Carfilzomib

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatRelapsed or refractory multiple myelomaRegimen in combination with: Hyaluronidase (human recombinant) (DB06205), Dexamethasone (DB01234), Daratumumab (DB09331)••••••••••••••••••••••••• • •• • ••••• ••••• •• ••••••••••••••••
Used in combination to treatRelapsed or refractory multiple myelomaRegimen in combination with: Dexamethasone (DB01234), Daratumumab (DB09331)••••••••••••••••••••••••• • •• • ••••• ••••• •• ••••••••••••••••
Used in combination to treatRelapsed or refractory multiple myelomaRegimen in combination with: Dexamethasone (DB01234)••••••••••••••••••••••••• • •• • ••••• ••••• •• ••••••••••••••••
Used in combination to treatRelapsed or refractory multiple myelomaRegimen in combination with: Dexamethasone (DB01234), Lenalidomide (DB00480)••••••••••••••••••••••••• • •• • ••••• ••••• •• ••••••••••••••••
Treatment ofRelapsed or refractory multiple myeloma••••••••••••••••••• ••••• ••• ••••• ••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
AProteasome subunit beta type-5
inhibitor
Humans
AProteasome subunit beta type-8
inhibitor
Humans
AProteasome subunit beta type-1
inhibitor
Humans
AProteasome subunit beta type-9
inhibitor
Humans
AProteasome subunit beta type-2
inhibitor
Humans
AProteasome subunit beta type-10
inhibitor
Humans
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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Toxicity

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Carfilzomib.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Carfilzomib.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Carfilzomib.
AbrocitinibThe serum concentration of Carfilzomib can be increased when it is combined with Abrocitinib.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Carfilzomib.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KyprolisInjection, powder, lyophilized, for solution10 mg/5mLIntravenousOnyx Pharmaceuticals, Inc.2018-05-23Not applicableUS flag
KyprolisInjection, powder, for solution10 mgIntravenousAmgen Europe B.V.2021-02-11Not applicableEU flag
KyprolisPowder, for solution10 mg / vialIntravenousAmgen2017-02-13Not applicableCanada flag
KyprolisInjection, powder, lyophilized, for solution30 mg/15mLIntravenousOnyx Pharmaceuticals, Inc.2016-07-15Not applicableUS flag
KyprolisInjection, powder, for solution60 mgIntravenousAmgen Europe B.V.2021-02-11Not applicableEU flag

Categories

ATC Codes
L01XG02 — Carfilzomib
Drug Categories
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
  1. Kortuem KM, Stewart AK: Carfilzomib. Blood. 2013 Feb 7;121(6):893-7. doi: 10.1182/blood-2012-10-459883. [Article]
  2. 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]
  3. FDA Approved Drug Products: KYPROLIS (carfilzomib) for injection, for intravenous use [Link]
  4. FDA Approved Drug Products: KYPROLIS (carfilzomib) for injection, for intravenous use 2022 [Link]
KEGG Drug
D08880
PubChem Compound
11556711
PubChem Substance
175427135
ChemSpider
9731489
BindingDB
50277889
RxNav
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
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentRelapsed/Refractory Multiple Myeloma (RRMM)1
4CompletedTreatmentRelapsed/Refractory Multiple Myeloma (RRMM)1
3Active Not RecruitingTreatmentMultiple Myeloma (MM)6
3Active Not RecruitingTreatmentMultiple Myeloma (MM) / New Diagnosis Tumor1
3Active Not RecruitingTreatmentNewly Diagnosed Multiple Myeloma2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntravenous10 mg
Injection, powder, for solutionIntravenous30 mg
Injection, powder, lyophilized, for solutionIntravenous10 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous30 mg/15mL
Injection, powder, lyophilized, for solutionIntravenous60 mg/30mL
Powder, for solutionIntravenous10 mg / vial
Powder, for solutionIntravenous30 mg / vial
Powder, for solutionIntravenous60 mg / vial
Powder, for solutionIntravenous; Parenteral10 MG
Powder, for solutionIntravenous; Parenteral30 MG
Powder, for solutionIntravenous; Parenteral60 MG
Injection, powder, for solutionIntravenous60 mg/1vial
Powder, for solution60 mg/mg
Injection, solutionIntravenous10 mg
Injection, solutionIntravenous30 mg
Injection, solutionIntravenous60 mg
Injection, powder, lyophilized, for solutionIntravenous30 mg
Injection, powder, lyophilized, for solutionIntravenous60 mg
PowderIntravenous60 mg
Injection, powder, for solutionIntravenous60 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7491704No2009-02-172025-04-14US flag
US8129346No2012-03-062026-12-25US flag
US8207127No2012-06-262025-04-14US flag
US8207125No2012-06-262025-04-14US flag
US7417042No2008-08-262026-06-07US flag
US8207126No2012-06-262025-04-14US flag
US7232818No2007-06-192025-04-14US flag
US8207297No2012-06-262025-04-14US flag
US7737112No2010-06-152027-12-07US flag
US9493582No2016-11-152033-02-27US flag
US9511109No2016-12-062029-10-21US flag
USRE47954No2020-04-212029-10-21US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsoluble FDA
pKa3.5FDA
Predicted Properties
PropertyValueSource
Water Solubility0.00484 mg/mLALOGPS
logP3.21ALOGPS
logP4.2Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.91Chemaxon
pKa (Strongest Basic)4.96Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area158.47 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity198.02 m3·mol-1Chemaxon
Polarizability79.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7982
Blood Brain Barrier-0.8941
Caco-2 permeable-0.6924
P-glycoprotein substrateSubstrate0.9378
P-glycoprotein inhibitor IInhibitor0.8224
P-glycoprotein inhibitor IINon-inhibitor0.9045
Renal organic cation transporterNon-inhibitor0.8642
CYP450 2C9 substrateNon-substrate0.8812
CYP450 2D6 substrateNon-substrate0.7587
CYP450 3A4 substrateSubstrate0.6641
CYP450 1A2 substrateNon-inhibitor0.9031
CYP450 2C9 inhibitorNon-inhibitor0.8546
CYP450 2D6 inhibitorNon-inhibitor0.7152
CYP450 2C19 inhibitorNon-inhibitor0.6665
CYP450 3A4 inhibitorInhibitor0.6532
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9676
Ames testNon AMES toxic0.7119
CarcinogenicityNon-carcinogens0.8431
BiodegradationNot ready biodegradable0.9942
Rat acute toxicity2.6381 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9831
hERG inhibition (predictor II)Non-inhibitor0.6044
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1212212900-d855a20810c7f1030579
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gi0-1701005900-6406552ecd4d89283e92
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-6349284000-c32f62082c65ff32d452
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-6943453400-08992a9398f61fd86f35
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-6877279000-abf6d25e519aae001150
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-3985210000-2ee67a1cd419a6fba173
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-285.384888
predicted
DarkChem Lite v0.1.0
[M-H]-261.85406
predicted
DeepCCS 1.0 (2019)
[M+H]+285.131088
predicted
DarkChem Lite v0.1.0
[M+H]+263.74948
predicted
DeepCCS 1.0 (2019)
[M+Na]+285.892188
predicted
DarkChem Lite v0.1.0
[M+Na]+269.5814
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
Substrate
Inhibitor
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 March 28, 2024 03:23