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Merck

PHR1438

Simvastatin

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

Simvastatin

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1 G

CZK 2,541.50

CZK 2,541.50

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About This Item

Empirical Formula (Hill Notation):
C25H38O5
CAS Number:
Molecular Weight:
418.57
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:

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Product Name

Simvastatin, Pharmaceutical Secondary Standard; Certified Reference Material

InChI

1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

SMILES string

[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)C(C)(C)CC

InChI key

RYMZZMVNJRMUDD-HGQWONQESA-N

grade

certified reference material
pharmaceutical secondary standard

agency

traceable to Ph. Eur. S0650000
traceable to USP 1612700

API family

simvastatin

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

127-132 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

-10 to -25°C

Quality Level

Gene Information

human ... HMGCR(3156)

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1 of 4

This Item
S06500001612700BP739
application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical
pharmaceutical small molecule

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

format

neat

format

neat

format

neat

format

neat

Quality Level

300

Quality Level

-

Quality Level

-

Quality Level

-

grade

certified reference material, pharmaceutical secondary standard

grade

pharmaceutical primary standard

grade

pharmaceutical primary standard

grade

pharmaceutical primary standard

storage temp.

-10 to -25°C

storage temp.

-

storage temp.

-

storage temp.

−20°C

Analysis Note

These secondary standards offer multi-traceability to the USP and EP primary standards, where they are available.

Application

Simvastatin may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques.[1][2][3]
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Biochem/physiol Actions

Simvastatin is a specific inhibitor of HMG-CoA reductase and cholesterol lowering drug.
Simvastatin is a specific inhibitor of HMG-CoA reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonate, an early step in cholesterol biosynthesis. It is used in the treatment of hypercholesterolemia, as it reduces levels of low-density lipoproteins and triglycerides, and raises high-density lipoprotein levels. Simvastatin is a lactone that is readily hydrolyzed in vivo to the corresponding β-hydroxyacid, and can be activated prior to use with NaOH in EtOH treatment. It is a synthetic analog of lovastatin (Cat. No. M2147).

General description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to in-house working standards.
Simvastatin is a hypolipidemic drug, which lowers plasma cholesterol by inhibiting 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) reductase. It is widely used in the treatment of hypercholesterolemia.[4]

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
To see an example of a Certificate of Analysis for this material enter LRAB3719 in the slot below. This is an example certificate only and may not be the lot that you receive.

pictograms

Health hazard

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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HPLC determination of ezetimibe and simvastatin in pharmaceutical formulations.
Ashfaq M, et al.
Journal of the Chilean Chemical Society, 52(3), 1220-1223 (2007)
Development of self-microemulsifying drug delivery systems (SMEDDS) for oral bioavailability enhancement of simvastatin in beagle dogs.
Kang BK, et al.
International Journal of Pharmaceutics, 274(1-2), 65-73 (2004)
Determination of lovastatin and simvastatin in pharmaceutical dosage forms by MEKC.
Srinivasu MK, et al.
Journal of Pharmaceutical and Biomedical Analysis, 29(4), 715-721 (2002)
Simultaneous determination of ezetimibe and simvastatin in pharmaceutical formulations by dual-mode gradient LC.
Ozalt?n N & Ucakturk E
Chromatographia, 66(1), 87-91 (2007)
Joost Besseling et al.
JAMA, 313(10), 1029-1036 (2015-03-11)
Familial hypercholesterolemia is characterized by impaired uptake of cholesterol in peripheral tissues, including the liver and the pancreas. In contrast, statins increase the cellular cholesterol uptake and are associated with increased risk for type 2 diabetes mellitus. We hypothesize that

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. What is Product PHR1438, Simvastatin, soluble in? And how to keep the stock solution?

    1 answer
    1. This product can be prepared by dissolving 50 mg in 1 ml in ethanol plus 0.813 ml of 1N NaOH. Solutions are stable for at least 1 month at -20°C. Prior to use, adjust the pH to 7.2 by adding 1N HCl, dropwise. Neutralized solutions should be used immediately. Simvastatin is also soluble at >20 mg/mL in DMSO. Long term solution stability in DMSO has not been determined. See the links below for other Simvastatin products that provide additional helpful information in addition to use as an analytical standard.

      567020
      https://www.sigmaaldrich.com/product/mm/567020

      S6196
      https://www.sigmaaldrich.com/product/sigma/s6196

      567022
      https://www.sigmaaldrich.com/product/mm/567022

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