Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H14F3N3O4S2 |
Molecular Weight | 421.415 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NS(=O)(=O)C1=CC2=C(NC(CC3=CC=CC=C3)NS2(=O)=O)C=C1C(F)(F)F
InChI
InChIKey=HDWIHXWEUNVBIY-UHFFFAOYSA-N
InChI=1S/C15H14F3N3O4S2/c16-15(17,18)10-7-11-13(8-12(10)26(19,22)23)27(24,25)21-14(20-11)6-9-4-2-1-3-5-9/h1-5,7-8,14,20-21H,6H2,(H2,19,22,23)
Molecular Formula | C15H14F3N3O4S2 |
Molecular Weight | 421.415 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Bendroflumethiazide (INN), formerly bendrofluazide (BAN) is a thiazide diuretic used to treat hypertension. CORZIDE (Nadolol and Bendroflumethiazide Tablets) for oral administration combines two antihypertensive agents: CORGARD (nadolol), a nonselective beta-adrenergic blocking agent, and NATURETIN (bendroflumethiazide), a thiazide diuretic-antihypertensive. Bendroflumethiazide works by inhibiting sodium reabsorption at the beginning of the distal convoluted tubule (DCT). Bendroflumethiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like bendroflumethiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of bendroflumethiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. Thiazides do not affect normal blood pressure. Onset of action of thiazides occurs in two hours and the peak effect at about four hours. Duration of action persists for approximately six to 12 hours. Thiazides are eliminated rapidly by the kidney.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3038495 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14766795 |
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Target ID: CHEMBL1876 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10894798 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CORZIDE Approved Useis indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. These benefits have been seen in controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes including the classes to which this drug principally belongs. There are no controlled trials demonstrating risk reduction with CORZIDE. Launch Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.2 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
44.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
15.4 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
147 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
250 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
75 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7056277 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6369882 |
BENDROFLUMETHIAZIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
The effect of spray drying solutions of bendroflumethiazide/polyethylene glycol on the physicochemical properties of the resultant materials. | 2003 Aug 27 |
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Results of the pilot study for the Hypertension in the Very Elderly Trial. | 2003 Dec |
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Dose-effect relations of loop- and thiazide-diuretics on calcium homeostasis: a randomized, double-blinded Latin-square multiple cross-over study in postmenopausal osteopenic women. | 2003 Jan |
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Do pharmaceuticals affect freshwater invertebrates? A study with the cnidarian Hydra vulgaris. | 2003 May |
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The potential savings of using thiazides as the first choice antihypertensive drug: cost-minimisation analysis. | 2003 Sep 8 |
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Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats. | 2004 Apr |
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Effects of furosemide and bendroflumethiazide on saliva flow rate and composition. | 2004 Jul |
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A case of hypertension and hyperkalaemia. | 2004 Jun |
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Paradoxical antidiuretic effect of thiazides in diabetes insipidus: another piece in the puzzle. | 2004 Nov |
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FI-chemiluminometric study of thiazides by on-line photochemical reaction. | 2004 Nov 19 |
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Ongoing clinical trials of the pleiotropic effects of statins. | 2005 |
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Physicochemical evaluation of PVP-thiazide diuretic interactions in co-spray-dried composites--analysis of glass transition composition relationships. | 2005 Apr |
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Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. | 2005 Aug |
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[Prevention of cardiovascular events by the antihypertensive treatment using amlodipine and perindopril in comparison with the use of atenolol and bendroflumethiazide. The ASCOT (Anglo-Scandinavian Outcomes Trail: blood pressure lowering arm) study results--multicentre, randomised, controlled trial. Landmark in the development of opinions on combination therapy in hypertension? (comment)]. | 2005 Dec |
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Does aldosterone-to-renin ratio predict the antihypertensive effect of the aldosterone antagonist spironolactone? | 2005 Dec |
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[Antihypertensive therapy: campaign of the giants]. | 2005 Dec 15 |
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Aldosterone-to-renin ratio, arterial stiffness, and the response to aldosterone antagonism in essential hypertension. | 2005 Jan |
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[Old or new antihypertensives--which are better?]. | 2005 Mar 31 |
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ASCOT blood pressure-lowering arm--study of effects of two BP-lowering regimens in hypertensive patients with cardiovascular risk factors. | 2005 Mar-Apr |
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[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications]. | 2005 May 2 |
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Efficacy and safety of 24 weeks of therapy with bendroflumethiazide 1.25 mg/day or 2.5 mg/day and potassium chloride compared with enalapril 10 mg/day and amlodipine 5 mg/day in patients with mild to moderate primary hypertension : a multicentre, randomised, open study. | 2006 |
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[The most recent study into blood pressure lowering by amlodipine: the beginning of the end for the beta-blockers]. | 2006 Apr 22 |
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High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics. | 2006 Dec |
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Fracture risk and the use of a diuretic (indapamide SR) +/- perindopril: a substudy of the Hypertension in the Very Elderly Trial (HYVET). | 2006 Dec 19 |
|
Synthesis and application of mono-2A-azido-2A-deoxyperphenylcarbamoylated beta-cyclodextrin and mono-2A-azido-2A-deoxyperacetylated beta-cyclodextrin as chiral stationary phases for high-performance liquid chromatography. | 2006 Jan 6 |
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Comparison of the effect of diuretics on carotid blood flow in stroke patients. | 2006 Mar |
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Indirect laser-induced fluorescence detection of diuretics separated by capillary electrophoresis. | 2006 Mar |
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Amlodipine plus perindopril was better than atenolol plus bendroflumethiazide for reducing complications in hypertension. | 2006 Mar-Apr |
