Brequinar

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 205953

CAS#: 96187-53-0

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

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Brequinar, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205953
Name: Brequinar
CAS#: 96187-53-0
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


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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: 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. PubMed PMID: 9740540.

2: Joshi AS, King SY, Zajac BA, Makowka L, Sher LS, Kahan BD, Menkis AH, Stiller CR, Schaefle B, Kornhauser DM. Phase I safety and pharmacokinetic studies of brequinar sodium after single ascending oral doses in stable renal, hepatic, and cardiac allograft recipients. J Clin Pharmacol. 1997 Dec;37(12):1121-8. PubMed PMID: 9506007.

3: Cleaveland ES, Zaharevitz DW, Kelley JA, Paull K, Cooney DA, Ford H Jr. Identification of a novel inhibitor (NSC 665564) of dihydroorotate dehydrogenase with a potency equivalent to brequinar. Biochem Biophys Res Commun. 1996 Jun 25;223(3):654-9. PubMed PMID: 8687451.

4: Buzaid AC, Pizzorno G, Marsh JC, Ravikumar TS, Murren JR, Todd M, Strair RK, Poo WJ, Hait WN. Biochemical modulation of 5-fluorouracil with brequinar: results of a phase I study. Cancer Chemother Pharmacol. 1995;36(5):373-8. PubMed PMID: 7634378.

5: King SY, Agra AM, Shen HS, Chi CL, Adams DB, Currie VE, Bertino JR, Pieniaszek HJ Jr, Quon CY. Protein binding of brequinar in the plasma of healthy donors and cancer patients and analysis of the relationship between protein binding and pharmacokinetics in cancer patients. Cancer Chemother Pharmacol. 1994;35(2):101-8. PubMed PMID: 7987984.

6: Cody R, Stewart D, DeForni M, Moore M, Dallaire B, Azarnia N, Gyves J. Multicenter phase II study of brequinar sodium in patients with advanced breast cancer. Am J Clin Oncol. 1993 Dec;16(6):526-8. PubMed PMID: 8256771.

7: Moore M, Maroun J, Robert F, Natale R, Neidhart J, Dallaire B, Sisk R, Gyves J. Multicenter phase II study of brequinar sodium in patients with advanced gastrointestinal cancer. Invest New Drugs. 1993 Feb;11(1):61-5. PubMed PMID: 8349438.

8: de Forni M, Chabot GG, Armand JP, Fontana X, Recondo G, Domenge C, Carde P, Barbu M, Gouyette A. Phase I and pharmacokinetic study of brequinar (DUP 785; NSC 368390) in cancer patients. Eur J Cancer. 1993;29A(7):983-8. PubMed PMID: 8499153.

9: Maroun J, Ruckdeschel J, Natale R, Morgan R, Dallaire B, Sisk R, Gyves J. Multicenter phase II study of brequinar sodium in patients with advanced lung cancer. Cancer Chemother Pharmacol. 1993;32(1):64-6. PubMed PMID: 8384937.

10: Natale R, Wheeler R, Moore M, Dallaire B, Lynch W, Carlson R, Grillo-Lopez A, Gyves J. Multicenter phase II trial of brequinar sodium in patients with advanced melanoma. Ann Oncol. 1992 Sep;3(8):659-60. PubMed PMID: 1450049.