Structure via PubChem · Public domain (PubChem)
lumacaftor
Sign in to saveAlso known as VRT-826809, VX-809, VRT 826809, VX 809, 3-(6-{[1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)cyclopropane-1-carbonyl]amino}-3-methylpyridin-2-yl)benzoic acid
Lumacaftor (VX-809) is a pharmaceutical drug that acts as a chaperone during protein folding and increases the number of CFTR proteins that are trafficked to the cell surface. It is available in a single pill with ivacaftor; the combination, lumacaftor/ivacaftor (brand name Orkambi), is used to treat people with cystic fibrosis who are homozygous for the F508del mutation in the cystic fibrosis transmembrane conductance regulator (CFTR) gene, the defective protein that causes the disease. It was developed by Vertex Pharmaceuticals and the combination was approved by the FDA in 2015. As of 2015,
Chemical data
- Formula
- C24H18F2N2O5
- Molecular weight
- 452.4 g/mol
- IUPAC name
- 3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methyl-2-pyridinyl]benzoic acid
- SMILES
- CC1=C(N=C(C=C1)NC(=O)C2(CC2)C3=CC4=C(C=C3)OC(O4)(F)F)C5=CC(=CC=C5)C(=O)O
- InChIKey
- UFSKUSARDNFIRC-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 97.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2015
- Admin. routes
- oral
- Indications
- liver disease, cystic fibrosis
via ChEMBL · EBI
Wikidata facts
- Subclass of
- carboxylic acid
- Mass
- 452.118378
- Has use
- medication
Show 4 more facts
- chemical formula
- C₂₄H₁₈F₂N₂O₅
- canonical SMILES
- CC1=C(N=C(C=C1)NC(=O)C2(CC2)C3=CC4=C(C=C3)OC(O4)(F)F)C5=CC(=CC=C5)C(=O)O
- World Health Organisation international non-proprietary name
- lumacaftor
- Commons category
- Lumacaftor
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{Drugbox | Verifiedfields = changed | verifiedrevid = 458773847 | IUPAC_name = 3-{6-{[1-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino}-3-methylpyridin-2-yl}benzoic acid | image = Lumacaftor_skeletal.svg | image_class = skin-invert-image | alt = | caption =
| tradename = | Drugs.com = | MedlinePlus = | pregnancy_AU = | pregnancy_US = | pregnancy_category= | licence_EU = yes | legal_AU = | legal_CA = | legal_UK = | legal_US = rx-only | legal_US_comment = available only as Lumacaftor/ivacaftor | legal_status = | routes_of_administration = By mouth
Excerpted from Wikipedia’s “lumacaftor” article, available under the CC BY-SA 4.0 licence.