Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H29N5O3 |
Molecular Weight | 435.5188 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC(=O)N(CC1=CC=C(C=C1)C2=C(C=CC=C2)C3=NN=NN3)[C@@H](C(C)C)C(O)=O
InChI
InChIKey=ACWBQPMHZXGDFX-QFIPXVFZSA-N
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
Molecular Formula | C24H29N5O3 |
Molecular Weight | 435.5188 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdfhttps://www.pharma.us.novartis.com/sites/www.pharma.us.novartis.com/files/entresto.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/25052956Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19934029
https://www.ncbi.nlm.nih.gov/pubmed/26082640
http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207620Orig1s000PharmR.pdf
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdfhttps://www.pharma.us.novartis.com/sites/www.pharma.us.novartis.com/files/entresto.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/25052956
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19934029
https://www.ncbi.nlm.nih.gov/pubmed/26082640
http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207620Orig1s000PharmR.pdf
There is no information in the literature about pharmacological and biological application of definite isomer of valsatran, R – form (also known as VALSARTAN, D- or CGP-49309). However there were found, that in the tablets of valsartan, which are used to treat high blood pressure and to heart failure, the R-enantiomer was an impurity.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23227311https://www.ncbi.nlm.nih.gov/pubmed/26663387
Curator's Comment: LBQ657 (an LCZ696 metabolite) achieves CSF concentrations sufficient to inhibit neprilysin, but LCZ696 did not cause changes in CSF levels of aggregable Abeta isoforms (1-42 and 1-40) compared with placebo
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8505092https://www.novartis.com/news/media-releases/novartis-new-heart-failure-medicine-lcz696-now-called-entrestotm-approved-fda
Curator's Comment: # Novartis
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL227 |
2.38 nM [Ki] | ||
Target ID: CHEMBL1944 |
2.3 nM [IC50] | ||
Target ID: CHEMBL227 |
2.43 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ENTRESTO Approved UseENTRESTO is a combination of sacubitril, a neprilysin inhibitor, and valsartan, an angiotensin II receptor blocker, indicated to reduce the risk of cardiovascular death and hospitalization for heart failure in patients with chronic heart failure (NYHA Class II-IV) and reduced ejection fraction. ENTRESTO is usually administered in conjunction with other heart failure therapies, in place of an ACE inhibitor or other ARB. Launch Date1.43614083E12 |
|||
Primary | DIOVAN Approved UseDiovan is an angiotensin II receptor blocker (ARB) indicated for:
Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1)
Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2)
Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3) Launch Date1.31086077E12 |
|||
Primary | DIOVAN Approved UseDiovan is an angiotensin II receptor blocker (ARB) indicated for:
Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1)
Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2)
Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3) Launch Date1.31086077E12 |
|||
Palliative | DIOVAN Approved UseDiovan is an angiotensin II receptor blocker (ARB) indicated for:
Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1)
Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2)
Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3) Launch Date1.31086077E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2808 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5756 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.141 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21617777 |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20650 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
34310 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
22.56 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21617777 |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27128457 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21617777 |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2.24 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Other AEs: Muscle cramps... |
640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Disc. AE: Hyperkalemia... Other AEs: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Hyperkalemia (1 patient) Other AEs:Dizziness (8.3%) Sources: Headache (9.2%) Back pain (5.8%) Upper respiratory tract infection (5.8%) Nasopharyngitis (5%) Diarrhea (5%) Hypoglycemia (5%) Peripheral edema (4.2%) Nausea (4.2%) |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
pregnant Health Status: pregnant Sources: |
Disc. AE: Disorder fetal... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2316 Health Status: unhealthy Condition: hypertension Population Size: 2316 Sources: |
Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (2.3%) Sources: Dizziness (2.3%) |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2506 Health Status: unhealthy Condition: Heart Failure Population Size: 2506 Sources: |
Disc. AE: Creatinine increased, Potassium increased... AEs leading to discontinuation/dose reduction: Creatinine increased (0.5%) Sources: Potassium increased (0.5%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Muscle cramps | 1 patient | 2.24 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Hyperkalemia | 1 patient Disc. AE |
640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Nausea | 4.2% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Peripheral edema | 4.2% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Diarrhea | 5% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Hypoglycemia | 5% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Nasopharyngitis | 5% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Back pain | 5.8% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Upper respiratory tract infection | 5.8% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Dizziness | 8.3% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Headache | 9.2% | 640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: |
unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: |
Disorder fetal | Disc. AE | 320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
pregnant Health Status: pregnant Sources: |
Dizziness | 2.3% Disc. AE |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2316 Health Status: unhealthy Condition: hypertension Population Size: 2316 Sources: |
Headache | 2.3% Disc. AE |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2316 Health Status: unhealthy Condition: hypertension Population Size: 2316 Sources: |
Creatinine increased | 0.5% Disc. AE |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2506 Health Status: unhealthy Condition: Heart Failure Population Size: 2506 Sources: |
Potassium increased | 0.5% Disc. AE |
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: |
unhealthy n = 2506 Health Status: unhealthy Condition: Heart Failure Population Size: 2506 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Remodelling of resistance arteries in genetically hypertensive rats by treatment with valsartan, an angiotensin II receptor antagonist. | 1996 Jun-Jul |
|
Valsartan, a new angiotensin II antagonist for the treatment of essential hypertension: a comparative study of the efficacy and safety against amlodipine. | 1996 Sep |
Sample Use Guides
The recommended starting dose of DIOVAN® is 80 mg or 160 mg once daily when used as monotherapy in patients who are not volume-depleted. Patients requiring greater reductions may be started at the higher dose. DIOVAN® may be used over a dose range of 80 mg to 320 mg daily, administered once a day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8242249
Curator's Comment: ...
