Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H11ClN2O5S |
Molecular Weight | 330.744 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NS(=O)(=O)C1=CC(C(O)=O)=C(NCC2=CC=CO2)C=C1Cl
InChI
InChIKey=ZZUFCTLCJUWOSV-UHFFFAOYSA-N
InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
Molecular Formula | C12H11ClN2O5S |
Molecular Weight | 330.744 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00695Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/furosemide.html
Sources: http://www.drugbank.ca/drugs/DB00695
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/furosemide.html
Furosemide, a sulfonamide-type loop diuretic structurally related to bumetanide, is used to manage hypertension and edema associated with congestive heart failure, cirrhosis, and renal disease, including the nephrotic syndrome. Furosemide inhibits water reabsorption in the nephron by blocking the sodium-potassium-chloride cotransporter (NKCC2) in the thick ascending limb of the loop of Henle. This is achieved through competitive inhibition at the chloride binding site on the cotransporter, thus preventing the transport of sodium from the lumen of the loop of Henle into the basolateral interstitium. Consequently, the lumen becomes more hypertonic while the interstitium becomes less hypertonic, which in turn diminishes the osmotic gradient for water reabsorption throughout the nephron. Because the thick ascending limb is responsible for 25% of sodium reabsorption in the nephron, furosemide is a very potent diuretic. Furosemide is sold under the brand name Lasix among others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15356425
Curator's Comment: furosemide did not cross the barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1874 Sources: http://www.drugbank.ca/drugs/DB00695 |
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Target ID: P05370 Gene ID: 24377.0 Gene Symbol: G6pdx Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.13 mM [IC50] | ||
Target ID: P85968 Gene ID: 1.00360176E8 Gene Symbol: Pgd Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.14 mM [IC50] | ||
Target ID: CHEMBL3286088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.08 mM [IC50] | ||
Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10713865 |
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Target ID: CHEMBL3510 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
52.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LASIX Approved UseEdema
Furosemide is indicated in adults and pediatric patients for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Furosemide is particularly useful when an agent with greater diuretic potential is desired.
Hypertension
Oral Furosemide may be used in adults for the treatment of hypertension alone or in combination with other antihypertensive agents. Launch Date-1.10678401E11 |
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Primary | LASIX Approved UseEdema
Furosemide is indicated in adults and pediatric patients for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Furosemide is particularly useful when an agent with greater diuretic potential is desired.
Hypertension
Oral Furosemide may be used in adults for the treatment of hypertension alone or in combination with other antihypertensive agents. Launch Date-1.10678401E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1315.34 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3014.77 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.2% |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
major | |||
Page: 9.0 |
major | yes (co-administration study) Comment: probe drug substrate for renal transporters OAT1 and OAT3; clinical investigation of a probe drug cocktail containing substrates of key drug transporters (digoxin, furosemide, metformin and rosuvastatin) Page: 9.0 |
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Page: 9.0 |
major | yes (co-administration study) Comment: probe drug substrate for renal transporters OAT1 and OAT3; clinical investigation of a probe drug cocktail containing substrates of key drug transporters (digoxin, furosemide, metformin and rosuvastatin) Page: 9.0 |
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Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Page: 6.0 |
yes | |||
Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19126296/ Page: 1.0 |
yes | yes (co-administration study) Comment: The time-averaged non-renal clearance (CLNR) of furosemide tended to be faster (but not significantly so) among smokers (3-methylcholanthrene (3-MC) type; a main inducer of CYP1A1/2 Sources: https://pubmed.ncbi.nlm.nih.gov/19126296/ Page: 1.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15950494/ Page: 8.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Permanent deafness associated with furosemide administration. | 1975 Jan-Feb |
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[Hypokalemic paralysis in furosemide therapy and simultaneous laxative abuse]. | 1999 Jul 15 |
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Acetazolamide and furosemide for posthemorrhagic hydrocephalus of the newborn. | 1999 Mar |
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Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
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[A case of pulmonary tuberculosis with acute renal failure caused by readministration of rifampicin]. | 1999 Nov |
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Influence of the M235T polymorphism of human angiotensinogen (AGT) on plasma AGT and renin concentrations after ethinylestradiol administration. | 2000 Nov |
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Endogenous bradykinin and the renin and pressor responses to furosemide in humans. | 2000 Nov |
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The loop diuretic torasemide interferes with endothelin-1 actions in the aorta of hypertensive rats. | 2001 |
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Diuretic-enhanced gadolinium excretory MR urography: comparison of conventional gradient-echo sequences and echo-planar imaging. | 2001 |
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Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. Frusemide or nitrates in acute left ventricular failure. | 2001 Jan |
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Self-retaining aural speculum: a valuable aid to middle-ear surgery. | 2001 Jan |
