Identification
- Summary
Carfilzomib is a proteasome inhibitor used either alone or in conjunction with a chemotherapy regimen to treat patients with relapsed or refractory multiple myeloma.
- Brand Names
- Kyprolis
- Generic Name
- Carfilzomib
- DrugBank Accession Number
- DB08889
- Background
Carfilzomib is an injectable antineoplastic agent (IV only). Chemically, it is a modified tetrapeptidyl epoxide and an analog of epoxomicin. It is also a selective proteasome inhibitor. FDA approved carfilzomib in July 2012 for the treatment of adults with relapsed or refractory multiple myeloma as monotherapy or combination therapy.3
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Carfilzomib (DB08889)
- Weight
- Average: 719.9099
Monoisotopic: 719.425799203 - Chemical Formula
- C40H57N5O7
- Synonyms
- Carfilzomib
- External IDs
- PR-171
Pharmacology
- Indication
Carfilzomib is indicated for the treatment of adult patients with relapsed or refractory multiple myeloma who have received one to three lines of therapy in combination with lenalidomide and dexamethasone; or dexamethasone; or daratumumab and dexamethasone; or daratumumab and hyaluronidase-fihj and dexamethasone; or isatuximab and dexamethasone. It is also indicated as a single agent for the treatment of patients with relapsed or refractory multiple myeloma who have received one or more lines of therapy.3,4
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Relapsed or refractory multiple myeloma Regimen in combination with: Hyaluronidase (human recombinant) (DB06205), Dexamethasone (DB01234), Daratumumab (DB09331) •••••••••••• ••••• •••••••• • •• • ••••• ••••• •• ••••••• ••••••••• Used in combination to treat Relapsed or refractory multiple myeloma Regimen in combination with: Dexamethasone (DB01234), Daratumumab (DB09331) •••••••••••• ••••• •••••••• • •• • ••••• ••••• •• ••••••• ••••••••• Used in combination to treat Relapsed or refractory multiple myeloma Regimen in combination with: Dexamethasone (DB01234) •••••••••••• ••••• •••••••• • •• • ••••• ••••• •• ••••••• ••••••••• Used in combination to treat Relapsed or refractory multiple myeloma Regimen in combination with: Dexamethasone (DB01234), Lenalidomide (DB00480) •••••••••••• ••••• •••••••• • •• • ••••• ••••• •• ••••••• ••••••••• Treatment of Relapsed or refractory multiple myeloma •••••••••••• ••••• •• ••••• ••• ••••• ••••••• ••••••••• - Contraindications & Blackbox Warnings
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Intravenous carfilzomib administration resulted in suppression of proteasome chymotrypsin-like activity when measured in blood 1 hour after the first dose. On Day 1 of Cycle 1, proteasome inhibition in peripheral blood mononuclear cells (PBMCs) ranged from 79% to 89% at 15 mg/m2, and from 82% to 83% at 20 mg/m2. In addition, carfilzomib administration resulted in inhibition of the LMP2 and MECL1 subunits of the immunoproteasome ranging from 26% to 32% and 41% to 49%, respectively, at 20 mg/m2. Proteasome inhibition was maintained for ≥ 48 hours following the first dose of carfilzomib for each week of dosing. Resistance against carfilzomib has been observed and although the mechanism has not been confirmed, it is thought that up-regulation of P-glycoprotein may be a contributing factor. Furthermore, studies suggest that carfilzomib is more potent than bortezomib.
- Mechanism of action
Carfilzomib is made up of four modified peptides and acts as a proteasome inhibitor. Carfilzomib irreversibly and selectively binds to N-terminal threonine-containing active sites of the 20S proteasome, the proteolytic core particle within the 26S proteasome. This 20S core has 3 catalytic active sites: the chymotrypsin, trypsin, and caspase-like sites. Inhibition of the chymotrypsin-like site by carfilzomib (β5 and β5i subunits) is the most effective target in decreasing cellular proliferation, ultimately resulting in cell cycle arrest and apoptosis of cancerous cells. At higher doses, carfilzomib will inhibit the trypsin-and capase-like sites.
Target Actions Organism AProteasome subunit beta type-5 inhibitorHumans AProteasome subunit beta type-8 inhibitorHumans AProteasome subunit beta type-1 inhibitorHumans AProteasome subunit beta type-9 inhibitorHumans AProteasome subunit beta type-2 inhibitorHumans AProteasome subunit beta type-10 inhibitorHumans - Absorption
Cmax, single IV dose of 27 mg/m^2 = 4232 ng/mL; AUC, single IV dose of 27 mg/m^2 = 379 ng•hr/mL; Carfilzomib does not accumulation in the systemic. At doses between 20 and 36 mg/m2, there was a dose-dependent increase in exposure.
