Methasquin | CAS#18921-70-5 | Folic Acid Antagonist

MedKoo Cat#: 535224 | Name: Methasquin

Description:

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

Methasquin is a folic acid antagonist that has been used in the treatment of experimental leukemia; acts by inhibiting the dihydrofolate reductase in the cell.

Chemical Structure

Methasquin

CAS#18921-70-5

Theoretical Analysis

MedKoo Cat#: 535224

Name: Methasquin

CAS#: 18921-70-5

Chemical Formula: C21H22N6O5

Exact Mass: 438.1652

Molecular Weight: 438.44

Elemental Analysis: C, 57.53; H, 5.06; N, 19.17; O, 18.25

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Methasquin

IUPAC/Chemical Name

Aspartic acid, N-(p-(((2,4-diamino-5-methyl-6-quinazolinyl)methyl)amino) benzoyl)-, L- (8CI)

InChi Key

NTKNUVXCGJPJQP-HNNXBMFYSA-N

InChi Code

InChI=1S/C21H22N6O5/c1-10-12(4-7-14-17(10)18(22)27-21(23)26-14)9-24-13-5-2-11(3-6-13)19(30)25-15(20(31)32)8-16(28)29/h2-7,15,24H,8-9H2,1H3,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,26,27)/t15-/m0/s1

SMILES Code

O=C(O)C[C@@H](C(O)=O)NC(C1=CC=C(NCC2=C(C)C3=C(N)N=C(N)N=C3C=C2)C=C1)=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

Shelf Life

>3 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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 438.44 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.

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

1: Sirotnak FM, Donsbach RC. A basis for the difference in toxicity of methotrexate, aminopterin and methasquin in mice. Biochem Pharmacol. 1975 Jan 1;24(1):156-8. doi: 10.1016/0006-2952(75)90332-9. PMID: 1168470. 2: Philips FS, Sirotnak FM, Sodergren JE, Hutchison DJ. Uptake of methotrexate, aminopterin, and methasquin and inhibition of dihydrofolate reductase and of DNA synthesis in mouse small intestine. Cancer Res. 1973 Jan;33(1):153-8. PMID: 4682318. 3: Rader JI, Hutchison DJ. Dihydrofolate reductase activity in strains of Streptococcus faecium var. durans resistant to methasquin and amethopterin. J Bacteriol. 1972 Apr;110(1):139-45. doi: 10.1128/JB.110.1.139-145.1972. PMID: 4401600; PMCID: PMC247390. 4: Sirotnak FM, Donsbach RC. Comparative studies on the transport of aminopterin, methotrexate, and methasquin by the L1210 leukemia cell. Cancer Res. 1972 Oct;32(10):2120-6. PMID: 4404161. 5: Rader JI, Hutchison DJ. Selection and characterization of mutant strains of Streptococcus faecium var. durans resistant to methasquin and amethopterin. Cancer Res. 1972 Apr;32(4):688-95. PMID: 5014779. 6: Albrecht AM, Biedler JL, Hutchison DJ. Two different species of dihydrofolate reductase in mammalian cells differentially resistant to amethopterin and methasquin. Cancer Res. 1972 Jul;32(7):1539-46. PMID: 4402276. 7: Myers CE, Eliot HM, Chabner BA. Competitive dihydrofolate reductase binding assay of triazinate (NSC-139105), methasquin (NSC-122870), and aminopterin (NSC739). Cancer Treat Rep. 1976 May;60(5):615-6. PMID: 1033031. 8: Wolgemuth DJ, Biedler JL, Melera PW. Repetitive DNA sequences in methotrexate- and methasquin-sensitive and -resistant Chinese hamster cell lines. Biochem Genet. 1980 Aug;18(7-8):655-67. doi: 10.1007/BF00484583. PMID: 6258555. 9: Rader JI, Hutchison DJ, Sodergren JE, Vidal P, Philips FS. Urinary and biliary excretion of the 2,4-diaminoquinazoline antifolate, methasquin, in rats and dogs. Cancer Res. 1971 Jul;31(7):964-9. PMID: 4997848. 10: Biedler JL, Albrecht AM, Spengler BA. Biochemical and karyological properties of cells resistant to the quinazoline antifolate, methasquin. Eur J Cancer. 1978 Jan;14(1):41-9. doi: 10.1016/0014-2964(78)90136-6. PMID: 564273. 11: Albrecht AM, Hutchison DJ. Folate reductase of the amethopterin-resistant Streptococcus faecium var. durans-Ak. I. Inhibition by amethopterin and methasquin, a new quinazoline antifolate. Mol Pharmacol. 1970 Jul;6(4):323-34. PMID: 4393363. 12: Philips FS, Sternberg SS, Sodergren JE, Vidal P. Toxicologic studies of the 2,4-diamino-quinazoline antifolate, methasquin (NSC-122870). Cancer Chemother Rep. 1971 Feb;55(1):35-42. PMID: 5001089. 13: Grey D, Hamilton-Miller JM. Trimethoprim-resistant bacteria: cross- resistance patterns. Microbios. 1977;19(75):45-54. PMID: 567736. 14: Spengler BA, Ross RA, Biedler JL. Differential drug sensitivity of human neuroblastoma cells. Cancer Treat Rep. 1986 Aug;70(8):959-65. PMID: 3731152. 15: McCullough JL, Weinstein GD, Hynes JB. In vitro screening of biochemical activity of folic acid antagonists in skin. J Invest Dermatol. 1977 Jun;68(6):362-5. doi: 10.1111/1523-1747.ep12496503. PMID: 864277. 16: Biedler JL, Spengler BA. A novel chromosome abnormality in human neuroblastoma and antifolate-resistant Chinese hamster cell lives in culture. J Natl Cancer Inst. 1976 Sep;57(3):683-95. doi: 10.1093/jnci/57.3.683. PMID: 62055. 17: Hynes JB, Eason DE, Garrett CM, Colvin PL Jr. Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids. J Med Chem. 1977 Apr;20(4):588-91. doi: 10.1021/jm00214a030. PMID: 850245. 18: Totskiĭ VN, Bondarchuk NG. Biokhimicheskie aspekty transporta folatov [Biochemical aspects of folate transport]. Usp Sovrem Biol. 1979 Nov- Dec;88(3):353-66. Russian. PMID: 395787. 19: Reddy AV, Behnke WD, Freisheim JH. Binary and ternary complexes of dihydrofolate reductase with substrates, coenzymes and inhibitors. Circular dichroic and magnetic circular dichroic studies. Biochim Biophys Acta. 1978 Apr 26;533(2):415-27. doi: 10.1016/0005-2795(78)90387-2. PMID: 417736. 20: Melera PW, Davide JP, Hession CA, Scotto KW. Phenotypic expression in Escherichia coli and nucleotide sequence of two Chinese hamster lung cell cDNAs encoding different dihydrofolate reductases. Mol Cell Biol. 1984 Jan;4(1):38-48. doi: 10.1128/mcb.4.1.38. PMID: 6366511; PMCID: PMC368655.