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Details

Stereochemistry RACEMIC
Molecular Formula C19H20N2O3S.ClH
Molecular Weight 392.9014
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIOGLITAZONE HYDROCHLORIDE

SMILES

CCc1ccc(CCOc2ccc(cc2)CC3C(=NC(=O)S3)O)nc1.Cl

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H20N2O3S
Molecular Weight 356.4405
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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.

Originator

Curator's Comment:: # Takeda Chemical Industries, Ltd

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACTOS

Approved Use

Pioglitazone 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 Date

9.3199683E11
Primary
ACTOS

Approved Use

Pioglitazone 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 Date

9.3199683E11
Primary
ACTOS

Approved Use

Pioglitazone 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 Date

9.3199683E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
890 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
8662 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12.6 h
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

Doses

DosePopulationAdverse 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%)
ALT increased (grade 2-4, 1.67%)
Sources: Page: p.983, 984
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
Edema
Hepatic failure (grade 5)
Fractures
Bladder cancer
Hypoglycemia
Macular edema
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
15-Deoxy-delta 12,14-prostaglandin J2 and thiazolidinediones activate the MEK/ERK pathway through phosphatidylinositol 3-kinase in vascular smooth muscle cells.
2001 Dec 28
The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells.
2001 Jan
Thiazolidinedione derivatives ameliorate albuminuria in streptozotocin-induced diabetic spontaneous hypertensive rat.
2002 Apr
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.
2002 Jan 11
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.
2002 Jul
PPAR gamma ligands, troglitazone and pioglitazone, up-regulate expression of HMG-CoA synthase and HMG-CoA reductase gene in THP-1 macrophages.
2002 Jun 5
Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition.
2003 Apr
Adiponectin gene activation by thiazolidinediones requires PPAR gamma 2, but not C/EBP alpha-evidence for differential regulation of the aP2 and adiponectin genes.
2003 Sep 5
Effects of PPARg agonist pioglitazone on rat hepatic fibrosis.
2004 Apr 1
Peroxisome proliferator-activated receptor gamma ligands suppress liver carcinogenesis induced by diethylnitrosamine in rats.
2004 Dec 1
Identification of a novel mitochondrial protein ("mitoNEET") cross-linked specifically by a thiazolidinedione photoprobe.
2004 Feb
Growth arrest by troglitazone is mediated by p27Kip1 accumulation, which results from dual inhibition of proteasome activity and Skp2 expression in human hepatocellular carcinoma cells.
2004 Jan 1
Comparison of the effects of pioglitazone and rosiglitazone on macrophage foam cell formation.
2004 Oct 22
Thiazolidinediones expand body fluid volume through PPARgamma stimulation of ENaC-mediated renal salt absorption.
2005 Aug
Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism.
2005 Mar
Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone.
2005 May
Angiotensin II induces peroxisome proliferator-activated receptor gamma in PC12W cells via angiotensin type 2 receptor activation.
2005 Sep
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
Transcriptional regulation of nephrin gene by peroxisome proliferator-activated receptor-gamma agonist: molecular mechanism of the antiproteinuric effect of pioglitazone.
2006 Jun
Gene expression analysis of troglitazone reveals its impact on multiple pathways in cell culture: a case for in vitro platforms combined with gene expression analysis for early (idiosyncratic) toxicity screening.
2006 Mar-Apr
Peroxisome proliferator-activated receptor-gamma agonist is protective in podocyte injury-associated sclerosis.
2006 May
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
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.
2006 Oct
[Effects of pioglitazone on MKP-1 and TSP-1 expression in early stages of diabetic retinopathy induced by streptozotocin].
2006 Sep
Activating effect of benzbromarone, a uricosuric drug, on peroxisome proliferator-activated receptors.
2007
Resveratrol inhibits macrophage expression of EMMPRIN by activating PPARgamma.
2007 Feb
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
NR4A orphan nuclear receptors modulate insulin action and the glucose transport system: potential role in insulin resistance.
2007 Oct 26
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
Chronic, in vivo, PPARalpha activation prevents lipid overload in rat liver induced by high fat feeding.
2009
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
Patents

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
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 Fri Jun 25 21:06:36 UTC 2021
Edited
by admin
on Fri Jun 25 21:06:36 UTC 2021
Record UNII
JQT35NPK6C
Record Status Validated (UNII)
Record Version
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Name Type Language
PIOGLITAZONE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
PIOGLITAZONE HYDROCHLORIDE [USAN]
Common Name English
PIOGLITAZONE HCL
VANDF  
Common Name English
PIOMED
Brand Name English
PIOGLITAZONE HYDROCHLORIDE COMPONENT OF OSENI
Brand Name English
OSENI COMPONENT PIOGLITAZONE HYDROCHLORIDE
Brand Name English
PIOGLITAZONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PIOGLITAZONE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
ACTOS
Brand Name English
PIOGLITAZONE HYDROCHLORIDE [WHO-DD]
Common Name English
PIOGLITAZONE HYDROCHLORIDE COMPONENT OF ACTOPLUS MET
Common Name English
NSC-758876
Code English
PIOGLITAZONE (AS HYDROCHLORIDE)
Common Name English
PIOGLITAZONE HYDROCHLORIDE [MI]
Common Name English
PIOGLITAZONE HYDROCHLORIDE COMPONENT OF DUETACT
Common Name English
PIOGLITAZONE HCL [VANDF]
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-ETHYL-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-, MONOHYDROCHLORIDE, (+/-)-
Common Name English
PIOGLITAZONE HYDROCHLORIDE [JAN]
Common Name English
U-72107A
Code English
PIOGLITAZONE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
ACTOPLUS MET COMPONENT PIOGLITAZONE HYDROCHLORIDE
Common Name English
STR-001
Code English
PIOGLITAZONE HYDROCHLORIDE [MART.]
Common Name English
PIOGLITAZONE HYDROCHLORIDE [USP-RS]
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-ETHYL-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
(+/-)-5-(P-(2-(5-ETHYL-2-PYRIDYL)ETHOXY)BENZYL)-2,4-THIAZOLIDINEDIONE MONOHYDROCHLORIDE
Common Name English
PIOGLITAZONE HYDROCHLORIDE [VANDF]
Common Name English
DUETACT COMPONENT PIOGLITAZONE HYDROCHLORIDE
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-ETHYL-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-, MONOHYDROCHLORIDE
Common Name English
POZE
Brand Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1823
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
NCI_THESAURUS C98241
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
Code System Code Type Description
USP_CATALOG
1539905
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C29367
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
DRUG BANK
DBSALT000555
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
PUBCHEM
60560
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
MERCK INDEX
M8835
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL595
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
CAS
112529-15-4
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
EVMPD
SUB03834MIG
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
FDA UNII
JQT35NPK6C
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
EPA CompTox
112529-15-4
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY
CAS
127676-30-6
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
SUPERSEDED
RXCUI
259319
Created by admin on Fri Jun 25 21:06:37 UTC 2021 , Edited by admin on Fri Jun 25 21:06:37 UTC 2021
PRIMARY RxNorm
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