U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28BN3O5
Molecular Weight 413.275
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELANZOMIB

SMILES

CC(C)C[C@H](NC(=O)[C@@H](NC(=O)C1=NC(=CC=C1)C2=CC=CC=C2)[C@@H](C)O)B(O)O

InChI

InChIKey=SJFBTAPEPRWNKH-CCKFTAQKSA-N
InChI=1S/C21H28BN3O5/c1-13(2)12-18(22(29)30)24-21(28)19(14(3)26)25-20(27)17-11-7-10-16(23-17)15-8-5-4-6-9-15/h4-11,13-14,18-19,26,29-30H,12H2,1-3H3,(H,24,28)(H,25,27)/t14-,18+,19+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18057228 http://adisinsight.springer.com/drugs/800017288 https://newdrugapprovals.org/2015/11/08/cep-18770-delanzomib/

Delanzomib (CEP-18770), a proteasome inhibitor, was being developed by Cepahlon (a subsidiary of Teva) for the treatment of cancer and immunological disorders. Delanzomib (CEP-18770) induces apoptotic cell death in multiple myeloma (MM) cell lines and in primary purified CD138-positive explant cultures from untreated and bortezomib-treated MM patients. In vitro, Delanzomib (CEP-18770) has a strong antiangiogenic activity and potently represses RANKL-induced osteoclastogenesis. Delanzomib represses the proteasomal degradation of a variety of proteins, including inhibitory kappaBalpha (IkappaBalpha), resulting in the cytoplasmic sequestration of the transcription factor NF-kappaB; inhibition of NF-kappaB nuclear translocation and transcriptional up-regulation of a variety of cell growth-promoting factors; and apoptotic cell death in susceptible tumor cell populations. In vitro studies indicate that this agent exhibits a favorable cytotoxicity profile toward normal human epithelial cells, bone marrow progenitors, and bone marrow-derived stromal cells relative to the proteasome inhibitor bortezomib. Delanzomib has been in phase II clinical trials for the treatment of multiple myeloma (MM). However, this research has been discontinued. Currently Delanzomib is on Phase I clinical trial for Non-Hodgkin's lymphoma and Solid tumours.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
5.6 nM [IC50]
10.0 nM [IC50]
Target ID: HS-Sultan anaplastic non-Hodgkin lymphoma
8.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Development and validation of a high-performance liquid chromatography-tandem mass spectrometry method for the determination of the novel proteasome inhibitor CEP-18770 in human plasma and its application in a clinical pharmacokinetic study.
2010 Nov
Patents

Sample Use Guides

Delanzomib (CEP-18770) beginning at a dose of 1.5 mg/m2. Patients will receive I.V. administration on days 1, 8, 15 (up to 8 cycles of 28 days each).
Route of Administration: Intravenous
TNFa-induced IkappaBalpha degradation was completely blocked by pretreatment with 20nM Delanzomib (CEP-18770)
Name Type Language
DELANZOMIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
Delanzomib [WHO-DD]
Common Name English
NPH 007098
Code English
BORONIC ACID, B-((1R)-1-(((2S,3R)-3-HYDROXY-1-OXO-2-(((6-PHENYL-2-PYRIDINYL)CARBONYL)AMINO)BUTYL)AMINO)-3-METHYLBUTYL)-
Common Name English
CIP 18770
Code English
((1R)-1-((2S,3R)-3-HYDROXY-2-(6-PHENYLPYRIDINE-2-CARBOXAMIDO)BUTANAMIDO)-3-METHYLBUTYL)BORONIC ACID
Systematic Name English
CT-47098
Code English
delanzomib [INN]
Common Name English
DELANZOMIB [USAN]
Common Name English
CT 47098
Code English
NPH-007098
Code English
((1R)-1-(((2S,3R)-3-HYDROXY-2-(((6-PHENYLPYRIDIN-2-YL)CARBONYL)AMINO)-1-OXOBUTYL)AMINO)-3-METHYLBUTYL)BORONIC ACID
Systematic Name English
CEP 18770
Code English
NPH007098
Code English
CIP-18770
Code English
CEP-18770
Code English
B-((1R)-1-((N-((6-PHENYLPYRIDIN-2-YL)CARBONYL)-L-THREONYL)AMINO)-3-METHYLBUTYL)BORONIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2160
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C74075
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
FDA UNII
6IF28942WO
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
CAS
847499-27-8
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
CHEBI
141530
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
PUBCHEM
24800541
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
USAN
XX-141
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
INN
9451
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
SMS_ID
100000155574
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
EVMPD
SUB129623
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
DRUG BANK
DB11956
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID901025656
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY