Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H27ClO7 |
Molecular Weight | 450.909 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=CC(CC3=CC=C(O[C@H]4CCOC4)C=C3)=C(Cl)C=C2
InChI
InChIKey=OBWASQILIWPZMG-QZMOQZSNSA-N
InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19+,20+,21-,22+,23-/m0/s1
Molecular Formula | C23H27ClO7 |
Molecular Weight | 450.909 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=21985634; https://www.boehringer-ingelheim.com/press-release/jardiance-empagliflozin-be-studied-treatment-people-chronic-heart-failure
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=21985634; https://www.boehringer-ingelheim.com/press-release/jardiance-empagliflozin-be-studied-treatment-people-chronic-heart-failure
Empagliflozin is a selective sodium glucose cotransporter-2 (SGLT-2) inhibitor designed for the treatment of type 2 diabetes mellitus. By inhibiting SGLT2, empagliflozin reduces renal reabsorption of filtered glucose and lowers the renal threshold for glucose, and thereby increases urinary glucose excretion. Empagliflozin interacts with diuretics, blood presure medicine and insulin. Jardiance reduces the risk of cardiovascular death in diabetes patients at high cardiovascular risk.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3884 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21985634 |
3.1 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Secondary | JARDIANCE Approved UseJARDIANCE is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Is not recommended for patients with type 1 diabetes or for the treatment of diabetic ketoacidosis. Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
259 nM |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
687 nM |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1870 nM × h |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
4740 nM × h |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.4 h |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.8% |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMPAGLIFLOZIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
From victim to ally: the kidney as an emerging target for the treatment of diabetes mellitus. | 2009 Mar |
|
Sodium glucose cotransporter 2 inhibitors as a new treatment for diabetes mellitus. | 2010 Jan |
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Empagliflozin, a novel selective sodium glucose cotransporter-2 (SGLT-2) inhibitor: characterisation and comparison with other SGLT-2 inhibitors. | 2012 Jan |
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Empagliflozin as add-on to metformin in patients with type 2 diabetes: a 24-week, randomized, double-blind, placebo-controlled trial. | 2014 Jun |
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Empagliflozin for the treatment of Type 2 diabetes. | 2014 May |
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Empagliflozin for the treatment of type 2 diabetes. | 2014 Nov |
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Nonclinical safety of the sodium-glucose cotransporter 2 inhibitor empagliflozin. | 2014 Nov-Dec |
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Efficacy and safety of empagliflozin for type 2 diabetes: a systematic review and meta-analysis. | 2014 Oct |
|
Empagliflozin (Jardiance) for diabetes. | 2014 Oct 13 |
Sample Use Guides
The recommended dose of JARDIANCE is 10 mg once daily in the morning, taken with or without food. In patients tolerating JARDIANCE, the dose may be increased to 25 mg
In patients with volume depletion, correcting this condition prior to initiation of JARDIANCE is recommended. Assessment of renal function is recommended prior to initiation of JARDIANCE and periodically thereafter.
JARDIANCE should not be initiated in patients with an eGFR less than 45 mL/min/1.73 m^2. No dose adjustment is needed in patients with an eGFR greater than or equal to 45 mL/min/1.73 m^2. JARDIANCE should be discontinued if eGFR is persistently less than 45 mL/min/1.73 m^2.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21985634
In in vitro experiments empagliflozin is used at a concentration of 100 nM and 500 nM based on recommendations by Boehringer-Ingelheim as these doses effectively and selectively block SGLT2 without significant inhibition of SGLT1.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:16:23 GMT 2023
by
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on
Fri Dec 15 19:16:23 GMT 2023
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Record UNII |
HDC1R2M35U
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Record Status |
Validated (UNII)
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Record Version |
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A10BD20
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N0000187059
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CHEMBL2107830
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C158136
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Empagliflozin
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N0000187058
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Empagliflozin
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Related Record | Type | Details | ||
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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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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
A mean of 54.4% of the dose was excreted in urine and 41.2% was excreted in feces. Approximately 50% of the drug related radioactivity excreted in urine was unchanged parent (28.6%) and approximately 83% of the drug related radioactivity excreted in feces was unchanged parent (~34%).
URINE
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EXCRETED UNCHANGED |
A mean of 54.4% of the dose was excreted in urine and 41.2% was excreted in feces. Approximately 50% of the drug related radioactivity excreted in urine was unchanged parent (28.6%) and approximately 83% of the drug related radioactivity excreted in feces was unchanged parent (~34%).
FECAL
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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SINGLE DOSE ADMINISTRATION |
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