dapagliflozin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
sodium glucose co-transporter inhibitors, phlorizin derivatives 4304 461432-26-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dapagliflozin propanediol monohydrate
  • dapagliflozin propanediol
  • BMS 512148
  • forxiga
  • dapaglifozin
  • dapagliflozin
  • farxiga
  • dapagliflozin propylene glycolate hydrate
an Sodium-glucose cotransporter 2 (SGLT2) inhibitor, SGLT2 expressed in the proximal renal tubules, is responsible for the majority of the reabsorption of filtered glucose from the tubular lumen, by inhibiting SGLT2, dapagliflozin reduces reabsorption of filtered glucose and lowers the renal threshold for glucose, and thereby increases urinary glucose excretion
  • Molecular weight: 408.88
  • Formula: C21H25ClO6
  • CLOGP: 3.37
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 4
  • TPSA: 99.38
  • ALOGS: -3.37
  • ROTB: 6

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
Vd (Volume of distribution) 1.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.09 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 12, 2012 EMA
Jan. 8, 2014 FDA ASTRAZENECA AB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Diabetic ketoacidosis 3004.63 21.16 690 8057 17520 46659795
Ketoacidosis 1192.10 21.16 247 8500 3708 46673607
Euglycaemic diabetic ketoacidosis 648.30 21.16 133 8614 1883 46675432
Fungal infection 338.56 21.16 146 8601 29374 46647941
Glycosylated haemoglobin increased 162.33 21.16 65 8682 10811 46666504
Diabetes mellitus inadequate control 140.36 21.16 62 8685 13152 46664163
Blood glucose increased 118.27 21.16 102 8645 71911 46605404
Ketosis 115.97 21.16 25 8722 452 46676863
Urinary tract infection 100.27 21.16 161 8586 220105 46457210
Ketonuria 97.98 21.16 21 8726 369 46676946
Diabetic metabolic decompensation 79.36 21.16 22 8725 1163 46676152
Metabolic acidosis 78.36 21.16 62 8685 38718 46638597
Blood ketone body increased 75.59 21.16 16 8731 264 46677051
Weight decreased 66.03 21.16 131 8616 210718 46466597
Hyperglycaemia 64.34 21.16 53 8694 35018 46642297
Urine ketone body present 62.53 21.16 21 8726 2121 46675194
Hypoglycaemia 60.34 21.16 62 8685 54287 46623028
Pyelonephritis 52.90 21.16 34 8713 15323 46661992
Pruritus genital 52.62 21.16 14 8733 633 46676682
Temperature perception test abnormal 51.55 21.16 8 8739 17 46677298
Genital infection female 50.92 21.16 10 8737 111 46677204
Urosepsis 48.02 21.16 32 8715 15321 46661994
Dehydration 46.15 21.16 96 8651 159444 46517871
Glucose urine present 42.82 21.16 12 8735 660 46676655
Vulvovaginal pruritus 41.31 21.16 16 8731 2431 46674884
Genital infection fungal 40.88 21.16 9 8738 180 46677135
Polyuria 40.81 21.16 22 8725 7173 46670142
Acute kidney injury 40.44 21.16 116 8631 235739 46441576
Necrotising fasciitis 40.23 21.16 16 8731 2607 46674708
Genital infection 37.82 21.16 7 8740 55 46677260
Lactic acidosis 34.60 21.16 37 8710 33872 46643443
Candida infection 33.43 21.16 30 8717 22210 46655105
Glomerular filtration rate decreased 33.29 21.16 23 8724 11671 46665644
Decreased vibratory sense 32.36 21.16 8 8739 269 46677046
Acidosis 31.86 21.16 22 8725 11152 46666163
Cerebral infarction 30.24 21.16 29 8718 23337 46653978
Pyelonephritis acute 30.24 21.16 15 8732 4119 46673196
Toe amputation 29.84 21.16 12 8735 2012 46675303
Pollakiuria 29.32 21.16 29 8718 24232 46653083
Haematuria 28.63 21.16 30 8717 26828 46650487
Hyperglycaemic hyperosmolar nonketotic syndrome 27.20 21.16 8 8739 523 46676792
Rheumatoid arthritis 27.00 21.16 6 8741 240209 46437106
Vulvovaginal mycotic infection 26.63 21.16 14 8733 4337 46672978
Blood ketone body 26.61 21.16 5 8742 43 46677272
Compartment syndrome 26.56 21.16 11 8736 1988 46675327
Diabetic ketosis 24.96 21.16 6 8741 179 46677136
Diabetic ketoacidotic hyperglycaemic coma 24.46 21.16 5 8742 69 46677246
Dysuria 24.31 21.16 28 8719 27805 46649510
Capillary leak syndrome 23.73 21.16 10 8737 1887 46675428
Vulvovaginitis 21.96 21.16 6 8741 300 46677015
Glycosuria 21.64 21.16 8 8739 1070 46676245

