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 Date1966 |
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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 Date1966 |
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 |
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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 |
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Permanent deafness associated with furosemide administration. | 1975 Jan-Feb |
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Nephrotic syndrome and acute interstitial nephritis associated with the use of diclofenac. | 1999 Jul 9 |
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Acute interstitial nephritis induced by crack cocaine binge. | 1999 May |
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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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Activation of renal afferent pathways following furosemide treatment. I. Effects Of survival time and renal denervation. | 2000 Apr 10 |
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Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. | 2000 Feb 11 |
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Effects of the V(2)-receptor antagonist OPC-41061 and the loop diuretic furosemide alone and in combination in rats. | 2000 Jan |
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Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4. | 2000 Sep 29 |
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Effects of loop diuretics on angiotensin II-stimulated vascular smooth muscle cell growth. | 2001 |
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Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy. | 2001 |
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Release of furosemide from multiple-unit and single-unit preparations containing different viscosity grades of sodium alginate. | 2001 |
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Improvement in site-specific intestinal absorption of furosemide by Eudragit L100-55. | 2001 Apr |
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Acute effects of the anti-inflammatory cyclooxygenase-2 selective inhibitor, flosulide, on renal plasma flow and glomerular filtration rate in rats. | 2001 Apr |
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Pressure-independent enhancement of cardiac hypertrophy in natriuretic peptide receptor A-deficient mice. | 2001 Apr |
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Brown Norway chromosome 13 confers protection from high salt to consomic Dahl S rat. | 2001 Feb |
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Mechanisms of chloride transport in thymic lymphocytes. | 2001 Feb |
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Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. | 2001 Feb |
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Congestive heart failure associated with myxomatous degeneration of the left atrioventricular valve in a parakeet. | 2001 Feb 1 |
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Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells. | 2001 Feb 23 |
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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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Fluorodeoxyglucose positron emission tomography studies in diagnosis and staging of clinically organ-confined prostate cancer. | 2001 Jan |
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Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols. | 2001 Jan |
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Furosemide stimulates macula densa cyclooxygenase-2 expression in rats. | 2001 Jan |
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Renal follow up of premature infants with and without perinatal indomethacin exposure. | 2001 Jan |
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Effects of PMCA2 mutation on DPOAE amplitudes and latencies in deafwaddler mice. | 2001 Jan |
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[Rhabdomyolysis as a rare complication of theophylline poisoning]. | 2001 Jan 15 |
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Angiotensin converting enzyme inhibition worsens the excretory phase of diuretic renography for obstructive hydronephrosis. | 2001 Jun |
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Multi-slice CT urography after diuretic injection: initial results. | 2001 Mar |
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Humoral hypercalcemia of malignancy in squamous cell carcinoma of the skin: parathyroid hormone--related protein as a cause. | 2001 Mar |
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Estimation of the probability for exceeding a threshold concentration of furosemide at various intervals after intravenous administration in horses. | 2001 Mar |
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Aggressive diuresis for severe heart failure in the elderly. | 2001 Mar |
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Effects of inhalation of albuterol sulphate, ipratroprium bromide and frusemide on breathing mechanics and gas exchange in healthy exercising horses. | 2001 May |
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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 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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Record UNII |
7LXU5N7ZO5
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Record Status |
Validated (UNII)
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Record Version |
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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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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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4839
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CHEMBL35
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4603
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PRIMARY | RxNorm | ||
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FUROSEMIDE
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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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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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SUB07849MIG
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
POTENCY
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TRANSPORTER -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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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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TRANSPORTER -> INHIBITOR | |||
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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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TRANSPORTER -> INHIBITOR |
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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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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