An inhibitor of NPC1L1
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Ezetimibe

Item No. 16331

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4S)-1,4-fluorophenyl-3-[(3S-3-4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone
CAS Number
163222-33-1
Synonyms
  • Ezetrol
  • SCH 58235
Molecular Formula
C24H21F2NO3
Formula Weight
409.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:4): 0.2 mg/ml
λmax
233 nm
SMILES
OC(C=C1)=CC=C1[C@@H]2[C@@H](CC[C@H](O)C3=CC=C(F)C=C3)C(N2C4=CC=C(F)C=C4)=O
InChi Code
InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
InChi Key
OLNTVTPDXPETLC-XPWALMASSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $81

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    50 mg

    $121

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    100 mg

    $222

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    250 mg

    $515

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Ezetimibe is an inhibitor of NPC1-like intracellular cholesterol transporter 1 (NPC1L1; Ki = 220 nM), a cholesterol transporter found in the apical membrane of enterocytes.1 It reduces cholesterol absorption in hamsters fed a high-cholesterol diet (ED50 = 0.04 mg/kg per day).2 Ezetimibe (346 nM) also reduces the levels of helper T cells and memory T cells isolated from the blood of heart transplant recipients.3 Formulations containing ezetimibe have been used in the treatment of primary hypercholesterolemia and mixed hyperlipidemia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Garcia-Calvo, M., Lisnock, J., Bull, H.G., et al. The target of ezetimibe is Niemann-Pick C1-like 1 (NPC1L1). Proc. Natl. Acad. Sci. USA 102(23), 8132-8137 (2005).

    2. Rosenblum, S.B., Huynh, T., Afonso, A., et al. Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4 -hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption. J. Med. Chem. 41(6), 973-980 (1998).

    3. Shaw, S.M., Najam, O., Khan, U., et al. Ezetimibe and atorvastatin both immunoregulate CD4+ T cells from cardiac transplant recipients in vitro. Transpl. Immunol. 21(3), 179-182 (2009).