Ezetimibe
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
Molecular Identity
Ezetimibe
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
PubChem CID: 150311
Ezetimibe is a beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer). It has a role as an antimetabolite, an antilipemic drug and an anticholesteremic drug. It is a beta-lactam, an organofluorine compound and a member of azetidines.
2D Structure
Properties
C24H21F2NO3
Molecular Formula
409.40
Molecular Weight
g/mol
409.1489
Exact Mass
Da
4
XLogP
Drug-like (Lipinski: < 5)
60.8
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
5
H-Bond Acceptors
567
Complexity
SMILES
Canonical SMILES
SMILES: C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)OIsomeric SMILES
SMILES: C1=CC(=CC=C1[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@@H](C4=CC=C(C=C4)F)O)OSynonyms(20)
Ezetimibe163222-33-1ZetiaEzetrolEzedoc(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-oneSch 58235SCH-58235SCH58235ezetimibaEOR26LQQ24ezetimibumDTXSID10442232-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-, (3R,4S)-MK0653
Data from PubChem (NCBI)
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Drug Network
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