Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H24N2O4S |
Molecular Weight | 424.513 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC3=CC=C(C=C3)C(O)=O
InChI
InChIKey=OROAFUQRIXKEMV-LDADJPATSA-N
InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+
Molecular Formula | C23H24N2O4S |
Molecular Weight | 424.513 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00876Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/eprosartan.html
Sources: http://www.drugbank.ca/drugs/DB00876
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/eprosartan.html
Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It acts on the renin-angiotensin system in two ways to decrease total peripheral resistance. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. Eprosartan is indicated for the management of hypertension alone or in combination with other classes of antihypertensive agents. Also used as a first-line agent in the treatment of diabetic nephropathy, as well as a second-line agent in the treatment of congestive heart failure (only in those intolerant of ACE inhibitors).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11401417
Curator's Comment: Eprosartan readily crosses the blood-brain barrier in vivo and selectively inhibits binding to AT1 receptors in specific brain nuclei.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL227 Sources: http://www.drugbank.ca/drugs/DB00876 |
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Target ID: CHEMBL2094250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8576904 |
1.5 nM [IC50] | ||
Target ID: GO:0015747 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558420 |
60.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TEVETEN Approved UseTEVETEN® is indicated for the treatment of hypertension. Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1273 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
439 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
702 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1857 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2246 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1205 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1612 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4887 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1400 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2620 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7855 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9597557/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2671 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4950 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
5750 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9737815/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
20 h |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EPROSARTAN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: Page: p.38 |
healthy, 20-43 n = 23 Health Status: healthy Age Group: 20-43 Sex: M Population Size: 23 Sources: Page: p.38 |
Other AEs: Headache, Earache... |
12000 mg single, oral Overdose Dose: 12000 mg Route: oral Route: single Dose: 12000 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
Other AEs: Circulatory collapse... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 17.4% | 800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: Page: p.38 |
healthy, 20-43 n = 23 Health Status: healthy Age Group: 20-43 Sex: M Population Size: 23 Sources: Page: p.38 |
Earache | 4.3% | 800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: Page: p.38 |
healthy, 20-43 n = 23 Health Status: healthy Age Group: 20-43 Sex: M Population Size: 23 Sources: Page: p.38 |
Circulatory collapse | 12000 mg single, oral Overdose Dose: 12000 mg Route: oral Route: single Dose: 12000 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
no | |||
no | ||||
Page: 4.0 |
no | |||
Page: 4.0 |
no | |||
no | ||||
Page: 4.0 |
no | |||
Page: 4.0 |
no | |||
no | ||||
Page: 4.0 |
no | |||
no | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
no | |||
yes | ||||
yes | ||||
Page: 2.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/eprosartan.html
Usual Adult Dose for Hypertension
Initial dose: 600 mg orally once a day as monotherapy assuming euvolemia
Maintenance dose: 400 to 800 mg orally per day in 1 or 2 divided doses
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11259627
Eprosartan (1 uM) inhibited the tail amplitude of HERG currents elicited on repolarization after pulses to +60 mV from 239 +/- 78 to 179 +/- 72 pA.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:37:23 GMT 2023
by
admin
on
Fri Dec 15 16:37:23 GMT 2023
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Record UNII |
2KH13Z0S0Y
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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 |
N0000175561
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NCI_THESAURUS |
C66930
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WHO-VATC |
QC09DA02
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WHO-VATC |
QC09CA02
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LIVERTOX |
NBK548507
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WHO-ATC |
C09DA02
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WHO-ATC |
C09CA02
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NDF-RT |
N0000000070
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C068373
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7223
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C61749
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EPROSARTAN
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CHEMBL813
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SUB06586MIG
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FF-70
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7521
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83515
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588
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DB00876
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4814
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1037
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100000084574
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Eprosartan
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5281037
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2KH13Z0S0Y
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133040-01-4
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2KH13Z0S0Y
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DTXSID0022989
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m4961
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
Priority toxic pollutant.
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IMPURITY -> PARENT |
Probable human carcinogen.
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IMPURITY GENOTOXIC->PARENT |
NDMA is an organic chemical that is in a family of potent carcinogens.
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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