Canagliflozin

ChemicalBook > CAS DataBase List > Canagliflozin

Abstract Oral diabetes drugs Clinical study How it works Invokana tables Taboo References

Product Name: Canagliflozin
CAS No.: 842133-18-0
Chemical Name: Canagliflozin
Synonyms: Canaglifozin;Invokana;Cagliflozin;JNJ 28431754;Canaglifozion;(1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4 -methylphenyl]-D-glucitol;(2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;CS-183;TA 7284;Calaglizin
CBNumber: CB02510088
Molecular Formula: C24H25FO5S
Formula Weight: 444.52
MOL File: 842133-18-0.mol

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Canagliflozin Property

Melting point:: 68 - 72°C
Boiling point:: 642.9±55.0 °C(Predicted)
Density: 1.364
storage temp.: -20°C
solubility: Soluble in DMSO (40 mg/ml)
form: solid
pka: 13.34±0.70(Predicted)
color: White
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey: XTNGUQKDFGDXSJ-XDLHWMRXNA-N
SMILES: O[C@@H]1[C@H]([C@H](O)[C@@H](CO)O[C@H]1C1C=CC(C)=C(CC2=CC=C(C3C=CC(F)=CC=3)S2)C=1)O |&1:1,2,3,5,9,r|
CAS DataBase Reference: 842133-18-0

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Safety

Hazardous Substances Data: 842133-18-0(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H318Causes serious eye damage

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 11575
Product name: Canagliflozin
Purity: ≥98%
Packaging: 5mg
Price: $57
Updated: 2024/03/01

Cayman Chemical

Product number: 11575
Product name: Canagliflozin
Purity: ≥98%
Packaging: 10mg
Price: $100
Updated: 2024/03/01

Cayman Chemical

Product number: 11575
Product name: Canagliflozin
Purity: ≥98%
Packaging: 25mg
Price: $193
Updated: 2024/03/01

Cayman Chemical

Product number: 11575
Product name: Canagliflozin
Purity: ≥98%
Packaging: 50mg
Price: $356
Updated: 2024/03/01

Usbiological

Product number: 005544
Product name: Canagliflozin
Packaging: 5mg
Price: $460
Updated: 2021/12/16

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Canagliflozin Chemical Properties,Usage,Production

Abstract

Canagliflozin(Invokana) is an oral diabetes medicine that helps control blood sugar levels. It works by helping the kidneys get rid of glucose from your bloodstream. Invokana is used together with diet and exercise to treat type 2 diabetes. To mention the advantage, this drug helps patients to reduce blood sugars without increasing the likelihood of gaining weight as long as a healthy, balanced diet is followed and regular exercise taken.

Oral diabetes drugs

Canagliflozin is an Inhibitor drug for SGLT2. It can lower blood glucose levels by expelling the glucose from the body through the kidneys after its decomposition. In addition, Canagliflozin has a broad prospect due to its significant antiobesity effects and few hypoglycemic events.
According to the results of 2 phase III clinical trials on June 9th, 2012, Canagliflozin, which is an Experimental type 2 diabetes drug of JNJ is better than Januvia of Merck or an older drug called glimepiride. Meanwhile, Canagliflozin has a more significant antiobesity effect. Compared with glimepiride, it causes less hypoglycemic events. On January 11th, 2013, Janssen Pharmaceutical of JNJ announced that its diabetes drug canagliflozin (trade name INVOKANA?）was recommended and approved by the committee of experts of FDA by the vote of 10 to 5 to treat adult patients with type 2 diabetes. On march 29th, 2013, canagliflozin (trade name INVOKANA, Janssen Pharmaceutical China of JNJ）was approved by the US Food and Drug Administration (FDA) to control blood glucose of adult patients with type 2 diabetes. On December 25th, 2013, Janssen Pharmaceutical of JNJ announced that new diabetes drug INVOKANA（canagliflozin）was approved by European Commission（EC）to treat adult patients with type 2 diabetes and improve glucose control. In September, 2014, Canagliflozin Won the positive Suggestions for recommend approval of Committee for Medicinal Products for Human Use （CHMP） of European Medicines Agency (EMA). In addition, Canagliflozin has been approved by FDA in March this year, and approved by Australia rencently.
Canagliflozin is a once daily oral diabetes drug, which works by inhibiting sodium glucose co-transporter 2 (SGLT2）as a new drug. It can lower blood glucose levels by interdicting the blood glucose reabsorption of the kidneys and increasing the excretion of blood glucose in urine. Compared with non-diabetic population, the kidneys of adult patients with type 2 diabetes absorb a large number of glucose into the blood stream, which will push up the blood glucose levels. Canagliflozin is one of the most promising drug candidates of JNJ. The department of Janssen Pharmaceutical of JNJ has the rights to sell this drug in North America, South America, Europe, Middle East, Africa, Australia, New Zealand and some Asian countries.

