vanzacaftor   Click here for help

GtoPdb Ligand ID: 13694

Synonyms: VX-121 | VX121
Approved drug
vanzacaftor is an approved drug
Compound class: Synthetic organic
Comment: Vanzacaftor (VX-121) is a cystic fibrosis transmembrane regulator (CFTR) protein modulator/corrector for class II CFTR mutations (the most common being F508del). The principal action of vanzacaftor is to restore the folding/trafficking of mutated CFTR to the plasma membrane. VX-121 also stimulates a K+ secretory current that is mediated by the large-conductance calcium-activated potassium channel (BKCa, KCa1.1) [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 136.44
Molecular weight 617.76
XLogP 4.91
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1(C)C[C@@H]2CCCNC3=CC=CC(=N3)S(=O)(=O)NC(=O)C4=CC=C(N=C4N1C2)N5C=CC(=N5)OCCC6C7(CC7)C86CC8
Isomeric SMILES CC1(C[C@@H]2CCCNC3=NC(=CC=C3)S(=O)(=O)NC(=O)C4=C(N1C2)N=C(C=C4)N5C=CC(=N5)OCCC6C7(C68CC8)CC7)C
InChI InChI=1S/C32H39N7O4S/c1-30(2)19-21-5-4-16-33-24-6-3-7-27(34-24)44(41,42)37-29(40)22-8-9-25(35-28(22)38(30)20-21)39-17-10-26(36-39)43-18-11-23-31(12-13-31)32(23)14-15-32/h3,6-10,17,21,23H,4-5,11-16,18-20H2,1-2H3,(H,33,34)(H,37,40)/t21-/m0/s1
InChI Key VCSUIBJKYCVWNF-NRFANRHFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2024)
International Nonproprietary Names Click here for help
INN number INN
11971 vanzacaftor
Synonyms Click here for help
VX-121 | VX121
Database Links Click here for help
CAS Registry No. 2374124-49-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL5314934
DrugBank Ligand DB18373
GtoPdb PubChem SID 507750328
PubChem CID 139399801
Search Google for chemical match using the InChIKey VCSUIBJKYCVWNF-NRFANRHFSA-N
Search Google for chemicals with the same backbone VCSUIBJKYCVWNF
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UniChem Compound Search for chemical match using the InChIKey VCSUIBJKYCVWNF-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey VCSUIBJKYCVWNF-NRFANRHFSA-N