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MedKoo Cat#: 626663 | Name: Simvastatin ammonium
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Description:

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

Simvastatin, also known as MK-733, is a competitive inhibitor of HMG-CoA reductase. Simvastatin acts by inhibiting 3-hydroxy-3-methylglutaryl (HMG) coenzyme A reductase. HMG-CoA reductase, the rate-limiting enzyme of the HMG-CoA reductase pathway, the metabolic pathway responsible for the endogenous production of cholesterol. Simvastatin suppresses TNF-induced NF-κB activation and potentiates apoptosis in human myeloid leukemia cells. It also inhibits glutathione peroxidase 4 (GPX4) activity, increases malondialdehyde (MDA) levels, and induces ferroptosis in MDA-MB-231 and MCF-7 breast cancer cells.

Chemical Structure

Simvastatin ammonium
Simvastatin ammonium
CAS#139893-43-9 (ammonium)

Theoretical Analysis

MedKoo Cat#: 626663

Name: Simvastatin ammonium

CAS#: 139893-43-9 (ammonium)

Chemical Formula: C25H43NO6

Exact Mass: 0.0000

Molecular Weight: 453.62

Elemental Analysis: C, 66.20; H, 9.56; N, 3.09; O, 21.16

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 weeks
100mg USD 900.00 2 Weeks
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Related CAS #
139893-43-9 (ammonium) 79902-63-9 (free) 101314-97-0 (sodium)
Synonym
Simvastatin ammonium salt; Synvinolin; MK-733; Sinvacor; MK 733; MK-733; MK733;
IUPAC/Chemical Name
Ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
InChi Key
FFPDWNBTEIXJJF-OKDJMAGBSA-N
InChi Code
InChI=1S/C25H40O6.H3N/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29;/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29);1H3/t15-,16-,18+,19+,20-,21-,23-;/m0./s1
SMILES Code
O=C([O-])C[C@H](O)C[C@H](O)CC[C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@H](OC(C(C)(C)CC)=O)[C@]12[H].[NH4+]
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
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
All statins act by inhibiting 3-hydroxy-3-methylglutaryl (HMG) coenzyme A reductase. HMG-CoA reductase, the rate-limiting enzyme of the HMG-CoA reductase pathway, the metabolic pathway responsible for the endogenous production of cholesterol. Statins are more effective than other lipid-regulating drugs at lowering LDL-cholesterol concentration, but they are less effective than the fibrates in reducing triglyceride concentration. However, statins reduce cardiovascular disease events and total mortality irrespective of the initial cholesterol concentration. This is a major piece of evidence that statins work in another way than the lowering of cholesterol (called pleiotropic effects). The drug is in the form of an inactive lactone that is hydrolyzed after ingestion to produce the active agent. It is a white, nonhygroscopic, crystalline powder that is practically insoluble in water, and freely soluble in chloroform, methanol, and ethanol. Simvastatin is an effective serum lipid-lowering drug that can decrease low density lipoprotein (LDL) levels by up to 50%.[citation needed] Simvastatin had been shown to interact with lipid-lowering transcription factor PPAR-alpha[34] and that interaction might control the neurotrophic action of the drug. From https://en.wikipedia.org/wiki/Simvastatin.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Simvastatin is a competitive inhibitor of HMG-CoA reductase with a Ki of 0.2 nM.
In vitro activity:
Simvastatin induced autophagy and inhibited the proliferation of prostate cancer cell lines (PC-3, LNCaP-LA; cultured under androgen-depleted conditions, DU145, 22RV1). Simvastatin demonstrated a significant concentration-dependent growth inhibition effect on cell lines. Reference: Anticancer Res. 2023 Dec;43(12):5377-5386. https://pubmed.ncbi.nlm.nih.gov/38030198/
In vivo activity:
Simvastatin improved the memory deterioration in a mouse model of aluminium chloride (AlCl3) induced neurobehavioral impairments. There was also significant recovery of the histopathological changes. Simvastatin provided its neuroprotective effect by upregulating the protein expression of β-catenin, TGF-β1 and downregulating the expression of GSK3β, TLR4 and p SMAD2. Reference: Environ Toxicol Pharmacol. 2023 Sep;102:104220. https://pubmed.ncbi.nlm.nih.gov/37454825/
Solvent mg/mL mM
Solubility
DMF 1.0 2.20
DMSO 1.0 2.20
Ethanol 1.0 2.20
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 453.62 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.

