Lovastatin | CAS#75330-75-5

MedKoo Cat#: 318168 | Name: Lovastatin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lovastatin inhibits HMGCR, blocking the enzyme-catalyzed transformation of 3-hydroxy-3-methylglutaryl CoA into mevalonate. Lovastatin is a statin natural product isolated from numerous sources including the Pleurotus ostreatus oyster mushroom, demonstrating hypocholesterolemic and antiproliferative properties. The biosynthesis of cholesterol requires mevalonate as a building block and elimination of mevalonate generation subsequently interrupts cholesterol synthesis, leading to a reduction of circulating low-density lipoproteins. Lovastatin demonstrates arrest of the cell cycle at the G1 phase in bladder carcinoma T24 cells.

Chemical Structure

Lovastatin

CAS#75330-75-5

Theoretical Analysis

MedKoo Cat#: 318168

Name: Lovastatin

CAS#: 75330-75-5

Chemical Formula: C24H36O5

Exact Mass: 404.2563

Molecular Weight: 404.54

Elemental Analysis: C, 71.26; H, 8.97; O, 19.77

Price and Availability

Size	Price	Availability
1g	USD 90.00	Ready to ship
2g	USD 150.00	Ready to Ship
5g	USD 350.00	2 Weeks
10g	USD 480.00	2 Weeks
25g	USD 750.00	2 Weeks

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Related CAS #

75225-50-2 (sodium) 75330-75-5

Synonym

Lovastatin; Mevinolin; Mevacor; Monacolin K; Altoprev; MK 803; MK-803; MK803; Monacolin K;

IUPAC/Chemical 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

InChi Key

PCZOHLXUXFIOCF-UHFFFAOYSA-N

InChi Code

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

SMILES Code

CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TCI60919

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

In vitro activity:

MTT assay was employed to determine whether FaDu cell viability is altered in the presence of lovastatin. As shown in Fig. 1a, lovastatin concentration-dependently decreased FaDu cell viability after 24 h exposure. Longer exposure to lovastatin (48 h) further decreased FaDu cell viability (Fig. 1a). To determine whether lovastatin-decreased FaDu cell viability was a result of cell cycle arrest or apoptosis, flowcytometry was used. As shown in Fig. 1b, the percentage of propidium iodide (PI)-stained cells in the S region was significantly decreased in FaDu cells after exposure to lovastatin for 24 h. In addition, lovastatin increased the percentage of PI-stained cells in the G0/G1 region (Fig. 1b). Moreover, 24 h treatment of lovastatin only slightly induced cell apoptosis (sub-G1 region) (Fig. 1b). However, lovastatin significantly induced apoptosis in FaDu cells after 48 h exposure of lovastatin (Fig. 1c). To detect apoptosis in FaDu cells exposed to lovastatin, flowcytometry with PI and annexin V-FITC double-labeling was also employed. As shown in Fig. 1d, lovastatin increased the percentage of early apoptotic cells (annexin V+PI− cells) and advanced apoptotic cells and/or necrotic cells (annexin V+PI+ cells) after 48 h exposure. It was next determined whether lovastatin activates caspase 3. As shown in Fig. 1e, lovastatin increased the cleaved (active) form of caspase 3 and PARP, a selective caspase 3 substrate. These findings suggest that lovastatin induced apoptosis and inhibited cell proliferation in FaDu cells. Sci Rep. 2016; 6: 25082. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4848532/

In vivo activity:

