Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H21F2NO3 |
Molecular Weight | 409.4252 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H](CC[C@@H]1[C@H](N(C1=O)C2=CC=C(F)C=C2)C3=CC=C(O)C=C3)C4=CC=C(F)C=C4
InChI
InChIKey=OLNTVTPDXPETLC-XPWALMASSA-N
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
Molecular Formula | C24H21F2NO3 |
Molecular Weight | 409.4252 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00973Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/ezetimibe.html
Sources: http://www.drugbank.ca/drugs/DB00973
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/ezetimibe.html
Ezetimibe is an anti-hyperlipidemic medication which is used to lower cholesterol levels. Specifically, it appears to bind to a critical mediator of cholesterol absorption, the Niemann-Pick C1-Like 1 (NPC1L1) protein on the gastrointestinal tract epithelial cells as well as in hepatocytes. Ezetimibe is in a class of lipid-lowering compounds that selectively inhibits the intestinal absorption of cholesterol and related phytosterols. Ezetimibe, administered alone is indicated as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia. It is also used in combination therapy with HMG-CoA reductase inhibitors. Ezetimibe has a mechanism of action that differs from those of other classes of cholesterol-reducing compounds (HMG-CoA reductase inhibitors, bile acid sequestrants, fibric acid derivatives, and plant stanols). Ezetimibe does not inhibit cholesterol synthesis in the liver, or increase bile acid excretion but instead localizes and appears to act at the brush border of the small intestine and inhibits the absorption of cholesterol, leading to a decrease in the delivery of intestinal cholesterol to the liver. This causes a reduction of hepatic cholesterol stores and an increase in clearance of cholesterol from the blood; this distinct mechanism is complementary to that of HMG-CoA reductase inhibitors.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2027 Sources: http://www.drugbank.ca/drugs/DB00973 |
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Target ID: CHEMBL2782 Sources: http://www.drugbank.ca/drugs/DB00973 |
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Target ID: CHEMBL5161 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18063367 |
200.0 nM [Ki] | ||
Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27600041 |
30.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZETIA Approved UseEzetimibe, administered alone, is indicated as adjunctive therapy to diet for the reduction of elevated total cholesterol (total-C), low-density lipoprotein cholesterol (LDL-C), apolipoprotein B (Apo B), and non-high-density lipoprotein cholesterol (non-HDL-C) in patients with primary (heterozygous familial and non-familial) hyperlipidemia. Launch Date2002 |
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Primary | ZETIA Approved UseHomozygous Familial Hypercholesterolemia (HoFH)
The combination of Ezetimibe and atorvastatin or simvastatin is indicated for the reduction of elevated total-C and LDL-C levels in patients with HoFH, as an adjunct to other lipid-lowering treatments (e.g., LDL apheresis) or if such treatments are unavailable. Launch Date2002 |
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Primary | ZETIA Approved UseEzetimibe is indicated as adjunctive therapy to diet for the reduction of elevated sitosterol and campesterol levels in patients with homozygous familial sitosterolemia. Launch Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
64.2 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
70.1 ng/mL |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.4 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
726 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
743 ng × h/mL |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
EZETIMIBE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, 57 years n = 1 Health Status: unhealthy Age Group: 57 years Sex: M Population Size: 1 Sources: |
Disc. AE: Liver injury... AEs leading to discontinuation/dose reduction: Liver injury Sources: |
10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, children n = 92 Health Status: unhealthy Condition: Primary hypercholesterolemia Age Group: children Population Size: 92 Sources: |
Other AEs: Epilepsy congenital, Appendicitis... Other AEs: Epilepsy congenital (serious, 1 patient) Sources: Appendicitis (serious, 1 patient) Upper respiratory tract infection (below serious, 7 patients) |
50 mg 1 times / day multiple, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 15 Health Status: unhealthy Population Size: 15 Sources: |
|
10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy n = 75 Health Status: unhealthy Condition: Type 2 Diabetes Population Size: 75 Sources: |
Other AEs: Cataract, Abdominal pain upper... Other AEs: Cataract (serious, 1 patient) Sources: Abdominal pain upper (serious, 1 patient) Type 2 diabetes mellitus (below serious, 7 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Liver injury | Disc. AE | 10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, 57 years n = 1 Health Status: unhealthy Age Group: 57 years Sex: M Population Size: 1 Sources: |
Upper respiratory tract infection | below serious, 7 patients | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, children n = 92 Health Status: unhealthy Condition: Primary hypercholesterolemia Age Group: children Population Size: 92 Sources: |
