Page last updated: 2024-12-04

mevalonic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(R)-mevalonic acid : The (R)-enantiomer of mevalonic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID439230
CHEMBL ID1794734
CHEBI ID17710
SCHEMBL ID120275
MeSH IDM0013714

Synonyms (38)

Synonym
rs-mevalonic acid
dl-mevalonate
CHEBI:17710 ,
(r)-3,5-dihydroxy-3-methylvaleric acid
(3r)-3,5-dihydroxy-3-methylpentanoic acid
(r)-mevalonic acid
3r-methyl-3,5-dihydroxy-pentanoic acid
LMFA01050352
C00418
17817-88-8
3,5-dihydroxy-3-methylvaleric acid
mevalonic acid
MVA ,
DB03518
(r)-3,5-dihydroxy-3-methylpentanoic acid
AKOS006375830
mk 91
2,4-dideoxy-3-c-methylpentonic acid
3,5-dihydroxy-3-methylvalerate
2,4-dideoxy-3-c-methylpentonate
CHEMBL1794734
(3rs)-mevalonic acid
hiochic acid
SCHEMBL120275
(s)-mevalonic acid lithium salt
J-018740
3,5-dihydroxy-3-methyl-valerate
b,d-dihydroxy-b-methylvaleric acid
(3rs)-mevalonate
rs-mevalonate
3,5-dihydroxy-3-methyl-valeric acid
b,d-dihydroxy-b-methylvalerate
b,d-dihydroxy-beta-methylvalerate
b,d-dihydroxy-beta-methylvaleric acid
r-mevalonic acid
DTXSID801314151
(r)-(-)-mevalonic acid
pentanoic acid, 3,5-dihydroxy-3-methyl-, (3r)-

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" of mevalonic acid completely blocked and/or ameliorated the mortality, cardiac myopathy, and other adverse effects."( Prevention of fluvastatin-induced toxicity, mortality, and cardiac myopathy in pregnant rats by mevalonic acid supplementation.
Cox, RH; Hartman, HA; Hrab, RV, 1994
)
0.29
"Oxidized low density lipoprotein (oxLDL) is known to be toxic to a variety of cell types, but relatively little is known about the toxic effects of oxLDL on vascular smooth muscle cells (SMC)."( Toxicity of oxidized low density lipoproteins for vascular smooth muscle cells and partial protection by antioxidants.
Guyton, JR; Hughes, H; Karsan, D; Lenz, ML; Mathews, B; Selinger, E; Smith, CV, 1995
)
0.29
" In addition, uninfected neurons treated with squalestatin became resistant to the otherwise toxic effect of PrP peptides, a synthetic miniprion (sPrP106) or partially purified prion preparations."( Squalestatin cures prion-infected neurons and protects against prion neurotoxicity.
Bate, C; Diomede, L; Salmona, M; Williams, A, 2004
)
0.32
"To examine in a major cohort of patients whether or not musculoskeletal adverse effects (MAEs), similar to those seen in intravenous bisphosphonates (BP), might occur also in high dosage oral treatment regimens with alendronate (ALN) and risedronate (RSN)."( Common musculoskeletal adverse effects of oral treatment with once weekly alendronate and risedronate in patients with osteoporosis and ways for their prevention.
Bock, O; Boerst, H; Degner, C; Felsenberg, D; Stephan-Oelkers, M; Thomasius, FE; Valentine, SM,
)
0.13
" Although statins are generally well-tolerated, adverse effects may occur in some patients."( Adverse effects of statins - mechanisms and consequences.
Bełtowski, J; Jamroz-Wiśniewska, A; Wójcicka, G, 2009
)
0.35
" These results indicate that muscle cells may be particularly susceptible to a statin-induced suppression of essential antioxidant selenoproteins, which provides an explanation for the disposition of these drugs to evoke adverse muscular side-effects."( Prooxidative toxicity and selenoprotein suppression by cerivastatin in muscle cells.
Fuhrmeister, J; Kromer, A; Moosmann, B; Tews, M, 2012
)
0.38
" However, a recognized side-effect of statin therapy is myopathy, which in severe cases can present as potentially fatal rhabdomyolysis."( Inhibition of prenyltransferase activity by statins in both liver and muscle cell lines is not causative of cytotoxicity.
Gee, RH; Johnston, JD; Malia, JM; Plant, KE; Plant, NJ; Spinks, JN, 2015
)
0.42
" In conclusion, myoblasts were more susceptible to the toxic effects of simvastatin and simvastatin impaired myoblast proliferation and myotube formation."( C2C12 myoblasts are more sensitive to the toxic effects of simvastatin than myotubes and show impaired proliferation and myotube formation.
Bouitbir, J; Krähenbühl, S; Sanvee, GM, 2021
)
0.62
" Although these pleiotropic effects of statins may be a cause for enthusiasm, there are many adverse effects that, for the most part, are unappreciated and need to be highlighted."( Molecular targets of statins and their potential side effects: Not all the glitter is gold.
Kashfi, K; Patel, KK; Sehgal, VS, 2022
)
0.72