To determine the effect of LOV administered prior to viral (DENV-2-infected) inoculation (pre-treatment), groups of six mice were treated with a single dose (24 hrs) or three doses (72, 48 and 24 hrs) before inoculation with DENV-2 (Figure 1). Moreover, three different types of control groups were used (See Materials and Methods section). In the group pre-treated with three LOV doses, there was a significant 21.8% reduction in viremia compared to the control group without LOV (p<0.001) (Table 1). Viremia was not significantly reduced in mice treated with a single LOV dose (reduction of 3.0%) (Figure 3A). In the groups treated with one or three LOV doses, weight loss was reduced compared to the control group without LOV (18.6% and 15.1%, respectively, compared to 24.0%) (Figure 3B). Based on Kaplan-Meier analyses, significant increase of survival in the groups treated with one or three doses compared to the control group without LOV (p<0.05) was found. This result is consistent with the average survival rates, which significantly increased (p<0.001) in the groups treated with one or three doses compared to the control group without LOV (7.33±1.0 and 7.17±0.9 days, respectively, versus 4.8±1.6 days) (Figure 3C–D). The LOV treatment alone did not affect the weight or survival time of treated mice in the control group. However, despite the reductions in viremia and weight loss and the increased survival rate observed following LOV treatment, some animals in this experimental group (pre-treatment) developed severe paralysis and were sacrificed by CO2 asphyxiation the moment these signs started to develop.These results suggest that the effect of LOV on viremia depends on the timing of treatment and on the number of doses administered. PLoS One. 2014; 9(2): e87412. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931612/

	Solvent	mg/mL	mM
Solubility
	DMSO	60.0	148.32
	Ethanol	25.0	61.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 404.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yen CS, Chen JC, Chang YF, Hsu YF, Chiu PT, Shiue C, Chuang YF, Ou G, Hsu MJ. Lovastatin causes FaDu hypopharyngeal carcinoma cell death via AMPK-p63-survivin signaling cascade. Sci Rep. 2016 Apr 28;6:25082. doi: 10.1038/srep25082. PMID: 27122225; PMCID: PMC4848532. 2. Terada Y, Inoshita S, Nakashima O, Yamada T, Kuwahara M, Sasaki S, Marumo F. Lovastatin inhibits mesangial cell proliferation via p27Kip1. J Am Soc Nephrol. 1998 Dec;9(12):2235-43. doi: 10.1681/ASN.V9122235. PMID: 9848777. 3. Fernandez K, Spielbauer KK, Rusheen A, Wang L, Baker TG, Eyles S, Cunningham LL. Lovastatin protects against cisplatininduced hearing loss in mice. Hear Res. 2020 Apr;389:107905. doi: 10.1016/j.heares.2020.107905. Epub 2020 Feb 6. PMID: 32062294; PMCID: PMC7080598. 4. Martinez-Gutierrez M, Correa-Londoño LA, Castellanos JE, Gallego-Gómez JC, Osorio JE. Lovastatin delays infection and increases survival rates in AG129 mice infected with dengue virus serotype 2. PLoS One. 2014 Feb 21;9(2):e87412. doi: 10.1371/journal.pone.0087412. PMID: 24586275; PMCID: PMC3931612.

In vitro protocol:

In vivo protocol:

1. Fernandez K, Spielbauer KK, Rusheen A, Wang L, Baker TG, Eyles S, Cunningham LL. Lovastatin protects against cisplatininduced hearing loss in mice. Hear Res. 2020 Apr;389:107905. doi: 10.1016/j.heares.2020.107905. Epub 2020 Feb 6. PMID: 32062294; PMCID: PMC7080598. 2. Martinez-Gutierrez M, Correa-Londoño LA, Castellanos JE, Gallego-Gómez JC, Osorio JE. Lovastatin delays infection and increases survival rates in AG129 mice infected with dengue virus serotype 2. PLoS One. 2014 Feb 21;9(2):e87412. doi: 10.1371/journal.pone.0087412. PMID: 24586275; PMCID: PMC3931612.

