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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23O10PS
Molecular Weight 474.419
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BRICICLIB

SMILES

COC1=CC(OC)=C(\C=C\S(=O)(=O)CC2=CC(OP(O)(O)=O)=C(OC)C=C2)C(OC)=C1

InChI

InChIKey=LXENKEWVEVKKGV-BQYQJAHWSA-N
InChI=1S/C19H23O10PS/c1-25-14-10-17(27-3)15(18(11-14)28-4)7-8-31(23,24)12-13-5-6-16(26-2)19(9-13)29-30(20,21)22/h5-11H,12H2,1-4H3,(H2,20,21,22)/b8-7+

HIDE SMILES / InChI

Molecular Formula C19H23O10PS
Molecular Weight 474.419
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Briciclib (also known as ON-013105 and ON-014185) has the potential of targeting and inhibition of eukaryotic translation initiation factor 4E (eIF4E) for solid cancers. eIF4E is a proto-oncogene that promotes translation of several genes essential for cellular proliferation (cyclin D1, c-Myc, mTOR), survival (Akt), angiogenesis (VEGF), and metastasis (MMP9). Overexpression of eIF4E has been observed in almost all major groups of cancers and has been shown to induce increased expression of cyclin D1 and c-Myc). An intravenous formulation of briciclib was being investigated in the Phase 1 clinical trial. The purpose of the study was to determine the highest dose of briciclib that could be given safely in patients with relapsed/refractory Lymphoma or B-cell Acute Lymphocytic Leukemia (Philadelphia chromosome negative). However, this study was terminated because of the lack of available clinical drug supply. In addition, briciclib was also involved in phase I clinical trials with advanced cancer and solid tumors, to determine the highest dose that can be safely given.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Combined administration of rituximab and on 013105 induces apoptosis in mantle cell lymphoma cells and reduces tumor burden in a mouse model of mantle cell lymphoma.
2013 Jan 1
Patents

Sample Use Guides

The starting dose of briciclib in the Escalation Stage will be 17 mg/week, with subsequent dose escalation levels of 35 mg, 70 mg, 140 mg, 280 mg, 560 mg, and 1120 mg. At each dose level, briciclib will be administered as a 2-hour intravenous infusion, once-a-week per 3-week cycles.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:50:58 GMT 2023
Edited
by admin
on Fri Dec 15 19:50:58 GMT 2023
Record UNII
WG93X96336
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRICICLIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
ON-014185
Code English
ON014185
Code English
PHENOL, 2-METHOXY-5-((((1E)-2-(2,4,6-TRIMETHOXYPHENYL)ETHENYL)SULFONYL)METHYL)-, 1-(DIHYDROGEN PHOSPHATE)
Common Name English
Briciclib [WHO-DD]
Common Name English
briciclib [INN]
Common Name English
BRICICLIB [USAN]
Common Name English
(E)-5-(((2,4,6-TRIMETHOXYSTYRYL)SULFONYL)METHYL)-2-METHOXYPHENYL DIHYDROGEN PHOSPHATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2185
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
Code System Code Type Description
USAN
AB-86
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
NCI_THESAURUS
C141431
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
PUBCHEM
11248490
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
SMS_ID
100000181827
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL1206245
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
CAS
865783-99-9
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
INN
9895
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
DRUG BANK
DB12004
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
FDA UNII
WG93X96336
Created by admin on Fri Dec 15 19:50:58 GMT 2023 , Edited by admin on Fri Dec 15 19:50:58 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY