Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H28ClN3O5S |
Molecular Weight | 494.0054 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1ccc(cc1C(=NCCc2ccc(cc2)S(=O)(=O)NC(=NC3CCCCC3)O)O)Cl
InChI
InChIKey=ZNNLBTZKUZBEKO-UHFFFAOYSA-N
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
Molecular Formula | C23H28ClN3O5S |
Molecular Weight | 494.0054 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01016Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017532Orig1s034lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01016
Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017532Orig1s034lbl.pdf
Glyburide, a second-generation sulfonylurea antidiabetic agent, lowers blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. With chronic administration in Type II diabetic patients, the blood glucose lowering effect persists despite a gradual decline in the insulin secretory response to the drug. Extrapancreatic effects may be involved in the mechanism of action of oral sulfonyl-urea hypoglycemic drugs. The combination of glibenclamide and metformin may have a synergistic effect, since both agents act to improve glucose tolerance by different but complementary mechanisms. In addition to its blood glucose lowering actions, glyburide produces a mild diuresis by enhancement of renal free water clearance. Glyburide is twice as potent as the related second-generation agent glipizide. Sulfonylureas such as glyburide bind to ATP-sensitive potassium channels on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin. Glyburide is indicated as an adjunct to diet to lower the blood glucose in patients with NIDDM whose hyperglycemia cannot be satisfactorily controlled by diet alone. Glyburide is available as a generic, is manufactured by many pharmaceutical companies and is sold in doses of 1.25, 2.5 and 5 mg under many brand names including Gliben-J, Daonil, Diabeta, Euglucon, Gilemal, Glidanil, Glybovin, Glynase, Maninil, Micronase and Semi-Daonil. It is also available in a fixed-dose combination drug with metformin that is sold under various trade names, e.g. Bagomet Plus, Benimet, Glibomet, Gluconorm, Glucored, Glucovance, Metglib and many others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26225433
Curator's Comment:: Weak penetration in rodents was shown. Glyburide reaches the central nervous system when given systemically, is rapidly removed across the BBB when given intracranioventricularly, and any Glyburide that does enter (and is below detection limit) is insufficient to influence neuronal function
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11716850 |
7.1 nM [IC50] | ||
Target ID: CHEMBL3244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294453 |
5.2 nM [IC50] | ||
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163 |
2.4 µM [Ki] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163 |
42.5 µM [Ki] | ||
Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11032738 |
20.0 µM [IC50] | ||
Target ID: CHEMBL2096972 Sources: http://www.genome.jp/dbget-bin/www_bget?D00336 |
4.3 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Diaßeta Approved UseDiaßeta is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date4.52131193E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
91.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
323.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult n = 23 Health Status: unhealthy Condition: diabetes Age Group: adult Sex: M+F Population Size: 23 Sources: |
|
5 mg 1 times / day multiple, oral (median) Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, mean age 32.8 years n = 236 Health Status: unhealthy Condition: gestational diabetes mellitus Age Group: mean age 32.8 years Sex: F Population Size: 236 Sources: |
Disc. AE: Hypoglycemia... AEs leading to discontinuation/dose reduction: Hypoglycemia (5%) Sources: |
2.5 mg 1 times / day steady, oral (starting) Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: |
unhealthy|pregnant n = 189 Health Status: unhealthy|pregnant Condition: Mild Gestational Diabetes Sex: F Population Size: 189 Sources: |
Other AEs: Facial swelling... Other AEs: Facial swelling (serious, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoglycemia | 5% Disc. AE |
5 mg 1 times / day multiple, oral (median) Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, mean age 32.8 years n = 236 Health Status: unhealthy Condition: gestational diabetes mellitus Age Group: mean age 32.8 years Sex: F Population Size: 236 Sources: |
Facial swelling | serious, 1 patient | 2.5 mg 1 times / day steady, oral (starting) Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: |
unhealthy|pregnant n = 189 Health Status: unhealthy|pregnant Condition: Mild Gestational Diabetes Sex: F Population Size: 189 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
weak [IC50 90 uM] | weak (co-administration study) Comment: Glyburide reduced the mean AUCτ of bosentan and the phenol, hydroxy, and hydroxy-phenol metabolites 29%, 26%, 25%, and 22% (all P < .05), respectively Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
yes [IC50 11.3 uM] | weak (co-administration study) Comment: Glyburide reduced the mean AUCτ of bosentan and the phenol, hydroxy, and hydroxy-phenol metabolites 29%, 26%, 25%, and 22% (all P < .05), respectively Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
||
yes [IC50 15 uM] | ||||
yes [IC50 18.8 uM] | ||||
yes [IC50 199 uM] | ||||
yes [Ki 0.75 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Page: 5.0 |
|||
minor | ||||
minor | yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Page: 5.0 |
|||
no | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Glibenclamide induced chronic cholestasis simulating primary biliary cirrhosis: a case report. | 1996 Mar |
|
Glyburide-ciprofloxacin interaction with resistant hypoglycemia. | 2000 Aug |
|
Diflubenzuron, a benzoyl-urea insecticide, is a potent inhibitor of TCDD-induced CYP1A1 expression in HepG2 cells. | 2000 May 1 |
|
Drug interaction: omeprazole and phenprocoumon. | 2001 |
|
Role of pertussis toxin-sensitive G-proteins in intracellular Ca2+ release and apoptosis induced by inhibiting cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channels in HepG2 human hepatoblastoma cells. | 2001 |
|
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions. | 2001 Apr |
|
Levosimendan increases diastolic coronary flow in isolated guinea-pig heart by opening ATP-sensitive potassium channels. | 2001 Apr |
|
Effects of bezafibrate on insulin sensitivity and insulin secretion in non-obese Japanese type 2 diabetic patients. | 2001 Apr |
|
Troglitazone prevents the rise in visceral adiposity and improves fatty liver associated with sulfonylurea therapy--a randomized controlled trial. | 2001 Apr |
|
Protein kinase C isoform-dependent modulation of ATP-sensitive K+ channels during reoxygenation in guinea-pig ventricular myocytes. | 2001 Apr 1 |
|
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels. | 2001 Apr 17 |
|
Effects of phosphodiesterase inhibitors on hypoxic pulmonary vasoconstriction. Influence of K(+) channels and nitric oxide. | 2001 Apr 6 |
|
Changes in cell volume induced by activation of the cyclic amp-dependent chloride channel in guinea-pig cardiac myocytes. | 2001 Feb |
|
The sulphonylurea glibenclamide inhibits multidrug resistance protein (MRP1) activity in human lung cancer cells. | 2001 Feb |
|
K(ATP)(+) channels, nitric oxide, and adenosine are not required for local metabolic coronary vasodilation. | 2001 Feb |
|
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection. | 2001 Feb |
|
Altered effects of potassium channel modulation in the coronary circulation in experimental hypercholesterolemia. | 2001 Feb 1 |
|
Potassium ions as vasodilators: role of inward rectifier potassium channels. | 2001 Feb 2 |
|
[Gestational diabetes: an alternative to insulin therapy?]. | 2001 Feb 3 |
|
Effect of glibenclamide in gabapentin antinociception. | 2001 Jan |
|
Verapamil prevents stretch-induced shortening of atrial effective refractory period in langendorff-perfused rabbit heart. | 2001 Jan |
|
Experimental leishmaniasis: synergistic effect of ion channel blockers and interferon-gamma on the clearance of Leishmania major by macrophages. | 2001 Jan |
|
Near-normoglycaemic remission in African-Americans with Type 2 diabetes mellitus is associated with recovery of beta cell function. | 2001 Jan |
|
Three types of K(+) currents in murine osteocyte-like cells (MLO-Y4). | 2001 Jan |
|
In vivo evidence for K(Ca) channel opening properties of acetazolamide in the human vasculature. | 2001 Jan |
|
Involvement of Ca2+ -activated K+ channels in ginsenosides-induced aortic relaxation in rats. | 2001 Jan |
|
Adenosine A1 receptor activation reduces reactive oxygen species and attenuates stunning in ventricular myocytes. | 2001 Jan |
|
Cause of high variability in drug dissolution testing and its impact on setting tolerances. | 2001 Jan |
|
Intrahippocampal infusions of k-atp channel modulators influence spontaneous alternation performance: relationships to acetylcholine release in the hippocampus. | 2001 Jan 15 |
|
ATP-binding cassette transporter A1 (ABCA1) functions as a cholesterol efflux regulatory protein. | 2001 Jun 29 |
|
Hypoglycemic and antihyperglycemic activity of Syzygium alternifolium (Wt.) Walp. seed extracts in normal and diabetic rats. | 2001 Mar |
|
Hemodynamic, metabolic and hormonal responses to oral glibenclamide in patients with cirrhosis receiving glucose. | 2001 Mar |
|
The role of K+ATP channels in the control of pre- and post-ischemic left ventricular developed pressure in septic rat hearts. | 2001 Mar |
|
Improvement of glycemic control by 1 year of insulin therapy leads to a sustained decrease in sE-selectin concentrations in type 2 diabetes. | 2001 Mar |
|
Inhibitory effects of nicorandil on rat mesangial cell proliferation via the protein kinase G pathway. | 2001 Mar |
|
HNS-32, a novel azulene-1-carboxamidine derivative, inhibits nifedipine-sensitive and -insensitive contraction of the isolated rabbit aorta. | 2001 Mar |
|
Effect of Aloe vera leaves on blood glucose level in type I and type II diabetic rat models. | 2001 Mar |
|
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors. | 2001 Mar |
|
Mechanism of CGRP-induced relaxation in rat intramural coronary arteries. | 2001 Mar |
|
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel. | 2001 Mar |
|
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata. | 2001 Mar |
|
Concentration of the complement activation product, acylation-stimulating protein, is related to C-reactive protein in patients with type 2 diabetes. | 2001 Mar |
|
Multiple Ca(2+)-dependent modulators mediate alkalosis-induced vasodilation in newborn piglet lungs. | 2001 Mar |
|
Regulation of an outwardly rectifying chloride conductance in renal epithelial cells by external and internal calcium. | 2001 Mar 1 |
|
Gramicidin-perforated patch analysis on HCO3- secretion through a forskolin-activated anion channel in rat parotid intralobular duct cells. | 2001 Mar 1 |
|
Nicorandil--induced ATP release in endothelial cells of rat caudal artery is associated with increase in intracellular Ca(2+). | 2001 Mar 30 |
|
Functional roles of cardiac and vascular ATP-sensitive potassium channels clarified by Kir6.2-knockout mice. | 2001 Mar 30 |
