Metesind | 138384-68-6 | 157182-23-5 | hymidylate synthase inhibitor

MedKoo Cat#: 206755 | Name: Metesind

Description:

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

Metesind, also known as AG-331; AG-341, is a thymidylate synthase inhibitor potentially for the treatment of brain cancer and solid tumours.

Chemical Structure

Metesind

CAS#138384-68-6

Theoretical Analysis

MedKoo Cat#: 206755

Name: Metesind

CAS#: 138384-68-6

Chemical Formula: C23H24N4O3S

Exact Mass: 436.1569

Molecular Weight: 436.53

Elemental Analysis: C, 63.28; H, 5.54; N, 12.83; O, 11.00; S, 7.34

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

Metesind; AG-331; AG-341; AG331; AG341.

IUPAC/Chemical Name

N6-methyl-N6-(4-(morpholinosulfonyl)benzyl)benzo[cd]indole-2,6-diamine

InChi Key

CVEGTZWWWRJCFK-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H24N4O3S/c1-26(21-10-9-20-22-18(21)3-2-4-19(22)23(24)25-20)15-16-5-7-17(8-6-16)31(28,29)27-11-13-30-14-12-27/h2-10H,11-15H2,1H3,(H2,24,25)

SMILES Code

NC1=NC2=CC=C(N(C)CC3=CC=C(S(=O)(N4CCOCC4)=O)C=C3)C5=C2C1=CC=C5

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

>2 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

Related CAS# CAS No. 138384-68-6 (Metesind) 157182-23-5 (Metesind glucuronate)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 436.53 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: Bram E, Ifergan I, Shafran A, Berman B, Jansen G, Assaraf YG. Mutant Gly482 and Thr482 ABCG2 mediate high-level resistance to lipophilic antifolates. Cancer Chemother Pharmacol. 2006 Dec;58(6):826-34. PubMed PMID: 16612649. 2: Tsai WC, Wilke TL, Tyle P. Development and validation of an HPLC method for AG331 bulk drug substance and lyophilized powder for injection. J Pharm Biomed Anal. 2004 Jun 29;35(4):697-702. PubMed PMID: 15193714. 3: Wu Q, Dolnick BJ. Detection of thymidylate synthase modulators by a novel screening assay. Mol Pharmacol. 2003 Jan;63(1):167-73. PubMed PMID: 12488549. 4: Danenberg PV, Malli H, Swenson S. Thymidylate synthase inhibitors. Semin Oncol. 1999 Dec;26(6):621-31. Review. PubMed PMID: 10606255. 5: Newell DR. Clinical pharmacokinetics of antitumor antifolates. Semin Oncol. 1999 Apr;26(2 Suppl 6):74-81. Review. PubMed PMID: 10598559. 6: Koda RT, Garcia AA, Chatterjee DJ, Li WY, Parimoo D, Jeffers S, Rogers M, Leichman CG, Leichman L, Wu EY, Shetty BV, Webber S, Clendinnin N, Muggia FM. Phase I study of AG 331, a novel thymidylate synthase inhibitor, in patients with refractory solid tumors. Cancer Chemother Pharmacol. 1999;43(6):489-96. PubMed PMID: 10321509. 7: Bavetsias V, Jackman AL. Nonpolyglutamatable antifolates as inhibitors of thymidylate synthase (TS) and potential antitumour agents. Curr Med Chem. 1998 Aug;5(4):265-88. Review. PubMed PMID: 9668195. 8: O'Dwyer PJ, Laub PB, DeMaria D, Qian M, Reilly D, Giantonio B, Johnston AL, Wu EY, Bauman L, Clendeninn NJ, Gallo JM. Phase I trial of the thymidylate synthase inhibitor AG331 as a 5-day continuous infusion. Clin Cancer Res. 1996 Oct;2(10):1685-92. PubMed PMID: 9816117. 9: Van Cutsem E. A glimpse of the future. new directions in the treatment of colorectal cancer. Eur J Cancer. 1996;32A Suppl 5:S23-7. Review. PubMed PMID: 8958039. 10: Li WY, Chatterjee DJ, Shetty BV, Wu EY, Muggia F, Koda RT. High-performance liquid chromatographic method for the determination of a novel thymidylate synthase inhibitor, AG 331, in human serum. J Chromatogr B Biomed Appl. 1995 Nov 17;673(2):281-8. PubMed PMID: 8611962. 11: Jackman AL, Calvert AH. Folate-based thymidylate synthase inhibitors as anticancer drugs. Ann Oncol. 1995 Nov;6(9):871-81. Review. PubMed PMID: 8624289. 12: Pressacco J, Mitrovski B, Hedley DW, Tsang R, Erlichman C. Biochemical modulation of iododeoxyuridine by N6-[4-(morpholinosulfonyl)benzyl]-N6-methyl-2,6-diaminobenz[cd]indole glucuronate (AG-331) leading to enhanced cytotoxicity. Biochem Pharmacol. 1995 Jun 29;50(1):55-60. PubMed PMID: 7605345. 13: Qian M, O'Dwyer PJ, Gallo JM. High-performance liquid chromatographic method for the determination of AG-331, a novel anti-cancer agent, in human serum and urine using solid-phase extraction and photodiode-array detection. J Chromatogr B Biomed Appl. 1995 Apr 21;666(2):307-14. PubMed PMID: 7633607. 14: Pressacco J, Mitrovski B, Erlichman C, Hedley DW. Effects of thymidylate synthase inhibition on thymidine kinase activity and nucleoside transporter expression. Cancer Res. 1995 Apr 1;55(7):1505-8. PubMed PMID: 7882359. 15: Pressacco J, Mitrovski B, Erlichman C. Cytotoxic and biochemical implications of combining AZT and AG-331. Cancer Chemother Pharmacol. 1995;35(5):387-90. PubMed PMID: 7850919. 16: Panadero A, Yin MB, Voigt W, Rustum YM. Contrasting patterns of DNA fragmentation induced by thymidylate synthase inhibitors, ZD1694 and AG-331. Oncol Res. 1995;7(2):73-81. PubMed PMID: 7579730. 17: O'Connor BM, Webber S, Jackson RC, Galivan J, Rhee MS. Biological activity of a novel rationally designed lipophilic thymidylate synthase inhibitor. Cancer Chemother Pharmacol. 1994;34(3):225-9. PubMed PMID: 8004755. 18: Chiang CC, Fessler D, Freebern K, Thirucote R, Tyle P. Product development of AG-331 lyophilized powder for injection. J Pharm Sci Technol. 1994 Jan-Feb;48(1):24-9. PubMed PMID: 8004414. 19: Nord LD, Martin DS. Enhancement of thymidylate synthase inhibition. Curr Opin Oncol. 1993 Nov;5(6):1017-22. Review. PubMed PMID: 8305534.