Carfilzomib

Carfilzomib

Clinical data
Trade names	Kyprolis
License data	US FDA: Carfilzomib
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01XX45 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	97%
Metabolism	Extensive; plays a minor role
Identifiers
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
Synonyms	PX-171-007
CAS Number	868540-17-4
PubChem CID	11556711
IUPHAR/BPS	7420
ChemSpider	9731489
UNII	72X6E3J5AR
KEGG	D08880
ChEBI	CHEBI:65347
ChEMBL	CHEMBL451887
ECHA InfoCard	100.219.957
Chemical and physical data
Formula	C40H57N5O7
Molar mass	719.91 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)[C@@]1(OC1)C)CC(C)C)Cc2ccccc2)CC(C)C)CCc3ccccc3)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 Key:BLMPQMFVWMYDKT-NZTKNTHTSA-N

Carfilzomib (marketed under the trade name Kyprolis, developed by Onyx Pharmaceuticals) is an anti-cancer drug acting as a selective proteasome inhibitor. Chemically, it is a tetrapeptide epoxyketone and an analog of epoxomicin.

The U.S. Food and Drug Administration (FDA) approved it on 20 July 2012 for use in patients with multiple myeloma who have received at least two prior therapies, including treatment with bortezomib and an immunomodulatory therapy (such as lenalidomide) and have demonstrated disease progression on or within 60 days of completion of the last therapy. Approval is based on response rate. Clinical benefit, such as improvement in survival or symptoms, has not been verified.

The abbreviation CFZ is common for referring to carfilzomib, but abbreviating drug names is not best practice in medicine.

Carfilzomib is derived from epoxomicin, a natural product that was shown by the laboratory of Craig Crews at Yale University to inhibit the proteasome. The Crews laboratory subsequently invented a more specific derivative of epoxomicin named YU101, which was licensed to Proteolix, Inc. Scientists at Proteolix invented a new, distinct compound that had potential use as a drug in humans, known as carfilzomib. Proteolix advanced carfilzomib to multiple Phase 1 and 2 clinical trials, including a pivotal phase 2 clinical trial designed to seek accelerated approval. Clinical trials for carfilzomib continue under Onyx Pharmaceuticals, which acquired Proteolix in 2009.