Appendicitis | serious, 1 patient | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, children n = 92 Health Status: unhealthy Condition: Primary hypercholesterolemia Age Group: children Population Size: 92 Sources: |
Epilepsy congenital | serious, 1 patient | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, children n = 92 Health Status: unhealthy Condition: Primary hypercholesterolemia Age Group: children Population Size: 92 Sources: |
Type 2 diabetes mellitus | below serious, 7 patients | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy n = 75 Health Status: unhealthy Condition: Type 2 Diabetes Population Size: 75 Sources: |
Abdominal pain upper | serious, 1 patient | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy n = 75 Health Status: unhealthy Condition: Type 2 Diabetes Population Size: 75 Sources: |
Cataract | serious, 1 patient | 10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy n = 75 Health Status: unhealthy Condition: Type 2 Diabetes Population Size: 75 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
not significant | unlikely (co-administration study) Comment: administered using cocktail approach: caffeine, tolbutamide, dextromethorphan, IV midazolam, and dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes [IC50 0.25 uM] | |||
Page: 11.0 |
yes [IC50 2.2 uM] | unlikely Comment: page 8: R-value extrapolation indicate potential for DDI as unlikely Page: 11.0 |
||
Page: 11.0 |
yes [IC50 2.9 uM] | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes [IC50 24 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
no | |||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21445_Zetia_biopharmr_P1.pdf#page=18 Page: 18.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Ezetimibe, a potent cholesterol absorption inhibitor, inhibits the development of atherosclerosis in ApoE knockout mice. | 2001 Dec |
|
A population pharmacokinetic model that describes multiple peaks due to enterohepatic recirculation of ezetimibe. | 2001 Jun |
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Ezetimibe, a potent cholesterol absorption inhibitor, normalizes combined dyslipidemia in obese hyperinsulinemic hamsters. | 2001 Jun |
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[Other antihyperlipidemic drugs with novel mechanism]. | 2001 Mar |
|
Novel approaches to lipid lowering: what is on the horizon? | 2001 Mar 8 |
|
The synergistic hypocholesterolemic activity of the potent cholesterol absorption inhibitor, ezetimibe, in combination with 3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitors in dogs. | 2001 Oct |
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[Statins remain the standard. New methods for lipid lowering therapy]. | 2001 Oct 18 |
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Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function. | 2001 Sep |
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Cholesterol absorption inhibitors for the treatment of hypercholesterolaemia. | 2002 |
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Gateways to Clinical Trials. | 2002 Apr |
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Disposition of the selective cholesterol absorption inhibitor ezetimibe in healthy male subjects. | 2002 Apr |
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[Antilipemic agents in combined therapy]. | 2002 Aug 25 |
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Management of dyslipidemia in the high-risk patient. | 2002 Dec |
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Low-density lipoprotein lowering therapy: an analysis of the options. | 2002 Dec 18 |
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Ezetimibe coadministered with simvastatin in patients with primary hypercholesterolemia. | 2002 Dec 18 |
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Future outlook: changing perspectives on best practice. | 2002 Feb |
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State of the art in cholesterol management: targeting multiple pathways. | 2002 Feb |
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Synthesis of fluorescent biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors. | 2002 Feb 11 |
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Gateways to clinical trials. | 2002 Jan-Feb |
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Ezetimibe. Schering-Plough. | 2002 Mar |
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Managing dyslipidemia in the high-risk patient. | 2002 Mar 7 |
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Gateways to clinical trials. | 2002 May |
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Efficacy and safety of a potent new selective cholesterol absorption inhibitor, ezetimibe, in patients with primary hypercholesterolemia. | 2002 Nov 15 |
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Efficacy and safety of ezetimibe added to ongoing statin therapy for treatment of patients with primary hypercholesterolemia. | 2002 Nov 15 |
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[Cholesterol resorption inhibition prevents high statin doses. Lipid lowering in double-pack]. | 2002 Nov 28 |
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[Ezetimib plus statin combination. A strong duo]. | 2002 Nov 28 |
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[Ezetimib--the first selective cholesterol resorption inhibitors. Strengthening of statins]. | 2002 Nov 28 |
