Pioglitazone hydrochloride

Modify Date: 2024-01-02 15:53:12

Pioglitazone hydrochloride Structure
Pioglitazone hydrochloride structure
 Common Name Pioglitazone hydrochloride
CAS Number 112529-15-4 Molecular Weight 392.900
Density 1.26 g/cm3 Boiling Point 575.4ºC at 760 mmHg
Molecular Formula C19H21ClN2O3S Melting Point 193-194ºC
MSDS Chinese USA Flash Point 301.8ºC
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Pioglitazone hydrochloride


Pioglitazone hydrochloride is a potent and selective PPARγ agonist with EC50s of 0.93 and 0.99 μM for human and mouse PPARγ, respectively.

 Names

Name [5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride
Synonym More Synonyms

 Pioglitazone hydrochloride Biological Activity

Description Pioglitazone hydrochloride is a potent and selective PPARγ agonist with EC50s of 0.93 and 0.99 μM for human and mouse PPARγ, respectively.
Related Catalog
Target

PPARδ:0.01 μM (EC50, Human PPARδ)

PPARα:0.93 μM (EC50, Human PPARα)

PPARγ:43 μM (EC50, Human PPARγ)
In Vitro AGEs-induced beta cell necrosis is completely abrogated by adding Pioglitazone to the AGEs culture medium. Furthermore Pioglitazone completely prevented any AGEs-induced increment in caspase-3 activation, thereby restoring caspase-3 activity to the same levels as the control cells. As expected AG is able to counteract AGEs-induced impaired viability[2].
In Vivo The serum-free fatty acid and triglyceride levels as well as adipocyte sizes in ob/ob and adipo-/- ob/ob mice are unchanged after 10 mg/kg Pioglitazone but are significantly reduced to a similar degree after 30 mg/kg Pioglitazone. Moreover, the expressions of TNFα and resistin in adipose tissues of ob/ob and adipo-/- ob/ob mice are unchanged after 10 mg/kg Pioglitazone but are decreased after 30 mg/kg Pioglitazone. Thus, Pioglitazone-induced amelioration of insulin resistance and diabetes may occur adiponectin dependently in the liver and adiponectin independently in skeletal muscle[3]. Pioglitazone (10 mg/kg per d) treatment significantly attenuates the loss of body weight (BW) and cardiac hypertrophy. Pioglitazone treatment significantly reduces the elevated serum glucose levels and markedly improved the associated dyslipidemia. Furthermore, there is a slight but significant increase in serum creatinine level in D rats over their N controls (P <0.05). However, a marked renal dysfunction is observed in diabetic nephropathic (DN) group (P<0.05). Moreover, DN rats exhibits the highest serum activity of CK-MB, relative to both N and D rats (P<0.05). Pioglitazone is able to decrease the elevated serum levels of both creatinine and creatine kinase-MB (CK-MB)[4].
Cell Assay In order to evaluate cell proliferation, HIT-T15 cells are seeded on 96-well plates (3×104 cells/well) and cultured for 5 days as described. Viable cells are determined using the Cell Titer 96 Aqueous One Solution Cell Proliferation Assay. To evaluate cell apoptosis and cell necrosis, HIT-T15 cells are plated on 6-well dishes (7×105 cells/well) for 5 days in standard conditions (CTR) or in the presence of AGEs (AGEs) with or without Pioglitazone (0.5 or 1 μM) or AG (1 mM). They are then processed to measure both the activity of caspase-3 and the activity of lactate dehydrogenase (LDH) (a stable cytosolic enzyme that is a marker of cell membrane damage and cell death due to necrosis) using Cytotox 96 Non Radioactive Cytotoxicity Assay[2].
Animal Admin Mice[3] 10 mg/kg Pioglitazone HCl or vehicle (0.25% carboxymethylcellulose) is adnimistered to ob/ob and adipo-/- ob/ob mice by oral gavage once daily for 14 consecutive days. 30 mg/kg Pioglitazone or vehicle is also adnimistered to ob/ob and adipo-/- ob/ob mice by oral gavage once daily for 14 consecutive days. Rats[4] Male Wistar albino rats (weighing 250±20 g) are ued.Rats that achieved serum glucose level ≥250 mg/dL and serum creatinine level ≥1.5 mg/dL are divided into 2 groups (n=10 per each group): diabetic nephropathic (DN) group in which rats received an equal amount of vehicle (0.5% carboxy methyl cellulose) and Pioglitazone-treated (DN+Pio) group in which rats treated with Pioglitazone. Pioglitazone (10 mg/kg BW) is given orally by gastric gavage, once daily, for 4 weeks.
References

[1]. Kuwabara K, et al. A novel selective peroxisome proliferator-activated receptor alpha agonist, 2-methyl-c-5-[4-[5-methyl-2-(4-methylphenyl)-4-oxazolyl]butyl]-1,3-dioxane-r-2-carboxylic acid (NS-220), potently decreases plasma triglyceride and glucose leve

[2]. Puddu A, et al. Pioglitazone attenuates the detrimental effects of advanced glycation end-products in the pancreatic beta cell line HIT-T15. Regul Pept. 2012 Aug 20;177(1-3):79-84.

[3]. Kubota N, et al. Pioglitazone ameliorates insulin resistance and diabetes by both adiponectin-dependent and -independent pathways. J Biol Chem. 2006 Mar 31;281(13):8748-55.

[4]. Elrashidy RA, et al. Pioglitazone attenuates cardiac fibrosis and hypertrophy in a rat model of diabetic nephropathy. J Cardiovasc Pharmacol Ther. 2012 Sep;17(3):324-33.

 Chemical & Physical Properties

Density 1.26 g/cm3
Boiling Point 575.4ºC at 760 mmHg
Melting Point 193-194ºC
Molecular Formula C19H21ClN2O3S
Molecular Weight 392.900
Flash Point 301.8ºC
Exact Mass 392.096130
PSA 93.59000
LogP 4.29040
Vapour Pressure 0mmHg at 25°C
Index of Refraction 1.64
Storage condition Desiccate at RT

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H319
Precautionary Statements P305 + P351 + P338
Hazard Codes Xi:Irritant
Risk Phrases R36/38
Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Effects of pioglitazone
PIODLITAZONE HYDROCHLORIC
Pioglitazonehydrochloride
Pioglitazone hydrochloride
5-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride (1:1)
MFCD04975446
Pioditazone hydrochloride
5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride
5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride
5-{4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride
5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione Hydrochloride
5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride
2,4-Thiazolidinedione, 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-, hydrochloride (1:1)
UNII:JQT35NPK6C
5-{4-[2-(5-éthylpyridin-2-yl)éthoxy]benzyl}-1,3-thiazolidine-2,4-dione chlorhydrate
5-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidin-2,4-dionhydrochlorid
Actos
Pioglitazone HCl
5-{4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride (1:1)
Pioglitazone hydrochloride
AD-4833
Pioglitazone (hydrochloride)
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Pioglitazone hydrochloride impurity A [EP]
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Pioglitazone hydrochloride specified impurity C [EP]
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