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Diabetic ketoacidosis 2194.30 19.69 571 8216 15415 29928276
Ketoacidosis 720.25 19.69 176 8611 3570 29940121
Euglycaemic diabetic ketoacidosis 411.21 19.69 98 8689 1773 29941918
Glycosylated haemoglobin increased 188.41 19.69 79 8708 9412 29934279
Ketonuria 160.89 19.69 37 8750 567 29943124
Phimosis 137.63 19.69 33 8754 611 29943080
Balanoposthitis 125.48 19.69 34 8753 1042 29942649
Fungal infection 104.10 19.69 59 8728 13541 29930150
Blood glucose increased 103.72 19.69 108 8679 61422 29882269
Ketosis 94.35 19.69 22 8765 359 29943332
Weight decreased 93.21 19.69 162 8625 150759 29792932
Diabetes mellitus inadequate control 91.34 19.69 53 8734 12709 29930982
Bladder cancer 90.58 19.69 47 8740 9055 29934636
Lactic acidosis 90.03 19.69 74 8713 31139 29912552
Polyuria 85.20 19.69 42 8745 7264 29936427
Metabolic acidosis 84.15 19.69 77 8710 37384 29906307
Hyperglycaemia 82.29 19.69 74 8713 35126 29908565
Urinary tract infection 79.84 19.69 103 8684 73556 29870135
Toe amputation 70.31 19.69 26 8761 2215 29941476
Acquired phimosis 64.31 19.69 12 8775 59 29943632
Epididymitis 62.23 19.69 24 8763 2295 29941396
Dehydration 60.32 19.69 120 8667 123419 29820272
Necrotising fasciitis 56.22 19.69 25 8762 3424 29940267
Pollakiuria 54.92 19.69 43 8744 16863 29926828
Hypoglycaemia 54.72 19.69 71 8716 50910 29892781
Blood ketone body increased 54.01 19.69 14 8773 360 29943331
Urine ketone body present 52.68 19.69 17 8770 962 29942729
Cerebral infarction 49.28 19.69 49 8738 26324 29917367
Blood glucose abnormal 49.01 19.69 26 8761 5233 29938458
Diabetic ketosis 48.27 19.69 9 8778 44 29943647
Blood triglycerides increased 46.28 19.69 36 8751 13981 29929710
Glucose urine present 45.42 19.69 15 8772 913 29942778
Acute kidney injury 43.69 19.69 177 8610 273665 29670026
Glomerular filtration rate decreased 41.51 19.69 31 8756 11331 29932360
Hyperglycaemic hyperosmolar nonketotic syndrome 40.78 19.69 14 8773 960 29942731
Thrombotic cerebral infarction 37.26 19.69 10 8777 295 29943396
Pancreatitis 33.31 19.69 47 8740 36443 29907248
Glycosuria 33.16 19.69 13 8774 1298 29942393
Pancreatitis acute 32.70 19.69 39 8748 25656 29918035
Blood cholesterol increased 32.56 19.69 32 8755 16938 29926753
Thirst 32.40 19.69 22 8765 6927 29936764
Haematuria 28.67 19.69 49 8738 44785 29898906
Urosepsis 27.92 19.69 24 8763 10708 29932983
Genital rash 27.87 19.69 9 8778 510 29943181
Neutropenia 27.18 19.69 3 8784 128537 29815154
Dysuria 26.70 19.69 33 8754 22508 29921183
Acetonaemia 26.26 19.69 6 8781 89 29943602
Acute myocardial infarction 25.24 19.69 51 8736 52888 29890803
Foot amputation 24.55 19.69 8 8779 467 29943224
Type 2 diabetes mellitus 23.04 19.69 24 8763 13598 29930093
Brain stem infarction 23.01 19.69 10 8777 1296 29942395
Thrombocytopenia 22.86 19.69 6 8781 137038 29806653
Pyelonephritis 22.53 19.69 16 8771 5410 29938281
Toxicity to various agents 22.48 19.69 12 8775 177171 29766520
Genital infection fungal 22.07 19.69 6 8781 186 29943505
Urine output increased 21.62 19.69 9 8778 1049 29942642
Peripheral circulatory failure 21.48 19.69 6 8781 206 29943485
Immune-mediated hepatitis 21.16 19.69 9 8778 1107 29942584
Gangrene 20.07 19.69 14 8773 4600 29939091
Anaemia 19.95 19.69 19 8768 207973 29735718

