Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H20N2O3S.ClH |
Molecular Weight | 392.9 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1
InChI
InChIKey=GHUUBYQTCDQWRA-UHFFFAOYSA-N
InChI=1S/C19H20N2O3S.ClH/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17;/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23);1H
Molecular Formula | C19H20N2O3S |
Molecular Weight | 356.439 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/actos-pioglitazone-342726 | https://www.drugbank.ca/drugs/DB01132 | https://www.drugs.com/cdi/pioglitazone.html | https://www.ncbi.nlm.nih.gov/pubmed/25760794
Curator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/actos-pioglitazone-342726 | https://www.drugbank.ca/drugs/DB01132 | https://www.drugs.com/cdi/pioglitazone.html | https://www.ncbi.nlm.nih.gov/pubmed/25760794
Pioglitazone (brand name Actos) is a prescription drug of the thiazolidinedione class with hypoglycemic action used in the treatment of type 2 diabetes. Pioglitazone selectively stimulates the nuclear receptor peroxisome proliferator-activated receptor gamma (PPAR-γ) and to a lesser extent PPAR-α. It modulates the transcription of the genes involved in the control of glucose and lipid metabolism in the muscle, adipose tissue, and the liver. As a result, pioglitazone reduces insulin resistance in the liver and peripheral tissues, decreases gluconeogenesis in the liver, and reduces the quantity of glucose and glycated hemoglobin in the bloodstream. Pioglitazone is used to lower blood glucose levels in the treatment of diabetes mellitus type 2 (T2DM) either alone or in combination with a sulfonylurea, metformin, or insulin. Pioglitazone cannot be used in patients with a known hypersensitivity to pioglitazone, other thiazolidinediones or any of components of its pharmaceutical forms. It is ineffective and possibly harmful to diabetes mellitus type 1 and diabetic ketoacidosis. Pioglitazone can cause fluid retention and peripheral edema. As a result, it may precipitate congestive heart failure (which worsens with fluid overload in those at risk). It may cause anemia. Mild weight gain is common due to increase in subcutaneous adipose tissue. In studies, patients on pioglitazone had an increased proportion of upper respiratory tract infection, sinusitis, headache, myalgia and tooth problems.
CNS Activity
Originator
Sources: https://www.google.ch/patents/EP0193256
Curator's Comment: # Takeda Chemical Industries, Ltd
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26595749 |
200.0 nM [EC50] | ||
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11831892 |
6680.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ACTOS Approved UsePioglitazone tablets are a thiazolidinedione and an agonist for peroxisome proliferator-activated receptor (PPAR) gamma indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings. (1.1, 14) Important Limitation of Use: •Not for treatment of type 1 diabetes or diabetic ketoacidosis. (1.2) 1.1 Monotherapy and Combination Therapy Pioglitazone tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings [see Clinical Studies (14) Launch Date1999 |
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Primary | ACTOS Approved UsePioglitazone tablets are a thiazolidinedione and an agonist for peroxisome proliferator-activated receptor (PPAR) gamma indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings. (1.1, 14) Important Limitation of Use: •Not for treatment of type 1 diabetes or diabetic ketoacidosis. (1.2) 1.1 Monotherapy and Combination Therapy Pioglitazone tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings [see Clinical Studies (14) Launch Date1999 |
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Primary | ACTOS Approved UsePioglitazone tablets are a thiazolidinedione and an agonist for peroxisome proliferator-activated receptor (PPAR) gamma indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings. (1.1, 14) Important Limitation of Use: •Not for treatment of type 1 diabetes or diabetic ketoacidosis. (1.2) 1.1 Monotherapy and Combination Therapy Pioglitazone tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus in multiple clinical settings [see Clinical Studies (14) Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
890 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16172178 |
