Drug Information

General Information
Drug ID
DR00140
Drug Name
Ezetimibe
Synonyms
(-)-Sch 58235; (1-(4-fluorophenyl)-(3R)-(3-(4-fluorophenyl)-(3S)-hydroxypropyl)-(4S)-(4-hydroxyphenyl)-2-azetidinone); (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one; (3R,4S)-1-(p-Fluorophenyl)-3-((3S)-3-(p-fluorophenyl)-3-hydroxypropyl)-4-(p-hydroxyphenyl)-2-azetidinone; 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-(4-hydroxyphenyl)-2-azetidione; 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone; Essex brand of ezetimibe; Ezedoc; Ezetimib; Ezetimibe (JAN/USAN/INN); Ezetimibe [USAN:INN]; Ezetrol; Inegy (TN); MK-0653; MSD brand of ezetimibe; Merck brand of ezetimibe; SCH-58235; SCH58235; Sch 58235; Schering-Plough brand of ezetimibe; Vytorin (TN); Zetia; Zetia (TN); Zetia , Ezetrol, Ezetimibe; Zient
Drug Type
Small molecular drug
Indication Hypercholesterolemia [ICD11:5C80.0] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C24H21F2NO3
Canonical SMILES
C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O
InChI
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
InChIKey
OLNTVTPDXPETLC-XPWALMASSA-N
CAS Number
CAS 163222-33-1
Pharmaceutical Properties Molecular Weight 409.4 Topological Polar Surface Area 60.8
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
XLogP
4
PubChem CID
150311
PubChem SID
10250673 ,103326446 ,104179182 ,104253290 ,104428106 ,11528896 ,117884262 ,12014979 ,124658886 ,124757411 ,124801398 ,125164215 ,126592989 ,126621626 ,126653456 ,126667079 ,127315811 ,127315812 ,127315813 ,127315814 ,127315815 ,127315816 ,127315817 ,127315818 ,127315819 ,127315820 ,127315821 ,127315822 ,127315823 ,127315824 ,128826430 ,131854738 ,134338005 ,135107180 ,14879623 ,14928749 ,26719841 ,46226990 ,46386640 ,46507625 ,49681809 ,49693660 ,50539938 ,53787196 ,57347010 ,71821424 ,7849028 ,81146074 ,92308446 ,92718207
ChEBI ID
ChEBI:49040
TTD Drug ID
D09LWS
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
BSEP Transporter Info Bile salt export pump Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [2]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [6]
References
1 Ezetimibe was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702.
3 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
4 Intestinal expression of P-glycoprotein (ABCB1), multidrug resistance associated protein 2 (ABCC2), and uridine diphosphate-glucuronosyltransferase 1A1 predicts the disposition and modulates the effects of the cholesterol absorption inhibitor ezetimibe in humans. Clin Pharmacol Ther. 2006 Mar;79(3):206-17.
5 A LC-MS/MS method to quantify the novel cholesterol lowering drug ezetimibe in human serum, urine and feces in healthy subjects genotyped for SLCO1B1. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):143-50.
6 Pharmacokinetic and pharmacodynamic interactions between the immunosuppressant sirolimus and the lipid-lowering drug ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2010 Jun;87(6):663-7.

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