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 |
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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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Acetazolamide and furosemide for posthemorrhagic hydrocephalus of the newborn. | 1999 Mar |
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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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Co-administration of furosemide augments tacrolimus-induced impairment in kidney function in rats. | 2000 |
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Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4. | 2000 Sep 29 |
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The loop diuretic torasemide interferes with endothelin-1 actions in the aorta of hypertensive rats. | 2001 |
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Maxi K+ channels co-localised with CFTR in the apical membrane of an exocrine gland acinus: possible involvement in secretion. | 2001 Apr |
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Effect of salicis cortex extract on human platelet aggregation. | 2001 Apr |
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Improvement in site-specific intestinal absorption of furosemide by Eudragit L100-55. | 2001 Apr |
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Aspirin inhibits the acute venodilator response to furosemide in patients with chronic heart failure. | 2001 Apr |
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ATP stimulates calcium-dependent glutamate release from cultured astrocytes. | 2001 Apr |
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Systemic sclerosis (scleroderma). A case of recovery of cardiomyopathy after vitamin E treatment. | 2001 Apr |
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Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo). | 2001 Apr 13 |
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Hyponatremia and sensorineural hearing loss in preterm infants. | 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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Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols. | 2001 Jan |
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[Rhabdomyolysis as a rare complication of theophylline poisoning]. | 2001 Jan 15 |
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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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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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Long-term efficacy of torsemide compared with frusemide in cirrhotic patients with ascites. | 2001 Mar |
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Homogeneous enzyme immunoassay for triiodothyronine in serum. | 2001 Mar |
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[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus]. | 2001 Mar 20 |
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Natriuresis and "dilutional" hyponatremia after infusion of glycine 1.5%. | 2001 May |
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Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum. | 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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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Interaction of serotonin and cholecystokinin in the lateral parabrachial nucleus to control sodium intake. | 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
by
admin
on
Edited
Fri Dec 16 16:15:56 UTC 2022
by
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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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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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PRIMARY | |||
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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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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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TRANSPORTER -> INHIBITOR |
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TARGET -> INHIBITOR |
POTENCY
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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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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TRANSPORTER -> INHIBITOR | |||
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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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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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