1: Zhao Q, Li M, Chen M, Zhou L, Zhao L, Hu R, Yan R, Dai K. Lovastatin induces platelet apoptosis. Environ Toxicol Pharmacol. 2016 Mar;42:69-75. doi: 10.1016/j.etap.2016.01.002. Epub 2016 Jan 4. PubMed PMID: 26773364. 2: Zhao N, Dong Q, Qian C, Li S, Wu QF, Ding D, Li J, Wang BB, Guo KF, Xie JJ, Cheng X, Liao YH, Du YM. Corrigendum: Lovastatin blocks Kv1.3 channel in human T cells: a new mechanism to explain its immunomodulatory properties. Sci Rep. 2016 Mar 10;6:21655. doi: 10.1038/srep21655. PubMed PMID: 26961979; PubMed Central PMCID: PMC4785556. 3: Walther U, Emmrich K, Ramer R, Mittag N, Hinz B. Lovastatin lactone elicits human lung cancer cell apoptosis via a COX-2/PPARγ-dependent pathway. Oncotarget. 2016 Feb 5. doi: 10.18632/oncotarget.7213. [Epub ahead of print] PubMed PMID: 26863638. 4: Krüger K, Ziegler V, Hartmann C, Henninger C, Thomale J, Schupp N, Fritz G. Lovastatin prevents cisplatin-induced activation of pro-apoptotic DNA damage response (DDR) of renal tubular epithelial cells. Toxicol Appl Pharmacol. 2016 Feb 1;292:103-14. doi: 10.1016/j.taap.2015.12.023. Epub 2015 Dec 29. PubMed PMID: 26739623. 5: Lin CH, Lin HI, Chen ML, Lai TT, Cao LP, Farrer MJ, Wu RM, Chien CT. Lovastatin protects neurite degeneration in LRRK2-G2019S parkinsonism through activating the Akt/Nrf pathway and inhibiting GSK3β activity. Hum Mol Genet. 2016 Feb 29. pii: ddw068. [Epub ahead of print] PubMed PMID: 26931464. 6: Ziegler V, Albers A, Fritz G. Lovastatin protects keratinocytes from DNA damage-related pro-apoptotic stress responses stimulated by anticancer therapeutics. Biochim Biophys Acta. 2016 Feb 12. pii: S0167-4889(16)30025-8. doi: 10.1016/j.bbamcr.2016.02.009. [Epub ahead of print] PubMed PMID: 26876155. 7: Riekes MK, Engelen A, Appeltans B, Rombaut P, Stulzer HK, Van den Mooter G. New Perspectives for Fixed Dose Combinations of Poorly Water-Soluble Compounds: a Case Study with Ezetimibe and Lovastatin. Pharm Res. 2016 Feb 8. [Epub ahead of print] PubMed PMID: 26857899. 8: Whitehorn J, Nguyen CV, Khanh LP, Kien DT, Quyen NT, Tran NT, Hang NT, Truong NT, Hue Tai LT, Cam Huong NT, Nhon VT, Van Tram T, Farrar J, Wolbers M, Simmons CP, Wills B. Lovastatin for the Treatment of Adult Patients With Dengue: A Randomized, Double-Blind, Placebo-Controlled Trial. Clin Infect Dis. 2016 Feb 15;62(4):468-76. doi: 10.1093/cid/civ949. Epub 2015 Nov 12. PubMed PMID: 26565005; PubMed Central PMCID: PMC4725386. 9: Yang SH, Lin HY, Changou CA, Chen CH, Liu YR, Wang J, Jiang X, Luh F, Yen Y. Integrin β3 and LKB1 are independently involved in the inhibition of proliferation by lovastatin in human intrahepatic cholangiocarcinoma. Oncotarget. 2016 Jan 5;7(1):362-73. doi: 10.18632/oncotarget.6238. PubMed PMID: 26517522. 10: Lee BS, Lee CC, Wang YP, Chen HJ, Lai CH, Hsieh WL, Chen YW. Controlled-release of tetracycline and lovastatin by poly(d,l-lactide-co-glycolide acid)-chitosan nanoparticles enhances periodontal regeneration in dogs. Int J Nanomedicine. 2016 Jan 18;11:285-97. doi: 10.2147/IJN.S94270. eCollection 2016. PubMed PMID: 26848264; PubMed Central PMCID: PMC4723100. 