BIRICODAR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H41N3O7
Molecular Weight	603.7052
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=CGVWPQOFHSAKRR-NDEPHWFRSA-N

InChI=1S/C34H41N3O7/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/h8-9,12-13,17-18,20-23,27-28H,4-7,10-11,14-16,19H2,1-3H3/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

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
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
Safety and efficacy of the multidrug resistance inhibitor Incel (biricodar; VX-710) in combination with paclitaxel for advanced breast cancer refractory to paclitaxel.	2002 Mar	11895894
Biricodar. Vertex Pharmaceuticals.	2002 May	12090559
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
Safety and efficacy of the MDR inhibitor Incel (biricodar, VX-710) in combination with mitoxantrone and prednisone in hormone-refractory prostate cancer.	2003 Apr	12721757
Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting p-glycoprotein.	2003 Mar-Apr	12712010
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005 Oct 4	16202168
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
Strategies for enhanced drug delivery to the central nervous system.	2008 Mar-Apr	20046703
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.	2009 Oct 6	19807929
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 16:20:31 GMT 2023` Edited by `admin` on `Fri Dec 15 16:20:31 GMT 2023`
Record UNII	3KG76X4KJK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIRICODAR

Official Name

English

Biricodar [WHO-DD]

Common Name

English

BIRICODAR [MI]

Common Name

English

biricodar [INN]

Common Name

English

4-(3-PYRIDYL)-1-(3-(3-PYRIDYL)PROPYL)BUTYL(S)-1-((3,4,5-TRIMETHOXYPHENYL)GLYOXYLOYL)PIPECOLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1744