|
Characteristics of pancreatic beta-cell secretion in Type 2 diabetic patients treated with gliclazide and glibenclamide. | 2001 May |
|
Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. | 2001 May |
|
Phospholipids as modulators of K(ATP) channels: distinct mechanisms for control of sensitivity to sulphonylureas, K(+) channel openers, and ATP. | 2001 May |
Sample Use Guides
The usual starting dose is 2.5 to 5 mg daily, administered
with breakfast or the first main meal. Those patients who may be more sensitive to hypoglycemic drugs should be started at 1.25 mg daily. The usual maintenance dose is in the range of 1.25 to 20 mg daily, which may be given as a single dose or in divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22399138
Inhibition of ABCA1 by glibenclamide (Glyburide) has been reported to
occur in the concentration range of 100 to 1,000 uM
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:00:37 UTC 2021
by
admin
on
Fri Jun 25 21:00:37 UTC 2021
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Record UNII |
SX6K58TVWC
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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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NDF-RT |
N0000008054
Created by
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NDF-RT |
N0000008054
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FDA ORPHAN DRUG |
502615
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FDA ORPHAN DRUG |
518816
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LIVERTOX |
463
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WHO-VATC |
QA10BB01
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NDF-RT |
N0000175608
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FDA ORPHAN DRUG |
539316
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NDF-RT |
N0000008054
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FDA ORPHAN DRUG |
491215
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WHO-ESSENTIAL MEDICINES LIST |
18.5
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EU-Orphan Drug |
EU/3/15/1589
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NCI_THESAURUS |
C97936
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WHO-ATC |
A10BB01
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Code System | Code | Type | Description | ||
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SUB07916MIG
Created by
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PRIMARY | |||
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2386
Created by
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PRIMARY | |||
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GLYBURIDE
Created by
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water and ether R; slightly soluble in ethanol (~750 g/l) TS and methanol R. Category: Antidiabetic agent. Storage: Glibenclamide should be kept in a well-closed container. Definition: Glibenclamide contains not less than 98.5% and not more than 101.0% of C23H28ClN3O5S, calculated with reference to the dried substance. | ||
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1314
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PRIMARY | |||
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M5784
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PRIMARY | Merck Index | ||
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1295505
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PRIMARY | USP-RS | ||
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Glyburide
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PRIMARY | |||
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3488
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PRIMARY | |||
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10238-21-8
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PRIMARY | |||
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SX6K58TVWC
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PRIMARY | |||
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233-570-6
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PRIMARY | |||
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D005905
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PRIMARY | |||
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2414
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PRIMARY | |||
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GLIBENCLAMIDE
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PRIMARY | |||
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DB01016
Created by
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PRIMARY | |||
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4815
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PRIMARY | RxNorm | ||
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10238-21-8
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PRIMARY | |||
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C29076
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PRIMARY | |||
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CHEMBL472
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PRIMARY |
Related Record | Type | Details | ||
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PARENT->INNOVATOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
1/400 as active as the parent in rat
URINE
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METABOLITE -> PARENT |
1/40 as active as the parent in rat
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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