Drug Details

General Information of the Drug (ID: DR2521)
Name
Mevastatin
Synonyms
Mevastatin; compactin; 73573-88-3; ML-236B; Mevastatina; Mevastatine; Mevastatinum; Mevastatinum [INN-Latin]; Antibiotic ML 236B; CS 500; UNII-1UQM1K0W9X; ML 236 B; 1UQM1K0W9X; CHEMBL54440; [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate; CHEBI:34848; MFCD05662341; Mevastatin (Compactin); Mevastatin [INN]; Compactin (penicillium); Mevastatine [INN-French]; Mevastatina [INN-Spanish]; (1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate; (S)-((1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate; Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-; SMR000336944; CCRIS 4505; kompaktin; NCGC00095942-01; EC 700-442-0; SCHEMBL1116; DSSTox_CID_20684; DSSTox_RID_79540; DSSTox_GSID_40684; Lopac0_000754; MLS000721804; MLS000759452; MLS001424284; MLS002207227; GTPL3031; DTXSID4040684; Mevastatin, >=96% (HPLC); HMS2052P07; HMS2089D10; HMS2232N09; HMS3262G10; HMS3268A19; HMS3412H15; HMS3676H15; HMS3713B06; ZINC3833876; Tox21_111540; Tox21_500754; ANW-41687; BDBM50011036; CS-500; NSC779705; s4223; AKOS015994712; Mevastatin, >=95% (HPLC), powder; CCG-101174; CS-1234; DB06693; KS-1085; LP00754; NC00424; NSC 759322; NSC-779705; SDCCGSBI-0050732.P002; 7-(1,2,6,7,8,8a-Hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide; SMP1_000077; NCGC00025202-04; NCGC00261439-01; (1S,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2S)-2-methylbutanoate; Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-; Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta))-; HY-17408; I518; Mevastatin 100 microg/mL in Acetonitrile; AB0013739; CAS-73573-88-3; B1788; EU-0100754; M2275; C13963; M 2537; W-5323; AB00588266-06; AB00588266-08; AB00588266_09; 573M883; Q414407; SR-01000729493; L-637312; SR-01000729493-4; BRD-K94441233-001-03-1; BRD-K94441233-001-17-1; (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate; (S)-((1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate; (S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester; 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester; 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester((+)-compactin); 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester(compactin)
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Molecular Type
Small molecule
Disease Diabetic foot ulcer [ICD-11: BD54] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C23H34O5
PubChem CID
64715
Canonical SMILES
CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
InChI
1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChIKey
AJLFOPYRIVGYMJ-INTXDZFKSA-N
CAS Number
CAS 73573-88-3
ChEBI ID
CHEBI:34848
TTD Drug ID
D0J9GD
DrugBank ID
DB06693
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Gamma tocotrienol      Bixa orellana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of mevastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
Target and Pathway
Target(s) HMG-CoA reductase (HMGCR)  Molecule Info  [3]
BioCyc Superpathway of geranylgeranyldiphosphate biosynthesis I (via mevalonate) Click to Show/Hide
2 Superpathway of cholesterol biosynthesis
3 Mevalonate pathway
KEGG Pathway Terpenoid backbone biosynthesis Click to Show/Hide
2 Metabolic pathways
3 Biosynthesis of antibiotics
4 AMPK signaling pathway
5 Bile secretion
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
3 TSH Signaling Pathway
Panther Pathway Cholesterol biosynthesis Click to Show/Hide
Pathwhiz Pathway Steroid Biosynthesis Click to Show/Hide
WikiPathways Statin Pathway Click to Show/Hide
2 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
3 Activation of Gene Expression by SREBP (SREBF)
4 SREBF and miR33 in cholesterol and lipid homeostasis
5 Integrated Breast Cancer Pathway
6 SREBP signalling
7 Cholesterol Biosynthesis
References
Reference 1 Mevastatin promotes healing by targeting caveolin-1 to restore EGFR signaling. JCI Insight. 2019 Dec 5;4(23):e129320.
Reference 2 Synergistic antiproliferative effects of gamma-tocotrienol and statin treatment on mammary tumor cells. Lipids. 2007 Dec;42(12):1113-23.
Reference 3 Regulation of CYP2B6 and CYP3A expression by hydroxymethylglutaryl coenzyme A inhibitors in primary cultured human hepatocytes. Drug Metab Dispos. 2002 Dec;30(12):1400-5.
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