MEVINIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H36O6
Molecular Weight	408.5283
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12

InChI

InChIKey=BOZILQFLQYBIIY-INTXDZFKSA-N

InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H36O6
Molecular Weight	408.5283
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8121646https://www.ncbi.nlm.nih.gov/pubmed/15531275 | https://www.ncbi.nlm.nih.gov/pubmed/28147319
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27581384 | https://www.ncbi.nlm.nih.gov/pubmed/3981532

Mevastatin (compactin or ML-236B) is an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase. This drug induces apoptosis and arrest of cancer cells in G1 phase. Therapeutic effects of mevastatin on serum level of lipoproteins and unbiquinone-10 in patients with familial hypercholesterolemia were investigated. However, that study was discontinued. In addition, mevastatin was investigated for the treatment of melanoma. It was suggested, that mevastatin was unlikely to prevent melanoma at standard doses. However, higher doses could have a role to play in adjuvant therapy by inhibiting growth and invasion of melanoma cells. Also was revealed, that mevastatin increased histone deacetylase inhibitor, LBH589-induced cell death in triple-negative breast cancer (TNBC) cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3-hydroxy-3-methylglutaryl-coenzyme A reductase 9 Target ID: P04035 Gene ID: 3156.0 Gene Symbol: HMGCR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16386050	Inhibitor 8504
HMG-CoA reductase 49 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8121646	Inhibitor 8504		1.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Familial hypercholesterolemia 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15531275	Primary	Not Provided 511	Unknown Approved Use Unknown
Triple-negative breast cancer 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28147319	Primary	Basic research	Unknown Approved Use Unknown
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18199328	Palliative	Basic research	Unknown Approved Use Unknown
Unknown 2596

