Rosuvastatin lactone
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Hodoodo CAT#: H464675

CAS#: 503610-43-3

Description: Rosuvastatin lactone is the lactone form of the HMG-CoA reductase inhibitor rosuvastatin. It is found in vivo following rosuvastatin administration. Rosuvastatin lactone is an inhibitor of the cytochrome P450 (CYP) isoforms CYP2C9.1 and CYP2C9.3 (IC50s = 8.52 and 4.1 µM, respectively).

Chemical Structure

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Rosuvastatin lactone
CAS# 503610-43-3
Instruction

Theoretical Analysis

Hodoodo Cat#: H464675
Name: Rosuvastatin lactone
CAS#: 503610-43-3
Chemical Formula: C22H26FN3O5S
Exact Mass: 463.16
Molecular Weight: 463.520
Elemental Analysis: C, 57.01; H, 5.65; F, 4.10; N, 9.07; O, 17.26; S, 6.92

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 Weeks
25mg USD 650 2 Weeks
50mg USD 950 2 Weeks
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Synonym: Rosuvastatin lactone; (+)-Rosuvastatin lactone; (+) Rosuvastatin lactone; Rosuvastatin-5S-lactone; RSTL;

IUPAC/Chemical Name: N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

InChi Key: SOEGVMSNJOCVHT-VEUZHWNKSA-N

InChi Code: InChI=1S/C22H26FN3O5S/c1-13(2)20-18(10-9-17-11-16(27)12-19(28)31-17)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)32(4,29)30/h5-10,13,16-17,27H,11-12H2,1-4H3/b10-9+/t16-,17-/m1/s1

SMILES Code: O[C@H]1CC(O[C@H](/C=C/C2=C(N=C(N=C2C3=CC=C(F)C=C3)N(S(C)(=O)=O)C)C(C)C)C1)=O

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 64.72
DMSO 15.0 32.36

Preparing Stock Solutions

The following data is based on the product molecular weight 463.52 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:
In vitro protocol:
In vivo protocol:

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1: Bai X, Zhang B, Wang P, Wang GL, Li JL, Wen DS, Long XZ, Sun HS, Liu YB, Huang M, Zhong SL. Effects of SLCO1B1 and GATM gene variants on rosuvastatin- induced myopathy are unrelated to high plasma exposure of rosuvastatin and its metabolites. Acta Pharmacol Sin. 2019 Apr;40(4):492-499. doi: 10.1038/s41401-018-0013-y. Epub 2018 Jun 27. PMID: 29950617; PMCID: PMC6461793.

2: Bai X, Wang XP, He GD, Zhang B, Huang M, Li JL, Zhong SL. Simultaneous Determination of Rosuvastatin, Rosuvastatin-5 S-lactone, and N-desmethyl Rosuvastatin in Human Plasma by UPLC-MS/MS and Its Application to Clinical Study. Drug Res (Stuttg). 2018 Jun;68(6):328-334. doi: 10.1055/s-0043-123576. Epub 2017 Dec 12. PMID: 29232752.

3: Merlier F, Jellali R, Leclerc E. Online monitoring of hepatic rat metabolism by coupling a liver biochip and a mass spectrometer. Analyst. 2017 Sep 25;142(19):3747-3757. doi: 10.1039/c7an00973a. PMID: 28891561.

4: Huguet J, Lu J, Gaudette F, Chiasson JL, Hamet P, Michaud V, Turgeon J. No effects of pantoprazole on the pharmacokinetics of rosuvastatin in healthy subjects. Eur J Clin Pharmacol. 2016 Aug;72(8):925-31. doi: 10.1007/s00228-016-2065-6. Epub 2016 May 5. PMID: 27146814.

5: Birmingham BK, Bujac SR, Elsby R, Azumaya CT, Zalikowski J, Chen Y, Kim K, Ambrose HJ. Rosuvastatin pharmacokinetics and pharmacogenetics in Caucasian and Asian subjects residing in the United States. Eur J Clin Pharmacol. 2015 Mar;71(3):329-40. doi: 10.1007/s00228-014-1800-0. Epub 2015 Jan 30. PMID: 25630984.

6: Ana Cecilia PP, Victor Manuel PA, Isabel WF, Enrique CH, Pedro LS, Jorge Skiold LC, Maria del Carmen CH, Carlos CH. Mechanism of the relaxant effect of rosuvastatin lactone on rat aortic rings. Front Biosci (Elite Ed). 2012 Jan 1;4:1787-94. doi: 10.2741/499. PMID: 22201994.

7: Macwan JS, Ionita IA, Akhlaghi F. A simple assay for the simultaneous determination of rosuvastatin acid, rosuvastatin-5S-lactone, and N-desmethyl rosuvastatin in human plasma using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Anal Bioanal Chem. 2012 Jan;402(3):1217-27. doi: 10.1007/s00216-011-5548-4. Epub 2011 Nov 23. PMID: 22108655.

8: Casar Z, Steinbücher M, Kosmrlj J. Lactone pathway to statins utilizing the Wittig reaction. The synthesis of rosuvastatin. J Org Chem. 2010 Oct 1;75(19):6681-4. doi: 10.1021/jo101050z. PMID: 20815370.

9: Li XN, Xu HR, Chen WL, Chu NN, Zhu JR. Pharmacokinetics of rosuvastatin in healthy Chinese volunteers living in China: a randomized, open-label, ascending single- and multiple-dose study. Clin Ther. 2010 Mar;32(3):575-87. doi: 10.1016/j.clinthera.2010.03.015. PMID: 20399994.

10: Lee HB, Peart TE, Svoboda ML, Backus S. Occurrence and fate of rosuvastatin, rosuvastatin lactone, and atorvastatin in Canadian sewage and surface water samples. Chemosphere. 2009 Nov;77(10):1285-91. doi: 10.1016/j.chemosphere.2009.09.068. Epub 2009 Oct 27. PMID: 19863993.

11: Choi JH, Lee MG, Cho JY, Lee JE, Kim KH, Park K. Influence of OATP1B1 genotype on the pharmacokinetics of rosuvastatin in Koreans. Clin Pharmacol Ther. 2008 Feb;83(2):251-7. doi: 10.1038/sj.clpt.6100267. Epub 2007 Jun 13. PMID: 17568401.

12: Lee E, Ryan S, Birmingham B, Zalikowski J, March R, Ambrose H, Moore R, Lee C, Chen Y, Schneck D. Rosuvastatin pharmacokinetics and pharmacogenetics in white and Asian subjects residing in the same environment. Clin Pharmacol Ther. 2005 Oct;78(4):330-41. doi: 10.1016/j.clpt.2005.06.013. PMID: 16198652.

13: Schneck DW, Birmingham BK, Zalikowski JA, Mitchell PD, Wang Y, Martin PD, Lasseter KC, Brown CD, Windass AS, Raza A. The effect of gemfibrozil on the pharmacokinetics of rosuvastatin. Clin Pharmacol Ther. 2004 May;75(5):455-63. doi: 10.1016/j.clpt.2003.12.014. PMID: 15116058.

14: Cooper KJ, Martin PD, Dane AL, Warwick MJ, Schneck DW, Cantarini MV. Effect of itraconazole on the pharmacokinetics of rosuvastatin. Clin Pharmacol Ther. 2003 Apr;73(4):322-9. doi: 10.1016/s0009-9236(02)17633-8. PMID: 12709722.