Trimidox | CAS#95933-74-7 | Ribonucleotide reductase inhibitor

MedKoo Cat#: 112181 | Name: Trimidox

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Description:

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

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.

Chemical Structure

Trimidox

CAS#95933-74-7

Theoretical Analysis

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

Price and Availability

Size	Price	Availability
5mg	USD 260.00	2 Weeks
10mg	USD 510.00	2 Weeks
50mg	USD 1,030.00	2 Weeks
100mg	USD 1,550.00	2 Weeks

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Related CAS #

No Data

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

More Info

Instruction

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	Solvent	mg/mL	mM
Solubility
	DMF	20.0	108.61
	DMSO	25.0	135.76

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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: Yang CH, Wu CH, Lo SY, Lua AC, Chan YR, Li HC. Hepatitis C Virus Down- Regulates the Expression of Ribonucleotide Reductases to Promote Its Replication. Pathogens. 2023 Jun 29;12(7):892. doi: 10.3390/pathogens12070892. PMID: 37513740; PMCID: PMC10383090. 2: 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. 3: Basu A, Sinha BN. Understanding the molecular interactions of different radical scavengers with ribonucleotide reductase M2 (hRRM2) domain: opening the gates and gaining access. J Comput Aided Mol Des. 2012 Jul;26(7):865-81. doi: 10.1007/s10822-012-9581-y. Epub 2012 May 26. PMID: 22639080. 4: 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. 5: 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. 6: 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. 7: 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. 8: Kaul DK, Kollander R, Mahaseth H, Liu XD, Solovey A, Belcher J, Kelm RJ Jr, Vercellotti GM, Hebbel RP. Robust vascular protective effect of hydroxamic acid derivatives in a sickle mouse model of inflammation. Microcirculation. 2006 Sep;13(6):489-97. doi: 10.1080/10739680600778456. PMID: 16864415. 9: Madlener S, Illmer C, Horvath Z, Saiko P, Losert A, Herbacek I, Grusch M, Elford HL, Krupitza G, Bernhaus A, Fritzer-Szekeres M, Szekeres T. Gallic acid inhibits ribonucleotide reductase and cyclooxygenases in human HL-60 promyelocytic leukemia cells. Cancer Lett. 2007 Jan 8;245(1-2):156-62. doi: 10.1016/j.canlet.2006.01.001. Epub 2006 Feb 20. PMID: 16488533. 10: 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. 11: Novotny L, Rauko P, Liska J, Elford HL, Szekeres T. Potentiation of the activity of cisplatin and cyclophosphamide by trimidox, a novel ribonucleotide reductase inhibitor, in leukemia-bearing mice. Cancer Lett. 2006 Feb 20;233(1):178-84. doi: 10.1016/j.canlet.2005.03.013. PMID: 15885888. 12: Mayhew CN, Sumpter R, Inayat M, Cibull M, Phillips JD, Elford HL, Gallicchio VS. Combination of inhibitors of lymphocyte activation (hydroxyurea, trimidox, and didox) and reverse transcriptase (didanosine) suppresses development of murine retrovirus-induced lymphoproliferative disease. Antiviral Res. 2005 Jan;65(1):13-22. doi: 10.1016/j.antiviral.2004.09.003. PMID: 15652967. 13: Jordheim LP, Cros E, Gouy MH, Galmarini CM, Peyrottes S, Mackey J, Perigaud C, Dumontet C. Characterization of a gemcitabine-resistant murine leukemic cell line: reversion of in vitro resistance by a mononucleotide prodrug. Clin Cancer Res. 2004 Aug 15;10(16):5614-21. doi: 10.1158/1078-0432.CCR-04-0506. PMID: 15328204. 14: 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. 15: 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. 16: 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. 17: Turchan J, Pocernich CB, Gairola C, Chauhan A, Schifitto G, Butterfield DA, Buch S, Narayan O, Sinai A, Geiger J, Berger JR, Elford H, Nath A. Oxidative stress in HIV demented patients and protection ex vivo with novel antioxidants. Neurology. 2003 Jan 28;60(2):307-14. doi: 10.1212/01.wnl.0000042048.85204.3d. PMID: 12552050. 18: 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. 19: 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. 20: Fritzer-Szekeres M, Luxbacher C, Horvath Z, Grusch M, Krupitza G, Elford HL, Szekeres T. Apoptosis-inducing cleavage of caspases by trimidox, an inhibitor of ribonucleotide reductase. Adv Exp Med Biol. 2000;486:125-30. doi: 10.1007/0-306-46843-3_25. PMID: 11783468.