Recalculate based on batch purity %
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. Miyazawa Y, Sekine Y, Oka D, Nakazawa S, Tsuji Y, Nakayama H, Suzuki K. Simvastatin Induces Autophagy and Inhibits Proliferation in Prostate Cancer Cells. Anticancer Res. 2023 Dec;43(12):5377-5386. doi: 10.21873/anticanres.16741. PMID: 38030198. 2. Tu X, Zhang J, Yuan W, Wu X, Xu Z, Qing C. Simvastatin Enhanced Anti-tumor Effects of Bevacizumab against Lung Adenocarcinoma A549 Cells via Abating HIF-1α-Wnt/β-Catenin Signaling Pathway. Anticancer Agents Med Chem. 2023;23(19):2083-2094. doi: 10.2174/1871520623666230816090914. PMID: 37587804. 3. Atef MM, Mostafa YM, Ahmed AAM, El-Sayed NM. Simvastatin attenuates aluminium chloride-induced neurobehavioral impairments through activation of TGF-β1/ SMAD2 and GSK3β/β-catenin signalling pathways. Environ Toxicol Pharmacol. 2023 Sep;102:104220. doi: 10.1016/j.etap.2023.104220. Epub 2023 Jul 15. PMID: 37454825. 4. Pereira ENGDS, Araujo BP, Rodrigues KL, Silvares RR, Martins CSM, Flores EEI, Fernandes-Santos C, Daliry A. Simvastatin Improves Microcirculatory Function in Nonalcoholic Fatty Liver Disease and Downregulates Oxidative and ALE-RAGE Stress. Nutrients. 2022 Feb 8;14(3):716. doi: 10.3390/nu14030716. PMID: 35277075; PMCID: PMC8838100.
In vitro protocol:
1. Miyazawa Y, Sekine Y, Oka D, Nakazawa S, Tsuji Y, Nakayama H, Suzuki K. Simvastatin Induces Autophagy and Inhibits Proliferation in Prostate Cancer Cells. Anticancer Res. 2023 Dec;43(12):5377-5386. doi: 10.21873/anticanres.16741. PMID: 38030198. 2. Tu X, Zhang J, Yuan W, Wu X, Xu Z, Qing C. Simvastatin Enhanced Anti-tumor Effects of Bevacizumab against Lung Adenocarcinoma A549 Cells via Abating HIF-1α-Wnt/β-Catenin Signaling Pathway. Anticancer Agents Med Chem. 2023;23(19):2083-2094. doi: 10.2174/1871520623666230816090914. PMID: 37587804.
In vivo protocol:
1. Atef MM, Mostafa YM, Ahmed AAM, El-Sayed NM. Simvastatin attenuates aluminium chloride-induced neurobehavioral impairments through activation of TGF-β1/ SMAD2 and GSK3β/β-catenin signalling pathways. Environ Toxicol Pharmacol. 2023 Sep;102:104220. doi: 10.1016/j.etap.2023.104220. Epub 2023 Jul 15. PMID: 37454825. 2. Pereira ENGDS, Araujo BP, Rodrigues KL, Silvares RR, Martins CSM, Flores EEI, Fernandes-Santos C, Daliry A. Simvastatin Improves Microcirculatory Function in Nonalcoholic Fatty Liver Disease and Downregulates Oxidative and ALE-RAGE Stress. Nutrients. 2022 Feb 8;14(3):716. doi: 10.3390/nu14030716. PMID: 35277075; PMCID: PMC8838100.
1: Oliver W, Giugliano RP. Benefit of Combination Ezetimibe/Simvastatin Among High-Risk Populations: Lessons from the IMPROVE-IT Trial. Curr Atheroscler Rep. 2023 Mar;25(3):85-93. doi: 10.1007/s11883-023-01084-4. Epub 2023 Feb 10. PMID: 36763180. 2: Chauhan D, Memon F, Patwardhan V, Kotwani P, Shah P, Samala Venkata V. Comparing Simvastatin Monotherapy V/S Simvastatin-Ezetimibe Combination Therapy for the Treatment of Hyperlipidemia: A Meta-Analysis and Review. Cureus. 2022 Nov 2;14(11):e31007. doi: 10.7759/cureus.31007. PMID: 36475227; PMCID: PMC9717522. 3: Huang M, Prayson RA, Li Y. Genvoya-Associated and Simvastatin-Associated Noninflammatory and Nonautoimmune Myopathy: A Case Report and Literature Review. J Clin Neuromuscul Dis. 2022 Dec 1;24(2):75-79. doi: 10.1097/CND.0000000000000386. PMID: 36409337. 4: Zang H, Yang W, Tian X. Simvastatin in the Treatment of Colorectal Cancer: A Review. Evid Based Complement Alternat Med. 2022 Jul 14;2022:3827933. doi: 10.1155/2022/3827933. PMID: 35873646; PMCID: PMC9303163. 5: Jeffilano BA, Arozal W, Wahyuni UT, Soetikno V, Nafrialdi N. Simvastatin is Independently Improving Uremic Cardiomyopathy Through Intercommunication Between Macrophage and Cardiomyocyte in Renal Failure Model. Eur Cardiol. 