- Volume of distribution
Vd, steady state, 20 mg/m^2 = 28 L
- Protein binding
Over the concentration range of 0.4 - 4 micromolar, carfilzomib was 97% protein bound.
- Metabolism
Carfilzomib was rapidly and extensively metabolized by the liver. The predominant metabolites were the peptide fragments and the diol of carfilzomib which suggests that the main metabolic pathways are peptidase cleavage and epoxide hydrolysis. The cytochrome P450 enzyme system is minimally involved in the metabolism of carfilzomib. All metabolites are inactive.
- Route of elimination
Not Available
- Half-life
Following intravenous administration of doses ≥ 15 mg/m^2, carfilzomib was rapidly cleared from the systemic circulation with a half-life of ≤ 1 hour on Day 1 of Cycle 1.
- Clearance
Systemic clearance = 151 - 263 L/hour. As this value exceeds hepatic blood flow, it suggests that carfilozmib is cleared extrahepatically.
- Adverse Effects
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Most commonly reported adverse reactions (incidence ≥ 30%) are fatigue, anemia, nausea, thrombocytopenia, dyspnea, diarrhea, and pyrexia. The two dose limiting toxicities are thrombocytopenia and febrile neutropenia. Maximum tolerate dose = 15 mg/m^2
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Carfilzomib. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Carfilzomib. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Carfilzomib. Abrocitinib The serum concentration of Carfilzomib can be increased when it is combined with Abrocitinib. Acenocoumarol The risk or severity of bleeding can be increased when Acenocoumarol is combined with Carfilzomib. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Kyprolis Powder, for solution 60 mg / vial Intravenous Amgen 2016-02-11 Not applicable Canada 
Kyprolis Injection, powder, lyophilized, for solution 60 mg/30mL Intravenous Onyx Pharmaceuticals, Inc. 2012-07-20 Not applicable US 
Kyprolis Injection, powder, for solution 10 mg Intravenous Amgen Europe B.V. 2021-02-11 Not applicable EU 
Kyprolis Powder, for solution 30 mg / vial Intravenous Amgen 2017-02-06 Not applicable Canada Kyprolis Injection, powder, lyophilized, for solution 10 mg/5mL Intravenous Onyx Pharmaceuticals, Inc. 2018-05-23 Not applicable US
Categories
- ATC Codes
- L01XG02 — Carfilzomib
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Immunosuppressive Agents
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- P-glycoprotein substrates with a Narrow Therapeutic Index
- Peptides
- Proteasome Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Phenylalanine and derivatives / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / N-acyl amines / Morpholines / Trialkylamines / Secondary carboxylic acid amides / Ketones show 7 more
- Substituents
- Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group show 27 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- epoxide, tetrapeptide, morpholines (CHEBI:65347)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 72X6E3J5AR
- CAS number
- 868540-17-4
- InChI Key
- BLMPQMFVWMYDKT-NZTKNTHTSA-N
- 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
- IUPAC Name
- (2S)-4-methyl-N-[(1S)-1-{[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]-2-[(2S)-2-[2-(morpholin-4-yl)acetamido]-4-phenylbutanamido]pentanamide
- SMILES
- CC(C)C[C@H](NC(=O)[C@H](CCC1=CC=CC=C1)NC(=O)CN1CCOCC1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1
References
- General References
- Kortuem KM, Stewart AK: Carfilzomib. Blood. 2013 Feb 7;121(6):893-7. doi: 10.1182/blood-2012-10-459883. [Article]
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
- FDA Approved Drug Products: KYPROLIS (carfilzomib) for injection, for intravenous use [Link]
- FDA Approved Drug Products: KYPROLIS (carfilzomib) for injection, for intravenous use 2022 [Link]
- External Links
- KEGG Drug
- D08880
- PubChem Compound
- 11556711
- PubChem Substance
- 175427135
- ChemSpider
- 9731489
- BindingDB
- 50277889
- 1302966
- ChEBI
- 65347
- ChEMBL
- CHEMBL451887
- ZINC
- ZINC000049841054
- PharmGKB
- PA166165203
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carfilzomib
- FDA label
