An internal standard for the quantification of atorvastatin lactone
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Unlabeled Version(s)
20951Atorvastatin lactone
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Atorvastatin lactone-d5

Item No. 35171

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N-phenyl-4-(phenyl-d5)-1H-pyrrole-3-carboxamide
Molecular Formula
C33H28D5FN2O4
Formula Weight
545.7
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleMethanol: 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=C([2H])C([2H])=C([2H])C([2H])=C4[2H])NC5=CC=CC=C5
InChi Code
InChI=1S/C33H33FN2O4/c1-21(2)31-30(33(39)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-27-19-26(37)20-28(38)40-27/h3-16,21,26-27,37H,17-20H2,1-2H3,(H,35,39)/t26-,27-/m1/s1/i3D,5D,6D,9D,10D
InChi Key
OUCSEDFVYPBLLF-CCJPLZOUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $174

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    1 mg

    $329

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    Product Description

    Atorvastatin lactone-d5 is intended for use as an internal standard for the quantification of atorvastatin lactone (Item No. 20951) by GC- or LC-MS. Atorvastatin lactone is an active metabolite of the HMG-CoA reductase inhibitor atorvastatin.1,2 It is formed from atorvastatin by the UDP-glucuronosyltransferase (UGT) isoforms UGT1A3 and UGT1A1 in insect cell-derived supersomes expressing the human enzymes, and hydrolyzes to form atorvastatin in human serum at room temperature.2,3 Atorvastatin lactone inhibits HMG-CoA reductase (IC50 = 0.007 µM for the rat liver enzyme).1 It also inhibits the cytochrome P450 (CYP) isoforms CYP2C9.1 and CYP2C9.3 (IC50s = 16.8 and 5.62 µM, respectively), as well as P-glycoprotein (P-gp; IC50 = 3.1-5.2 µM).4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Roth, B.D., Blankley, C.J., Chucholowski, A.W., et al. Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran-2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus. J. Med. Chem. 34(1), 357-366 (1990).

    2. Schirris, T.J.J., Ritschel, T., Bilos, A., et al. Statin lactonization by uridine 5'-diphospho-glucuronosyltransferases (UGTs). Mol. Pharm. 12(11), 4048-4055 (2015).

    3. Jemal, M., Ouyang, Z., Chen, B.C., et al. Quantitation of the acid and lactone forms of atorvastatin and its biotransformation products in human serum by high-performance liquid chromatography with electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 13(11), 1003-1015 (1999).

    4. Shiozawa, A., Yamaori, S., Kamijo, S., et al. Effects of acid and lactone forms of statins on S-warfarin 7-hydroxylation catalyzed by human liver microsomes and recombinant CYP2C9 variants (CYP2C9.1 and CYP2C9.3). Drug Metab. Pharmacokinet. 36, 100364 (2021).

    5. Bogman, K., Peyer, A.-K., Török, M., et al. HMG-CoA reductase inhibitors and P-glycoprotein modulation. Br. J. Pharmacol. 132(6), 1183-1192 (2001).