2021 Dec 14;16:e62. doi: 10.15420/ecr.2021.16.PO6. PMID: 35106078; PMCID: PMC8785067. 6: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Simvastatin. 2021 Dec 1. PMID: 31644029. 7: Duarte JA, de Barros ALB, Leite EA. The potential use of simvastatin for cancer treatment: A review. Biomed Pharmacother. 2021 Sep;141:111858. doi: 10.1016/j.biopha.2021.111858. Epub 2021 Jul 10. PMID: 34323700. 8: Verma D, Hussain K, Namiq KS, Firoz A, Bouchama M, Raza M, Haris M, Khan S. Vitiligo: The Association With Metabolic Syndrome and the Role of Simvastatin as an Immunomodulator. Cureus. 2021 Mar 22;13(3):e14029. doi: 10.7759/cureus.14029. PMID: 33898117; PMCID: PMC8059484. 9: Jin H, Ji Y, Cui Y, Xu L, Liu H, Wang J. Simvastatin-Incorporated Drug Delivery Systems for Bone Regeneration. ACS Biomater Sci Eng. 2021 Jun 14;7(6):2177-2191. doi: 10.1021/acsbiomaterials.1c00462. Epub 2021 Apr 20. PMID: 33877804. 10: Hasan R, Agarwal K, Podder I, Misitzis A, Schwartz RA, Wollina U, Lotti T, Grabbe S, Goldust M. Simvastatin in vitiligo: an update with recent review of the literature. Int J Dermatol. 2021 Oct;60(10):e390-e396. doi: 10.1111/ijd.15330. Epub 2021 Feb 7. PMID: 33554328. 11: Yang G, Han D, Ma J, Zhang X. Efficacy of Ezetimibe/Simvastatin (10/10 mg) versus High Dose Statin in Dyslipidemia Patients: A Meta-Analysis of Randomized Controlled Trials. Iran J Public Health. 2019 Aug;48(8):1405-1417. PMID: 32292723; PMCID: PMC7145912. 12: Fattah TA, Saeed A, Shehzadi SA. Synthetic Approaches Towards Antihypercholesterolemic Drug Simvastatin. Curr Org Synth. 2019;16(5):652-670. doi: 10.2174/1570179416666190725095951. PMID: 31984887. 13: Gupta S, Del Fabbro M, Chang J. The impact of simvastatin intervention on the healing of bone, soft tissue, and TMJ cartilage in dentistry: a systematic review and meta-analysis. Int J Implant Dent. 2019 Apr 9;5(1):17. doi: 10.1186/s40729-019-0168-4. PMID: 30963362; PMCID: PMC6453984. 14: Han SN, Yang WH, Yin JJ, Tao HL, Zhang LR. Drug Treatment of Hyperlipidemia in Chinese Patients: Focus on the Use of Simvastatin and Ezetimibe Alone and in Combination. Am J Cardiovasc Drugs. 2019 Jun;19(3):237-247. doi: 10.1007/s40256-018-00317-1. PMID: 30714088. 15: de Faria CA, Zanette DL, Silva WA Jr, Ribeiro-Paes JT. PAI-1 inhibition by simvastatin as a positive adjuvant in cell therapy. Mol Biol Rep. 2019 Feb;46(1):1511-1517. doi: 10.1007/s11033-018-4562-4. Epub 2019 Jan 5. PMID: 30612281. 16: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Simvastatin. 2018 Oct 31. PMID: 30000419. 17: McAuley DF, Laffey JG, O’Kane CM, Perkins GD, Mullan B, Trinder TJ, Johnston P, Hopkins PA, Johnston AJ, Murphy L, McNally C, Agus AM, McDowell C, Jackson C. Simvastatin to reduce pulmonary dysfunction in patients with acute respiratory distress syndrome: the HARP-2 RCT. Southampton (UK): NIHR Journals Library; 2018 Jan. PMID: 29400921. 18: Cervantes J, Jimenez JJ, DelCanto GM, Tosti A. Treatment of Alopecia Areata with Simvastatin/Ezetimibe. J Investig Dermatol Symp Proc. 2018 Jan;19(1):S25-S31. doi: 10.1016/j.jisp.2017.10.013. PMID: 29273101. 19: Liu H, Xu X. Effect of simvastatin in patients with aneurysmal subarachnoid hemorrhage: A systematic review and meta-analysis. Am J Emerg Med. 2017 Dec;35(12):1940-1945. doi: 10.1016/j.ajem.2017.09.001. Epub 2017 Sep 5. PMID: 28966073. 20: Bove M, Fogacci F, Cicero AFG. Pharmacokinetic drug evaluation of ezetimibe + simvastatin for the treatment of hypercholesterolemia. Expert Opin Drug Metab Toxicol. 2017 Oct;13(10):1099-1104. doi: 10.1080/17425255.2017.1381085. Epub 2017 Sep 26. PMID: 28922021.