Canagliflozin

Cas：928672-86-0 (hemihydrate)

Product Information：

Canagliflozin, also known as JNJ-28431754 and TA 7284, is a drug of the gliflozin class or subtype 2 sodium-glucose transport (SGLT-2) inhibitors used for the treatment of type 2 diabetes. SGLT2 is responsible for at least 90% of renal glucose reabsorption (SGLT1 being responsible for the remaining 10%). Blocking this transporter causes up to 119 grams of blood glucose per day to be eliminated through the urine, corresponding to 476 kilocalories. Additional water is eliminated by osmotic diuresis, resulting in a lowering of blood pressure.

Chemical Formula: C48H52F2O11S2

Molecular Weight: 907.0498

Elemental Analysis: C, 63.56; H, 5.78; F, 4.19; O, 19.40; S, 7.07

Synonym: 

JNJ 28431754

JNJ-28431754

JNJ28431754

TA 7284

TA-7284

TA7284

NJ-24831754-ZAE

JNJ-28431754-AAA

Canagliflozin hemihydrate

brand name

Invokana

Sulisent.

Chemical Name: 

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

InChi Key: 

VHOFTEAWFCUTOS-HTDYLQHCSA-N

InChi Code: 

InChI=1S/2C24H25FO5S.H2O/c2*1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14;/h2*2-10,19,21-24,26-29H,11-12H2,1H3;1H2/t2*19-,21-,22+,23-,24?;/m11./s1

Smiles Code:

O[C@H]1C(O[C@@H]([C@H]([C@@H]1O)O)CO)C2=CC=C(C(CC3=CC=C(S3)C4=CC=C(C=C4)F)=C2)C.[H]O[H].O[C@H]5C(O[C@@H]([C@H]([C@@H]5O)O)CO)C6=CC=C(C(CC7=CC=C(S7)C8=CC=C(C=C8)F)=C6)C

Technical Data：

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

In Vitro:

Canagliflozin inhibits Na+-dependent 14C-AMG uptake in CHO-hSGLT2 cells, with an IC50 of 4.4±1.2 nM. Similar IC50 values are obtained in CHO-rSGLT2 and CHO-mSGLT2 cells (IC50 = 3.7 and 2.0 nM for rat and mouse SGLT2, respectively). Canagliflozin inhibits 14C-AMG uptake in CHO-hSGLT1 and mSGLT1 cells with IC50 of 684±159 nM and >1,000 nM, respectively.

In Vivo:

Canagliflozin (30 mg/kg treatment for 4 weeks) reduced blood glucose (BG) levels, respiratory exchange ratio, and body weight gain in DIO mice.

Canagliflozin (3 mg/kg for 3 weeks) increases urinary glucose excretion (UGE) with no significant change in total food intake compared with that in vehicle-treated rats, leading to a decrease in body weight In ZF rats.

References:

1. Qiu R, Balis D, Capuano G, Xie J, Meininger G. Canagliflozin: Efficacy and Safety in Combination with Metformin Alone or with Other Antihyperglycemic Agents in Type 2 Diabetes. Diabetes Ther. 2016 Oct 12. [Epub ahead of print] Review. PubMed PMID: 27734320.

2. 2.Canagliflozin (Invokana) for Type 2 Diabetes Mellitus [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Sep. Available from http://www.ncbi.nlm.nih.gov/books/NBK349575/ PubMed PMID: 26962611.

3. Kaur K, Likar N, Dang A, Kaur G. Efficacy and safety of canagliflozin among patients with type 2 diabetes mellitus: A systematic review and meta-analysis. Indian J Endocrinol Metab. 2015 Nov-Dec;19(6):705-21. doi: 10.4103/2230-8210.167562. Review. PubMed PMID: 26693420; PubMed Central PMCID: PMC4673798.

4. Parveen R, Agarwal NB, Kaushal N, Mali G, Raisuddin S. Efficacy and safety of canagliflozin in type 2 diabetes mellitus: systematic review of randomized controlled trials. Expert Opin Pharmacother. 2016;17(1):105-15. doi: 10.1517/14656566.2016.1109629. Review. PubMed PMID: 26650511.

5. Seufert J. SGLT2 inhibitors - an insulin-independent therapeutic approach for treatment of type 2 diabetes: focus on canagliflozin. Diabetes Metab Syndr Obes. 2015 Nov 9;8:543-54. doi: 10.2147/DMSO.S90662. Review. PubMed PMID: 26609242; PubMed Central PMCID: PMC4644173.

6. Syed SH, Gosavi S, Shami W, Bustamante M, Farah Z, Teleb M, Abbas A, Said S, Mukherjee D. A Review of Sodium Glucose Co-transporter 2 Inhibitors Canagliflozin, Dapagliflozin and Empagliflozin. Cardiovasc Hematol Agents Med Chem. 2015;13(2):105-12. Review. PubMed PMID: 26549321.

Products are for research use only. Not for human use.