Carfilzomib
Carfilzomib is a synthetic tetrapeptidyl epoxide tetrapeptide consisting of morpholin-4-acetyl, L-2-amino-4-phenylbutanoyl, L-leucyl and L-phenylalanyl residues joined in sequence with the C-terminus connected to the amino group of (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-1-one via an amide linkage. Used for the treatment of patients with multiple myeloma It has a role as an antineoplastic agent and a proteasome inhibitor. It is a tetrapeptide, a member of morpholines and an epoxide.
General
Type : Not AlphaBeta Hydrolase target, Drug, Epoxide, Peptide, Morpholine
Chemical_Nomenclature : (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
Canonical 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
Other name(s) : Kyprolis || PR-171 || NSC-758252 || 72X6E3J5AR || DTXSID4048690 || CHEBI:65347
MW : 719.9
Formula : C40H57N5O7
CAS_number : 868540-17-4
PubChem : 11556711
UniChem : BLMPQMFVWMYDKT-NZTKNTHTSA-N
Target
Structures : No structure
Families : Epoxide_hydrolase
References (6)
| Title : Hydroxylation near the epoxyketone of carfilzomib confers protection from microsomal epoxide hydrolase-mediated metabolism - Lee_2025_Drug.Metab.Dispos_53_100115 |
| Author(s) : Lee S , Jang JY , Bae C , Armstrong A , Kim J , Park S , Han BW , Kim KB , Jeong H , Lee W |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 53 :100115 , 2025 |
| Abstract : |
| PubMedSearch : Lee_2025_Drug.Metab.Dispos_53_100115 |
| PubMedID: 40674997 |
| Title : Hydroxylation near the epoxyketone of carfilzomib confers protection from microsomal epoxide hydrolase-mediated metabolism - Lee_2025_Drug.Metab.Dispos_53_100115 |
| Author(s) : Lee S , Jang JY , Bae C , Armstrong A , Kim J , Park S , Han BW , Kim KB , Jeong H , Lee W |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 53 :100115 , 2025 |
| Abstract : |
| PubMedSearch : Lee_2025_Drug.Metab.Dispos_53_100115 |
| PubMedID: 40674997 |
| Title : Hydroxylation near the epoxyketone of carfilzomib confers protection from microsomal epoxide hydrolase-mediated metabolism - Lee_2025_Drug.Metab.Dispos_53_100115 |
| Author(s) : Lee S , Jang JY , Bae C , Armstrong A , Kim J , Park S , Han BW , Kim KB , Jeong H , Lee W |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 53 :100115 , 2025 |
| Abstract : |
| PubMedSearch : Lee_2025_Drug.Metab.Dispos_53_100115 |
| PubMedID: 40674997 |
| Title : Pharmacokinetics, pharmacodynamics, metabolism, distribution, and excretion of carfilzomib in rats - Yang_2011_Drug.Metab.Dispos_39_1873 |
| Author(s) : Yang J , Wang Z , Fang Y , Jiang J , Zhao F , Wong H , Bennett MK , Molineaux CJ , Kirk CJ |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :1873 , 2011 |
| Abstract : |
| PubMedSearch : Yang_2011_Drug.Metab.Dispos_39_1873 |
| PubMedID: 21752943 |
| Title : Pharmacokinetics, pharmacodynamics, metabolism, distribution, and excretion of carfilzomib in rats - Yang_2011_Drug.Metab.Dispos_39_1873 |
| Author(s) : Yang J , Wang Z , Fang Y , Jiang J , Zhao F , Wong H , Bennett MK , Molineaux CJ , Kirk CJ |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :1873 , 2011 |
| Abstract : |
| PubMedSearch : Yang_2011_Drug.Metab.Dispos_39_1873 |
| PubMedID: 21752943 |
| Title : Pharmacokinetics, pharmacodynamics, metabolism, distribution, and excretion of carfilzomib in rats - Yang_2011_Drug.Metab.Dispos_39_1873 |
| Author(s) : Yang J , Wang Z , Fang Y , Jiang J , Zhao F , Wong H , Bennett MK , Molineaux CJ , Kirk CJ |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :1873 , 2011 |
| Abstract : |
| PubMedSearch : Yang_2011_Drug.Metab.Dispos_39_1873 |
| PubMedID: 21752943 |