergillus terreus

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like xylanase. It was also the initial source for the drug mevinolin (lovastatin), a drug for lowering serum cholesterol. Aspergillus terreus can cause...

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Medicinal uses of fungi

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of producing 70 mg lovastatin per kilogram of substrate. The red yeast rice fungus, Monascus purpureus, can synthesize lovastatin, mevastatin, and the...

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Swanson Health Products

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of SHP's red yeast rice supplements contained significant amounts of lovastatin, the active ingredient in Mevacor and its generic counterparts. The FDA...

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Secondary metabolite

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from Tolypocladium inflatum. Lovastatin was the first FDA approved secondary metabolite to lower cholesterol levels. Lovastatin occurs naturally in low concentrations...

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Pravastatin

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"Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin". Clinical Pharmacokinetics. 47 (7): 463–474...

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Pleurotus citrinopileatus

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oyster mushroom, has been found to contain the cholesterol-lowering drug lovastatin. In one study, among 11 other commonly cultivated or foraged mushroom...

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Simvastatin

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and colleagues isolated lovastatin from a strain of the fungus Aspergillus terreus. While developing and researching lovastatin, Merck scientists synthetically...

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Discovery and development of statins

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Atorvastatin Rosuvastatin Lovastatin is derived from a fungus source and simvastatin and pravastatin are chemical modifications of lovastatin and as a result do...

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Mexazolam

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HMG-CoA reductase inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of...

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Fluvastatin

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characteristic side effects for statins, can also occur. Contrary to lovastatin, simvastatin and atorvastatin, fluvastatin has no relevant interactions...

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WHO Model List of Essential Medicines

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high‐risk patients. Atorvastatin, fluvastatin, lovastatin, and pravastatin are alternatives fluvastatin, lovastatin, pravastatin, and simvastatin are alternatives...

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Mold

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USDA and by Pfizer. Several statin cholesterol-lowering drugs (such as lovastatin, from Aspergillus terreus) are derived from molds. The immunosuppressant...

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Monascus purpureus

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medical uses. It produces a number of statins. The naturally occurring lovastatins and analogs are called monacolins K, L, J, and also occur in their hydroxyl...

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Monacolin

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group of compounds found in yeast species: Monacolin J Monacolin K or lovastatin This article includes a list of related items that share the same name...

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Clarithromycin

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liver impairment. Concomitant use with cholesterol medications such as lovastatin or simvastatin. Hypersensitivity to clarithromycin or any component of...

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Diverted total synthesis

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ergot alkaloids one of which is lysergic acid and Simvastatin is based on Lovastatin. Diverted total synthesis is a topic in academic research. Design and...

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Medication

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chlorpromazine, reserpine, chlordiazepoxide, diazepam, and alprazolam Statins: lovastatin, pravastatin, and simvastatin Pharmaceuticals may also be described as...

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Erythromycin

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— drugs that are broken down by CYP3A — such as simvastatin (Zocor), lovastatin (Mevacor), or atorvastatin (Lipitor) — are taken concomitantly with erythromycin...

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Fungus

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statins found in fungi include mevastatin from Penicillium citrinum and lovastatin from Aspergillus terreus and the oyster mushroom. Psilocybin from fungi...

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Omeprazole

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Linolenic acid: α-Linolenic acid and γ-linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone...

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Niacin

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combined with lovastatin (Advicor), and with simvastatin (Simcor), as prescription drug combinations. The combination niacin/lovastatin was approved by...

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Permethrin

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Linolenic acid: α-Linolenic acid and γ-linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone...

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Loratadine

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Linolenic acid: α-Linolenic acid and γ-linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone...

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Karine Auclair

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"Modulation of Polyketide Synthase Activity by Accessory Proteins During Lovastatin Biosynthesis". Science. 284 (5418): 1368–1372. Bibcode:1999Sci...284.1368K...

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