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 |
---|---|---|---|
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 |
---|---|---|
Oxalate nephrocalcinosis in renal tubular dysgenesis. | 1999 Nov |
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Persistent nephrocalcinosis for acetazolamide and furosemide in a pediatric patient. | 2000 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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The loop diuretic torasemide interferes with endothelin-1 actions in the aorta of hypertensive rats. | 2001 |
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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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Furosemide-probenecid interaction as a laboratory exercise for undergraduate education in clinical pharmacology. | 2001 Apr |
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Chronic tubulointerstitial nephritis and distal renal tubular acidosis in a patient with frusemide abuse. | 2001 Apr |
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Renal interstitial atp responses to changes in arterial pressure during alterations in tubuloglomerular feedback activity. | 2001 Feb |
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Brown Norway chromosome 13 confers protection from high salt to consomic Dahl S rat. | 2001 Feb |
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Effect of furosemide on renal excretion of oxypurinol and purine bases. | 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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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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Acute congestive heart failure associated with a limited form of systemic sclerosis and primary biliary cirrhosis. | 2001 Jan |
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Furosemide stimulates macula densa cyclooxygenase-2 expression in rats. | 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 intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2. | 2001 Jul 27 |
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The effects of enalapril-digoxin-diuretic combination therapy on nutritional and anthropometric indices in chronic congestive heart failure: preliminary findings in cardiac cachexia. | 2001 Jun |
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Urolithiasis in the low birth weight infant: the role and efficacy of extracorporeal shock wave lithotripsy. | 2001 Jun |
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Angiotensin converting enzyme inhibition worsens the excretory phase of diuretic renography for obstructive hydronephrosis. | 2001 Jun |
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Supranormal differential renal function is real but may be pathological: assessment by 99m technetium mercaptoacetyltriglycine renal scan of congenital unilateral hydronephrosis. | 2001 Jun |
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Dynamic characteristics and underlying mechanisms of renal blood flow autoregulation in the conscious dog. | 2001 Jun |
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Perturbation of the pump-leak balance for Na(+) and K(+) in malaria-infected erythrocytes. | 2001 Jun |
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Pediatric renal transplantation: anesthesia and perioperative complications. | 2001 Mar |
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The appropriateness of drug use in an older nondemented and demented population. | 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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Optical imaging reveals cation--Cl(-) cotransporter-mediated transient rapid decrease in intracellular Cl(-) concentration induced by oxygen--glucose deprivation in rat neocortical slices. | 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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Role of diuretics in the preservation of residual renal function in patients on continuous ambulatory peritoneal dialysis. | 2001 Mar |
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Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum. | 2001 May |
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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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Long-term treatment of patients with inappropriate secretion of antidiuretic hormone by the vasopressin receptor antagonist conivaptan, urea, or furosemide. | 2001 May |
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Nephrocalcinosis induced by furosemide in an adult patient with incomplete renal tubular acidosis. | 2001 May |
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Effects of albumin/furosemide mixtures on responses to furosemide in hypoalbuminemic patients. | 2001 May |
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Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. | 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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Fatal portal hypertension, liver failure, and mitochondrial dysfunction after HIV-1 nucleoside analogue-induced hepatitis and lactic acidaemia. | 2001 May 5 |
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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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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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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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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7LXU5N7ZO5
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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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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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