Carfilzomib, proteasome inhibitor

Key facts

CAS number

868540-17-4

Purity

>98%

Form

Solid

form

Molecular weight

719.9 Da

Molecular formula

C₄₀H₅₇N₅O₇

PubChem

11556711

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Soluble in ethanol to 25 mM

Biochemical name

Carfilzomib

Biological description

Potent, irreversible proteasome inhibitor. Synthetic analog of the microbial product epoxomcin. Compared to bortezomib it displays equal potency but greater selectivity for the chymotrypsin-like activity of the proteasome. In cell culture it is more cytotoxic than bortezomib and hematologic tumor cells exhibit greater sensitivity than solid tumor cells. Treatment of cells with carfilzomib results in the accumulation of proteasome substrates and induction of cell cycle arrest and/or apoptosis. Effective against multiple myeloma. Active in vivo.

Canonical smiles

CC(C)CC(C(=O)C1(CO1)C)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(C)C)NC(=O)C(CCC3=CC=CC=C3)NC(=O)CN4CCOCC4

Isomeric smiles

CC(C)C[C@@H](C(=O)[C@]1(CO1)C)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC3=CC=CC=C3)NC(=O)CN4CCOCC4

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

InChiKey

BLMPQMFVWMYDKT-NZTKNTHTSA-N

IUPAC Name

(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