Identification
- Generic Name
- Biricodar
- DrugBank Accession Number
- DB04851
- Background
The pipecolinate derivative biricodar (VX-710) is a clinically applicable modulator of P-glycoprotein (Pgp) and multidrug resistance protein (MRP-1).
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Biricodar (DB04851)
- Weight
- Average: 603.716
Monoisotopic: 603.294450672 - Chemical Formula
- C34H41N3O7
- Synonyms
- Biricodar
- External IDs
- VX 710
- VX-710
Pharmacology
- Indication
Administered intravenously, biricodar dicitrate is to be used in combination with cancer chemotherapy agents.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Biricodar dicitrate blocks two major multi-drug resistance mechanisms: P-glycoprotein (MDR-1) and multi-drug resistance-associated protein (MRP).
- Mechanism of action
Vertex’s research shows that biricodar dicitrate can enhance the accumulation of chemotherapy agents in tumor cells by blocking the drug pumps P-gp and MRP, and that it is capable of restoring the sensitivity of tumors to treatment with chemotherapeutic agents.
Target Actions Organism UATP-binding cassette sub-family B member 5 Not Available Humans UMultidrug resistance-associated protein 1 Not Available Humans UATP-binding cassette sub-family G member 2 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Biricodar. Afatinib The serum concentration of Afatinib can be increased when it is combined with Biricodar. Ambrisentan The serum concentration of Ambrisentan can be increased when it is combined with Biricodar. Apixaban The serum concentration of Apixaban can be increased when it is combined with Biricodar. Avanafil The serum concentration of Avanafil can be increased when it is combined with Biricodar. Avatrombopag The serum concentration of Avatrombopag can be increased when it is combined with Biricodar. Axitinib The serum concentration of Axitinib can be increased when it is combined with Biricodar. Belantamab mafodotin The serum concentration of Belantamab mafodotin can be increased when it is combined with Biricodar. Belinostat The serum concentration of Belinostat can be increased when it is combined with Biricodar. Bendamustine The serum concentration of Bendamustine can be increased when it is combined with Biricodar. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Biricodar dicitrate 9WQP0L619L 174254-13-8 VDMKJSJJXQDICL-ZXVJYWQYSA-N - International/Other Brands
- Incel
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3KG76X4KJK
- CAS number
- 159997-94-1
- InChI Key
- CGVWPQOFHSAKRR-NDEPHWFRSA-N
- InChI
- 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
- IUPAC Name
- 1,7-bis(pyridin-3-yl)heptan-4-yl (2S)-1-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
- SMILES
- COC1=CC(=CC(OC)=C1OC)C(=O)C(=O)N1CCCC[C@H]1C(=O)OC(CCCC1=CN=CC=C1)CCCC1=CN=CC=C1
References
- General References
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D03128
- PubChem Compound
- 9963148
- PubChem Substance
- 175426862
- ChemSpider
- 2301309
- BindingDB
- 50109811
- ChEBI
- 135847
- ChEMBL
- CHEMBL350775
- PharmGKB
- PA164924560
- Wikipedia
- Biricodar
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Terminated Treatment Lung Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00129 mg/mL ALOGPS logP 4.54 ALOGPS logP 4.77 Chemaxon logS -5.7 ALOGPS pKa (Strongest Basic) 5.86 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 117.15 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 164.5 m3·mol-1 Chemaxon Polarizability 64.13 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9372 Blood Brain Barrier - 0.9496 Caco-2 permeable - 0.6555 P-glycoprotein substrate Substrate 0.7999 P-glycoprotein inhibitor I Inhibitor 0.5124 P-glycoprotein inhibitor II Non-inhibitor 0.5093 Renal organic cation transporter Non-inhibitor 0.8498 CYP450 2C9 substrate Non-substrate 0.7975 CYP450 2D6 substrate Non-substrate 0.8208 CYP450 3A4 substrate Substrate 0.7234 CYP450 1A2 substrate Non-inhibitor 0.8485 CYP450 2C9 inhibitor Non-inhibitor 0.766 CYP450 2D6 inhibitor Non-inhibitor 0.8887 CYP450 2C19 inhibitor Non-inhibitor 0.8673 CYP450 3A4 inhibitor Non-inhibitor 0.907 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9154 Ames test Non AMES toxic 0.8794 Carcinogenicity Non-carcinogens 0.9466 Biodegradation Not ready biodegradable 0.9876 Rat acute toxicity 2.6263 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9909 hERG inhibition (predictor II) Inhibitor 0.5328
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Efflux transmembrane transporter activity
- Specific Function
- Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
- Gene Name
- ABCB5
- Uniprot ID
- Q2M3G0
- Uniprot Name
- ATP-binding cassette sub-family B member 5
- Molecular Weight
- 138639.48 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- NCI Dictionary: Biricodar [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- General Function
- Transporter activity
- Specific Function
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- Grzywacz MJ, Yang JM, Hait WN: Effect of the multidrug resistance protein on the transport of the antiandrogen flutamide. Cancer Res. 2003 May 15;63(10):2492-8. [Article]
Drug created at October 18, 2007 23:04 / Updated at June 17, 2022 22:04