Brequinar
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MedKoo CAT#: 205953

CAS#: 96187-53-0 (free acid)

Description: Brequinar is a synthetic quinolinecarboxylic acid analogue with antineoplastic properties. Brequinar inhibits the enzyme dihydroorotate dehydrogenase, thereby blocking de novo pyrimidine biosynthesis. This agent may also enhance the in vivo antitumor effect of antineoplastic agents such as 5-FU.


Price and Availability

Size Price Shipping out time Quantity
20mg USD 325 2 Weeks
100mg USD 1050 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-08-14. Prices are subject to change without notice.

Brequinar, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205953
Name: Brequinar
CAS#: 96187-53-0 (free acid)
Chemical Formula: C23H15F2NO2
Exact Mass: 375.10709
Molecular Weight: 375.37
Elemental Analysis: C, 73.59; H, 4.03; F, 10.12; N, 3.73; O, 8.52


Related CAS #: 96201-88-6 (sodium)   96187-53-0 (free acid)   Brequinar sodium hydrate    

Synonym: Brequinar; Bipenquinate; DUP 785; DUP785; DUP-785; NSC 368390.

IUPAC/Chemical Name: 6-fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid

InChi Key: PHEZJEYUWHETKO-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)

SMILES Code: O=C(C1=C(C)C(C2=CC=C(C3=CC=CC=C3F)C=C2)=NC4=CC=C(F)C=C14)O


Technical Data

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:
>5 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


Additional Information

  
 
 
 


References

1: Andersen PI, Krpina K, Ianevski A, Shtaida N, Jo E, Yang J, Koit S, Tenson T, Hukkanen V, Anthonsen MW, Bjoras M, Evander M, Windisch MP, Zusinaite E, Kainov DE. Novel Antiviral Activities of Obatoclax, Emetine, Niclosamide, Brequinar, and Homoharringtonine. Viruses. 2019 Oct 18;11(10):964. doi: 10.3390/v11100964. PMID: 31635418; PMCID: PMC6832696.

2: Li SF, Gong MJ, Sun YF, Shao JJ, Zhang YG, Chang HY. Antiviral activity of brequinar against foot-and-mouth disease virus infection in vitro and in vivo. Biomed Pharmacother. 2019 Aug;116:108982. doi: 10.1016/j.biopha.2019.108982. Epub 2019 May 27. PMID: 31146110.

3: Peters GJ. Re-evaluation of Brequinar sodium, a dihydroorotate dehydrogenase inhibitor. Nucleosides Nucleotides Nucleic Acids. 2018;37(12):666-678. doi: 10.1080/15257770.2018.1508692. Epub 2019 Jan 19. PMID: 30663496.

4: Dorasamy MS, Ab A, Nellore K, Wong PF. Synergistic inhibition of melanoma xenografts by Brequinar sodium and Doxorubicin. Biomed Pharmacother. 2019 Feb;110:29-36. doi: 10.1016/j.biopha.2018.11.010. Epub 2018 Nov 17. PMID: 30458345.

5: Madak JT, Cuthbertson CR, Chen W, Showalter HD, Neamati N. Design, Synthesis, and Characterization of Brequinar Conjugates as Probes to Study DHODH Inhibition. Chemistry. 2017 Oct 9;23(56):13875-13878. doi: 10.1002/chem.201702999. Epub 2017 Sep 12. PMID: 28833638.

6: He T, Haapa-Paananen S, Kaminskyy VO, Kohonen P, Fey V, Zhivotovsky B, Kallioniemi O, Perälä M. Inhibition of the mitochondrial pyrimidine biosynthesis enzyme dihydroorotate dehydrogenase by doxorubicin and brequinar sensitizes cancer cells to TRAIL-induced apoptosis. Oncogene. 2014 Jul 3;33(27):3538-49. doi: 10.1038/onc.2013.313. Epub 2013 Sep 9. PMID: 24013224.

7: Schnellrath LC, Damaso CR. Potent antiviral activity of brequinar against the emerging Cantagalo virus in cell culture. Int J Antimicrob Agents. 2011 Nov;38(5):435-41. doi: 10.1016/j.ijantimicag.2011.07.002. Epub 2011 Aug 12. PMID: 21840180.

8: Qing M, Zou G, Wang QY, Xu HY, Dong H, Yuan Z, Shi PY. Characterization of dengue virus resistance to brequinar in cell culture. Antimicrob Agents Chemother. 2010 Sep;54(9):3686-95. doi: 10.1128/AAC.00561-10. Epub 2010 Jul 6. PMID: 20606073; PMCID: PMC2934995.

