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MedKoo Cat#: 314204 | Name: Dapagliflozin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Dapagliflozin
Dapagliflozin
CAS#461432-26-8 (free base)

Theoretical Analysis

MedKoo Cat#: 314204

Name: Dapagliflozin

CAS#: 461432-26-8 (free base)

Chemical Formula: C21H25ClO6

Exact Mass: 408.1340

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
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 350.00 Ready to ship
5g USD 650.00 Ready to ship
10g USD 1,050.00 Ready to ship
20g USD 1,750.00 Ready to ship
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Related CAS #
960404-48-2 (propanediol monohydrate) 461432-26-8 (free base)
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
More Info
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.         
Biological target:
Dapagliflozin (BMS-512148) is a competitive sodium/glucose cotransporter 2 (SGLT2) inhibitor.
In vitro activity:
Here, the study showed that the expression of PGC-1α was suppressed following H/R (hypoxia/reoxygenation) injury whereas treatment of DAPA (Dapagliflozin) maintained the amount of PGC-1α. Moreover, the silence of AMPK abrogated this effect (Fig. 3a, b), suggesting that reservation of PGC-1α expression by DAPA was related to AMPK activation. Downregulation of PGC-1α by I/R injury attenuated by DAPA treatment was confirmed by animal study (Fig. 3c, d). Besides, treatment of DPI to inhibit Nox attenuated the downregulation of PGC-1α under H/R injury (Fig. 3a, b), suggesting oxidative stress participated in the downregulation of PGC-1α after H/R injury. Taken together, the downregulation of PGC-1α by H/R or I/R injury could be attenuated via oxidative stress inhibition, and via AMPK activation by DAPA treatment. Reference: Cell Biosci. 2021; 11: 44. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7913252/
In vivo activity:
Mice were treated for 5 weeks with either saline or PDF with or without addition of dapagliflozin (1 mg/kg) via a peritoneal catheter (Figure 2A). A systemic action of dapagliflozin was observed, as reflected by the presence of glucosuria in 24 h urine collections of mice treated with the SGLT2 inhibitor (Figure S1, Supplementary Materials). The study then evaluated the peritoneal transcriptional expression of SGLT2, SGLT1, and several GLUTs known to be expressed in the peritoneum. The study found a strong upregulation of SGLT2 expression in mice receiving high-glucose PDF, whereas SGLT1 expression was unaltered (Figure 2B). Most notably, pharmacological inhibition of SGLT2 with dapagliflozin completely abrogated PD-induced upregulation of SGLT2. Glucose transporters demonstrated differential regulation, with GLUT1 and 3 being upregulated and GLUT4 being downregulated in response to chronic exposure to PDF. This regulation was unaffected by dapagliflozin (Figure 2C). Reference: Biomolecules. 2020 Nov; 10(11): 1573. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7699342/
Solvent mg/mL mM
Solubility
DMSO 91.0 222.56
Ethanol 82.0 200.55
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. Dai C, Walker JT, Shostak A, Bouchi Y, Poffenberger G, Hart NJ, Jacobson DA, Calcutt MW, Bottino R, Greiner DL, Shultz LD, McGuinness OP, Dean ED, Powers AC. Dapagliflozin Does Not Directly Affect Human α or β Cells. Endocrinology. 2020 Aug 1;161(8):bqaa080. doi: 10.1210/endocr/bqaa080. PMID: 32428240; PMCID: PMC7375801. 2. Tsai KL, Hsieh PL, Chou WC, Cheng HC, Huang YT, Chan SH. Dapagliflozin attenuates hypoxia/reoxygenation-caused cardiac dysfunction and oxidative damage through modulation of AMPK. Cell Biosci. 2021 Feb 26;11(1):44. doi: 10.1186/s13578-021-00547-y. PMID: 33637129; PMCID: PMC7913252. 3. Balzer MS, Rong S, Nordlohne J, Zemtsovski JD, Schmidt S, Stapel B, Bartosova M, von Vietinghoff S, Haller H, Schmitt CP, Shushakova N. SGLT2 Inhibition by Intraperitoneal Dapagliflozin Mitigates Peritoneal Fibrosis and Ultrafiltration Failure in a Mouse Model of Chronic Peritoneal Exposure to High-Glucose Dialysate. Biomolecules. 2020 Nov 19;10(11):1573. doi: 10.3390/biom10111573. PMID: 33228017; PMCID: PMC7699342. 4. Nugrahaningrum DA, Marcelina O, Liu C, Wu S, Kasim V. Dapagliflozin Promotes Neovascularization by Improving Paracrine Function of Skeletal Muscle Cells in Diabetic Hindlimb Ischemia Mice Through PHD2/HIF-1α Axis. Front Pharmacol. 2020 Aug 10;11:1104. doi: 10.3389/fphar.2020.01104. PMID: 32848736; PMCID: PMC7424065.
In vitro protocol:
1. Dai C, Walker JT, Shostak A, Bouchi Y, Poffenberger G, Hart NJ, Jacobson DA, Calcutt MW, Bottino R, Greiner DL, Shultz LD, McGuinness OP, Dean ED, Powers AC. Dapagliflozin Does Not Directly Affect Human α or β Cells. Endocrinology. 2020 Aug 1;161(8):bqaa080. doi: 10.1210/endocr/bqaa080. PMID: 32428240; PMCID: PMC7375801. 2. Tsai KL, Hsieh PL, Chou WC, Cheng HC, Huang YT, Chan SH. Dapagliflozin attenuates hypoxia/reoxygenation-caused cardiac dysfunction and oxidative damage through modulation of AMPK. Cell Biosci. 2021 Feb 26;11(1):44. doi: 10.1186/s13578-021-00547-y. PMID: 33637129; PMCID: PMC7913252.
In vivo protocol:
1. Balzer MS, Rong S, Nordlohne J, Zemtsovski JD, Schmidt S, Stapel B, Bartosova M, von Vietinghoff S, Haller H, Schmitt CP, Shushakova N. SGLT2 Inhibition by Intraperitoneal Dapagliflozin Mitigates Peritoneal Fibrosis and Ultrafiltration Failure in a Mouse Model of Chronic Peritoneal Exposure to High-Glucose Dialysate. Biomolecules. 2020 Nov 19;10(11):1573. doi: 10.3390/biom10111573. PMID: 33228017; PMCID: PMC7699342. 2. Nugrahaningrum DA, Marcelina O, Liu C, Wu S, Kasim V. Dapagliflozin Promotes Neovascularization by Improving Paracrine Function of Skeletal Muscle Cells in Diabetic Hindlimb Ischemia Mice Through PHD2/HIF-1α Axis. Front Pharmacol. 2020 Aug 10;11:1104. doi: 10.3389/fphar.2020.01104. PMID: 32848736; PMCID: PMC7424065.
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.