Valsartan competed with [125I]-angiotensin II (AII) at its specific binding sites in rat aortic smooth muscle cell membranes (AT1-receptor subtype) with a Ki of 2.38 nM, but was about 30,000 times less active in human myometrial membranes (AT2-receptor subtype). In rabbit aortic rings incubated for 5 min with valsartan, at concentrations of 2, 20 and 200 nM, the concentration-response curve of AII was displaced to the right and the maximum response was reduced by 33%, 36% and 40%, respectively. Prolongation of the incubation time with valsartan to 1 h or 3 h, further reduced the maximum response by 48% or 59% (after 20 nM) and by 59% or 60% (after 200 nM), respectively. After 3 h incubation an apparent pKb value of 9.26 was calculated. Contractions induced by noradrenaline, 5-hydroxytryptamine, or potassium chloride were not affected by valsartan.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 20:21:52 UTC 2022
by
admin
on
Fri Dec 16 20:21:52 UTC 2022
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Record UNII |
80M03YXJ7I
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-ATC |
C09CA03
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EMA ASSESSMENT REPORTS |
IMPRADA-HCT (WITHDRAWN: HYPERTENSION)
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WHO-ATC |
C10BX10
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EMA ASSESSMENT REPORTS |
EXFORGE (AUTHORIZED: HYPERTENSION)
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WHO-VATC |
QC09CA03
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NDF-RT |
N0000175561
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WHO-ATC |
C09DX02
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EMA ASSESSMENT REPORTS |
COPALIA (AUTHORIZED: HYPERTENSION)
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WHO-ATC |
C09DX01
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WHO-VATC |
QC09DA03
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EMA ASSESSMENT REPORTS |
EXFORGE-HCT (AUTHORIZED: HYPERTENSION)
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NCI_THESAURUS |
C66930
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WHO-ATC |
C09DB08
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EMA ASSESSMENT REPORTS |
DARFIRO-HCT (AUTHORIZED: HYPERTENSION)
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LIVERTOX |
NBK547944
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EMA ASSESSMENT REPORTS |
COPALIA-HCT (AUTHORIZED: HYPERTENSION)
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WHO-ATC |
C09DA03
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NDF-RT |
N0000000070
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EMA ASSESSMENT REPORTS |
DAFIRO (AUTHORIZED: HYPERTENSION)
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FDA ORPHAN DRUG |
494115
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WHO-VATC |
QC09DX01
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EMA ASSESSMENT REPORTS |
IMPRIDA (AUTHORIZED: HYPERTENSION)
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WHO-ATC |
C09DX05
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WHO-ATC |
C09DX04
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WHO-VATC |
QC09DX02
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WHO-ATC |
C09DB01
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WHO-VATC |
QC09DB01
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C081489
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VALSARTAN
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C47781
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Valsartan
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9927
Created by
admin on Fri Dec 16 20:21:53 UTC 2022 , Edited by admin on Fri Dec 16 20:21:53 UTC 2022
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HH-50
Created by
admin on Fri Dec 16 20:21:53 UTC 2022 , Edited by admin on Fri Dec 16 20:21:53 UTC 2022
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M11372
Created by
admin on Fri Dec 16 20:21:53 UTC 2022 , Edited by admin on Fri Dec 16 20:21:53 UTC 2022
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PRIMARY | Merck Index | ||
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60846
Created by
admin on Fri Dec 16 20:21:53 UTC 2022 , Edited by admin on Fri Dec 16 20:21:53 UTC 2022
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PRIMARY | |||
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SUB00017MIG
Created by
admin on Fri Dec 16 20:21:53 UTC 2022 , Edited by admin on Fri Dec 16 20:21:53 UTC 2022
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PRIMARY |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
SALT/SOLVATE -> PARENT |
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||
|
TRANSPORTER -> INHIBITOR | |||
|
SALT/SOLVATE -> PARENT |
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||
|
TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE INACTIVE -> PARENT | |||
|
METABOLITE INACTIVE -> PARENT |
Valsartan was metabolized to a small extent only. The only notable metabolite in plasma, urine and faecs
MAJOR
FECAL; PLASMA; URINE
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Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
Probable human carcinogen.
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Priority toxic pollutant.
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> 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 |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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ROUTE OF ADMINISTRATION: ORAL |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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PROTEIN BINDING | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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ROUTE OF ADMINISTRATION: ORAL |
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RENAL CLEARANCE | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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