45 mg 1 times / day steady-state, oral dose: 45 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIOGLITAZONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8662 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16172178 |
45 mg 1 times / day steady-state, oral dose: 45 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIOGLITAZONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16172178 |
45 mg 1 times / day steady-state, oral dose: 45 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIOGLITAZONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.75 mg/kg 1 times / day multiple, oral MTD Dose: 0.75 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.75 mg/kg, 1 times / day Sources: Page: p.7, 9 |
unhealthy, 5-12 n = 18 Health Status: unhealthy Condition: Autistic disorder|Asperger syndrome Age Group: 5-12 Sex: M+F Population Size: 18 Sources: Page: p.7, 9 |
|
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.983, 984 |
unhealthy, 58.1 n = 60 Health Status: unhealthy Condition: Nonalcoholic Steatohepatitis and Prediabetes|Type 2 Diabetes Mellitus Age Group: 58.1 Sex: M+F Population Size: 60 Sources: Page: p.983, 984 |
Disc. AE: Edema, ALT increased... AEs leading to discontinuation/dose reduction: Edema (mild, 1.67%) Sources: Page: p.983, 984ALT increased (grade 2-4, 1.67%) |
180 mg 1 times / day multiple, oral Overdose Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: Page: p.21 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.21 |
|
45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 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, Edema... AEs leading to discontinuation/dose reduction: Congestive heart failure Sources: Page: p.1Edema Hepatic failure (grade 5) Fractures Bladder cancer Hypoglycemia Macular edema |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
ALT increased | grade 2-4, 1.67% Disc. AE |
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.983, 984 |
unhealthy, 58.1 n = 60 Health Status: unhealthy Condition: Nonalcoholic Steatohepatitis and Prediabetes|Type 2 Diabetes Mellitus Age Group: 58.1 Sex: M+F Population Size: 60 Sources: Page: p.983, 984 |
Edema | mild, 1.67% Disc. AE |
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.983, 984 |
unhealthy, 58.1 n = 60 Health Status: unhealthy Condition: Nonalcoholic Steatohepatitis and Prediabetes|Type 2 Diabetes Mellitus Age Group: 58.1 Sex: M+F Population Size: 60 Sources: Page: p.983, 984 |
Bladder cancer | Disc. AE | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 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 | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Edema | Disc. AE | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Fractures | Disc. AE | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Hypoglycemia | Disc. AE | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 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 | 45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.1 |
Hepatic failure | grade 5 Disc. AE |
45 mg 1 times / day multiple, oral Recommended Dose: 45 mg, 1 times / day Route: oral Route: multiple Dose: 45 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 |
---|---|---|
Augmentation of myocardial production of 15-epi-lipoxin-a4 by pioglitazone and atorvastatin in the rat. | 2006 Aug 29 |
|
Rosiglitazone inhibits mouse liver regeneration. | 2006 Dec |
|
In vitro screening of 200 pesticides for agonistic activity via mouse peroxisome proliferator-activated receptor (PPAR)alpha and PPARgamma and quantitative analysis of in vivo induction pathway. | 2006 Dec 15 |
|
[Resveratrol inhibits expression of EMMPRIN from macrophages]. | 2006 Jul |
|
The direct antioxidative and anti-inflammatory effects of peroxisome proliferator-activated receptors ligands are associated with the inhibition of angiotensin converting enzyme expression in streptozotocin-induced diabetic rat aorta. | 2006 Nov 7 |
|
Acetaldehyde inhibits PPARgamma via H2O2-mediated c-Abl activation in human hepatic stellate cells. | 2006 Oct |
|
Modulation of airway remodeling and airway inflammation by peroxisome proliferator-activated receptor gamma in a murine model of toluene diisocyanate-induced asthma. | 2006 Oct 15 |
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[Effects of pioglitazone on MKP-1 and TSP-1 expression in early stages of diabetic retinopathy induced by streptozotocin]. | 2006 Sep |