Pharmacologic Action:

SourceCodeDescription
ATC A10BD15 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Combinations of oral blood glucose lowering drugs
ATC A10BD21 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Combinations of oral blood glucose lowering drugs
ATC A10BD25 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Combinations of oral blood glucose lowering drugs
ATC A10BK01 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Sodium-glucose co-transporter 2 (SGLT2) inhibitors
MeSH PA D007004 Hypoglycemic Agents
MeSH PA D000077203 Sodium-Glucose Transporter 2 Inhibitors
FDA MoA N0000187058 Sodium-Glucose Transporter 2 Inhibitors
FDA EPC N0000187059 Sodium-Glucose Cotransporter 2 Inhibitor
CHEBI has role CHEBI:35526 hypoglycemic drug
CHEBI has role CHEBI:73273 sodium glucose co-transporter 2 inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Diabetes mellitus type 2 indication 44054006 DOID:9352

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.62 acidic
pKa2 13.26 acidic
pKa3 13.7 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
10MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL Feb. 22, 2022 INFORMATION ADDED TO THE PRESCRIBING INFORMATION TO REFLECT THAT NO DOSE ADJUSTMENT IS NEEDED FOR PATIENTS WITH AN ESTIMATED GLOMERULAR FILTRATION RATE (EGFR) OF 45 ML/MIN/1.73 M2 OR GREATER AS SUPPORTED BY CLINICAL STUDY REPORT
5MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL Feb. 22, 2022 INFORMATION ADDED TO THE PRESCRIBING INFORMATION TO REFLECT THAT NO DOSE ADJUSTMENT IS NEEDED FOR PATIENTS WITH AN ESTIMATED GLOMERULAR FILTRATION RATE (EGFR) OF 45 ML/MIN/1.73 M2 OR GREATER AS SUPPORTED BY CLINICAL STUDY REPORT
10MG;EQ 5MG BASE QTERN ASTRAZENECA AB N209091 Feb. 27, 2017 RX TABLET ORAL May 2, 2022 EXPANDED INDICATION FOR USE AS AN ADJUNCT TO DIET AND EXERCISE TO IMPROVE GLYCEMIC CONTROL IN ADULTS WITH TYPE 2 DIABETES MELLITUS
5MG;EQ 5MG BASE QTERN ASTRAZENECA AB N209091 May 2, 2019 RX TABLET ORAL May 2, 2022 NEW STRENGTH
10MG;1GM;EQ 5MG BASE QTERNMET XR ASTRAZENECA AB N210874 May 2, 2019 DISCN TABLET, EXTENDED RELEASE ORAL May 2, 2022 NEW PRODUCT
2.5MG;1GM;EQ 2.5MG BASE QTERNMET XR ASTRAZENECA AB N210874 May 2, 2019 DISCN TABLET, EXTENDED RELEASE ORAL May 2, 2022 NEW PRODUCT
5MG;1GM;EQ 2.5MG BASE QTERNMET XR ASTRAZENECA AB N210874 May 2, 2019 DISCN TABLET, EXTENDED RELEASE ORAL May 2, 2022 NEW PRODUCT
5MG;1GM;EQ 5MG BASE QTERNMET XR ASTRAZENECA AB N210874 May 2, 2019 DISCN TABLET, EXTENDED RELEASE ORAL May 2, 2022 NEW PRODUCT
10MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
5MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
10MG;1GM XIGDUO XR ASTRAZENECA AB N205649 Oct. 29, 2014 RX TABLET, EXTENDED RELEASE ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
10MG;500MG XIGDUO XR ASTRAZENECA AB N205649 Oct. 29, 2014 RX TABLET, EXTENDED RELEASE ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
2.5MG;1GM XIGDUO XR ASTRAZENECA AB N205649 July 28, 2017 RX TABLET, EXTENDED RELEASE ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
5MG;1GM XIGDUO XR ASTRAZENECA AB N205649 Oct. 29, 2014 RX TABLET, EXTENDED RELEASE ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
5MG;500MG XIGDUO XR ASTRAZENECA AB N205649 Oct. 29, 2014 RX TABLET, EXTENDED RELEASE ORAL Oct. 18, 2022 TO REDUCE THE RISK OF HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH TYPE 2 DIABETES MELLITUS AND ESTABLISHED CARDIOVASCULAR DISEASE OR MULTIPLE CARDIOVASCULAR RISK FACTORS
10MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL May 5, 2023 TO REDUCE THE RISK OF CARDIOVASCULAR DEATH AND HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH HEART FAILURE (NYHA CLASS II-IV) WITH REDUCED EJECTION FRACTION
5MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL May 5, 2023 TO REDUCE THE RISK OF CARDIOVASCULAR DEATH AND HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH HEART FAILURE (NYHA CLASS II-IV) WITH REDUCED EJECTION FRACTION
10MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL April 30, 2024 TO REDUCE THE RISK OF SUSTAINED EGFR DECLINE, END-STAGE KIDNEY DISEASE, CARDIOVASCULAR DEATH, AND HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH CHRONIC KIDNEY DISEASE AT RISK OF PROGRESSION
5MG FARXIGA ASTRAZENECA AB N202293 Jan. 8, 2014 RX TABLET ORAL April 30, 2024 TO REDUCE THE RISK OF SUSTAINED EGFR DECLINE, END-STAGE KIDNEY DISEASE, CARDIOVASCULAR DEATH, AND HOSPITALIZATION FOR HEART FAILURE IN ADULTS WITH CHRONIC KIDNEY DISEASE AT RISK OF PROGRESSION