Pharmacokinetics

ExcerptReferenceRelevance
" Indeed, pharmacokinetic interactions (e."( New insights into the pharmacodynamic and pharmacokinetic properties of statins.
Baetta, R; Bellosta, S; Bernini, F; Corsini, A; Fumagalli, R; Paoletti, R, 1999
)
0.3

Compound-Compound Interactions

ExcerptReferenceRelevance
" Herein, we investigated in human monocytes the effect of statins alone, and in combination with PPAR-gamma ligands on CD36 expression, as well as the molecular mechanisms underlying the regulatory action of statins."( Statins upregulate CD36 expression in human monocytes, an effect strengthened when combined with PPAR-gamma ligands Putative contribution of Rho GTPases in statin-induced CD36 expression.
Domínguez, A; Ruiz-Velasco, N; Vega, MA, 2004
)
0.32
" Here, we demonstrated that VPA combined with ZOL revealed the synergistic effect in enhancing antitumor efficacy of γδ T cells against osteosarcoma cells."( Valproic Acid Combined with Zoledronate Enhance γδ T Cell-Mediated Cytotoxicity against Osteosarcoma Cells
Li, B; Li, H; Lin, N; Lin, P; Sun, L; Teng, W; Wang, S; Wang, Z; Xue, D; Ye, C; Ye, Z; Zhang, W; Zhou, X, 2018
)
0.48
" In this study, atmospheric and room temperature plasma (ARTP) mutagenesis, in combination with adaptive laboratory evolution (ALE), is used to generate a mutant with high methanol tolerance (referred to as CLY-2533)."( Breeding of Methanol-Tolerant Methylobacterium extorquens AM1 by Atmospheric and Room Temperature Plasma Mutagenesis Combined With Adaptive Laboratory Evolution.
Cui, LY; Guan, CG; Liang, WF; Wang, SS; Xing, XH; Xue, ZL; Zhang, C, 2018
)
0.48

