Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H19N3O3S |
Molecular Weight | 357.427 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C3=CC=CC=N3
InChI
InChIKey=YASAKCUCGLMORW-UHFFFAOYSA-N
InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)
Molecular Formula | C18H19N3O3S |
Molecular Weight | 357.427 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/rosiglitazone.html
http://www.rxlist.com/avandia-drug.htm
http://www.wikidoc.org/index.php/Rosiglitazone
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/rosiglitazone.html
http://www.rxlist.com/avandia-drug.htm
http://www.wikidoc.org/index.php/Rosiglitazone
Rosiglitazone acts as a highly selective and potent agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. It is FDA approved for the treatment of as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Inhibitors of CYP2C8 (e.g., gemfibrozil) may increase rosiglitazone levels; inducers of CYP2C8 (e.g., rifampin) may decrease rosiglitazone levels. Common adverse reactions include edema, weight gain, and headache.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
40.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AVANDIA Approved UseAfter consultation with a healthcare professional who has considered and advised the patient of the risks and benefits of rosiglitazone, AVANDAMET® is indicated as an adjunct to diet and exercise to improve glycemic control when treatment with both rosiglitazone and metformin is appropriate in adults with type 2 diabetes mellitus who either are: already taking rosiglitazone, or not already taking rosiglitazone and unable to achieve glycemic control on other diabetes medications and, in consultation with their healthcare provider, have decided not to take pioglitazone (ACTOS®) or pioglitazone-containing products (ACTOPLUS MET®, ACTOPLUS MET XR®, DUETACT®) for medical reasons. Other Important Limitations of Use: Due to its mechanism of action, rosiglitazone is active only in the presence of endogenous insulin. Therefore, AVANDAMET should not be used in patients with type 1 diabetes. Coadministration of AVANDAMET with insulin is not recommended [see Warnings and Precautions (5.2, 5.3) Launch Date9.2759038E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
432 ng/mL DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FED |
|
598 ng/mL DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2890 ng × h/mL DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FED |
|
2971 ng × h/mL DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.59 h DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FED |
|
3.37 h DRUG LABEL https://www.fda.gov/media/75754/download |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ROSIGLITAZONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.105 |
unhealthy, 53.1 n = 32 Health Status: unhealthy Condition: Nonalcoholic steatohepatitis Age Group: 53.1 Sex: M+F Population Size: 32 Sources: Page: p.105 |
DLT: Headache, Malaise... Disc. AE: Pain in leg... Dose limiting toxicities: Headache (3.1%) AEs leading toMalaise (3.1%) Oedema legs (9.4%) discontinuation/dose reduction: Pain in leg (3.1%) Sources: Page: p.105 |
20 mg single, oral Overdose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: Page: p.73,74 |
unhealthy, 60 n = 1 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 60 Sex: M Population Size: 1 Sources: Page: p.73,74 |
Disc. AE: Macular edema... AEs leading to discontinuation/dose reduction: Macular edema Sources: Page: p.73,74 |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Disc. AE: Congestive heart failure, Myocardial ischemia... AEs leading to discontinuation/dose reduction: Congestive heart failure Sources: Page: p.1Myocardial ischemia (2%) Fluid retention Edema Weight gain Anemia Macular edema Fracture bone |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 3.1% DLT |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.105 |
unhealthy, 53.1 n = 32 Health Status: unhealthy Condition: Nonalcoholic steatohepatitis Age Group: 53.1 Sex: M+F Population Size: 32 Sources: Page: p.105 |
Malaise | 3.1% DLT |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.105 |
unhealthy, 53.1 n = 32 Health Status: unhealthy Condition: Nonalcoholic steatohepatitis Age Group: 53.1 Sex: M+F Population Size: 32 Sources: Page: p.105 |
Pain in leg | 3.1% Disc. AE |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.105 |
unhealthy, 53.1 n = 32 Health Status: unhealthy Condition: Nonalcoholic steatohepatitis Age Group: 53.1 Sex: M+F Population Size: 32 Sources: Page: p.105 |
Oedema legs | 9.4% DLT |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.105 |
unhealthy, 53.1 n = 32 Health Status: unhealthy Condition: Nonalcoholic steatohepatitis Age Group: 53.1 Sex: M+F Population Size: 32 Sources: Page: p.105 |
Macular edema | Disc. AE | 20 mg single, oral Overdose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: Page: p.73,74 |
unhealthy, 60 n = 1 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 60 Sex: M Population Size: 1 Sources: Page: p.73,74 |
