Biricodar dicitrate

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MedKoo CAT#: 100086

CAS#: 174254-13-8 (dicitrate)

Description: Biricodar, also known as VX-710, is a synthetic pipecolinate derivative with potential chemosensitizing activity. Biricodar binds directly to the plasma membrane drug-efflux pumps P-glycoprotein (Pgp) and multidrug resistance protein 1 (MRP-1) and inhibits their activities, which may result in increased intracellular accumulation and retention of cytotoxic agents.


Chemical Structure

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Biricodar dicitrate
CAS# 174254-13-8 (dicitrate)

Theoretical Analysis

MedKoo Cat#: 100086
Name: Biricodar dicitrate
CAS#: 174254-13-8 (dicitrate)
Chemical Formula: C34H41N3O7
Exact Mass:
Molecular Weight: 603.7
Elemental Analysis: C, 67.64; H, 6.85; N, 6.96; O, 18.55

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Related CAS #: 159997-94-1 (free base)   174254-13-8 (dicitrate)  

Synonym: VX710; VX-710; VX 710. Biricodar. US brand name: Incel.

IUPAC/Chemical Name: (S)-1,7-di(pyridin-3-yl)heptan-4-yl 1-(2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl)piperidine-2-carboxylate dicitrate

InChi Key: VDMKJSJJXQDICL-ZXVJYWQYSA-N

InChi Code: 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

SMILES Code: O=C([C@H]1N(C(C(C2=CC(OC)=C(OC)C(OC)=C2)=O)=O)CCCC1)OC(CCCC3=CC=CN=C3)CCCC4=CC=CN=C4.OC(C(O)=O)(CC(O)=O)CC(O)=O.OC(C(O)=O)(CC(O)=O)CC(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 603.7 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Gandhi L, Harding MW, Neubauer M, Langer CJ, Moore M, Ross HJ, Johnson BE, Lynch TJ. A phase II study of the safety and efficacy of the multidrug resistance inhibitor VX-710 combined with doxorubicin and vincristine in patients with recurrent small cell lung cancer. Cancer. 2007 Mar 1;109(5):924-32. PubMed PMID: 17285598.

2: Mullin S, Mani N, Grossman TH. Inhibition of antibiotic efflux in bacteria by the novel multidrug resistance inhibitors biricodar (VX-710) and timcodar (VX-853). Antimicrob Agents Chemother. 2004 Nov;48(11):4171-6. PubMed PMID: 15504837; PubMed Central PMCID: PMC525397.

3: Minderman H, O'Loughlin KL, Pendyala L, Baer MR. VX-710 (biricodar) increases drug retention and enhances chemosensitivity in resistant cells overexpressing P-glycoprotein, multidrug resistance protein, and breast cancer resistance protein. Clin Cancer Res. 2004 Mar 1;10(5):1826-34. PubMed PMID: 15014037.

4: Rago RP, Einstein A Jr, Lush R, Beer TM, Ko YJ, Henner WD, Bubley G, Merica EA, Garg V, Ette E, Harding MW, Dalton WS. Safety and efficacy of the MDR inhibitor Incel (biricodar, VX-710) in combination with mitoxantrone and prednisone in hormone-refractory prostate cancer. Cancer Chemother Pharmacol. 2003 Apr;51(4):297-305. Epub 2003 Mar 13. PubMed PMID: 12721757.

5: Seiden MV, Swenerton KD, Matulonis U, Campos S, Rose P, Batist G, Ette E, Garg V, Fuller A, Harding MW, Charpentier D. A phase II study of the MDR inhibitor biricodar (INCEL, VX-710) and paclitaxel in women with advanced ovarian cancer refractory to paclitaxel therapy. Gynecol Oncol. 2002 Sep;86(3):302-10. PubMed PMID: 12217752.

6: Toppmeyer D, Seidman AD, Pollak M, Russell C, Tkaczuk K, Verma S, Overmoyer B, Garg V, Ette E, Harding MW, Demetri GD. Safety and efficacy of the multidrug resistance inhibitor Incel (biricodar; VX-710) in combination with paclitaxel for advanced breast cancer refractory to paclitaxel. Clin Cancer Res. 2002 Mar;8(3):670-8. PubMed PMID: 11895894.

7: Bramwell VH, Morris D, Ernst DS, Hings I, Blackstein M, Venner PM, Ette EI, Harding MW, Waxman A, Demetri GD. Safety and efficacy of the multidrug-resistance inhibitor biricodar (VX-710) with concurrent doxorubicin in patients with anthracycline-resistant advanced soft tissue sarcoma. Clin Cancer Res. 2002 Feb;8(2):383-93. PubMed PMID: 11839653.

8: Yanagisawa T, Newman A, Coley H, Renshaw J, Pinkerton CR, Pritchard-Jones K. BIRICODAR (VX-710; Incel): an effective chemosensitizer in neuroblastoma. Br J Cancer. 1999 Jun;80(8):1190-6. PubMed PMID: 10376971; PubMed Central PMCID: PMC2362368.

9: Germann UA, Ford PJ, Shlyakhter D, Mason VS, Harding MW. Chemosensitization and drug accumulation effects of VX-710, verapamil, cyclosporin A, MS-209 and GF120918 in multidrug resistant HL60/ADR cells expressing the multidrug resistance-associated protein MRP. Anticancer Drugs. 1997 Feb;8(2):141-55. PubMed PMID: 9073310.

10: Germann UA, Shlyakhter D, Mason VS, Zelle RE, Duffy JP, Galullo V, Armistead DM, Saunders JO, Boger J, Harding MW. Cellular and biochemical characterization of VX-710 as a chemosensitizer: reversal of P-glycoprotein-mediated multidrug resistance in vitro. Anticancer Drugs. 1997 Feb;8(2):125-40. PubMed PMID: 9073309.



Additional Information

Biricodar (INN, codename VX-170, marketed as the dicitrate salt under the trade name Incel) is a pharmaceutical drug released by Vertex Pharmaceuticals in 1999 to help treat ovarian cancer patients.