Dapagliflozin
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MedKoo CAT#: 314204

CAS#: 461432-26-8

Description: Dapagliflozin, also known as BMS-512148, is a drug used to treat type 2 diabetes approved in 2012 by FDA. Dapagliflozin inhibits subtype 2 of the sodium-glucose transport proteins (SGLT2) which are responsible for at least 90% of the glucose reabsorption in the kidney. Blocking this transporter mechanism causes blood glucose to be eliminated through the urine. In clinical trials, dapagliflozin lowered HbA1c by 0.6 versus placebo percentage points when added to metformin.


Chemical Structure

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Dapagliflozin
CAS# 461432-26-8

Theoretical Analysis

MedKoo Cat#: 314204
Name: Dapagliflozin
CAS#: 461432-26-8
Chemical Formula: C21H25ClO6
Exact Mass: 408.13397
Molecular Weight: 408.87
Elemental Analysis: C, 61.69; H, 6.16; Cl, 8.67; O, 23.48

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Same day
1.0g USD 250.0 Same day
2.0g USD 450.0 Same day
5.0g USD 850.0 Same day
10.0g USD 1450.0 Same day
20.0g USD 2550.0 Same day
100.0g USD 6450.0 Same day
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Synonym: BMS512148; BMS-512148; BMS 512148; Dapagliflozin; trade name Farxiga in the US and Forxiga in the EU.

IUPAC/Chemical Name: (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key: JVHXJTBJCFBINQ-ADAARDCZSA-N

InChi Code: InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1

SMILES Code: O[C@H]1[C@H](C2=CC=C(Cl)C(CC3=CC=C(OCC)C=C3)=C2)O[C@H](CO)[C@@H](O)[C@@H]1O

Appearance: white 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

Preparing Stock Solutions

The following data is based on the product molecular weight 408.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hinnen D. Glucuretic effects and renal safety of dapagliflozin in patients with type 2 diabetes. Ther Adv Endocrinol Metab. 2015 Jun;6(3):92-102. doi: 10.1177/2042018815575273. Review. PubMed PMID: 26137213; PubMed Central PMCID: PMC4480550.

2: Liakos A, Karagiannis T, Bekiari E, Boura P, Tsapas A. Update on long-term efficacy and safety of dapagliflozin in patients with type 2 diabetes mellitus. Ther Adv Endocrinol Metab. 2015 Apr;6(2):61-7. doi: 10.1177/2042018814560735. Review. PubMed PMID: 25941564; PubMed Central PMCID: PMC4406879.

3: Vivian EM. Dapagliflozin: a new sodium-glucose cotransporter 2 inhibitor for treatment of type 2 diabetes. Am J Health Syst Pharm. 2015 Mar 1;72(5):361-72. doi: 10.2146/ajhp140168. Review. PubMed PMID: 25694411.

4: Filippatos TD, Liberopoulos EN, Elisaf MS. Dapagliflozin in patients with type 2 diabetes mellitus. Ther Adv Endocrinol Metab. 2015 Feb;6(1):29-41. doi: 10.1177/2042018814558243. Review. PubMed PMID: 25678954; PubMed Central PMCID: PMC4321869.

5: Sposetti G, MacKinnon I, Barengo NC. Dapagliflozin: drug profile and its role in individualized treatment. Expert Rev Cardiovasc Ther. 2015 Feb;13(2):129-39. doi: 10.1586/14779072.2015.995636. Epub 2015 Jan 6. Review. PubMed PMID: 25560982.

6: Anderson SL. Dapagliflozin efficacy and safety: a perspective review. Ther Adv Drug Saf. 2014 Dec;5(6):242-54. doi: 10.1177/2042098614551938. Review. PubMed PMID: 25436106; PubMed Central PMCID: PMC4232499.

7: Maranghi M, Carnovale A, Durante C, Tarquini G, Tiseo G, Filetti S. Pharmacokinetics, pharmacodynamics and clinical efficacy of dapagliflozin for the treatment of type 2 diabetes. Expert Opin Drug Metab Toxicol. 2015 Jan;11(1):125-37. doi: 10.1517/17425255.2015.986457. Epub 2014 Nov 24. Review. PubMed PMID: 25418019.

8: Plosker GL. Dapagliflozin: a review of its use in patients with type 2 diabetes. Drugs. 2014 Dec;74(18):2191-209. doi: 10.1007/s40265-014-0324-3. Review. PubMed PMID: 25389049.