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Activating effect of benzbromarone, a uricosuric drug, on peroxisome proliferator-activated receptors. | 2007 |
|
Peroxisome proliferator-activated receptor-gamma agonists induce neuroprotection following transient focal ischemia in normotensive, normoglycemic as well as hypertensive and type-2 diabetic rodents. | 2007 Apr |
|
Resveratrol inhibits macrophage expression of EMMPRIN by activating PPARgamma. | 2007 Feb |
|
Peroxisome proliferated-activated receptor gamma ligand, Pioglitazone, does not prevent hepatic fibrosis in mice. | 2007 Jan |
|
Effect of pioglitazone treatment on behavioral symptoms in autistic children. | 2007 Jan 5 |
|
[Effects of peroxisome proliferators activated receptors on caveolin-1 expression in foam cells]. | 2007 Jul |
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The PPARgamma agonist pioglitazone inhibits early neoplastic occurrence in the rat liver. | 2007 Jul |
|
Pioglitazone inhibits androgen production in NCI-H295R cells by regulating gene expression of CYP17 and HSD3B2. | 2007 Mar |
|
Troglitazone and pioglitazone interactions via PPAR-gamma-independent and -dependent pathways in regulating physiological responses in renal tubule-derived cell lines. | 2007 Mar |
|
Ligands of peroxisome proliferator-activated receptor inhibit homocysteine-induced DNA methylation of inducible nitric oxide synthase gene. | 2007 May |
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Peroxisome proliferator-activated receptor gamma activation relieves expression of behavioral sensitization to methamphetamine in mice. | 2007 May |
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Inhibitory effect of PPAR on the expression of EMMPRIN in macrophages and foam cells. | 2007 May 2 |
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NR4A orphan nuclear receptors modulate insulin action and the glucose transport system: potential role in insulin resistance. | 2007 Oct 26 |
|
Pioglitazone and risk of cardiovascular events in patients with type 2 diabetes mellitus: a meta-analysis of randomized trials. | 2007 Sep 12 |
|
MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. | 2007 Sep 4 |
|
Inhibition of advanced glycation end products: an implicit goal in clinical medicine for the treatment of diabetic nephropathy? | 2008 Apr |
|
Telmisartan inhibits CD4-positive lymphocyte migration independent of the angiotensin type 1 receptor via peroxisome proliferator-activated receptor-gamma. | 2008 Feb |
|
Treating Hispanic patients for type 2 diabetes mellitus: special considerations. | 2008 May |
|
JNK- and IkappaB-dependent pathways regulate MCP-1 but not adiponectin release from artificially hypertrophied 3T3-L1 adipocytes preloaded with palmitate in vitro. | 2008 May |
|
Bezafibrate prevents hepatic stellate cell activation and fibrogenesis in a murine steatohepatitis model, and suppresses fibrogenic response induced by transforming growth factor-beta1 in a cultured stellate cell line. | 2008 Oct |
|
Aldosterone induces interleukin-18 through endothelin-1, angiotensin II, Rho/Rho-kinase, and PPARs in cardiomyocytes. | 2008 Sep |
|
Chronic, in vivo, PPARalpha activation prevents lipid overload in rat liver induced by high fat feeding. | 2009 |
|
Effects of benzbromarone and allopurinol on adiponectin in vivo and in vitro. | 2009 Apr |
|
Type 2 deiodinase expression is induced by peroxisomal proliferator-activated receptor-gamma agonists in skeletal myocytes. | 2009 Apr |
|
On the mechanism for PPAR agonists to enhance ABCA1 gene expression. | 2009 Aug |
|
Risk of cardiovascular disease and all cause mortality among patients with type 2 diabetes prescribed oral antidiabetes drugs: retrospective cohort study using UK general practice research database. | 2009 Dec 3 |
|
Distinct functions of vascular endothelial and smooth muscle PPARgamma in regulation of blood pressure and vascular tone. | 2009 Jan |
|
Retinol saturase promotes adipogenesis and is downregulated in obesity. | 2009 Jan 27 |
|
Differential effects of in vivo PPAR alpha and gamma activation on fatty acid transport proteins expression and lipid content in rat liver. | 2009 Mar |
|
Chronic administration of voglibose, an alpha-glucosidase inhibitor, increases active glucagon-like peptide-1 levels by increasing its secretion and decreasing dipeptidyl peptidase-4 activity in ob/ob mice. | 2009 May |
