Details
Stereochemistry | ACHIRAL |
Molecular Formula | C33H30N4O2 |
Molecular Weight | 514.6169 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1=NC2=C(C)C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(O)=O)C5=NC6=C(C=CC=C6)N5C
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 | 514.6169 |
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 |
|
[Angiotensin receptor blockers--significance for the therapy of hypertension]. | 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 |
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Renal effects of angiotensin II receptor antagonists. | 2001 |
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Study at up to 700 sites will build on landmark HOPE trial. | 2001 Apr-May |
|
Combination treatment with telmisartan and hydrochlorothiazide in black patients with mild to moderate hypertension. | 2001 Jan |
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Effect of telmisartan on angiotensin II-mediated collagen gel contraction by adult rat cardiac fibroblasts. | 2001 Jul |
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AT1 receptor antagonist telmisartan administered peripherally inhibits central responses to angiotensin II in conscious rats. | 2001 Jul |
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Comparative antihypertensive and renoprotective effects of telmisartan and lisinopril after long-term treatment in hypertensive diabetic rats. | 2001 Mar |
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[Hypotensive effects of telmisartan on blood pressure during rest and exercise in patients with mild and moderate arterial hypertension]. | 2002 |
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Telmisartan. BIBR 277, Micardis, Pritor. | 2002 |
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Can angiotensin receptor antagonists be used safely in patients with previous ACE inhibitor-induced angioedema? | 2002 |
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Gateways to clinical trials. | 2002 Dec |
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The 24-hour blood pressure pattern: does it have implications for morbidity and mortality? | 2002 Jan 24 |
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From the HOPE to the ONTARGET and the TRANSCEND studies: challenges in improving prognosis. | 2002 Jan 24 |
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Angiotensin II and trials of cardiovascular outcomes. | 2002 Jan 24 |
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Comparative effects of telmisartan in the treatment of hypertension. | 2002 Jul-Aug |
|
Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
A multicenter, open-label study of the efficacy and safety of telmisartan in mild to moderate hypertensive patients. | 2002 Oct |
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The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension. | 2002 Sep |
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Experimental design approach for the optimisation of a HPLC-fluorimetric method for the quantitation of the angiotensin II receptor antagonist telmisartan in urine. | 2003 Aug 8 |
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Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis. | 2003 Feb 26 |
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Angiotensin II receptor blockade: is there truly a benefit of adding an ACE inhibitor? | 2003 Jan |
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Comparison of telmisartan versus losartan: meta-analysis of titration-to-response studies. | 2003 Jun |
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Angioedema induced by angiotensin II blocker telmisartan. | 2003 May |
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How cost-effective are new preventive strategies for cardiovascular disease? | 2003 May 22 |
|
[Diurnal blood pressure control in the optimal treatment of hypertension]. | 2003 May 4 |
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 Dec 16 17:27:16 UTC 2022
by
admin
on
Fri Dec 16 17:27:16 UTC 2022
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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 |
NBK548042
Created by
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EMA ASSESSMENT REPORTS |
TELMISARTAN ACTAVIS (AUTHORIZED: HYPERTENSION)
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WHO-VATC |
QC09DA07
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EMA ASSESSMENT REPORTS |
KINZALKOMB (AUTHORIZED: HYPERTENSION)
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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]
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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)
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WHO-ATC |
C09CA07
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WHO-ATC |
C09DA07
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EMA ASSESSMENT REPORTS |
PRITOR (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
KINZALMONO (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
TELMISARTAN TEVA PHARMA (AUTHORIZED: HYPERTENSION)
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NDF-RT |
N0000175561
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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)
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NDF-RT |
N0000000070
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EMA ASSESSMENT REPORTS |
MICARDIS (AUTHORIZED: HYPERTENSION)
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EMA ASSESSMENT REPORTS |
PRITORPLUS (AUTHORIZED: HYPERTENSION)
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C084178
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TELMISARTAN
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Telmisartan
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II-75
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U5SYW473RQ
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592
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1643419
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M10541
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CHEMBL1017
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2583
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65999
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DB00966
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144701-48-4
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73494
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9434
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U5SYW473RQ
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SUB10874MIG
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DTXSID8023636
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C47746
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7590
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7144
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TRANSPORTER -> INHIBITOR |
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> AGONIST |
SELECTIVE
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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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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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