Trimetrexate glucuronate

For research use only. Not for therapeutic Use.

  • CAT Number: I037525
  • CAS Number: 82952-64-5
  • Molecular Formula: C25H33N5O10
  • Molecular Weight: 563.56
  • Purity: 98%
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Trimetrexate glucuronate(Cat No.:I037525)is an active metabolite of trimetrexate, a potent inhibitor of dihydrofolate reductase (DHFR), which plays a critical role in folate metabolism and DNA synthesis. This compound has shown efficacy in treating certain types of cancer, particularly in patients with reduced response to conventional methotrexate therapy. Trimetrexate glucuronate enhances the therapeutic effects of trimetrexate by improving its solubility and bioavailability. Ongoing research focuses on its pharmacokinetics, mechanisms of action, and potential applications in combination therapies to optimize treatment outcomes for various malignancies.


Catalog Number I037525
CAS Number 82952-64-5
Synonyms

Trimetrexate glucuronate; DRG0183; DRG 0183; DRG-0183; CI898; CI-898; CI 898

Molecular Formula C25H33N5O10
Purity 98%
Solubility To be determined
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine;(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
InChI InChI=1S/C19H23N5O3.C6H10O7/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3;7-1-2(8)3(9)4(10)5(11)6(12)13/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24);1-5,8-11H,(H,12,13)/t;2-,3+,4-,5-/m.0/s1
InChIKey ZCJXQWYMBJYJNB-LRDBBFHQSA-N
SMILES CC1=C(C=CC2=C1C(=NC(=N2)N)N)CNC3=CC(=C(C(=C3)OC)OC)OC.C(=O)[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O)O)O)O
Reference

1: Blanke CD, Chansky K, Christman KL, Hundahl SA, Issell BF, Van Veldhuizen PJ Jr, Budd GT, Abbruzzese JL, Macdonald JS. S9511: a Southwest Oncology Group phase II study of trimetrexate, 5-fluorouracil, and leucovorin in unresectable or metastatic adenocarcinoma of the stomach. Am J Clin Oncol. 2010 Apr;33(2):117-20. doi: 10.1097/COC.0b013e318199fb84. PubMed PMID: 19770625; PubMed Central PMCID: PMC2967385.
2: Senkovich O, Schormann N, Chattopadhyay D. Structures of dihydrofolate reductase-thymidylate synthase of Trypanosoma cruzi in the folate-free state and in complex with two antifolate drugs, trimetrexate and methotrexate. Acta Crystallogr D Biol Crystallogr. 2009 Jul;65(Pt 7):704-16. doi: 10.1107/S090744490901230X. Epub 2009 Jun 20. PubMed PMID: 19564691.
3: Short CE, Gilleece YC, Fisher MJ, Churchill DR. Trimetrexate and folinic acid: a valuable salvage option for Pneumocystis jirovecii pneumonia. AIDS. 2009 Jun 19;23(10):1287-90. doi: 10.1097/QAD.0b013e32832d0792. PubMed PMID: 19424049.
4: Das JR, Fryar EB, Green S, Southerland WM, Bowen D. The protection against trimetrexate cytotoxicity in human bone marrow by sequence-dependent administration of raloxifene, 5-fluorouracil/trimetrexate. Anticancer Res. 2006 Nov-Dec;26(6B):4279-86. PubMed PMID: 17201145.
5: Matin K, Jacobs SA, Richards T, Wong MK, Earle M, Evans T, Troetschel M, Ferri W, Friedland D, Pinkerton R, Volkin R, Wieand S, Ramanathan RK. A phase I/II study of trimetrexate and capecitabine in patients with advanced refractory colorectal cancer. Am J Clin Oncol. 2005 Oct;28(5):439-44. PubMed PMID: 16199980.
6: Senkovich O, Bhatia V, Garg N, Chattopadhyay D. Lipophilic antifolate trimetrexate is a potent inhibitor of Trypanosoma cruzi: prospect for chemotherapy of Chagas’ disease. Antimicrob Agents Chemother. 2005 Aug;49(8):3234-8. PubMed PMID: 16048931; PubMed Central PMCID: PMC1196212.
7: Szabolcs P, Park KD, Marti L, Deoliveria D, Lee YA, Colvin MO, Kurzberg J. Superior depletion of alloreactive T cells from peripheral blood stem cell and umbilical cord blood grafts by the combined use of trimetrexate and interleukin-2 immunotoxin. Biol Blood Marrow Transplant. 2004 Nov;10(11):772-83. PubMed PMID: 15505608.
8: Garcia AA, Leichman L, Baranda J, Pandit L, Lenz HJ, Leichman CG. Phase II clinical trial of 5-fluorouracil, trimetrexate, and leucovorin (NFL) in patients with advanced pancreatic cancer. Int J Gastrointest Cancer. 2003;34(2-3):79-86. PubMed PMID: 15361639.
9: Machiavelli MR, Salum G, Pérez JE, Ortiz EH, Romero AO, Bologna F, Vallejo CT, Lacava JA, Dominguez ME, Leone BA. Double modulation of 5-fluorouracil by trimetrexate and leucovorin in patients with advanced colorectal carcinoma. Am J Clin Oncol. 2004 Apr;27(2):149-54. PubMed PMID: 15057154.
10: Faessel HM, Slocum HK, Rustum YM, Greco WR. Thymidine and hypoxanthine protection patterns of the folic acid-enhanced synergies for combinations of trimetrexate plus a polyglutamylatable inhibitor of purine or thymidylate synthesis against human ileocecal HCT-8 cells. Int J Oncol. 2003 Aug;23(2):401-9. PubMed PMID: 12851689.

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