WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 112181
CAS#: 95933-74-7
Description: Trimidox is a specific ribonucleotide reductase inhibitor that reduces levels of dGTP and dCTP in HL-60 cells, inducing apoptosis via activation of caspases without altering the cell cycle distribution.
MedKoo Cat#: 112181
Name: Trimidox
CAS#: 95933-74-7
Chemical Formula: C7H8N2O4
Exact Mass: 184.0484
Molecular Weight: 184.15
Elemental Analysis: C, 45.66; H, 4.38; N, 15.21; O, 34.75
Synonym: Trimidox; VF 233; VF233; VF-233
IUPAC/Chemical Name: N,3,4,5-tetrahydroxybenzimidamide
InChi Key: MSLJYSGFUMYUDX-UHFFFAOYSA-N
InChi Code: InChI=1S/C7H8N2O4/c8-7(9-13)3-1-4(10)6(12)5(11)2-3/h1-2,10-13H,(H2,8,9)
SMILES Code: OC1=C(O)C(O)=CC(/C(N([H])O)=N\[H])=C1
Appearance: To be determined
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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 20.0 | 108.61 | |
| DMSO | 25.0 | 135.76 |
The following data is based on the product molecular weight 184.15 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: Kanno S, Uwai K, Tomizawa A, Hiura T, Osanai Y, Ujibe M, Takeshita M, Ohtake T, Kimura K, Ishikawa M. Trimidox induces apoptosis via cytochrome c release in NALM-6 human B cell leukaemia cells. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):44-50. doi: 10.1111/j.1742-7843.2006.pto_188.x. PMID: 16433890.
2: Kanno S, Kakuta M, Kitajima Y, Osanai Y, Kurauchi K, Ohtake T, Ujibe M, Uwai K, Takeshita M, Ishikawa M. Preventive effect of trimidox on oxidative stress in U937 cell line. Biol Pharm Bull. 2007 May;30(5):994-8. doi: 10.1248/bpb.30.994. PMID: 17473450.
3: Fritzer-Szekeres M, Salamon A, Grusch M, Horvath Z, Höchtl T, Steinbrugger R, Jäger W, Krupitza G, Elford HL, Szekeres T. Trimidox, an inhibitor of ribonucleotide reductase, synergistically enhances the inhibition of colony formation by Ara-C in HL-60 human promyelocytic leukemia cells. Biochem Pharmacol. 2002 Aug 1;64(3):481-5. doi: 10.1016/s0006-2952(02)01186-3. PMID: 12147300.
4: Kanno S, Ohtake T, Osanai Y, Kurauchi K, Ujibe M, Uwai K, Takeshita M, Satoh S, Ishikawa M. Trimidox-induced apoptosis is mediated through induction of p53 in NALM-6 cells. J Pharmacol Sci. 2008 Mar;106(3):521-4. doi: 10.1254/jphs.sc0070384. Epub 2008 Mar 12. PMID: 18344606.
5: Szekeres T, Gharehbaghi K, Fritzer M, Woody M, Srivastava A, van't Riet B, Jayaram HN, Elford HL. Biochemical and antitumor activity of trimidox, a new inhibitor of ribonucleotide reductase. Cancer Chemother Pharmacol. 1994;34(1):63-6. doi: 10.1007/BF00686113. PMID: 8174204.
6: Leyden D, Ahmed N, Hassan HT. Hydroxyurea and trimidox enhance the radiation effect in human pancreatic adenocarcinoma cells. Anticancer Res. 2000 Jan- Feb;20(1A):133-8. PMID: 10769645.
7: Iyamu EW, Adunyah SE, Elford HL, Fasold H, Turner EA. Trimidox-mediated morphological changes during erythroid differentiation is associated with the stimulation of hemoglobin and F-cell production in human K562 cells. Biochem Biophys Res Commun. 1998 Jun 29;247(3):759-64. doi: 10.1006/bbrc.1998.8534. PMID: 9647767.
8: Rosenberger G, Fuhrmann G, Grusch M, Fassl S, Elford HL, Smid K, Peters GJ, Szekeres T, Krupitza G. The ribonucleotide reductase inhibitor trimidox induces c-myc and apoptosis of human ovarian carcinoma cells. Life Sci. 2000 Nov 17;67(26):3131-42. doi: 10.1016/s0024-3205(00)00901-2. PMID: 11191620.
9: Szekeres T, Fritzer M, Strobl H, Gharehbaghi K, Findenig G, Elford HL, Lhotka C, Schoen HJ, Jayaram HN. Synergistic growth inhibitory and differentiating effects of trimidox and tiazofurin in human promyelocytic leukemia HL-60 cells. Blood. 1994 Dec 15;84(12):4316-21. PMID: 7994048.
10: Fritzer-Szekeres M, Grusch M, Luxbacher C, Horvath S, Krupitza G, Elford HL, Szekeres T. Trimidox, an inhibitor of ribonucleotide reductase, induces apoptosis and activates caspases in HL-60 promyelocytic leukemia cells. Exp Hematol. 2000 Aug;28(8):924-30. doi: 10.1016/s0301-472x(00)00484-7. PMID: 10989193.