Clinical study

Canagliflozin is the first FDA approved inhibitor for SGLT2 and used to treat adult patients with type 2 diabetes. As a kind of glucose transporter, SGLT has two subtypes of SGLT1and SGLT2, which are distributed in the intestinal mucosa and renal tubular respectively, and able to transport glucose into the blood. Canagliflozin can inhibit SLCT2 and, interdict the reabsorption of glucose in Renal tubular and increase the excretion of blood glucose in urine. Thus, the blood glucose levels can be lowered. Glucose was passed into the urine through the kidneys, accompanied by renal impairment, symptomatic hypotension, fungal infections and other side effects. 9 clinical trials involving 10285 patients have demonstrated the safety and efficacy of Invokana, either used alone or in combination with other hypoglycemic agents. In a double-blind controlled trial for 26 weeks, 584 adult patients with type 2 diabetes were divided into three groups, namely 100mg Canagliflozin group, 300mg Canagliflozin group and placebo group. Compared with placebo group, the HbA1c of the 100mg Canagliflozin group and 300mg Canagliflozin group was lowed extra 0.91% and 1.16% respectively.

How it works

Invokana is in a class of drugs called sodium-glucose transport protein 2 (or SGLT2) inhibitors, which drugs work by increasing the amount of glucose that gets passed out in the urine.
When blood passes through the kidneys, the kidneys filter glucose out of the blood and the SGLT proteins then help reabsorb glucose back into the blood.
SGLT2 proteins are responsible for 90% of the glucose that is reabsorbed, so by blocking the action these proteins, less glucose is reabsorbed and so more glucose is excreted via the urine.

Invokana tables

Invokana is supplied as film-coated tablets for oral administration, containing 102 and 306 mg of canagliflozin in each tablet strength, corresponding to 100 mg and 300 mg of canagliflozin (anhydrous), respectively.
Inactive ingredients of the core tablet are croscarmellose sodium, hydroxypropyl cellulose, lactose anhydrous, magnesium stearate, and microcrystalline cellulose. The magnesium stearate is vegetable-sourced. The tablets are finished with a commercially available film-coating consisting of the following excipients: polyvinyl alcohol (partially hydrolyzed), titanium dioxide, macrogol/PEG, talc, and iron oxide yellow, E172 (100 mg tablet only).

Taboo

You should not use Invokana if you have severe kidney disease (or if you are on dialysis).
Invokana is not for treating type 1 diabetes.

References

https://www.drugs.com/cdi/canagliflozin.html
http://www.diabetes.co.uk/diabetes-medication/invokana-canagliflozin.html

Description

In March 2013, the US FDA approved canagliflozin (JNJ-28431754; TA-7284) for the treatment of type 2 diabetes in adults. Canagliflozin is the first US-approved sodium-glucose co-transporter (SGLT) inhibitor for the treatment of type 2 diabetes. Inhibition of renal SGLT suppresses glucose reabsorption, which permits glucose excretion into urine and reduction of hyperglycemia. Canagliflozin was discovered through structural modifications of phlorizin, a known inhibitor of renal glucose reabsorption. Early modifications of OH groups on the glucose moiety were insufficient to adequately impair hydrolysis by intestinal β-glucosidase. Introduction of the C-glucoside moiety, as in the clinical candidate dapagliflozin, afforded sufficient resistance to hydrolysis. Finally, incorporation of the thiophene moiety in canagliflozin provided improved potency for hSGLT2 (exclusive to kidney), IC₅₀=2.2 nM, while offering significant selectivity over hSGLT1 (in kidney and heart), IC₅₀=910 nM. Hyperglycemic, high-fat (HF) diet fedmice (KKstrain) that received a single 3 mg/kg oral dose of canagliflozin had a 48% reduction in blood glucose levels after 6 h versus vehicle-treatedmice. Noteworthy in themultistep synthesis of canagliflozin is the stereoselective formation of the β-C-glucoside which is accomplished by coupling of the aryllithiumaglycone with 2,3,4,6-tetra-O-trimethylsilyl-β-Dgluconolactone followed by desilylation and stereoselective reduction with triethylsilane and boron trifluoride etherate.

Chemical Properties

Pale Yellow Solid

Originator

Mitsubishi Tanabe Pharma (Japan)

Uses

Canagliflozin is a sodium/glucose cotransporter 2 (SGLT2) inhibitor. Canagliflozin has been shown to dose dependently reduce calculated renal threshold for glucose excretion and increase urinary glucose excretion. Canagliflozin is a candidate for the treatment of type 2 diabetes and obesity.