9: Thomas MC. Renal effects of dapagliflozin in patients with type 2 diabetes. Ther Adv Endocrinol Metab. 2014 Jun;5(3):53-61. doi: 10.1177/2042018814544153. Review. PubMed PMID: 25126408; PubMed Central PMCID: PMC4132377.

10: Orme M, Fenici P, Lomon ID, Wygant G, Townsend R, Roudaut M. A systematic review and mixed-treatment comparison of dapagliflozin with existing anti-diabetes treatments for those with type 2 diabetes mellitus inadequately controlled by sulfonylurea monotherapy. Diabetol Metab Syndr. 2014 Jun 11;6:73. doi: 10.1186/1758-5996-6-73. eCollection 2014. Review. PubMed PMID: 25006351; PubMed Central PMCID: PMC4085736.

11: Aylsworth A, Dean Z, VanNorman C, Nkemdirim Okere A. Dapagliflozin for the Treatment of Type 2 Diabetes Mellitus. Ann Pharmacother. 2014 Jun 20;48(9):1202-1208. [Epub ahead of print] Review. PubMed PMID: 24951310.

12: Salvo MC, Brooks AD, Thacker SM. Patient considerations in the management of type 2 diabetes - critical appraisal of dapagliflozin. Patient Prefer Adherence. 2014 Apr 22;8:493-502. doi: 10.2147/PPA.S59169. eCollection 2014. Review. PubMed PMID: 24790417; PubMed Central PMCID: PMC4003262.

13: Balakumar P, Sundram K, Dhanaraj SA. Dapagliflozin: glucuretic action and beyond. Pharmacol Res. 2014 Apr;82:34-9. doi: 10.1016/j.phrs.2014.03.008. Epub 2014 Apr 3. Review. PubMed PMID: 24705156.

14: Albarrán OG, Ampudia-Blasco FJ. [Dapagliflozin, the first SGLT-2 inhibitor in the treatment of type 2 diabetes]. Med Clin (Barc). 2013 Sep;141 Suppl 2:36-43. doi: 10.1016/S0025-7753(13)70062-9. Review. Spanish. PubMed PMID: 24444523.

15: Goring S, Hawkins N, Wygant G, Roudaut M, Townsend R, Wood I, Barnett AH. Dapagliflozin compared with other oral anti-diabetes treatments when added to metformin monotherapy: a systematic review and network meta-analysis. Diabetes Obes Metab. 2014 May;16(5):433-42. doi: 10.1111/dom.12239. Epub 2013 Dec 16. Review. PubMed PMID: 24237939.

16: Kilov G, Leow S, Thomas M. SGLT2 inhibition with dapagliflozin -- a novel approach for the management of type 2 diabetes. Aust Fam Physician. 2013 Oct;42(10):706-10. Review. PubMed PMID: 24130972.

17: Zhang M, Zhang L, Wu B, Song H, An Z, Li S. Dapagliflozin treatment for type 2 diabetes: a systematic review and meta-analysis of randomized controlled trials. Diabetes Metab Res Rev. 2014 Mar;30(3):204-21. doi: 10.1002/dmrr.2479. Review. PubMed PMID: 24115369.

18: Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW. Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. Review. PubMed PMID: 24105299.

19: Kleefstra N, Drion I, van Hateren KJ, Holleman F, Goudswaard AN, Bilo HJ. [SGLT-2 inhibitors: diabetes treatment by glycosuria; literature review on the effect of dapagliflozin]. Ned Tijdschr Geneeskd. 2013;157(38):A5969. Review. Dutch. PubMed PMID: 24050445.

20: Abdul-Ghani MA, DeFronzo RA. Dapagliflozin for the treatment of type 2 diabetes. Expert Opin Pharmacother. 2013 Aug;14(12):1695-703. doi: 10.1517/14656566.2013.812632. Epub 2013 Jun 26. Review. PubMed PMID: 23800130.



Additional Information

Dapagliflozin inhibits subtype 2 of the sodium-glucose transport proteins (SGLT2), which is responsible for at least 90% of the glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine. The efficacy of the this medication class has yet to be determined, but in initial clinical trials, dapagliflozin lowers HbA1c by 0.90 percentage points when added to metformin.