BIRICODAR DICITRATE

Investigational

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

Molecular Formula	C34H41N3O7
Molecular Weight	603.7052
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Clinical trials and progress with paclitaxel in ovarian cancer.	2010-11-19	21270965
Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin.	2010-09-28	20927189
In vitro and in vivo multidrug resistance reversal activity by a Betti-base derivative of tylosin.	2010-07-13	20551959
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.	2010-01	21589765
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.	2009-10-06	19807929
Resistance to chemotherapy: new treatments and novel insights into an old problem.	2008-08-05	18665178
Epigenetic mechanisms involved in differential MDR1 mRNA expression between gastric and colon cancer cell lines and rationales for clinical chemotherapy.	2008-08-01	18673531
Strategies for enhanced drug delivery to the central nervous system.	2007-02-20	20046703
Pharmacological strategies for overcoming multidrug resistance.	2006-07	16842217
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005-10-04	16202168
Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting p-glycoprotein.	2003-04-25	12712010
Safety and efficacy of the MDR inhibitor Incel (biricodar, VX-710) in combination with mitoxantrone and prednisone in hormone-refractory prostate cancer.	2003-04	12721757
A phase II study of the MDR inhibitor biricodar (INCEL, VX-710) and paclitaxel in women with advanced ovarian cancer refractory to paclitaxel therapy.	2002-09	12217752
Biricodar. Vertex Pharmaceuticals.	2002-05	12090559
Safety and efficacy of the multidrug resistance inhibitor Incel (biricodar; VX-710) in combination with paclitaxel for advanced breast cancer refractory to paclitaxel.	2002-03	11895894
Safety and efficacy of the multidrug-resistance inhibitor biricodar (VX-710) with concurrent doxorubicin in patients with anthracycline-resistant advanced soft tissue sarcoma.	2002-02	11839653
Phase I and pharmacokinetic study of the novel MDR1 and MRP1 inhibitor biricodar administered alone and in combination with doxorubicin.	2001-06-15	11408511

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:26 GMT 2025`
Record UNII	9WQP0L619L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIRICODAR DICITRATE

Official Name

English

INCEL

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C1744