Bioavailability

ExcerptReferenceRelevance
" The enhancement was not due to increased bioavailability because cellular uptake of [3H]tamoxifen was not increased and the lipoprotein fraction of serum had negligible [3H]tamoxifen-binding capacity."( Cytostatic effect of antiestrogens in lymphoid cells: relationship to high affinity antiestrogen-binding sites and cholesterol.
Kon, OL; Ng, ML; Sim, KY; Tang, BL; Teo, CC, 1989
)
0.28
" Orally administered tracer doses of phytol-U-(14)C were well absorbed both by seven normal control subjects (61 to 94%) and by two patients with Refsum's disease (74 and 80%)."( Studies on the metabolic error in Refsum's disease.
Avigan, J; Eldjarn, L; Fales, HM; Mize, CE; Refsum, S; Steinberg, D; Stokke, O; Try, K, 1967
)
0.25
"Atherogenic levels of native low density lipoproteins (nLDLs) decrease the bioavailability of endothelium-derived NO and downregulate endothelial NO synthase (eNOS) expression in cultured human endothelial cells."( 3-hydroxy-3-methylglutaryl coenzyme a reductase inhibition prevents endothelial NO synthase downregulation by atherogenic levels of native LDLs: balance between transcriptional and posttranscriptional regulation.
Badimon, L; Martínez-González, J; Raposo, B; Rodríguez, C, 2001
)
0.31
" Although improvement in NO bioavailability has been attributed to the lowering of serum cholesterol levels, recent studies suggest that HMG-CoA reductase inhibitors, statins, may have direct effects on NO bioavailability by little known mechanisms that are independent of serum cholesterol levels."( Cerivastatin potentiates nitric oxide release and enos expression through inhibition of isoprenoids synthesis.
Dobrucki, IT; Kalinowski, L; Malinski, T, 2002
)
0.31
" Some of the activity associated with bisphosphonates is observed in non-osteoclast cells; therefore, the bioavailability of bisphosphonates is briefly discussed."( The molecular basis of bisphosphonate activity: a preclinical perspective.
Clézardin, P; Green, J, 2010
)
0.36
" These critical steps are responsible for reducing NADPH-oxidase activity and improving tetrahydrobiopterin bioavailability and nitric oxide synthase (NOS) coupling in human vessels."( Translating the effects of statins: from redox regulation to suppression of vascular wall inflammation.
Antoniades, C; Antonopoulos, AS; Margaritis, M; Shirodaria, C, 2012
)
0.38
" However, the disturbance of this pathway paralleled by increased bioavailability of its products and their direct involvement in several steps of tumorigenesis has highlighted the mevalonate pathway as a promising hub in cancer treatment."( The mevalonate pathway in breast cancer biology.
Göbel, A; Hofbauer, LC; Rachner, TD; Riffel, RM, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" Patients were treated with progressively increasing doses of simvastatin (20, 40, and 80 mg day-1) taken in a twice-daily dosage for a period of 6 weeks on each dose."( The effects of simvastatin on plasma lipoproteins and cholesterol homeostasis in patients with heterozygous familial hypercholesterolaemia.
Hagemenas, FC; Illingworth, DR; Pappu, AS, 1990
)
0.28
" The dosage of MV-GABA which caused locomotor hypoactivity produced an impairment of the rotarod performance."( [Behavioral pharmacological action of Ca-4-(3,5-dihydroxy-3-methylpenthylamido) butyrate (mevalonic GABA, MV-GABA)].
Kameyama, T; Nabeshima, T; Noda, Y, 1987
)
0.27
"Steroidogenesis was investigated in Leydig cell-enriched fractions isolated from the testes of rats dosed dermally with 130 mg/kg/day hexafluoroacetone (HFA) for 14 days and from pair-fed control rats."( Effects of hexafluoroacetone on Leydig cell steroidogenesis and spermatogenesis in the rat.
Gillies, PJ; Lee, KP, 1985
)
0.27
" The effects of cholestyramine rapidly disappeared when it was withdrawn from the diet, while the effects of gemfibrozil persisted after dosage was stopped."( Some comparative effects of gemfibrozil, clofibrate, bezafibrate, cholestyramine and compactin on sterol metabolism in rats.
Maxwell, RE; Nawrocki, JW; Uhlendorf, PD, 1983
)
0.27
" at a level corresponding to the human dosage of 1-2 mg/kg/day."( Reduction of mouse mammary tumor formation and metastasis by lovastatin, an inhibitor of the mevalonate pathway of cholesterol synthesis.
Alonso, DF; De Lorenzo, MS; Farina, HG; Gabri, MR; Gomez, DE; Skilton, G, 1998
)
0.3
", the use of intermittent dosing rather than continuous), intravenous vs."( Bisphosphonates: from the laboratory to the clinic and back again.
Rogers, MJ; Russell, RG, 1999
)
0.3
" LDL cholesterol levels were reduced by 17% at the 40 mg/day and by 28% at the 80 mg/day dosage (P<0."( Inhibition of cholesterol synthesis by atorvastatin in homozygous familial hypercholesterolaemia.
Black, DM; Firth, JC; Heinonen, TM; Illingworth, DR; Kotze, MJ; Marais, AD; Pappu, AS; Pilcher, GJ; Raal, FJ, 2000
)
0.31
