Trimetrexate

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

MedKoo CAT#: 407165

CAS#: 52128-35-5

Description: Trimetrexate is a quinazoline derivative. It is a dihydrofolate reductase inhibitor. It has been used with leucovorin in treating pneumocystis pneumonia. It has been investigated for use in treating leiomyosarcoma. It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Other uses include skin lymphoma.


Chemical Structure

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Trimetrexate
CAS# 52128-35-5

Theoretical Analysis

MedKoo Cat#: 407165
Name: Trimetrexate
CAS#: 52128-35-5
Chemical Formula: C19H23N5O3
Exact Mass: 369.18009
Molecular Weight: 369.43
Elemental Analysis: C, 61.77; H, 6.28; N, 18.96; O, 12.99

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Synonym: Trimetrexate

IUPAC/Chemical Name: 5-methyl-6-(((3,4,5-trimethoxyphenyl)amino)methyl)quinazoline-2,4-diamine

InChi Key: NOYPYLRCIDNJJB-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H23N5O3/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/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)

SMILES Code: NC1=NC(N)=C2C(C)=C(CNC3=CC(OC)=C(OC)C(OC)=C3)C=CC2=N1

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: >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

Preparing Stock Solutions

The following data is based on the product molecular weight 369.43 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.

Recalculate based on batch purity %
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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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.