ICI 198583 | CAS#112887-62-4 | antifolate thymidylate synthase inhibitor

MedKoo Cat#: 597163 | Name: ICI 198583

Description:

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

ICI 198583 is an antifolate thymidylate synthase inhibitor.

Chemical Structure

ICI 198583

CAS#112887-62-4

Theoretical Analysis

MedKoo Cat#: 597163

Name: ICI 198583

CAS#: 112887-62-4

Chemical Formula: C25H24N4O6

Exact Mass: 476.1696

Molecular Weight: 476.48

Elemental Analysis: C, 63.02; H, 5.08; N, 11.76; O, 20.15

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

ICI 198583; CB 3819; ICI-198583; ICI198583;

IUPAC/Chemical Name

(4-(((2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-yn-1-yl)amino)benzoyl)-L-glutamic acid

InChi Key

PMTUUSDTAKQWQJ-NRFANRHFSA-N

InChi Code

InChI=1S/C25H24N4O6/c1-3-12-29(14-16-4-9-20-19(13-16)24(33)27-15(2)26-20)18-7-5-17(6-8-18)23(32)28-21(25(34)35)10-11-22(30)31/h1,4-9,13,21H,10-12,14H2,2H3,(H,28,32)(H,30,31)(H,34,35)(H,26,27,33)/t21-/m0/s1

SMILES Code

O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(N(CC2=CC3=C(NC(C)=NC3=O)C=C2)CC#C)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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 476.48 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

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Cytometry. 1998 Sep 1;33(1):56-66. PubMed PMID: 9725559. 5: Bavetsias V, Jackman AL, Marriott JH, Kimbell R, Gibson W, Boyle FT, Bisset GM. Folate-based inhibitors of thymidylate synthase: synthesis and antitumor activity of gamma-linked sterically hindered dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583). J Med Chem. 1997 May 9;40(10):1495-510. PubMed PMID: 9154971. 6: Springer CJ, Bavetsias V, Jackman AL, Boyle FT, Marshall D, Pedley RB, Bisset GM. Prodrugs of thymidylate synthase inhibitors: potential for antibody directed enzyme prodrug therapy (ADEPT). Anticancer Drug Des. 1996 Dec;11(8):625-36. PubMed PMID: 9022750. 7: Bavetsias V, Jackman AL, Kimbell R, Gibson W, Boyle FT, Bisset GM. Quinazoline antifolate thymidylate synthase inhibitors: gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583). J Med Chem. 1996 Jan 5;39(1):73-85. PubMed PMID: 8568829. 8: Jackman AL, Kimbell R, Brown M, Brunton L, Bisset GM, Bavetsias V, Marsham P, Hughes LR, Boyle FT. Quinazoline-based thymidylate synthase inhibitors: relationship between structural modifications and polyglutamation. Anticancer Drug Des. 1995 Oct;10(7):573-89. PubMed PMID: 7495480. 9: Jackman AL, Kelland LR, Kimbell R, Brown M, Gibson W, Aherne GW, Hardcastle A, Boyle FT. Mechanisms of acquired resistance to the quinazoline thymidylate synthase inhibitor ZD1694 (Tomudex) in one mouse and three human cell lines. Br J Cancer. 1995 May;71(5):914-24. PubMed PMID: 7537518; PubMed Central PMCID: PMC2033796. 10: Marsham PR, Jackman AL, Barker AJ, Boyle FT, Pegg SJ, Wardleworth JM, Kimbell R, O'Connor BM, Calvert AH, Hughes LR. Quinazoline antifolate thymidylate synthase inhibitors: replacement of glutamic acid in the C2-methyl series. J Med Chem. 1995 Mar 17;38(6):994-1004. 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The duration of the inhibition of thymidylate synthase in intact L1210 cells exposed to two different classes of quinazoline analogues. Adv Exp Med Biol. 1993;338:597-600. PubMed PMID: 8304189. 15: Bavetsias V, Jackman AL, Thornton TJ, Pawelczak K, Boyle FT, Bisset GM. Quinazoline antifolates inhibiting thymidylate synthase: synthesis of gamma-linked peptide and amide analogues of 2-desamino-2-methyl-N10-propargyl- 5,8-dideazafolic acid (ICI 198583). Adv Exp Med Biol. 1993;338:593-6. PubMed PMID: 8304188. 16: Boyle FT, Matusiak ZS, Hughes LR, Slater AM, Stephens TC, Smith MN, Brown M, Kimbell R, Jackman AL. Substituted-2-desamino-2-methyl-quinazolinones. A series of novel antitumour agents. Adv Exp Med Biol. 1993;338:585-8. PubMed PMID: 8304185. 17: Jackman AL, Bisset GM, Jodrell DI, Gibson W, Kimbell R, Bavetsias V, Calvert AH, Harrap KR, Stephens TC, Smith MN, et al. Gamma-linked dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8- dideazafolate as antitumour agents. 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