Myocardial ischemia | 2% Disc. AE |
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Anemia | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Congestive heart failure | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Edema | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Fluid retention | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Fracture bone | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Macular edema | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Weight gain | Disc. AE | 8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Rosiglitazone (BRL49653), a PPARgamma-selective agonist, causes peroxisome proliferator-like liver effects in obese mice. | 1999 Jul |
|
Regulation of gene expression by activation of the peroxisome proliferator-activated receptor gamma with rosiglitazone (BRL 49653) in human adipocytes. | 1999 Nov |
|
PPARalpha activation by Wy 14643 induces transactivation of the rat UCP-1 promoter without increasing UCP-1 mRNA levels and attenuates PPARgamma-mediated increases in UCP-1 mRNA levels induced by rosiglitazone in fetal rat brown adipocytes. | 1999 Oct 22 |
|
Differential activation of peroxisome proliferator-activated receptor-gamma by troglitazone and rosiglitazone. | 2000 Apr |
|
Troglitazone inhibits mitogenic signaling by insulin in vascular smooth muscle cells. | 2000 May |
|
Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists. | 2001 Jan 15 |
|
A novel potent antagonist of peroxisome proliferator-activated receptor gamma blocks adipocyte differentiation but does not revert the phenotype of terminally differentiated adipocytes. | 2001 Jul |
|
In vivo myocardial protection from ischemia/reperfusion injury by the peroxisome proliferator-activated receptor-gamma agonist rosiglitazone. | 2001 Nov 20 |
|
Novel genes regulated by the insulin sensitizer rosiglitazone during adipocyte differentiation. | 2002 Apr |
|
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002 Jul |
|
Lipid metabolome-wide effects of the PPARgamma agonist rosiglitazone. | 2002 Nov |
|
Accelerated hypertension due to rosiglitazone therapy. | 2002 Nov-Dec |
|
PPAR gamma-dependent anti-inflammatory action of rosiglitazone in human monocytes: suppression of TNF alpha secretion is not mediated by PTEN regulation. | 2003 Apr 11 |
|
Peroxisome proliferator-activated receptor-gamma represses GLUT4 promoter activity in primary adipocytes, and rosiglitazone alleviates this effect. | 2003 Aug 15 |
|
Reduction in the evolution of murine type II collagen-induced arthritis by treatment with rosiglitazone, a ligand of the peroxisome proliferator-activated receptor gamma. | 2003 Dec |
|
Resistin and type 2 diabetes: regulation of resistin expression by insulin and rosiglitazone and the effects of recombinant resistin on lipid and glucose metabolism in human differentiated adipocytes. | 2003 Dec |
|
Diminished production of nitric oxide synthase cofactor tetrahydrobiopterin by rosiglitazone in adipocytes. | 2003 Feb 15 |
|
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
|
Effects of rosiglitazone and linoleic acid on human preadipocyte differentiation. | 2003 Jul |
|
Regulation of retinoic acid receptor beta expression by peroxisome proliferator-activated receptor gamma ligands in cancer cells. | 2003 Jul 1 |
|
AhR- and ERK-dependent pathways function synergistically to mediate 2,3,7,8-tetrachlorodibenzo-p-dioxin suppression of peroxisome proliferator-activated receptor-gamma1 expression and subsequent adipocyte differentiation. | 2003 May 15 |
|
PPARgamma ligands induce prostaglandin production in vascular smooth muscle cells: indomethacin acts as a peroxisome proliferator-activated receptor-gamma antagonist. | 2003 Oct |
|
Effects of rosiglitazone and metformin on liver fat content, hepatic insulin resistance, insulin clearance, and gene expression in adipose tissue in patients with type 2 diabetes. | 2004 Aug |
|
The PPARgamma ligands PGJ2 and rosiglitazone show a differential ability to inhibit proliferation and to induce apoptosis and differentiation of human glioblastoma cell lines. | 2004 Aug |
|
Decreased expression of peroxisome proliferator activated receptor gamma in cftr-/- mice. | 2004 Aug |
|
Effect of peroxisome proliferator-activated receptor gamma agonist, rosiglitazone, on dedifferentiated thyroid cancers. | 2004 Dec |
|
Peroxisome proliferator-activated receptor gamma ligands suppress liver carcinogenesis induced by diethylnitrosamine in rats. | 2004 Dec 1 |
|
A yeast two-hybrid technology-based system for the discovery of PPARgamma agonist and antagonist. | 2004 Dec 15 |
|
Rosiglitazone, a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation. | 2004 Jan 1 |
|
Reduction of intracellular cholesterol accumulation in THP-1 macrophages by a combination of rosiglitazone and atorvastatin. | 2004 Jul 1 |
|
Evidence for a potent antiinflammatory effect of rosiglitazone. | 2004 Jun |
|
Rosiglitazone induction of Insig-1 in white adipose tissue reveals a novel interplay of peroxisome proliferator-activated receptor gamma and sterol regulatory element-binding protein in the regulation of adipogenesis. | 2004 Jun 4 |