PubMed

Title	Date	PubMed
Statins revert doxorubicin resistance via nitric oxide in malignant mesothelioma.	2006-07-01	16450390
Statins inhibit growth of human endometrial stromal cells independently of cholesterol availability.	2006-07	16571871
Involvement of Rho signaling in PAR2-mediated regulation of neutrophil adhesion to lung epithelial cells.	2006-04-24	16564523
HMG-CoA reductase inhibitors induce apoptosis in pericytes.	2006-03	16427097
Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies.	2006-02-22	16478276
Activators of the energy sensing kinase AMPK inhibit random cell movement and chemotaxis in U937 cells.	2006-02	16405649
Alkylamines cause Vgamma9Vdelta2 T-cell activation and proliferation by inhibiting the mevalonate pathway.	2006-01-15	16179378
HMG-CoA reductase inhibitors upregulate heme oxygenase-1 expression in murine RAW264.7 macrophages via ERK, p38 MAPK and protein kinase G pathways.	2006-01	16214041
Statins decrease serotonin-induced contractions in coronary arteries of swine in vitro.	2006	16428899
Statins prevent beta-amyloid inhibition of sympathetic alpha7-nAChR-mediated nitrergic neurogenic dilation in porcine basilar arteries.	2005-12	16192990
Cholesterol biosynthesis and the pro-apoptotic effects of the p75 nerve growth factor receptor in PC12 pheochromocytoma cells.	2005-10-03	15967538
Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil.	2005-09-09	16081098
Fast analysis of pravastatin in production media.	2005-08-05	15990369
Kruppel-like factor 2 as a novel mediator of statin effects in endothelial cells.	2005-08-02	16043642
Genomic effect of vitamin 'C' and statins within human mononuclear cells involved in atherogenic process.	2005-08	15970944
In vivo and in vitro effects of statins on lymphocytes in patients with Hashimoto's thyroiditis.	2005-07	15994744
Statins prevent oxidized LDL-induced injury of glomerular podocytes by activating the phosphatidylinositol 3-kinase/AKT-signaling pathway.	2005-07	15843472
Induction of macrophage elastase (MMP-12) gene expression by statins.	2005-07	15605420
Cholesterol modulation of the expression of mitochondrial aconitase in human prostatic carcinoma cells.	2005-06-30	16201454
Regulation of HMG-CoA reductase in MCF-7 cells by genistein, EPA, and DHA, alone and in combination with mevastatin.	2005-06-28	15914273
Chlamydophila pneumoniae induces expression of toll-like receptor 4 and release of TNF-alpha and MIP-2 via an NF-kappaB pathway in rat type II pneumocytes.	2005-06-03	15935092
4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway.	2005-06	16222778
FOXO-dependent expression of the proapoptotic protein Bim: pivotal role for apoptosis signaling in endothelial progenitor cells.	2005-06	15824087
Novel and simple high-performance liquid chromatographic method for determination of 3-hydroxy-3-methylglutaryl-coenzyme A reductase activity.	2005-05-25	15833295
HMG CoA reductase inhibitors (statins) to treat Epstein-Barr virus-driven lymphoma.	2005-05-09	15856040
Interleukin-6 and mevastatin regulate plasminogen activator inhibitor-1 through CCAAT/enhancer-binding protein-delta.	2005-05	15718495
Statins potentiate the IFN-gamma-induced upregulation of group IIA phospholipase A2 in human aortic smooth muscle cells and HepG2 hepatoma cells.	2005-04-15	15863363
Induction of de novo volatile terpene biosynthesis via cytosolic and plastidial pathways by methyl jasmonate in foliage of Vitis vinifera L.	2005-04-06	15796607
Disruption of lipid rafts causes apoptotic cell death in HaCaT keratinocytes.	2005-04	15810884
Effector gammadelta T cells and tumor cells as immune targets of zoledronic acid in multiple myeloma.	2005-04	15744346
Progesterone-receptor antagonists and statins decrease de novo cholesterol synthesis and increase apoptosis in rat and human periovulatory granulosa cells in vitro.	2005-03	15385411
Three-dimensional quantitative structure (3-D QSAR) activity relationship studies on imidazolyl and N-pyrrolyl heptenoates as 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitors by comparative molecular similarity indices analysis (CoMSIA).	2005-02-15	15686906
Inhibitory effects of mevastatin and a geranylgeranyl transferase I inhibitor (GGTI-2166) on mononuclear osteoclast formation induced by receptor activator of NF kappa B ligand (RANKL) or tumor necrosis factor-alpha (TNF-alpha).	2005-01-01	15588717
Mevastatin induces apoptosis in HL60 cells dependently on decrease in phosphorylated ERK.	2005-01	15786722
High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line.	2005-01	15466163
Inhibition of geranylgeranylation mediates the effects of 3-hydroxy-3-methylglutaryl (HMG)-CoA reductase inhibitors on microglia.	2004-11-12	15364922
Mevastatin inhibits ovarian theca-interstitial cell proliferation and steroidogenesis.	2004-10	15474095
Statins inhibit reoxygenation-induced cardiomyocyte apoptosis: role for glycogen synthase kinase 3beta and transcription factor beta-catenin.	2004-09	15350841
Antioxidant effects of statins via S-nitrosylation and activation of thioredoxin in endothelial cells: a novel vasculoprotective function of statins.	2004-08-17	15289372
Chronic mevastatin modulates receptor-dependent vascular contraction in eNOS-deficient mice.	2004-08	15130878
Mevastatin-induced apoptosis and growth suppression in U266 myeloma cells.	2004-07-28	15274361
Depletion of membrane cholesterol causes ligand-independent activation of Fas and apoptosis.	2004-07-16	15207716
[In vitro effects of mevastatin on the proliferation and apoptosis in human multiple myeloma cell line U266].	2004-06	15228663
Isolation and characterization of a novel trans-factor for luteinizing hormone receptor mRNA from ovary.	2004-04-09	14749336
Statins inhibit osteoblast migration by inhibiting Rac-Akt signaling.	2004-03-12	14975748
De novo biosynthesis and radiolabeling of mammalian digitalis-like factors.	2004-03	14981028
Statins prevent bisphosphonate-induced gamma,delta-T-cell proliferation and activation in vitro.	2004-02	14969398
[Mevastatin induced apoptosis in U266 human myeloma cell line].	2004	15655579
Rhabdomyolysis due to red yeast rice (Monascus purpureus) in a renal transplant recipient.	2002-10-27	12438974
Competitive inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase by ML-236A and ML-236B fungal metabolites, having hypocholesterolemic activity.	1976-12-31	16386050

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:22:07 GMT 2025` Edited by `admin` on `Tue Apr 01 16:22:07 GMT 2025`
Record UNII	1R89KK61YI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEVINIC ACID

Common Name

English

ML-236B ACID

Preferred Name

English

1-NAPHTHALENEHEPTANOIC ACID, 1,2,6,7,8,8A-HEXAHYDRO-.BETA.,.DELTA.-DIHYDROXY-2-METHYL-8-((2S)-2-METHYL-1-OXOBUTOXY)-, (.BETA.R,.DELTA.R,1S,2S,8S,8AR)-

Systematic Name

English

ML236B ACID

Code

English

MEVASTATIN (ACID FORM)

Common Name

English

COMPACTIN ACID

Common Name

English

MEVASTATIN ACID

Common Name

English

MEVASTATIN HYDROXY ACID

Common Name

English

Code System Code Type Description

CHEBI

39508