BIRICODAR DICITRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H41N3O7.2C6H8O7
Molecular Weight	987.9523
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=CC(=CC(OC)=C1OC)C(=O)C(=O)N2CCCC[C@H]2C(=O)OC(CCCC3=CC=CN=C3)CCCC4=CC=CN=C4

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12090559 | https://www.ncbi.nlm.nih.gov/pubmed/12217752 | https://www.ncbi.nlm.nih.gov/pubmed/11895894 | https://adisinsight.springer.com/drugs/800004179 | https://www.ncbi.nlm.nih.gov/pubmed/20691230

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
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	11839653
A phase II study of the MDR inhibitor biricodar (INCEL, VX-710) and paclitaxel in women with advanced ovarian cancer refractory to paclitaxel therapy.	2002 Sep	12217752
Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting p-glycoprotein.	2003 Mar-Apr	12712010

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

BIRICODAR DICITRATE

Official 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

Biricodar dicitrate [WHO-DD]

Common Name

English

VX-710

Code

English

INCEL

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1744