carfilzomib   Click here for help

GtoPdb Ligand ID: 7420

Synonyms: Kyprolis® | PR-171
Approved drug
carfilzomib is an approved drug (FDA (2012), EMA (2015))
Compound class: Synthetic organic
Comment: Carfilzomib is a tetrapeptide analogue of epoxomicin, an Actinomycete derived selective proteasome inhibitor [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 24
Topological polar surface area 158.47
Molecular weight 719.43
XLogP 3.71
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(CC(C(=O)NC(C(=O)NC(C(=O)C1(C)CO1)CC(C)C)Cc1ccccc1)NC(=O)C(NC(=O)CN1CCOCC1)CCc1ccccc1)C
Isomeric SMILES CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)[C@@]1(C)CO1)CC(C)C)Cc1ccccc1)NC(=O)[C@@H](NC(=O)CN1CCOCC1)CCc1ccccc1)C
InChI InChI=1S/C40H57N5O7/c1-27(2)22-32(36(47)40(5)26-52-40)42-39(50)34(24-30-14-10-7-11-15-30)44-38(49)33(23-28(3)4)43-37(48)31(17-16-29-12-8-6-9-13-29)41-35(46)25-45-18-20-51-21-19-45/h6-15,27-28,31-34H,16-26H2,1-5H3,(H,41,46)(H,42,50)(H,43,48)(H,44,49)/t31-,32-,33-,34-,40+/m0/s1
InChI Key BLMPQMFVWMYDKT-NZTKNTHTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2015))
IUPAC Name Click here for help
(2S)-4-methyl-N-[(2S)-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]-4-phenylbutanoyl]amino]pentanamide
International Nonproprietary Names Click here for help
INN number INN
8859 carfilzomib
Synonyms Click here for help
Kyprolis® | PR-171
Database Links Click here for help
CAS Registry No. 868540-17-4
ChEMBL Ligand CHEMBL451887
DrugBank Ligand DB08889
DrugCentral Ligand 4483
GtoPdb PubChem SID 178103992
PubChem CID 11556711
Search Google for chemical match using the InChIKey BLMPQMFVWMYDKT-NZTKNTHTSA-N
Search Google for chemicals with the same backbone BLMPQMFVWMYDKT
Search PubMed clinical trials carfilzomib
Search PubMed titles carfilzomib
Search PubMed titles/abstracts carfilzomib
Search UniChem for chemical match using the InChIKey BLMPQMFVWMYDKT-NZTKNTHTSA-N
Search UniChem for chemicals with the same backbone BLMPQMFVWMYDKT
Wikipedia Carfilzomib