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

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H41N3O7.2C6H8O7
Molecular Weight 987.9541
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIRICODAR DICITRATE

SMILES

COc1cc(cc(c1OC)OC)C(=O)C(=O)N2CCCC[C@@]2([H])C(=O)OC(CCCc3cccnc3)CCCc4cccnc4.C(C(=O)O)C(CC(=O)O)(C(=O)O)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=VDMKJSJJXQDICL-ZXVJYWQYSA-N
InChI=1S/C34H41N3O7.2C6H8O7/c1-41-29-20-26(21-30(42-2)32(29)43-3)31(38)33(39)37-19-5-4-16-28(37)34(40)44-27(14-6-10-24-12-8-17-35-22-24)15-7-11-25-13-9-18-36-23-25;2*7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,12-13,17-18,20-23,27-28H,4-7,10-11,14-16,19H2,1-3H3;2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t28-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula C34H41N3O7
Molecular Weight 603.7065
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Biricodar (also known as VX-710) was developed by Vertex as a chemosensitizing agent designed to restore the effectiveness of chemotherapeutic agents in tumor multidrug resistance. The phase II trials had commenced for biricodar, in combination with chemotherapy, for five common cancer indications: breast, ovarian, soft-tissue sarcomas, small cell lung cancer, and prostate cancer. In spite of completed trials, development of biricodar was discontinued because of the adverse effects.

Approval Year

PubMed

PubMed

TitleDatePubMed
Safety and efficacy of the multidrug-resistance inhibitor biricodar (VX-710) with concurrent doxorubicin in patients with anthracycline-resistant advanced soft tissue sarcoma.
2002 Feb
Safety and efficacy of the MDR inhibitor Incel (biricodar, VX-710) in combination with mitoxantrone and prednisone in hormone-refractory prostate cancer.
2003 Apr
Evaluation of the effects of galbanic acid from Ferula szowitsiana and conferol from F. badrakema, as modulators of multi-drug resistance in clinical isolates of Escherichia coli and Staphylococcus aureus.
2010 Jan
Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin.
2010 Sep 28

Sample Use Guides

Patients received 80 mg/m(2) paclitaxel over 3 h starting 4 h after initiation of a 24-h continuous intravenous infusion of 120 mg/m(2)/h biricodar (VX-710). Cycles were repeated every 3 weeks.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:50:42 UTC 2021
Edited
by admin
on Sat Jun 26 01:50:42 UTC 2021
Record UNII
9WQP0L619L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BIRICODAR DICITRATE
MI   USAN   WHO-DD  
USAN  
Official Name English
BIRICODAR DICITRATE [WHO-DD]
Common Name English
VX-710-3
Code English
BIRICODAR DICITRATE [MI]
Common Name English
BIRICODAR DICITRATE [USAN]
Common Name English
4-(3-PYRIDINYL)-1-(3-(3-PYRIDINYL)PROPYL)BUTYL (S)-1-(OXO(3,4,5-TRIMETHOXYPHENYL)ACETYL)-2-PIPERIDINECARBOXYLATE 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:2)
Common Name English
4-(3-PYRIDYL)-1-(3-(3-PYRIDYL)PROPYL)BUTYL (S)-1-((3,4,5-TRIMETHOXYPHENYL)GLYOXYLOYL)PIPECOLATE, CITRATE (1:2)
Common Name English
VX-710
Code English
INCEL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1744
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
Code System Code Type Description
FDA UNII
9WQP0L619L
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
NCI_THESAURUS
C1653
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
CAS
174254-13-8
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL350775
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
DRUG BANK
DBSALT002850
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
MERCK INDEX
M2514
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY Merck Index
PUBCHEM
9963148
Created by admin on Sat Jun 26 01:50:42 UTC 2021 , Edited by admin on Sat Jun 26 01:50:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY