nirogacestat   Click here for help

GtoPdb Ligand ID: 7746

Synonyms: Ogsiveo® | PF-03084014 | PF3084014 | Z-3181
Approved drug PDB Ligand
nirogacestat is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Nirogacestat (PF-3084014) is compound 14f in [2] where it is described as a centrally active γ-secretase inhibitor. It is a reversible, non-competitive, and orally bioactive agent. It was proposed an an anti-tumour agent [1,3,11-12].
PF-3084014 was also reported as an inhibitor of the NOTCH signalling pathway which bolstered its oncology credentials [8,11], since NOTCH inhibition promotes cell cycle arrest and induces apoptosis in tumour cells.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 70.98
Molecular weight 489.33
XLogP 5.14
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
Click here for help

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/)

✖
Canonical SMILES CCCC(C(=O)Nc1ncn(c1)C(CNCC(C)(C)C)(C)C)NC1CCc2c(C1)c(F)cc(c2)F
Isomeric SMILES CCC[C@@H](C(=O)Nc1ncn(c1)C(CNCC(C)(C)C)(C)C)N[C@H]1CCc2c(C1)c(F)cc(c2)F
InChI InChI=1S/C27H41F2N5O/c1-7-8-23(32-20-10-9-18-11-19(28)12-22(29)21(18)13-20)25(35)33-24-14-34(17-31-24)27(5,6)16-30-15-26(2,3)4/h11-12,14,17,20,23,30,32H,7-10,13,15-16H2,1-6H3,(H,33,35)/t20-,23-/m0/s1
InChI Key VFCRKLWBYMDAED-REWPJTCUSA-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 (2023))
IUPAC Name Click here for help
(2S)-2-[[(2S)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-N-[1-[1-(2,2-dimethylpropylamino)-2-methylpropan-2-yl]imidazol-4-yl]pentanamide
International Nonproprietary Names Click here for help
INN number INN
10404 nirogacestat
Synonyms Click here for help
Ogsiveo® | PF-03084014 | PF3084014 | Z-3181
Database Links Click here for help
CAS Registry No. 1290543-63-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1770916
GtoPdb PubChem SID 223366079
PubChem CID 46224413
RCSB PDB Ligand O6U
Search Google for chemical match using the InChIKey VFCRKLWBYMDAED-REWPJTCUSA-N
Search Google for chemicals with the same backbone VFCRKLWBYMDAED
Search PubMed clinical trials nirogacestat
Search PubMed titles nirogacestat
Search PubMed titles/abstracts nirogacestat
UniChem Compound Search for chemical match using the InChIKey VFCRKLWBYMDAED-REWPJTCUSA-N
UniChem Connectivity Search for chemical match using the InChIKey VFCRKLWBYMDAED-REWPJTCUSA-N