Dapagliflozin

  • CAT Number: A000545
  • CAS Number: 461432-26-8
  • Molecular Formula: C₂₁H₂₅ClO₆
  • Molecular Weight: 408.87
  • Purity: ≥95%
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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.

Catalog Number A000545
CAS Number 461432-26-8
Molecular Formula

C₂₁H₂₅ClO₆

Purity 95%
Target SGLT
Solubility >15.1mg/mL in DMSO
Storage -20°C
InChI 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
InChIKey JVHXJTBJCFBINQ-ADAARDCZSA-N
SMILES CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)CO)O)O)O)Cl
Reference

1: Miyaoka D, Tsuda A, Hayashi N, Toi N, Yamasaki A, Nagata Y, Nakatani S,
Kurajoh M, Yamada S, Morioka T, Imanishi Y, Emoto M, Inaba M. Development of
hyperkalemia following treatment with dapagliflozin (DAPA) in a patient with type
2 diabetes after bilateral adrenalectomy. CEN Case Rep. 2017 Nov 13. doi:
10.1007/s13730-017-0286-x. [Epub ahead of print] PubMed PMID: 29134558.
<br>

2: Hayashi T, Fukui T, Nakanishi N, Yamamoto S, Tomoyasu M, Osamura A, Ohara M,
Yamamoto T, Ito Y, Hirano T. Correction to: Dapagliflozin decreases small dense
low-density lipoprotein-cholesterol and increases high-density lipoprotein
2-cholesterol in patients with type 2 diabetes: comparison with sitagliptin.
Cardiovasc Diabetol. 2017 Nov 13;16(1):149. doi: 10.1186/s12933-017-0608-5.
PubMed PMID: 29132354.
<br>

3: Pleros C, Stamataki E, Papadaki A, Damianakis N, Poulidaki R, Gakiopoulou C,
Tzanakis I. Dapagliflozin as a cause of acute tubular necrosis with heavy
consequences: a case report. CEN Case Rep. 2017 Nov 10. doi:
10.1007/s13730-017-0283-0. [Epub ahead of print] PubMed PMID: 29127652.
<br>

4: Min SH, Oh TJ, Baek SI, Lee DH, Kim KM, Moon JH, Choi SH, Park KS, Jang HC,
Lim S. Degree of ketonaemia and its association with insulin resistance after
dapagliflozin treatment in type 2 diabetes. Diabetes Metab. 2017 Oct 23. pii:
S1262-3636(17)30518-9. doi: 10.1016/j.diabet.2017.09.006. [Epub ahead of print]
PubMed PMID: 29074329.
<br>

5: Solini A, Giannini L, Seghieri M, Vitolo E, Taddei S, Ghiadoni L, Bruno RM.
Dapagliflozin acutely improves endothelial dysfunction, reduces aortic stiffness
and renal resistive index in type 2 diabetic patients: a pilot study. Cardiovasc
Diabetol. 2017 Oct 23;16(1):138. doi: 10.1186/s12933-017-0621-8. PubMed PMID:
29061124; PubMed Central PMCID: PMC5654086.
<br>

6: CORRIGENDUM FOR /Dapagliflozin lowers plasma glucose concentration and
improves β-cell function/. J Clin Endocrinol Metab. 2017 Oct 5. doi:
10.1210/jc.2017-02166. [Epub ahead of print] PubMed PMID: 29029092.
<br>

7: Díaz-Rodríguez E, Agra RM, Fernández áL, Adrio B, García-Caballero T,
González-Juanatey JR, Eiras S. Novel effects of dapagliflozin on epicardial
adipose tissue with insulin resistance, high levels of inflammatory chemokines
production and low differentiation ability. Cardiovasc Res. 2017 Sep 11. doi:
10.1093/cvr/cvx186. [Epub ahead of print] PubMed PMID: 29016744.
<br>

8: Scheen AJ. Dapagliflozin and saxagliptin tablets for adults with type 2
diabetes. Expert Rev Clin Pharmacol. 2017 Oct 18:1-14. doi:
10.1080/17512433.2017.1389645. [Epub ahead of print] PubMed PMID: 28984487.
<br>

9: Gaspari T, Spizzo I, Liu H, Hu Y, Simpson RW, Widdop RE, Dear AE.
Dapagliflozin attenuates human vascular endothelial cell activation and induces
vasorelaxation: A potential mechanism for inhibition of atherogenesis. Diab Vasc
Dis Res. 2017 Oct 1:1479164117733626. doi: 10.1177/1479164117733626. [Epub ahead
of print] PubMed PMID: 28976221.

<br>
10: Fadini GP, Zatti G, Consoli A, Bonora E, Sesti G, Avogaro A; DARWIN-T2D
Network. Rationale and design of the DARWIN-T2D (DApagliflozin Real World
evIdeNce in Type 2 Diabetes): A multicenter retrospective nationwide Italian
study and crowdsourcing opportunity. Nutr Metab Cardiovasc Dis. 2017 Aug 8. pii:
S0939-4753(17)30181-3. doi: 10.1016/j.numecd.2017.08.001. [Epub ahead of print]
PubMed PMID: 28967594.

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