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium/glucose cotransporter 2 Transporter INHIBITOR IC50 9.30 IUPHAR IUPHAR
Low affinity sodium-glucose cotransporter Transporter IC50 8.87 CHEMBL
Sodium/glucose cotransporter 1 Transporter IC50 8.49 CHEMBL
Sodium/myo-inositol cotransporter 2 Transporter IC50 6.42 CHEMBL
Sodium/glucose cotransporter 2 Transporter EC50 8.52 CHEMBL

External reference:

IDSource
D08897 KEGG_DRUG
960404-48-2 SECONDARY_CAS_RN
4033035 VANDF
C2353950 UMLSCUI
CHEBI:85078 CHEBI
CHEMBL429910 ChEMBL_ID
CHEMBL2103802 ChEMBL_ID
DB06292 DRUGBANK_ID
C529054 MESH_SUPPLEMENTAL_RECORD_UI
9887712 PUBCHEM_CID
4594 IUPHAR_LIGAND_ID
8886 INN_ID
1ULL0QJ8UC UNII
1486966 RXNORM
210769 MMSL
28989 MMSL
29986 MMSL
d07928 MMSL
014949 NDDF
014950 NDDF
703674001 SNOMEDCT_US
703675000 SNOMEDCT_US
703678003 SNOMEDCT_US
783086004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 0310-6205 TABLET, FILM COATED 5 mg ORAL NDA 27 sections
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 0310-6210 TABLET, FILM COATED 10 mg ORAL NDA 27 sections
XIGDUOXR HUMAN PRESCRIPTION DRUG LABEL 2 0310-6225 TABLET, FILM COATED, EXTENDED RELEASE 2.50 mg ORAL NDA 30 sections
XIGDUOXR HUMAN PRESCRIPTION DRUG LABEL 2 0310-6250 TABLET, FILM COATED, EXTENDED RELEASE 5 mg ORAL NDA 30 sections
XIGDUOXR HUMAN PRESCRIPTION DRUG LABEL 2 0310-6260 TABLET, FILM COATED, EXTENDED RELEASE 5 mg ORAL NDA 30 sections
XIGDUOXR HUMAN PRESCRIPTION DRUG LABEL 2 0310-6270 TABLET, FILM COATED, EXTENDED RELEASE 10 mg ORAL NDA 30 sections
XIGDUOXR HUMAN PRESCRIPTION DRUG LABEL 2 0310-6280 TABLET, FILM COATED, EXTENDED RELEASE 10 mg ORAL NDA 30 sections
QTERN HUMAN PRESCRIPTION DRUG LABEL 2 0310-6770 TABLET, FILM COATED 5 mg ORAL NDA 28 sections
QTERN HUMAN PRESCRIPTION DRUG LABEL 2 0310-6780 TABLET, FILM COATED 10 mg ORAL NDA 28 sections
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 50090-3481 TABLET, FILM COATED 10 mg ORAL NDA 27 sections
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 50090-3482 TABLET, FILM COATED 5 mg ORAL NDA 27 sections
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 55154-6932 TABLET, FILM COATED 5 mg ORAL NDA 28 sections
FARXIGA HUMAN PRESCRIPTION DRUG LABEL 1 55154-6933 TABLET, FILM COATED 10 mg ORAL NDA 28 sections