9: Hurt DE, Sutton AE, Clardy J. Brequinar derivatives and species-specific drug design for dihydroorotate dehydrogenase. Bioorg Med Chem Lett. 2006 Mar 15;16(6):1610-5. doi: 10.1016/j.bmcl.2005.12.029. Epub 2006 Jan 10. PMID: 16406782.

10: Boa AN, Canavan SP, Hirst PR, Ramsey C, Stead AM, McConkey GA. Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase. Bioorg Med Chem. 2005 Mar 15;13(6):1945-67. doi: 10.1016/j.bmc.2005.01.017. PMID: 15727850.

11: McLean JE, Neidhardt EA, Grossman TH, Hedstrom L. Multiple inhibitor analysis of the brequinar and leflunomide binding sites on human dihydroorotate dehydrogenase. Biochemistry. 2001 Feb 20;40(7):2194-200. doi: 10.1021/bi001810q. PMID: 11329288.

12: Wennberg L, Song Z, Wijkström M, Zhang J, Bari S, Sundberg B, Groth CG, Korsgren O. Brequinar in combination with cyclosporine a inhibits islet xenograft rejection for up to 24 days: a study in the pig-to-rat model. Transplant Proc. 2000 Aug;32(5):1026. doi: 10.1016/s0041-1345(00)01097-6. PMID: 10936333.

13: Knecht W, Henseling J, Löffler M. Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76. doi: 10.1016/s0009-2797(99)00144-1. PMID: 10658902.

14: Antoniou EA, Deroover A, Howie AJ, Chondros K, McMaster P, D'Silva M. Immunosuppressive effect of combination schedules of brequinar with leflunomide or tacrolimus on rat cardiac allotransplantation. Microsurgery. 1999;19(2):98-102. doi: 10.1002/(sici)1098-2752(1999)19:2<98::aid- micr11>3.0.co;2-c. PMID: 10188834.

15: Batt DG, Petraitis JJ, Sherk SR, Copeland RA, Dowling RL, Taylor TL, Jones EA, Magolda RL, Jaffee BD. Heteroatom- and carbon-linked biphenyl analogs of Brequinar as immunosuppressive agents. Bioorg Med Chem Lett. 1998 Jul 7;8(13):1745-50. doi: 10.1016/s0960-894x(98)00308-4. PMID: 9873427.

16: Pitts WJ, Jetter JW, Pinto DJ, Orwat MJ, Batt DG, Sherk SR, Petraitis JJ, Jacobson IC, Copeland RA, Dowling RL, Jaffee BD, Gardner TL, Jones EA, Magolda RL. Structure-activity relationships (SAR) of some tetracyclic heterocycles related to the immunosuppressive agent Brequinar Sodium. Bioorg Med Chem Lett. 1998 Feb 3;8(3):307-12. doi: 10.1016/s0960-894x(98)00010-9. PMID: 9871675.

17: Burris HA 3rd, Raymond E, Awada A, Kuhn JG, O'Rourke TJ, Brentzel J, Lynch W, King SY, Brown TD, Von Hoff DD. Pharmacokinetic and phase I studies of brequinar (DUP 785; NSC 368390) in combination with cisplatin in patients with advanced malignancies. Invest New Drugs. 1998;16(1):19-27. doi: 10.1023/a:1016066529642. PMID: 9740540.

18: Chastanet S, Cursio R, Gugenheim J, Baldini E, Chevallier A, Damais A, Charpentier B, Mouiel J. Brequinar sodium and liver hemoperfusion in xenotransplantation. Transplant Proc. 1998 Aug;30(5):2244-5. doi: 10.1016/s0041-1345(98)00606-x. PMID: 9723457.

19: Schuurman HJ, Tanner M, Pally C, Jaffee BD. Brequinar and brequinar analogues in rat allo- and xenotransplantation. Transplant Proc. 1998 Aug;30(5):2240-3. doi: 10.1016/s0041-1345(98)00605-8. PMID: 9723456.

20: Pally C, Smith D, Jaffee B, Magolda R, Zehender H, Dorobek B, Donatsch P, Papageorgiou C, Schuurman HJ. Side effects of brequinar and brequinar analogues, in combination with cyclosporine, in the rat. Toxicology. 1998 May 15;127(1-3):207-22. doi: 10.1016/s0300-483x(98)00026-2. PMID: 9699807.