Chemicals and Drugs

Simvastatin

A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.

Chemical Identity

Chemical Information

Molecular Formula
C25H38O5
Molecular Weight
418.6 g/mol
CAS Registry No.
79902-63-9
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] 2,2-dimethylbutanoate
InChIKey
RYMZZMVNJRMUDD-HGQWONQESA-N
SMILES
CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C
MeSH Unique ID
D019821
Source
PubChem CID 54454

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

See Also

MeSH Record

Synonyms

5 entry terms
  • MK-733
  • Synvinolin
  • Zocor
  • MK 733
  • MK733

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

98; use SIMVASTATIN (NM) 1986-97

MeSH Record

Previous Indexing

  • Lovastatin/analogs & derivatives (1988-1997)
  • Naphthalenes (1986-1987)

MeSH Hierarchy

Tree Numbers

  1. D02w.455w.426w.559w.847w.638.400w.900w
  2. D04w.615w.638.400w.900w

AMA Style

References

  1. National Library of Medicine. Simvastatin. Medical Subject Headings (MeSH). 2026. Unique ID D019821. http://id.nlm.nih.gov/mesh/2026/D019821
  2. Simvastatin. In: Wikipedia. https://en.wikipedia.org/wiki/Simvastatin
  3. Simvastatin. In: Wikidata. https://www.wikidata.org/wiki/Q670131
  4. Simvastatin. In: PubChem Compound. CID 54454. https://pubchem.ncbi.nlm.nih.gov/compound/54454