11: Fritzer-Szekeres M, Novotny L, Romanova D, Göbl R, Sedlak J, Vachalkova A, Rauko P, Elford HL, Szekeres T. Enhanced effects of adriamycin by combination with a new ribonucleotide reductase inhibitor, trimidox, in murine leukemia. Life Sci. 1998;63(7):545-52. doi: 10.1016/s0024-3205(98)00305-1. PMID: 9718080.
12: Bhave S, Elford H, McVoy MA. Ribonucleotide reductase inhibitors hydroxyurea, didox, and trimidox inhibit human cytomegalovirus replication in vitro and synergize with ganciclovir. Antiviral Res. 2013 Oct;100(1):151-8. doi: 10.1016/j.antiviral.2013.07.016. Epub 2013 Aug 6. PMID: 23933116; PMCID: PMC3843955.
13: Iyamu WE, Adunyah SE, Fasold H, Horiuchi K, Elford HL, Asakura T, Turner EA. Enhancement of hemoglobin and F-cell production by targeting growth inhibition and differentiation of K562 cells with ribonucleotide reductase inhibitors (didox and trimidox) in combination with streptozotocin. Am J Hematol. 2000 Apr;63(4):176-83. doi: 10.1002/(sici)1096-8652(200004)63:4<176::aid- ajh3>3.0.co;2-g. PMID: 10706760.
14: Findenig G, Vielnascher E, Göbl R, Fritzer-Szekeres M, Szekeres T. Das Enzym Ribonukleotid-Reduktase als Target für enzymgerichtete Chemotherapie-Wirkungen von Trimidox (3,4,5-Trihydroxybenzohydroxamidoxim), einem neuen Inhibitor der Ribonukleotid-Reduktase [The ribonucleotide reductase enzyme as a target for enzyme-directed chemotherapy effects of trimidox (3,4,5-trihydroxybenzohydroxamidoxim), a new inhibitor of ribonucleotide reductases]. Wien Klin Wochenschr. 1995;107(22):694-7. German. PMID: 8533431.
15: Inayat MS, El-Amouri IS, Bani-Ahmad M, Elford HL, Gallicchio VS, Oakley OR. Inhibition of allogeneic inflammatory responses by the Ribonucleotide Reductase Inhibitors, Didox and Trimidox. J Inflamm (Lond). 2010 Aug 18;7:43. doi: 10.1186/1476-9255-7-43. PMID: 20718971; PMCID: PMC2933664.
16: Mayhew CN, Mampuru LJ, Chendil D, Ahmed MM, Phillips JD, Greenberg RN, Elford HL, Gallicchio VS. Suppression of retrovirus-induced immunodeficiency disease (murine AIDS) by trimidox and didox: novel ribonucleotide reductase inhibitors with less bone marrow toxicity than hydroxyurea. Antiviral Res. 2002 Nov;56(2):167-81. doi: 10.1016/s0166-3542(02)00108-0. PMID: 12367722.
17: Kanno S, Kakuta M, Kitajima Y, Osanai Y, Kurauchi K, Ohtake T, Ujibe M, Uwai K, Takeshita M, Ishikawa M. Inhibitory effect of trimidox on lipopolysaccharide- induced nitric oxide production in RAW 264.7 macrophages. J Pharmacol Sci. 2007 Jul;104(3):278-81. doi: 10.1254/jphs.sc0070073. Epub 2007 Jul 3. PMID: 17609582.
18: Figul M, Söling A, Dong HJ, Chou TC, Rainov NG. Combined effects of temozolomide and the ribonucleotide reductase inhibitors didox and trimidox in malignant brain tumor cells. Cancer Chemother Pharmacol. 2003 Jul;52(1):41-6. doi: 10.1007/s00280-003-0611-2. Epub 2003 Apr 11. PMID: 12690517.
19: Sumpter LR, Inayat MS, Yost EE, Duvall W, Hagan E, Mayhew CN, Elford HL, Gallicchio VS. In vivo examination of hydroxyurea and the novel ribonucleotide reductase inhibitors trimidox and didox in combination with the reverse transcriptase inhibitor abacavir: suppression of retrovirus-induced immunodeficiency disease. Antiviral Res. 2004 Jun;62(3):111-20. doi: 10.1016/j.antiviral.2003.11.007. PMID: 15130534.
20: Mayhew CN, Phillips JD, Cibull ML, Elford HL, Gallicchio VS. Short-term treatment with novel ribonucleotide reductase inhibitors Trimidox and Didox reverses late-stage murine retrovirus-induced lymphoproliferative disease with less bone marrow toxicity than hydroxyurea. Antivir Chem Chemother. 2002 Sep;13(5):305-14. doi: 10.1177/095632020201300506. PMID: 12630679.
