Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H16ClN3O3S |
Molecular Weight | 365.835 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1CC2=C(C=CC=C2)N1NC(=O)C3=CC=C(Cl)C(=C3)S(N)(=O)=O
InChI
InChIKey=NDDAHWYSQHTHNT-UHFFFAOYSA-N
InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)
Molecular Formula | C16H16ClN3O3S |
Molecular Weight | 365.835 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00808Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/indapamide.html
Sources: http://www.drugbank.ca/drugs/DB00808
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/indapamide.html
Indapamide is an antihypertensive and a diuretic. It contains both a polar sulfamoyl chlorobenzamide moiety and a lipid- soluble methylindoline moiety. Indapamide blocks the slow component of delayed rectifier potassium current (IKs) without altering the rapid component (IKr) or the inward rectifier current. Specifically it blocks or antagonizes the action the proteins KCNQ1 and KCNE1. Indapamide is also thought to stimulate the synthesis of the vasodilatory hypotensive prostaglandin PGE2. Indapamide is used for the treatment of hypertension, alone or in combination with other antihypertensive drugs, as well as for the treatment of salt and fluid retention associated with congestive heart failure or edema from pregnancy (appropriate only in the management of edema of pathologic origin during pregnancy when clearly needed). Also used for the management of edema as a result of various causes.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1866 Sources: http://www.drugbank.ca/drugs/DB00808 |
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Target ID: CHEMBL4872 Sources: http://www.drugbank.ca/drugs/DB00808 |
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Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
36.0 nM [Ki] | ||
Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
10.0 nM [Ki] | ||
Target ID: CHEMBL2326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
0.23 nM [Ki] | ||
Target ID: CHEMBL1876 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D00345 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Indapamide Approved UseIndapamide tablets are indicated for the treatment of hypertension, alone or in combination with other antihypertensive drugs.
Indapamide tablets are also indicated for the treatment of salt and fluid retention associated with congestive heart failure. Launch Date1998 |
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Primary | Indapamide Approved UseIndapamide tablets are indicated for the treatment of hypertension, alone or in combination with other antihypertensive drugs.
Indapamide tablets are also indicated for the treatment of salt and fluid retention associated with congestive heart failure. Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
260 ng/mL |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
47.79 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23447043 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
919.52 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23447043 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14 h |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
23.23 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23447043 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
INDAPAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: Page: p.261 |
unhealthy, 21 - 73 n = 311 Health Status: unhealthy Condition: Hypertension Age Group: 21 - 73 Sex: M+F Population Size: 311 Sources: Page: p.261 |
Disc. AE: Hypokalemia... AEs leading to discontinuation/dose reduction: Hypokalemia (0.64%) Sources: Page: p.261 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypokalemia | 0.64% Disc. AE |
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: Page: p.261 |
unhealthy, 21 - 73 n = 311 Health Status: unhealthy Condition: Hypertension Age Group: 21 - 73 Sex: M+F Population Size: 311 Sources: Page: p.261 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [IC50 11 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Perindopril/indapamide 2/0.625 mg/day: a review of its place in the management of hypertension. | 2001 |
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Indapamide plus perindopril--simpler treatment, better compliance. | 2001 Apr-May |
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Comparison of spectrophotometric and an LC method for the determination perindopril and indapamide in pharmaceutical formulations. | 2001 Aug |
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Recommendations for the use of low-dose diuretics. | 2001 Aug-Sep |
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Academic support for combination therapy in hypertension. | 2001 Aug-Sep |
|
Progress in reducing the burden of stroke. | 2001 Dec |
|
The lowering of blood pressure after stroke. | 2001 Dec 8 |
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The lowering of blood pressure after stroke. | 2001 Dec 8 |
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The lowering of blood pressure after stroke. | 2001 Dec 8 |
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The lowering of blood pressure after stroke. | 2001 Dec 8 |
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Significant hypertrophy regression with indapamide sustained release 1.5 mg. | 2001 Feb-Mar |
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[PROGRESS Study examines transient cerebral ischemia and stroke patients. Future goal: attaining basic blood pressure control]. | 2001 Jul 5 |
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Effects of combination of low doses of angiotensin-converting enzyme inhibitor and diuretics on renal function in spontaneously hypertensive rats: comparison between acute and chronic treatment. | 2001 Jun |
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Clinical benefit of very-low-dose perindopril-indapamide combination in hypertension. | 2001 Nov |
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Amelioration of arterial properties with a perindopril-indapamide very-low-dose combination. | 2001 Nov |
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[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study]. | 2001 Nov |
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Sodium intake, large artery stiffness, and proteoglycans in the spontaneously hypertensive rat. | 2001 Nov |
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A double-blind trial of perindopril and nitrendipine in incipient diabetic nephropathy. | 2001 Oct |
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Indapamide-induced pemphigus foliaceus. | 2001 Sep |
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Blood pressure and stroke; the PROGRESS trial. | 2001 Sep |
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[Tolerability and efficacy of retard form of indapamide in the treatment of hypertension in elderly patients (results of multicenter open non-comparative trial in Russian program ARGUS)]. | 2002 |
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Effects of antihypertensive therapy on hemorheological profiles in female hypertensive patients with initially low or high whole blood viscosity. | 2002 |
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The effects of the addition of micronised fenofibrate on uric acid metabolism in patients receiving indapamide. | 2002 |
