Details of the Drug

General Information of Drug (ID: DM28UJG)

Drug Name
Dapagliflozin
Synonyms BMS 512148; BMS-512148; BMS-512148, Dapagliflozin; Dapagliflozin (INN/USAN); 2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol
Indication
Disease Entry ICD 11 Status REF
Non-insulin dependent diabetes 5A11 Approved [1]
Type-2 diabetes 5A11 Approved [2]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 3 [3]
Affected Organisms
Humans and other mammals
ATC Code
A10BK01: Dapagliflozin
A10BK: Sodium-glucose co-transporter 2 (SGLT2) inhibitors
A10B: BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
A10: DRUGS USED IN DIABETES
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 408.9
Logarithm of the Partition Coefficient (xlogp) 2.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3 mL/min/kg [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 12.2 hours [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.09% [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.7 L/kg [5]
Chemical Identifiers
Formula
C21H25ClO6
IUPAC Name
(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
Canonical SMILES
CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl
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
Cross-matching ID
PubChem CID
9887712
ChEBI ID
CHEBI:85078
CAS Number
461432-26-8
UNII
1ULL0QJ8UC
DrugBank ID
DB06292
TTD ID
D01TNW
VARIDT ID
DR00918
INTEDE ID
DR0412
ACDINA ID
D00167
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium/glucose cotransporter 2 (SGLT2) TTLWPVF SC5A2_HUMAN Modulator [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [7]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [7]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [7]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Sodium/glucose cotransporter 2 (SLC5A2) OT93UUDI SC5A2_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dapagliflozin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Arn-509 DMT81LZ Moderate Increased metabolism of Dapagliflozin caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [9]
Regorafenib DMHSY1I Minor Decreased metabolism of Dapagliflozin caused by Regorafenib mediated inhibition of UGT. Colorectal cancer [2B91] [10]
PF-06463922 DMKM7EW Moderate Increased metabolism of Dapagliflozin caused by PF-06463922 mediated induction of UGT. Lung cancer [2C25] [11]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Crospovidone E00626 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 4000 E00654 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Colcothar yellow E00436 518696 Colorant
Cellulose microcrystalline E00698 Not Available Adsorbent; Suspending agent; Diluent
⏷ Show the Full List of 10 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Dapagliflozin Propanediol 5mg tablet 5mg Tablet Oral
Dapagliflozin Propanediol 10mg tablet 10mg Tablet Oral
Dapagliflozin 10 mg tablet 10 mg Oral Tablet Oral
Dapagliflozin 5 mg tablet 5 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Dapagliflozin FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4594).
3 Dapagliflozin in Respiratory Failure in Patients With COVID-19 (DARE-19)
4 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
7 Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27.
8 Discovery of novel N--D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes. J Med Chem. 2011 Jan 13;54(1):166-78. doi: 10.1021/jm101072y. Epub 2010 Dec 3.
9 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
10 Product Information. Farxiga (dapagliflozin). Bristol-Myers Squibb, Princeton, NJ.
11 Cerner Multum, Inc. "Australian Product Information.".