|
PPAR(gamma) agonist rosiglitazone improves vascular function and lowers blood pressure in hypertensive transgenic mice. | 2004 Mar |
|
Rosiglitazone improves insulin sensitivity, glucose tolerance and ambulatory blood pressure in subjects with impaired glucose tolerance. | 2004 May |
|
Transactivation of the PPAR-responsive enhancer module in chemopreventive glutathione S-transferase gene by the peroxisome proliferator-activated receptor-gamma and retinoid X receptor heterodimer. | 2004 May 15 |
|
Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism. | 2004 Nov |
|
Chronic heart failure-related interventions after starting rosiglitazone in patients receiving insulin. | 2004 Oct |
|
Comparison of the effects of pioglitazone and rosiglitazone on macrophage foam cell formation. | 2004 Oct 22 |
|
The antidiabetic agent rosiglitazone upregulates SERCA2 and enhances TNF-alpha- and LPS-induced NF-kappaB-dependent transcription and TNF-alpha-induced IL-6 secretion in ventricular myocytes. | 2005 |
|
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury. | 2005 Feb |
|
Rosiglitazone up-regulates lipoprotein lipase, hormone-sensitive lipase and uncoupling protein-1, and down-regulates insulin-induced fatty acid synthase gene expression in brown adipocytes of Wistar rats. | 2005 Jun |
|
The peroxisome proliferator-activated receptor gamma ligand rosiglitazone delays the onset of inflammatory bowel disease in mice with interleukin 10 deficiency. | 2005 Mar |
|
Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism. | 2005 Mar |
|
Development of a complex scintillation proximity assay for high-throughput screening of PPARgamma modulators. | 2005 Mar |
|
Comparison of pioglitazone with other antidiabetic drugs for associated incidence of liver failure: no evidence of increased risk of liver failure with pioglitazone. | 2005 Mar |
|
Rosiglitazone causes bone loss in mice by suppressing osteoblast differentiation and bone formation. | 2005 Mar |
|
Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway. | 2005 May |
|
Selective activation of PPARgamma in breast, colon, and lung cancer cell lines. | 2005 May 12 |
|
Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions. | 2005 Oct |
|
Peroxisome proliferator-activated receptor-gamma ligands suppress fibronectin gene expression in human lung carcinoma cells: involvement of both CRE and Sp1. | 2005 Sep |
Sample Use Guides
Start at 4 mg daily in single or divided doses; do not exceed 8 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18039959
Rosiglitazone treatment (5 uM) prevents NO and prostacyclin overproduction by inhibiting microparticles-induced iNOS and COX-2 expression.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 19:50:28 UTC 2022
by
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on
Fri Dec 16 19:50:28 UTC 2022
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Record UNII |
05V02F2KDG
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C98241
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NDF-RT |
N0000011272
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WHO-ATC |
A10BD03
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LIVERTOX |
NBK548114
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N0000180190
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A10BD04
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WHO-VATC |
QA10BG02
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NDF-RT |
N0000175374
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NCI_THESAURUS |
C1934
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WHO-VATC |
QA10BD04
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WHO-ATC |
A10BG02
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NDF-RT |
N0000170119
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N0000011272
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QA10BD03
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NDF-RT |
N0000180186
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N0000170119
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NDF-RT |
N0000011272
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Rosiglitazone
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ROSIGLITAZONE
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1056
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C089730
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M9666
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122320-73-4
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CHEMBL121
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84108
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR |
SUBSTRATE USED: Bromsulphthalein (BSP)
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MINOR
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METABOLITE ACTIVE -> PARENT |
MAJOR
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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