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

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
Phase I and pharmacokinetic study of the novel MDR1 and MRP1 inhibitor biricodar administered alone and in combination with doxorubicin.	2001 Jun 15	11408511
Biricodar. Vertex Pharmaceuticals.	2002 May	12090559
Pharmacological strategies for overcoming multidrug resistance.	2006 Jul	16842217
Epigenetic mechanisms involved in differential MDR1 mRNA expression between gastric and colon cancer cell lines and rationales for clinical chemotherapy.	2008 Aug 1	18673531
Resistance to chemotherapy: new treatments and novel insights into an old problem.	2008 Aug 5	18665178
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	21589765
In vitro and in vivo multidrug resistance reversal activity by a Betti-base derivative of tylosin.	2010 Jul 13	20551959
Clinical trials and progress with paclitaxel in ovarian cancer.	2010 Nov 19	21270965
Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin.	2010 Sep 28	20927189

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 `Fri Dec 15 15:57:17 UTC 2023` Edited by `admin` on `Fri Dec 15 15:57:17 UTC 2023`
Record UNII	9WQP0L619L
Record Status	`Validated (UNII)`
Record Version

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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