A metabolite of atorvastatin
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4-hydroxy Atorvastatin lactone

Item No. 23358

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(4-fluorophenyl)-N-(4-hydroxyphenyl)-2-(1-methylethyl)-4-phenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide
CAS Number
163217-70-7
Synonyms
  • p-hydroxy Atorvastatin lactone
  • para-hydroxy Atorvastatin lactone
Molecular Formula
C33H33FN2O5
Formula Weight
556.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Slightly soluble
SMILES
O=C(C1=C(C(C)C)N(CC[C@H](C[C@@H](O)C2)OC2=O)C(C3=CC=C(F)C=C3)=C1C4=CC=CC=C4)NC5=CC=C(O)C=C5
InChi Code
InChI=1S/C33H33FN2O5/c1-20(2)31-30(33(40)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-27-18-26(38)19-28(39)41-27/h3-15,20,26-27,37-38H,16-19H2,1-2H3,(H,35,40)/t26-,27-/m1/s1
InChi Key
KDJMDZSAAFACAM-KAYWLYCHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $436

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    Product Description

    4-hydroxy Atorvastatin lactone is a metabolite of atorvastatin (Item No. 10493), an HMG-CoA reductase inhibitor present in formulations that have been used to treat hypercholesterolemia and certain dyslipidemias.1,2,3,4 Atorvastatin is metabolized by the cytochrome P450 (CYP) isoform CYP3A4 to form 4-hydroxy atorvastatin (Item No. 22575) and 2-hydroxy atorvastatin, which can be interconverted between their acid and lactone forms.1 Atorvastatin can itself be lactonized to atorvastatin lactone (Item No. 20951) then metabolized by CYP3A4 directly to 4-hydroxy atorvastatin lactone and 2-hydroxy atorvastatin lactone.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lennernäs, H. Clinical pharmacokinetics of atorvastatin. Clin. Pharmacokinet. 42(13), 1141-1160 (2003).

    2. Dart, A., Jerums, G., Nicholson, G., et al. A multicenter, double-blind, one-year study comparing safety and efficacy of atorvastatin versus simvastatin in patients with hypercholesterolemia. Am. J. Cardiol. 80(1), 39-44 (1997).

    3. Group, T.D.A.L.I.S. The effect of aggressive versus standard lipid lowering by atorvastatin on diabetic dyslipidemia. The DALI study: A double-blind, randomized, placebo-controlled trial in patients with type 2 diabetes and diabetic dyslipidemia. Diabetes Care 24(8), 1335-1341 (2001).

    4. van Dam, M., Zwart, M., de Beer, F., et al. Long term efficacy and safety of atorvastatin in the treatment of severe type III and combined dyslipidaemia. Heart 88(3), 234-238 (2002).