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Cutaneous drug reaction case reports: from the world literature. | 2002 |
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[Efficacy of 12-week monotherapy with arifon-retard of patients with isolated systolic hypertension]. | 2002 |
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[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study]. | 2002 Aug |
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[Indapamide-induced pemphigus foliaceus a sulfurous affair?]. | 2002 Aug-Sep |
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Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study. | 2002 Dec |
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Hypokalaemia and hyponatraemia due to indapamide. | 2002 Dec |
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Very-low-dose combination of the angiotensin-converting enzyme inhibitor perindopril and the diuretic indapamide induces an early and sustained increase in neovascularization in rat ischemic legs. | 2002 Dec |
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Molecular and functional characterization of ERG, KCNQ, and KCNE subtypes in rat stomach smooth muscle. | 2002 Feb |
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The PROGRESS Trial: preventing strokes by lowering blood pressure in patients with cerebral ischemia. Emerging therapies: critique of an important advance. | 2002 Jan |
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Efficacious response with low-dose indapamide therapy in the treatment of type II diabetic patients with normal renal function or moderate renal insufficiency and moderate hypertension. | 2002 Jan-Feb |
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Hyponatraemia and hypokalaemia caused by indapamide. | 2002 Jul 1 |
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Hyponatraemia and hypokalaemia due to indapamide. | 2002 Mar 4 |
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Combined therapy with indapamide and perindopril but not perindopril alone reduced the risk for recurrent stroke. | 2002 Mar-Apr |
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Stroke prevention: management of modifiable vascular risk factors. | 2002 May |
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[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke]. | 2002 May 16 |
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[The challenge to treat hypertensive patients with type 2 diabetes]. | 2002 Oct |
|
[Arterial hypertension in elderly individuals]. | 2002 Oct |
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[Management of hypertensive patients with left ventricular hypertrophy]. | 2002 Oct |
|
Water vapor absorption into amorphous hydrophobic drug/poly(vinylpyrrolidone) dispersions. | 2002 Oct |
|
Drug-induced long QT in isolated rabbit Purkinje fibers: importance of action potential duration, triangulation and early afterdepolarizations. | 2002 Oct 4 |
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Efficacy of very low dose perindopril 2 mg/indapamide 0.625 mg combination on left ventricular hypertrophy in hypertensive patients: the P.I.C.X.E.L. study rationale and design. | 2002 Sep |
|
Drug-drug interactions among elderly patients hospitalized for drug toxicity. | 2003 Apr 2 |
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Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study. | 2003 Jan |
|
Blinded test in isolated female rabbit heart reliably identifies action potential duration prolongation and proarrhythmic drugs: importance of triangulation, reverse use dependence, and instability. | 2003 Jan |
|
[Secondary prevention after ischemic stroke]. | 2003 Jan 29 |
|
Effect of low-dose perindopril/indapamide on albuminuria in diabetes: preterax in albuminuria regression: PREMIER. | 2003 May |
|
Optimization of a solid-phase extraction method for determination of indapamide in biological fluids using high-performance liquid chromatography. | 2003 May 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/indapamide.html
Usual Adult Dose for Edema
Initial dose: 2.5 mg orally once a day.
Usual Adult Dose for Hypertension
Initial dose: 1.25 mg orally once a day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11204436
10(-4) M Indapamide decreased bone resorption in organ cultures and in cocultures of osteoblast-like cells and bone marrow cells in the presence of 10(-8) M 1,25-dihydroxyvitamin D3
Substance Class |
Chemical
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on
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Record UNII |
F089I0511L
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Validated (UNII)
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NCI_THESAURUS |
C49185
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NDF-RT |
N0000175420
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QC03BA11
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C03BA11
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N0000175359
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LIVERTOX |
503
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WHO-ATC |
C09BX01
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C10BX13
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QC09BX01
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1433
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248-012-7
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INDAPAMIDE
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m6245
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D007190
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7203
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F089I0511L
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F089I0511L
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Indapamide
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CHEMBL406
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1338801
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SUB08169MIG
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C29119
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26807-65-8
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DB00808
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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EXCRETED UNCHANGED |
Lozol is an extensively metabolized drug, with only about 7% of the total dose administered,
recovered in the urine as unchanged drug during the first 48 hours after administration.
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
From 71 to 79% of the Lozol in plasma is reversibly bound to plasma
proteins.
REVERSIBLE
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SOLVATE->ANHYDROUS |
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TARGET -> INHIBITOR |
indapamide has both diuretic and vasodilator properties. A low urinary excretion and specific accumulation into arterial smooth muscle of this lipophilic molecule may provide a rationale for this dual activity.
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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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 |
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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 |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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