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10% hydroxyethyl starch for plasma expansion in the treatment of severe ovarian hyperstimulation syndrome. A case report. | 2001 Jan |
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Acute congestive heart failure associated with a limited form of systemic sclerosis and primary biliary cirrhosis. | 2001 Jan |
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[Life threatening hypercalcemia in a young man with ALL]. | 2001 Jan 5 |
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Pamidronate and calcitonin as therapy of acute cancer-related hypercalcemia in children. | 2001 Jan-Feb |
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The appropriateness of drug use in an older nondemented and demented population. | 2001 Mar |
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Statistical evaluation of the regulatory guidelines for use of furosemide in race horses. | 2001 Mar |
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Intraplatelet calcium levels in patients with acute renal failure before and after the administration of loop diuretics. | 2001 Mar |
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[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus]. | 2001 Mar 20 |
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Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. | 2001 May |
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Heterogeneous susceptibility of GABA(A) receptor-mediated IPSCs to depolarization-induced suppression of inhibition in rat hippocampus. | 2001 May 1 |
Patents
Sample Use Guides
The usual initial dose of LASIX is 20 to 80 mg given as a single dose. Ordinarily a prompt diuresis ensues. If needed, the same dose can be administered 6 to 8 hours later or the dose may be increased. The dose may be raised by 20 or 40 mg and given not sooner than 6 to 8 hours after the previous dose until the desired diuretic effect has been obtained. The individually determined single dose should then be given once or twice daily (eg, at 8 am and 2 pm). The dose of LASIX may be carefully titrated up to 600 mg/day in patients with clinically severe edematous states.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10619350
There was a significant reduction in levels of TNF-alpha and IL-6 at a furosemide concentration of 0.5 x 10(-2) M and a reduction in IL-8 levels at 10(-2) M in human peripheral blood mononuclear cells.
Substance Class |
Chemical
Created
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on
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Wed Jul 05 22:39:38 UTC 2023
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Record UNII |
7LXU5N7ZO5
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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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WHO-ESSENTIAL MEDICINES LIST |
12.4
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CFR |
21 CFR 522.1010
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NDF-RT |
N0000175590
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WHO-VATC |
QC03CB01
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WHO-ATC |
C03EB01
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LIVERTOX |
445
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NCI_THESAURUS |
C49184
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WHO-VATC |
QC03EB01
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WHO-ESSENTIAL MEDICINES LIST |
16
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WHO-ATC |
C03CA01
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NDF-RT |
N0000175366
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WHO-ATC |
C03CB01
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CFR |
21 CFR 520.1010
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WHO-VATC |
QC03CA01
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Code System | Code | Type | Description | ||
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4839
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CHEMBL35
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PRIMARY | |||
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4603
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PRIMARY | RxNorm | ||
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FUROSEMIDE
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PRIMARY | |||
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47426
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7LXU5N7ZO5
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D005665
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200-203-6
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269420
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1287008
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DTXSID6020648
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DB00695
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M5608
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PRIMARY | Merck Index | ||
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100000090317
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PRIMARY | |||
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FUROSEMIDE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 75 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Diuretic. Storage: Furosemide should be kept in a well-closed container, protected from light. Definition: Furosemide contains not less than 98.0% and not more than 101.0% of C12H11ClN2O5S, calculated with reference to the dried substance. | ||
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54-31-9
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C515
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Furosemide
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3086
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3440
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7LXU5N7ZO5
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1584
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1258
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SUB07849MIG
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
POTENCY
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 2.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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Tmax | PHARMACOKINETIC |
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ORAL SOLUTION PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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