Structure via PubChem · Public domain (PubChem)
dapagliflozin
Sign in to saveAlso known as (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Dapagliflozin, sold under the brand names Farxiga (US) and Forxiga (EU) among others, is a medication used to treat type2 diabetes. It is also used to treat adults with heart failure and chronic kidney disease. It reversibly inhibits sodium-glucose co-transporter 2 (SGLT-2) in the renal proximal convoluted tubule to reduce glucose reabsorption and increase urinary glucose excretion.
Key facts
- Drug.image
- Dapagliflozin skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 275
- Drug.image2
- Haworth projection of dapagliflozin.svg
- Drug.image_class2
- skin-invert-image
- Drug.width2
- 225
- Drug.caption
- Haworth projection (bottom)
- Drug.imageR
- Dapagliflozin-from-xtal-Mercury-3D-bs.png
- Drug.image_classR
- bg-transparent
- Drug.widthR
- 250
- Drug.tradename
- Farxiga, Forxiga, others
- Drug.MedlinePlus
- a614015
- Drug.DailyMedID
- Dapagliflozin
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth
- Drug.class
- Sodium-glucose co-transporter 2 (SGLT2) inhibitor
- Drug.ATC_prefix
- A10
- Drug.ATC_suffix
- BK01
via Wikipedia infobox
Chemical data
- Formula
- C21H25ClO6
- Molecular weight
- 408.9 g/mol
- IUPAC name
- (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
- 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
- InChIKey
- JVHXJTBJCFBINQ-ADAARDCZSA-N
- XLogP
- 2.3
- Polar surface area
- 99.4 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Official website
FARXIGA for CKD | Heart Failure | Type 2 Diabetes
FARXIGA® (dapagliflozin), a medication for people with chronic kidney disease (CKD), heart failure, and type 2 diabetes.
farxiga.com →Link to the official site · 40,000 chars · not written by Vinony
~15 min read
Encyclopedic overview
12 sectionsContents
- Medical uses
- Effects in nondiabetic chronic kidney disease
- Adverse effects
- Chemistry
- Mechanism of action
- Selectivity
- Names
- History
- Society and culture
- Legal status
- Research
- References
{{Infobox drug | image = Dapagliflozin skeletal.svg | image_class = skin-invert-image | width = 275 | alt = | image2 = Haworth projection of dapagliflozin.svg | image_class2 = skin-invert-image | width2 = 225 | alt2 = | caption = Haworth projection (bottom) | imageR = Dapagliflozin-from-xtal-Mercury-3D-bs.png | image_classR = bg-transparent | widthR = 250 | altR =
| pronounce = | tradename = Farxiga, Forxiga, others | Drugs.com = | MedlinePlus = a614015 | DailyMedID = Dapagliflozin | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category= | routes_of_administration = By mouth | class = Sodium-glucose co-transporter 2 (SGLT2) inhibitor | ATC_prefix = A10 | ATC_suffix = BK01 | ATC_supplemental =
Excerpted from Wikipedia’s “dapagliflozin” article, available under the CC BY-SA 4.0 licence.