11: Yang T, Yao H, He G, Song L, Liu N, Wang Y, Yang Y, Keller ET, Deng X. Effects of Lovastatin on MDA-MB-231 Breast Cancer Cells: An Antibody Microarray Analysis. J Cancer. 2016 Jan 1;7(2):192-9. doi: 10.7150/jca.13414. eCollection 2016. PubMed PMID: 26819643; PubMed Central PMCID: PMC4716852. 12: Cacho RA, Thuss J, Xu W, Sanichar R, Gao Z, Nguyen A, Vederas JC, Tang Y. Understanding Programming of Fungal Iterative Polyketide Synthases: The Biochemical Basis for Regioselectivity by the Methyltransferase Domain in the Lovastatin Megasynthase. J Am Chem Soc. 2015 Dec 23;137(50):15688-91. doi: 10.1021/jacs.5b11814. Epub 2015 Dec 10. PubMed PMID: 26630357. 13: Chen CC, Liu TY, Huang SP, Ho CT, Huang TC. Differentiation and apoptosis induction by lovastatin and γ-tocotrienol in HL-60 cells via Ras/ERK/NF-κB and Ras/Akt/NF-κB signaling dependent down-regulation of glyoxalase 1 and HMG-CoA reductase. Cell Signal. 2015 Nov;27(11):2182-90. doi: 10.1016/j.cellsig.2015.07.014. Epub 2015 Jul 21. PubMed PMID: 26208883. 14: Chen CB, Chen J, Wang J, Zhu YY, Shi JH. Combined spectroscopic and molecular docking approach to probing binding interactions between lovastatin and calf thymus DNA. Luminescence. 2015 Nov;30(7):1004-10. doi: 10.1002/bio.2851. Epub 2015 Feb 1. PubMed PMID: 25640921. 15: Zhao N, Dong Q, Qian C, Li S, Wu QF, Ding D, Li J, Wang BB, Guo KF, Xie JJ, Cheng X, Liao YH, Du YM. Lovastatin blocks Kv1.3 channel in human T cells: a new mechanism to explain its immunomodulatory properties. Sci Rep. 2015 Nov 30;5:17381. doi: 10.1038/srep17381. PubMed PMID: 26616555; PubMed Central PMCID: PMC4663632. 16: Mulder KC, Mulinari F, Franco OL, Soares MS, Magalhães BS, Parachin NS. Lovastatin production: From molecular basis to industrial process optimization. Biotechnol Adv. 2015 Nov 1;33(6 Pt 1):648-65. doi: 10.1016/j.biotechadv.2015.04.001. Epub 2015 Apr 11. Review. PubMed PMID: 25868803. 17: Dikshit R, Tallapragada P. Bio-synthesis and screening of nutrients for lovastatin by Monascus sp. under solid-state fermentation. J Food Sci Technol. 2015 Oct;52(10):6679-86. doi: 10.1007/s13197-014-1678-y. Epub 2015 Feb 11. PubMed PMID: 26396416; PubMed Central PMCID: PMC4573169. 18: Guimarães MR, Murad LB, Paganelli A, de Oliveira CA, Vianna LM. Effects of alpha-tocopherol associated with lovastatin on brain tissue and memory function in SHRSPs. Physiol Behav. 2015 Oct 1;149:303-9. doi: 10.1016/j.physbeh.2015.06.025. Epub 2015 Jun 19. PubMed PMID: 26095118. 19: He H, Zhang M, Liu L, Zhang S, Liu J, Zhang W. Suppression of Remodeling Behaviors with Arachidonic Acid Modification for Enhanced in vivo Antiatherogenic Efficacies of Lovastatin-loaded Discoidal Recombinant High Density Lipoprotein. Pharm Res. 2015 Oct;32(10):3415-31. doi: 10.1007/s11095-015-1719-x. Epub 2015 Jun 4. PubMed PMID: 26040661. 20: Kuzma-Kuzniarska M, Cornell HR, Moneke MC, Carr AJ, Hulley PA. Lovastatin-Mediated Changes in Human Tendon Cells. J Cell Physiol. 2015 Oct;230(10):2543-51. doi: 10.1002/jcp.25010. PubMed PMID: 25846724.