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Blunted non-nitric oxide vasodilatory neurotransmission in penile arteries from renal hypertensive rats. | 2006 May |
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Aliskiren--an orally active renin inhibitor. Review of pharmacology, pharmacodynamics, kinetics, and clinical potential in the treatment of hypertension. | 2007 |
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Can combining different risk interventions into a single formulation contribute to improved cardiovascular disease risk reduction? The single pill of amlodipine/atorvastatin. | 2007 |
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Fast quantitative determination of diuretic drugs in tablets and human urine by microchip electrophoresis with native fluorescence detection. | 2007 Aug |
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Low-dose quadruple antihypertensive combination: more efficacious than individual agents--a preliminary report. | 2007 Feb |
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Treatments with losartan or enalapril are equally sensitive to deterioration in renal function from cyclooxygenase inhibition. | 2007 Feb |
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Effects of "newer" and "older" antihypertensive drugs on hemorrheological, platelet, and endothelial factors. A substudy of the Anglo-Scandinavian Cardiac Outcomes Trial. | 2007 Jun |
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Delayed cardiotoxicity in chronic lithium poisoning: discrepancy between serum lithium concentrations and clinical status. | 2007 May |
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[Treating essential hypertension. Are beta blockers still first choice?]. | 2007 May 3 |
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Does the aldosterone:renin ratio predict the efficacy of spironolactone over bendroflumethiazide in hypertension? A clinical trial protocol for RENALDO (RENin-ALDOsterone) study. | 2007 May 9 |
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Hirshfeld surface analysis of two bendroflumethiazide solvates. | 2007 Nov |
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Are patients reliable when self-reporting medication use? Validation of structured drug interviews and home visits by drug analysis and prescription data in acutely hospitalized patients. | 2007 Nov |
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Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds. | 2007 Sep 7 |
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Upregulation of apical sodium-chloride cotransporter and basolateral chloride channels is responsible for the maintenance of salt-sensitive hypertension. | 2008 Aug |
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Economic evaluation of ASCOT-BPLA: antihypertensive treatment with an amlodipine-based regimen is cost effective compared with an atenolol-based regimen. | 2008 Feb |
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[Serious debate on unconventional treatment, thank you]. | 2008 Feb 25 |
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Acute angiotensin II infusions elicit pressure natriuresis in mice and reduce distal fractional sodium reabsorption. | 2008 Jul |
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Burden and rates of treatment and control of cardiovascular disease risk factors in obesity: the Framingham Heart Study. | 2008 Jul |
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Comparison of effects of combined ACE inhibitor and low-dose thiazide diuretic with ACE inhibitor alone on insulin action in patients with hypertension and Type 2 diabetes: a double-blind crossover study. | 2008 May |
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Effective management of hypertension with dihydropyridine calcium channel blocker-based combination therapy in patients at high cardiovascular risk. | 2008 May |
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Acetazolamide prevents vacuolar myopathy in skeletal muscle of K(+) -depleted rats. | 2008 May |
|
LC-high-resolution multiple stage spectrometric analysis of diuretic compounds Unusual mass fragmentation pathways. | 2008 Sep 29 |
Patents
Sample Use Guides
The initial dose of CORZIDE (Nadolol and Bendroflumethiazide Tablets) may therefore be the 40 mg/5 mg tablet once daily. When the antihypertensive response is not satisfactory, the dose may be increased by administering the 80 mg/5 mg tablet once daily. When necessary, another antihypertensive agent may be added gradually beginning with 50 percent of the usual recommended starting dose to avoid an excessive fall in blood pressure.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8866635
Incubation in vitro of human recombinant and erythrocyte (RBC) thiopurine methyl transferase (TPMT) with furosemide, bendroflumethiazide and trichlormethiazide demonstrated inhibition of both enzyme preparations, with IC50 values of 170 microM, 360 microM and 1 mM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:51:15 GMT 2023
by
admin
on
Sat Dec 16 17:51:15 GMT 2023
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Record UNII |
5Q52X6ICJI
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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 |
N0000175359
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NCI_THESAURUS |
C49185
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WHO-VATC |
QC03EA13
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NDF-RT |
N0000166469
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WHO-ATC |
C03EA13
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NDF-RT |
N0000175419
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N0000166469
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LIVERTOX |
95
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QC03AA01
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C03AA01
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QC03AB01
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C03AB01
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7122
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73-48-3
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3293
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C47410
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200-800-1
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SUB20550
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CHEMBL1684
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m2309
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1049000
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2315
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D001539
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BENDROFLUMETHIAZIDE
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SUB05711MIG
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1369
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3013
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305
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Bendroflumethiazide
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DTXSID5022647
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758229
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5Q52X6ICJI
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TARGET -> INHIBITOR |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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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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