Definition

ChEBI: A C-glycosyl compound that is used (in its hemihydrate form) for treatment of type II diabetes via inhibition of sodium-glucose transport protein subtype 2.

brand name

Invokana

Clinical Use

Sodium-glucose co-transporter 2 inhibitor:

Treatment of type 2 diabetes

target

hSGLT2

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration reduced by rifampicin.
Lipid-regulating drugs: avoid canagliflozin for 1 hour before or 4-6 hours after bile acid sequestrants.

Metabolism

O-glucuronidation is the major metabolic elimination pathway mainly by UGT1A9 and UGT2B4 to two inactive metabolites. CYP3A4-mediated (oxidative) metabolism of canagliflozin is minimal (approximately 7%) in humans.

References

Nomura et al. (2010), Discovery of canagliflozin, a novel C-glucoside with thiophene ring, as sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes mellitus; J. Med. Chem., 53 6355 Shaw et al. (2011), Canagliflozin, a novel inhibitor of sodium glucose co-transporter 2, dose dependently reduces calculated renal threshold for glucose excretion and increases urinary glucose excretion in healthy subjects; Diabetes Obes. Metab., 13 669 Mantovani et al. (2020), Sodium-Glucose Cotransporter-2 Inhibitors for Treatment of Nonalcoholic Fatty Liver Disease: A Meta-Analysis of Randomized Controlled Trials; Metabolites, 11 22 Miller et al. (2020), Canagliflozin extends life span in genetically heterogeneous male but not female mice; JCI Insight, 5 e140019 Vilani et al. (2016), The diabetes medication Canagliflozin reduces cancer cell proliferation by inhibiting mitochondrial complex-I supported respiration; Mol. Metab., 5 1048 Xu et al. (2020), Inhibitory effects of canagliflozin on pancreatic cancer are mediated via the downregulation of glucose transporter-1 and lactate dehydrogenase A; Int. J. Oncol. 57 1223

Canagliflozin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Canagliflozin manufacturers

Sinoway Industrial co., ltd.

Product: Canagliflozin 842133-18-0
Price: US $0.00/Kg/Bag
Min. Order: 2Kg/Bag
Purity: 99% up, High Density
Supply Ability: 20 tons
Release date: 2023-05-29

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Canagliflozin 842133-18-0
Price: US $0.00/g
Min. Order: 1g
Purity: 98%min
Supply Ability: 1000g
Release date: 2021-09-18

Nanjing Fred Technology Co., Ltd

Product: Canagliflozin 842133-18-0
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%，single impurity＜0.1
Supply Ability: 1 ton
Release date: 2024-01-02

842133-18-0, CanagliflozinRelated Search:

Canagliflozin heMihydrate 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone LIPOPHILIC SEPHADEX 2-(4-Fluorophenyl)-thiophene BCP19353 D-Glucitol, 1,5-dideoxy-1,5-epithio-1-C-[5-[(4-ethoxyphenyl)Methyl]-2-Methoxy-4-Methylphenyl]-, (1S)- Tofogliflozin LX-4211 Ipragliflozin PF-04971729 Bortezomib Y27632 (hydrochloride) Selumetinib Pictilisib Olaparib Empagliflozin Dapagliflozin N1,N3-Bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanamido)-2,4,6-triiodoisophthalamide

Canaglifozion

D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, (1S)-

Cango coluMn net

TA 7284

Cagliflozin

CS-183

Invokana

Canagliflozin(TA-7284)

(2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Canaglifozin

Canagliflozin, >=98%

Canagliflozin-D6

D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl

(1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4 -methylphenyl]-D-glucitol

Canagliflozin WS

Canagliflozi

(1S)-1,5-Anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-D-glucitol

JNJ 24831754ZAE

JNJ 28431754

JNJ 28431754AAA

Canagliflozin

Canagliflozin USP/EP/BP

(2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

Canagliflozin (JNJ 28431754)

CanagliflozinQ: What is Canagliflozin Q: What is the CAS Number of Canagliflozin Q: What is the storage condition of Canagliflozin Q: What are the applications of Canagliflozin

Kangglijing

Calaglizin

JNJ 24831754

JNJ24831754

JNJ-24831754

JNJ24831754AAA

(2R,4S,5S,6R)-2-butyl-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-4,5-dihydroxy-6-(hydroxymethyl)dihydro-2H-pyran-3(4H)-one

Canagliflozin Impurity 112

Canagliflozin Impurity 93

842133-18-0

842133--86-0

C24H25FO5S

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