" 3) INC induced Cbfa1-nuclear localization within hours; and in an in vivo experiment using ovariectomized mice, its 3 weeks dosing exhibited the same effect in tibial extracts."( Incadronate and etidronate accelerate phosphate-primed mineralization of MC4 cells via ERK1/2-Cbfa1 signaling pathway in a Ras-independent manner: further involvement of mevalonate-pathway blockade for incadronate.
Fujita, T; Fukuyama, R; Izumo, N; Koida, M; Meguro, T; Nakamuta, H; Yasutomi, C, 2001
)
0.31
" No consistent effect of vitamin A deficiency or of vitamin A dosage on the incorporation of mevalonate into cholesterol or squalene was found."( VITAMIN A AND ISOPRENOID SYNTHESIS IN THE RAT.
BUNYAN, J; DIPLOCK, AT; GREEN, J, 1965
)
0.24
" Neonatal mortality has been observed following PFOS exposure in a two-generation reproduction study in rats and after dosing pregnant rats and mice during gestation."( Neonatal mortality from in utero exposure to perfluorooctanesulfonate (PFOS) in Sprague-Dawley rats: dose-response, and biochemical and pharamacokinetic parameters.
Butenhoff, JL; Hansen, KJ; Luebker, DJ; Moore, JA; York, RG, 2005
)
0.33
"To examine in a major cohort of patients whether or not musculoskeletal adverse effects (MAEs), similar to those seen in intravenous bisphosphonates (BP), might occur also in high dosage oral treatment regimens with alendronate (ALN) and risedronate (RSN)."( Common musculoskeletal adverse effects of oral treatment with once weekly alendronate and risedronate in patients with osteoporosis and ways for their prevention.
Bock, O; Boerst, H; Degner, C; Felsenberg, D; Stephan-Oelkers, M; Thomasius, FE; Valentine, SM,
)
0.13
" They are observed exclusively in patients starting ALN or RSN treatment with once weekly dosage regimens."( Common musculoskeletal adverse effects of oral treatment with once weekly alendronate and risedronate in patients with osteoporosis and ways for their prevention.
Bock, O; Boerst, H; Degner, C; Felsenberg, D; Stephan-Oelkers, M; Thomasius, FE; Valentine, SM,
)
0.13
" Estimations were done at predose on day 1 of dosing (baseline) and 24 h postdose after days 7 and 14."( The effects of rosuvastatin on the serum cortisol, serum lipid, and serum mevalonic acid levels in the healthy Indian male population.
Pillai, KK; Saini, GS; Samad, A; Sharma, PL; Tandon, M; Wani, TA, 2010
)
0.36
" We characterized the PK/PD model of plasma mevalonic acid (MVA) profiles after rosuvastatin administration and simulated the plasma MVA concentration in various dosage regimens."( Pharmacokinetic/pharmacodynamic modeling and simulation of rosuvastatin using an extension of the indirect response model by incorporating a circadian rhythm.
Aoyama, T; Fukuda, N; Matsumoto, Y; Omori, T; Shioya, A; Ueno, T; Watabe, S, 2010
)
0.36
" This microstructural disorder exhibited a strong dependence on both the dosage and the duration of treatment, indicating a possibility to assess the severity of muscle injury according to the altered length of the sarcomeres."( Imaging of zebrafish in vivo with second-harmonic generation reveals shortened sarcomeres associated with myopathy induced by statin.
Chang, CJ; Chow, CY; Hsiao, CD; Huang, SH; Liau, I; Lin, DS, 2011
)
0.37
"Farnesol pretreatment decreased infarct size in a U-shaped dose-response manner where 1 mg/kg/day dose reached a statistically significant reduction (22."( Cardioprotection by farnesol: role of the mevalonate pathway.
Csonka, C; Csont, T; Ferdinandy, P; Görbe, A; Kocsis, GF; Murlasits, Z; Pálóczi, J; Szűcs, G; Török, S, 2013
)
0.39
" Taken together, our work indicates that Zol, a drug already widely used to prevent osteoporosis and dosed only once a year, modulates important mechanisms of aging."( Zoledronate Extends Health Span and Survival via the Mevalonate Pathway in a FOXO-dependent Manner.
Alqarni, AM; Bellantuono, I; Chen, Z; Cordero, J; Slack, C; Zeidler, MP, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
3,5-dihydroxy-3-methylpentanoic acidA dihydroxy monocarboxylic acid comprising valeric acid having two hydroxy groups at the 3- and 5-positions together with a methyl group at the 3-position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (9)

PathwayProteinsCompounds
Steroids metabolism ( Steroids metabolism )1627
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways039
Mevalonate Pathway1126
Cholesterol synthesis disorders015
Ergosterol biosynthesis332
Biochemical pathways: part I0466
Ferroptosis133
Glycosylation and related congenital defects2426
Sterols biosynthesis pathway015

Bioassays (1)

Assay IDTitleYearJournalArticle
AID679719TP_TRANSPORTER: uptake of Mevalonic acid at a concentration of 67uM in MCT1-expressing MDA-MB231 cells1999The Journal of pharmacy and pharmacology, Oct, Volume: 51, Issue:10
Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (3,728)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901419 (38.06)18.7374
1990's653 (17.52)18.2507
2000's670 (17.97)29.6817
2010's757 (20.31)24.3611
2020's229 (6.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials33 (0.87%)5.53%
Reviews332 (8.71%)6.00%
Case Studies32 (0.84%)4.05%
Observational1 (0.03%)0.25%
Other3,412 (89.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]