|
Emerging treatments in cystic fibrosis. | 2009 Oct 1 |
|
Peroxisome proliferator-activated receptor gamma agonist rosiglitazone increases expression of very low density lipoprotein receptor gene in adipocytes. | 2009 Oct 30 |
|
Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma. | 2010 Apr |
|
Rational design of a pirinixic acid derivative that acts as subtype-selective PPARgamma modulator. | 2010 Apr 15 |
|
Pioglitazone ameliorates behavioral, biochemical and cellular alterations in quinolinic acid induced neurotoxicity: possible role of peroxisome proliferator activated receptor-Upsilon (PPARUpsilon) in Huntington's disease. | 2010 Aug |
|
Effects of pioglitazone, a peroxisome proliferator-activated receptor gamma agonist, on the urine and urothelium of the rat. | 2010 Feb |
|
Rosiglitazone attenuates development of polycystic kidney disease and prolongs survival in Han:SPRD rats. | 2010 Jul 9 |
|
Troglitazone, a ligand of peroxisome proliferator-activated receptor-{gamma}, stabilizes NUCB2 (Nesfatin) mRNA by activating the ERK1/2 pathway: isolation and characterization of the human NUCB2 gene. | 2010 Jun |
|
Different effects of pioglitazone and rosiglitazone on lipid metabolism in mouse cultured liver explants. | 2010 May |
|
The role of adiponectin in the pathogenesis and treatment of non-alcoholic fatty liver disease. | 2010 May |
|
Suppression of NF-kappaB and GSK-3beta is involved in colon cancer cell growth inhibition by the PPAR agonist troglitazone. | 2010 Oct 6 |
|
Differential modulatory effects of rosiglitazone and pioglitazone on white adipose tissue in db/db mice. | 2010 Sep 25 |
Sample Use Guides
Initiate ACTOS (Pioglitazone) at 15 mg or 30 mg once daily. Limit initial dose to 15 mg once daily in patients with NYHA Class I or II heart failure.
If there is inadequate glycemic control, the dose can be increased in 15 mg increments up to a maximum of 45 mg once daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27703271
For the cell counting assay, Human aortic smooth muscle cells (HASMCs) were seeded at 3× 10^3 cells on to a 96-well dish; 24 hours after the plating, the cells were serum-starved to render them quiescent by replacing the medium with DMEM containing 0.2% FBS. The quiescent SMCs were then preincubated with globular adiponectin (1μg/mL or 3μg/mL) or pioglitazone (1μM or 10μM) for 30min. PDGF-BB (10ng/mL) was added to stimulate the cells for 24hours. These cells were incubated with 10 μl of CCK (cell counting kit)-8 (DOJINDO) or WST-1 (Roche) solution for 2hours before conducting the measurements. We measured the absorbance at 450nm using a microplate reader. 10 μl of BrdU (Roche) solution was added these cells simultaneously with PDGF-BB. BrdU incorporation was measured by chemiluminescent assay
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:08:53 GMT 2023
by
admin
on
Fri Dec 15 16:08:53 GMT 2023
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Record UNII |
JQT35NPK6C
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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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FDA ORPHAN DRUG |
890822
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EU-Orphan Drug |
EU/3/16/1823
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NCI_THESAURUS |
C98241
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JQT35NPK6C
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C29367
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DBSALT000555
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60560
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m8835
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CHEMBL595
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112529-15-4
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SUB03834MIG
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100000091439
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127676-30-6
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758876
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AA-22
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1539905
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259319
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |