Details
Stereochemistry | ACHIRAL |
Molecular Formula | C33H30N4O2 |
Molecular Weight | 514.6181 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCc1nc2c(C)cc(cc2n1Cc3ccc(cc3)-c4ccccc4C(=O)O)-c5nc6ccccc6n5C
InChI
InChIKey=RMMXLENWKUUMAY-UHFFFAOYSA-N
InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39)
Molecular Formula | C33H30N4O2 |
Molecular Weight | 514.6181 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00966Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00966
Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf
Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT1 receptor subtype. It was discovered by Boehringer Ingelheim and launched in 1999 as Micardis. It has the highest affinity for the AT1 receptor among commercially available ARBS and has minimal affinity for the AT2 receptor. New studies suggest that telmisartan may also have PPARγ agonistic properties that could potentially confer beneficial metabolic effects, as PPARγ is a nuclear receptor that regulates specific gene transcription, and whose target genes are involved in the regulation of glucose and lipid metabolism, as well as anti-inflammatory responses. This observation is currently being explored in clinical trials. Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme (ACE, kininase II). Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Telmisartan works by blocking the vasoconstrictor and aldosterone secretory effects of angiotensin II. Telmisartan interferes with the binding of angiotensin II to the angiotensin II AT1-receptor by binding reversibly and selectively to the receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in decreases in systemic vascular resistance. Telmisartan does not inhibit the angiotensin converting enzyme, other hormone receptors, or ion channels. Studies also suggest that telmisartan is a partial agonist of PPARγ, which is an established target for antidiabetic drugs. This suggests that telmisartan can improve carbohydrate and lipid metabolism, as well as control insulin resistance without causing the side effects that are associated with full PPARγ activators. Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Telmisartan is used in the treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes mellitus, as well as the treatment of congestive heart failure (only in patients who cannot tolerate ACE inhibitors).
Originator
Sources: http://adisinsight.springer.com/drugs/800002511
Curator's Comment:: # Boehringer Ingelheim Pharma KG
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map00590 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26632190 |
49.5 µM [IC50] | ||
Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00966 |
12.2 µM [IC50] | ||
Target ID: CHEMBL227 |
3.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MICARDIS Approved UseMICARDIS is an angiotensin II receptor blocker (ARB) indicated for:
• Treatment of hypertension
• Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors Launch Date9.1056957E11 |
|||
Preventing | MICARDIS Approved UseMICARDIS is an angiotensin II receptor blocker (ARB) indicated for:
• Treatment of hypertension
• Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors Launch Date9.1056957E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3200 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323 |
160 mg single, intravenous dose: 160 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TELMISARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3320 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323 |
160 mg single, intravenous dose: 160 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TELMISARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323 |
160 mg single, intravenous dose: 160 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TELMISARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
160 mg single, intravenous Highest studied dose Dose: 160 mg Route: intravenous Route: single Dose: 160 mg Sources: Page: p.159 |
healthy, 18 – 50 n = 12 Health Status: healthy Age Group: 18 – 50 Sex: M Population Size: 12 Sources: Page: p.159 |
|
320 mg 1 times / day multiple, oral Highest studied dose Dose: 320 mg, 1 times / day Route: oral Route: multiple Dose: 320 mg, 1 times / day Sources: Page: p.161 |
healthy, 18 – 50 n = 10 Health Status: healthy Age Group: 18 – 50 Sex: M Population Size: 10 Sources: Page: p.161 |
|
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension|Cardiovascular Risk Reduction Sources: Page: p.1 |
Disc. AE: Disorder fetal, Hypotension... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: Page: p.1Hypotension |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Disorder fetal | Disc. AE | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension|Cardiovascular Risk Reduction Sources: Page: p.1 |
Hypotension | Disc. AE | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension|Cardiovascular Risk Reduction Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Use of ambulatory blood pressure monitoring to evaluate the selective angiotensin II receptor antagonist, telmisartan, and other antihypertensive drugs. | 2000 |
|
Telmisartan: a review of its use in hypertension. | 2001 |
|
The comparative pharmacology of angiotensin II receptor antagonists. | 2001 |
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Angiotensin II receptor antagonists: new paradigms in the treatment of hypertension. Introduction. | 2001 |
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Ambulatory blood pressure monitoring to assess the comparative efficacy and duration of action of a novel new angiotensin II receptor blocker--telmisartan. | 2001 |
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The role of angiotensin II receptor antagonists in the management of diabetes. | 2001 |
|
Effects of the replacement of the angiotensin converting enzyme inhibitor enalapril by the angiotensin II receptor blocker telmisartan in patients with congestive heart failure. The replacement of angiotensin converting enzyme inhibition (REPLACE) investigators. | 2001 Feb |
|
[Angiotensin II antagonism. Critical morning hours are covered]. | 2001 Feb 22 |
|
Comparison of 26-week efficacy and tolerability of telmisartan and atenolol, in combination with hydrochlorothiazide as required, in the treatment of mild to moderate hypertension: a randomized, multicenter study. | 2001 Jan |
|
Combination treatment with telmisartan and hydrochlorothiazide in black patients with mild to moderate hypertension. | 2001 Jan |
|
Effects of telmisartan, hydrochlorothiazide and their combination on blood pressure and renal excretory parameters in spontaneously hypertensive rats. | 2001 Jun |
|
Angiotensin II-induced stimulation of collagen secretion and production in cardiac fibroblasts is mediated via angiotensin II subtype 1 receptors. | 2001 Jun |
|
Comparative antihypertensive and renoprotective effects of telmisartan and lisinopril after long-term treatment in hypertensive diabetic rats. | 2001 Mar |
|
Effects of telmisartan on renal excretory function in conscious dogs. | 2001 Mar-Apr |
|
Effect of telmisartan on arterial distensibility and central blood pressure in patients with mild to moderate hypertension and Type 2 diabetes mellitus. | 2001 Sep |
|
Long-term efficacy and tolerability of telmisartan as monotherapy and in combination with other antihypertensive medications. | 2002 |
|
Telmisartan. BIBR 277, Micardis, Pritor. | 2002 |
|
Gateways to clinical trials. | 2002 Dec |
|
Comparison of trough effect of telmisartan vs perindopril using self blood pressure measurement: EVERESTE study. | 2002 Dec |
|
Application of capillary zone electrophoresis to the screening of some angiotensin II receptor antagonists. | 2002 Jan |
|
[Coronary heart disease patient with hypertension. Dangerously increased blood pressure despite gigantic therapy arsenal]. | 2002 Jan 24 |
|
Angiotensin II receptor antagonists role in arterial hypertension. | 2002 Mar |
|
Gateways to clinical trials. | 2002 May |
|
Angiotensin blockade prevents type 2 diabetes by formation of fat cells. | 2002 Nov |
|
Amlodipine versus Angiotensin-receptor blockers for nonhypertension indications. | 2002 Nov |
|
[These hypertensive patients are especially at risk for myocardial infarct in the morning. Screen for non-dippers]. | 2002 Nov 14 |
|
[Lowering blood pressure with sartans. Are there differences?]. | 2002 Nov 21 |
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Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
ABPM comparison of the anti-hypertensive profiles of telmisartan and enalapril in patients with mild-to-moderate essential hypertension. | 2002 Nov-Dec |
|
A multicenter, open-label study of the efficacy and safety of telmisartan in mild to moderate hypertensive patients. | 2002 Oct |
|
The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension. | 2002 Sep |
|
Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis. | 2003 Feb 26 |
|
[Despite therapy morning dangerous RR spikes. Headache and vertigo are alarm signals]. | 2003 Jan 23 |
|
Evaluation of angiotensin II receptor blockers for 24-hour blood pressure control: meta-analysis of a clinical database. | 2003 Jan-Feb |
Sample Use Guides
Hypertension - 40 to 80 mg once daily
Cardiovascular Risk Reduction - 80 mg once daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12195125
Telmisartan (0.01-10 nmol/l) concentration dependently attenuated the angiotensin II-mediated (1 nmol/l) enhancement of EFS-evoked sympathetic outflow in the isolated rabbit thoracic aorta.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:03:21 UTC 2021
by
admin
on
Fri Jun 25 21:03:21 UTC 2021
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Record UNII |
U5SYW473RQ
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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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LIVERTOX |
930
Created by
admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
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EMA ASSESSMENT REPORTS |
TELMISARTAN ACTAVIS (AUTHORIZED: HYPERTENSION)
Created by
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WHO-VATC |
QC09DA07
Created by
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EMA ASSESSMENT REPORTS |
KINZALKOMB (AUTHORIZED: HYPERTENSION)
Created by
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NCI_THESAURUS |
C66930
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EMA ASSESSMENT REPORTS |
TOLURA (AUTHORIZED: HYPERTENSION)
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WHO-ATC |
C09DB04
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WHO-VATC |
QC09DB04
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EMA VETERINARY ASSESSMENT REPORTS |
SEMINTRA [AUTHORIZED]
Created by
admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
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EMA ASSESSMENT REPORTS |
TOLUCOMBI (AUTHORIZED: HYPERTENSION)
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WHO-VATC |
QC09CA07
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EMA ASSESSMENT REPORTS |
ONDUARP (WITHDRAWN: HYPERTENSION)
Created by
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WHO-ATC |
C09CA07
Created by
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WHO-ATC |
C09DA07
Created by
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EMA ASSESSMENT REPORTS |
PRITOR (AUTHORIZED: HYPERTENSION)
Created by
admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
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EMA ASSESSMENT REPORTS |
KINZALMONO (AUTHORIZED: HYPERTENSION)
Created by
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EMA ASSESSMENT REPORTS |
TELMISARTAN TEVA PHARMA (AUTHORIZED: HYPERTENSION)
Created by
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NDF-RT |
N0000175561
Created by
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EMA ASSESSMENT REPORTS |
TELMISARTAN TEVA (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
TWYNSTA (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
MICARDISPLUS (AUTHORIZED: HYPERTENSION)
Created by
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NDF-RT |
N0000000070
Created by
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EMA ASSESSMENT REPORTS |
MICARDIS (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
PRITORPLUS (AUTHORIZED: HYPERTENSION)
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Code System | Code | Type | Description | ||
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C084178
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PRIMARY | |||
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TELMISARTAN
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PRIMARY | |||
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Telmisartan
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PRIMARY | |||
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592
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PRIMARY | |||
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M10541
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PRIMARY | Merck Index | ||
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CHEMBL1017
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PRIMARY | |||
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2583
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1643419
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65999
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PRIMARY | |||
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DB00966
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144701-48-4
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PRIMARY | |||
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73494
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U5SYW473RQ
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SUB10874MIG
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144701-48-4
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PRIMARY | |||
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C47746
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7590
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PRIMARY | |||
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7144
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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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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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TARGET -> AGONIST |
SELECTIVE
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT |
only metabolite that has been identified in human plasma and urine
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Probable human carcinogen.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY GENOTOXIC->PARENT |
NDMA is an organic chemical that is in a family of potent carcinogens.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Priority toxic pollutant.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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