- Download (310 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Relapsed/Refractory Multiple Myeloma (RRMM) 1 4 Completed Treatment Relapsed/Refractory Multiple Myeloma (RRMM) 1 3 Active Not Recruiting Treatment Multiple Myeloma (MM) 6 3 Active Not Recruiting Treatment Multiple Myeloma (MM) / New Diagnosis Tumor 1 3 Active Not Recruiting Treatment Newly Diagnosed Multiple Myeloma 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous 10 mg Injection, powder, for solution Intravenous 30 mg Injection, powder, lyophilized, for solution Intravenous 10 mg/5mL Injection, powder, lyophilized, for solution Intravenous 30 mg/15mL Injection, powder, lyophilized, for solution Intravenous 60 mg/30mL Powder, for solution Intravenous 10 mg / vial Powder, for solution Intravenous 30 mg / vial Powder, for solution Intravenous 60 mg / vial Powder, for solution Intravenous; Parenteral 10 MG Powder, for solution Intravenous; Parenteral 30 MG Powder, for solution Intravenous; Parenteral 60 MG Injection, powder, for solution Intravenous 60 mg/1vial Powder, for solution 60 mg/mg Injection, solution Intravenous 10 mg Injection, solution Intravenous 30 mg Injection, solution Intravenous 60 mg Injection, powder, lyophilized, for solution Intravenous 30 mg Injection, powder, lyophilized, for solution Intravenous 60 mg Powder Intravenous 60 mg Injection, powder, for solution Intravenous 60 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7491704 No 2009-02-17 2025-04-14 US US8129346 No 2012-03-06 2026-12-25 US US8207127 No 2012-06-26 2025-04-14 US US8207125 No 2012-06-26 2025-04-14 US US7417042 No 2008-08-26 2026-06-07 US US8207126 No 2012-06-26 2025-04-14 US US7232818 No 2007-06-19 2025-04-14 US US8207297 No 2012-06-26 2025-04-14 US US7737112 No 2010-06-15 2027-12-07 US US9493582 No 2016-11-15 2033-02-27 US US9511109 No 2016-12-06 2029-10-21 US USRE47954 No 2020-04-21 2029-10-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Insoluble FDA pKa 3.5 FDA - Predicted Properties
Property Value Source Water Solubility 0.00484 mg/mL ALOGPS logP 3.21 ALOGPS logP 4.2 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 11.91 Chemaxon pKa (Strongest Basic) 4.96 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 158.47 Å2 Chemaxon Rotatable Bond Count 20 Chemaxon Refractivity 198.02 m3·mol-1 Chemaxon Polarizability 79.45 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7982 Blood Brain Barrier - 0.8941 Caco-2 permeable - 0.6924 P-glycoprotein substrate Substrate 0.9378 P-glycoprotein inhibitor I Inhibitor 0.8224 P-glycoprotein inhibitor II Non-inhibitor 0.9045 Renal organic cation transporter Non-inhibitor 0.8642 CYP450 2C9 substrate Non-substrate 0.8812 CYP450 2D6 substrate Non-substrate 0.7587 CYP450 3A4 substrate Substrate 0.6641 CYP450 1A2 substrate Non-inhibitor 0.9031 CYP450 2C9 inhibitor Non-inhibitor 0.8546 CYP450 2D6 inhibitor Non-inhibitor 0.7152 CYP450 2C19 inhibitor Non-inhibitor 0.6665 CYP450 3A4 inhibitor Inhibitor 0.6532 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9676 Ames test Non AMES toxic 0.7119 Carcinogenicity Non-carcinogens 0.8431 Biodegradation Not ready biodegradable 0.9942 Rat acute toxicity 2.6381 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9831 hERG inhibition (predictor II) Non-inhibitor 0.6044
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 285.384888 predictedDarkChem Lite v0.1.0 [M-H]- 261.85406 predictedDeepCCS 1.0 (2019) [M+H]+ 285.131088 predictedDarkChem Lite v0.1.0 [M+H]+ 263.74948 predictedDeepCCS 1.0 (2019) [M+Na]+ 285.892188 predictedDarkChem Lite v0.1.0 [M+Na]+ 269.5814 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB5
- Uniprot ID
- P28074
- Uniprot Name
- Proteasome subunit beta type-5
- Molecular Weight
- 28480.01 Da
References
- Kortuem KM, Stewart AK: Carfilzomib. Blood. 2013 Feb 7;121(6):893-7. doi: 10.1182/blood-2012-10-459883. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB8
- Uniprot ID
- P28062
- Uniprot Name
- Proteasome subunit beta type-8
- Molecular Weight
- 30354.035 Da
References
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB1
- Uniprot ID
- P20618
- Uniprot Name
- Proteasome subunit beta type-1
- Molecular Weight
- 26489.09 Da
References
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB9
- Uniprot ID
- P28065
- Uniprot Name
- Proteasome subunit beta type-9
- Molecular Weight
- 23264.1 Da
References
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB2
- Uniprot ID
- P49721
- Uniprot Name
- Proteasome subunit beta type-2
- Molecular Weight
- 22836.02 Da
References
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Threonine-type endopeptidase activity
- Specific Function
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly ...
- Gene Name
- PSMB10
- Uniprot ID
- P40306
- Uniprot Name
- Proteasome subunit beta type-10
- Molecular Weight
- 28936.08 Da
References
- Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 2007 Nov 1;110(9):3281-90. Epub 2007 Jun 25. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
Drug created at May 29, 2013 22:03 / Updated at February 20, 2024 23:54