BGC-945

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

MedKoo CAT#: 209490

CAS#: 501332-69-0

Description: ONX-0801, also known as BGC 945, is a cyclopenta[g]quinazoline–based, thymidylate synthase inhibitor specifically transported into α-folate receptor (α-FR)–overexpressing tumors. Affinity of BGC 945 for the α-FR is 70% of the high-affinity ligand folic acid. In contrast to conventional antifolates, BGC 945 has low affinity for the widely expressed reduced-folate carrier (RFC). The Ki for isolated thymidylate synthase is 1.2 nmol/L and the IC50 for inhibition of the growth of α-FR-negative mouse L1210 or human A431 cells is ~ 7 μmol/L. In contrast, BGC 945 is highly potent in a range of α-FR-overexpressing human tumor cell lines (IC50 ~1-300 nmol/L). BGC 945 selectively inhibits thymidylate synthase in α-FR-overexpressing tumors and should cause minimal toxicity to humans at therapeutic doses.


Price and Availability

Size
Price

1g
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Size
Price

2g
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Size
Price

5g
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BGC-945, 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#: 209490
Name: BGC-945
CAS#: 501332-69-0
Chemical Formula: C32H33N5O10
Exact Mass: 647.22274
Molecular Weight: 647.63
Elemental Analysis: C, 59.35; H, 5.14; N, 10.81; O, 24.70


Synonym: ONX 0801; ONX-0801; ONX0801; BGC 945; BGC945; BGC 945; CB 300945.

IUPAC/Chemical Name: (R)-2-((S)-4-carboxy-4-(4-(((S)-2-(hydroxymethyl)-4-oxo-4,6,7,8-tetrahydro-3H-cyclopenta[g]quinazolin-6-yl)(prop-2-yn-1-yl)amino)benzamido)butanamido)pentanedioic acid

InChi Key: NVHRBQOZEMFKLD-CUYJMHBOSA-N

InChi Code: InChI=1S/C32H33N5O10/c1-2-13-37(25-10-5-18-14-24-21(15-20(18)25)30(43)36-26(16-38)33-24)19-6-3-17(4-7-19)29(42)35-23(32(46)47)8-11-27(39)34-22(31(44)45)9-12-28(40)41/h1,3-4,6-7,14-15,22-23,25,38H,5,8-13,16H2,(H,34,39)(H,35,42)(H,40,41)(H,44,45)(H,46,47)(H,33,36,43)/t22-,23+,25+/m1/s1

SMILES Code: O=C(O)[C@H](NC(CC[C@@H](C(O)=O)NC(C1=CC=C(N([C@H]2CCC3=C2C=C4C(NC(CO)=NC4=C3)=O)CC#C)C=C1)=O)=O)CCC(O)=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: Gonen N, Assaraf YG. Antifolates in cancer therapy: Structure, activity and mechanisms of drug resistance. Drug Resist Updat. 2012 Aug 22. [Epub ahead of print] PubMed PMID: 22921318.

2: Jarmuła A. Antifolate inhibitors of thymidylate synthase as anticancer drugs. Mini Rev Med Chem. 2010 Nov;10(13):1211-22. Review. PubMed PMID: 20854257.

3: Pillai RG, Forster M, Perumal M, Mitchell F, Leyton J, Aibgirhio FI, Golovko O, Jackman AL, Aboagye EO. Imaging pharmacodynamics of the alpha-folate receptor-targeted thymidylate synthase inhibitor BGC 945. Cancer Res. 2008 May 15;68(10):3827-34. PubMed PMID: 18483267.

4: Gibbs DD, Theti DS, Wood N, Green M, Raynaud F, Valenti M, Forster MD, Mitchell F, Bavetsias V, Henderson E, Jackman AL. BGC 945, a novel tumor-selective thymidylate synthase inhibitor targeted to alpha-folate receptor-overexpressing tumors. Cancer Res. 2005 Dec 15;65(24):11721-8. PubMed PMID: 16357184.

5: Wood N, Gibbs DD, Jackman AL, Henley A, Workman P, Raynaud F. A liquid chromatographic-tandem mass spectrometric method for the determination of two selective thymidylate synthase inhibitors, BGC945 and BGC638, in mouse plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):181-8. PubMed PMID: 16061428.