An active metabolite of atorvastatin
Related Products
Labeled Version(s)
35171Atorvastatin lactone-d5
Parent Compound(s)
10493Atorvastatin (calcium salt hydrate)
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Atorvastatin lactone

Item No. 20951

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide
CAS Number
125995-03-1
Molecular Formula
C33H33FN2O4
Formula Weight
540.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:3): 0.25 mg/mlDMSO: 15 mg/mlEthanol: 10 mg/ml
λmax
248 nm
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=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
InChi Key
OUCSEDFVYPBLLF-KAYWLYCHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $186

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    25 mg

    $294

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    Product Description

    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).