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Inhibition of intestinal cholesterol absorption by ezetimibe in humans. | 2002 Oct 8 |
|
[Statins plus cholesterol resorption inhibitor. LDL goal values attainable]. | 2002 Sep 19 |
|
Ezetimibe. | 2003 Apr |
|
Synthesis of a biotin-tagged photoaffinity probe of 2-azetidinone cholesterol absorption inhibitors. | 2003 Apr 17 |
|
Beyond statins. New drugs can work with, or in place of, cholesterol-lowering statins. | 2003 Feb |
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Fresh from the pipeline. Ezetimibe. | 2003 Feb |
|
Ezetimibe added to ongoing statin therapy reduced LDL cholesterol in primary hypercholesterolemia. | 2003 Jul-Aug |
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Ezetimibe for management of hypercholesterolemia. | 2003 Jun |
|
Combination lipid-lowering therapy in diabetes. | 2003 Jun |
|
Statins, super-statins and cholesterol absorption inhibitors. | 2003 May |
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Treating dyslipidemic patients with lipid-modifying and combination therapies. | 2003 May |
|
[Controlling LDL cholesterol from 2 sides. "I have never seen such low LDL values"]. | 2003 May 15 |
|
New lipid-lowering combo proves successful. | 2003 May 20 |
|
The intestinal absorption of biliary and dietary cholesterol as a drug target for lowering the plasma cholesterol level. | 2003 Winter |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ezetimibe.html
10 mg orally once a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26167075
10uM/L ezetimibe treatment of Huh7 hepatocytes significantly decreased PA-induced fat accumulation and increased PA-reduced mRNA and protein expression involved in autophagy
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:57:43 GMT 2023
by
admin
on
Fri Dec 15 15:57:43 GMT 2023
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Record UNII |
EOR26LQQ24
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008553
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WHO-ATC |
C10BA05
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WHO-VATC |
QC10AX09
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WHO-VATC |
QC10BA06
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WHO-ATC |
C10BA06
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WHO-ATC |
C10BA02
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WHO-ATC |
C10AX09
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WHO-VATC |
QC10BA05
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NCI_THESAURUS |
C29703
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WHO-VATC |
QC10BA02
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LIVERTOX |
NBK548095
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NDF-RT |
N0000175911
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8010
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EOR26LQQ24
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C47529
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1269028
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ZETIA
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PRIMARY | APPROVE APRIL 2007 | ||
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150311
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m5228
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SUB16430MIG
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163222-33-1
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CHEMBL1138
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100000091598
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7737
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DB00973
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Ezetimibe
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1125
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DTXSID1044223
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N0000008553
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PRIMARY | Decreased Cholesterol Absorption [PE] | ||
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341248
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LL-18
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EZETIMIBE
Created by
admin on Fri Dec 15 15:57:43 GMT 2023 , Edited by admin on Fri Dec 15 15:57:43 GMT 2023
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6816
Created by
admin on Fri Dec 15 15:57:43 GMT 2023 , Edited by admin on Fri Dec 15 15:57:43 GMT 2023
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758923
Created by
admin on Fri Dec 15 15:57:43 GMT 2023 , Edited by admin on Fri Dec 15 15:57:43 GMT 2023
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49040
Created by
admin on Fri Dec 15 15:57:43 GMT 2023 , Edited by admin on Fri Dec 15 15:57:43 GMT 2023
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C108606
Created by
admin on Fri Dec 15 15:57:43 GMT 2023 , Edited by admin on Fri Dec 15 15:57:43 GMT 2023
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Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
MAJOR
FECAL
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TARGET->INHIBITOR OF ABSORPTION |
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET->INHIBITOR OF ABSORPTION |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
TRACE
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
MINOR
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
From ANDA on applications
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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