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MedKoo Cat#: 206031 | Name: Etanidazole
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Description:

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

Etanidazole (SR-2508) is a 2-nitroimidazole drug with radiosensitizing properties. Etanidazole depletes glutathione and inhibits glutathione transferase, thereby enhancing the cytotoxicity of ionizing radiation. This agent may also be useful as an imaging agent for identifying hypoxic, drug-resistant regions of primary tumors or metastases. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Etanidazole
Etanidazole
CAS#22668-01-5 (free base)

Theoretical Analysis

MedKoo Cat#: 206031

Name: Etanidazole

CAS#: 22668-01-5 (free base)

Chemical Formula: C7H10N4O4

Exact Mass: 214.0702

Molecular Weight: 214.18

Elemental Analysis: C, 39.25; H, 4.71; N, 26.16; O, 29.88

Price and Availability

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10mg USD 425.00 Ready to ship
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Related CAS #
182323-12-2 (hydrate) 22668-01-5 (free base)
Synonym
Etanidazole; SR2508; SR 2508; SR-2508
IUPAC/Chemical Name
N-(2-Hydroxyethyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
InChi Key
WCDWBPCFGJXFJZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H10N4O4/c12-4-2-8-6(13)5-10-3-1-9-7(10)11(14)15/h1,3,12H,2,4-5H2,(H,8,13)
SMILES Code
O=C(NCCO)CN1C=CN=C1[N+]([O-])=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, not in water
Shelf Life
>5 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
More Info
        
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T8R01C16
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Etanidazole is a hypoxic cell radiosensitizer.
In vitro activity:
The in vitro action of an hydrosoluble 2-nitroimidazole, Etanidazole (EZL), against Trypanosoma cruzi, the etiologic agent of Chagas disease, was evaluated. As shown in Fig. 2a, EZL treatment provoked a dose-dependent reduction in the number of RA trypomastigotes of T. cruzi, with the most remarkable effect achieved at 48 h. EZL was again notably active against the clinically relevant intracellular amastigote forms of T. cruzi. Indeed, amastigotes infecting Vero cells or J774 macrophages were more susceptible to the new compound than trypo-mastigotes (Fig. 2b). At the observation timepoint after infection (72 h), only intracellular forms of the parasite could be seen in drug-treated cell cultures. No change in the viability of Vero cells or J774 macrophages could be observed even at the highest concentration of the drugs tested, indicating that T. cruzi and not host cells is the target for EZL (Fig. 2b, d). Reference: Mem Inst Oswaldo Cruz. 2004 Mar;99(2):233-5. https://www.scielo.br/j/mioc/a/CBMVB8MyBvDmLYVJ7pXgYCy/?lang=en
In vivo activity:
The in vivo radiosensitizing activity of etanidazole, a well-known hypoxic cell radiosensitizer, was evaluated using tumor-bearing chick embryo. On the basis of tumor growth, drug administration and X-ray irradiation were performed on day 15 chick embryo, with the endpoint being day 18 chick embryo. In day 15 chick embryo, an X-ray irradiation dose of equal or less than 10 Gy did not cause significant tumor growth suppression. Intravenous administration of equal or less than 1.0 mg of etanidazole did not cause tumor growth suppression. Neither doses of equal or less than 8 Gy of irradiation nor 1.0 mg of etanidazole caused fatality of the chick embryo. On the basis of these results, the radiosensitizing effect of a combination treatment with 8 Gy of irradiation and 1.0 mg of etanidazole was evaulated. As noted above, 1.0 mg of etanidazole alone and 8 Gy of irradiation alone did not show tumor growth suppression. In contrast, a combination treatment with 8 Gy of irradiation and 1.0 mg of etanidazole showed 35% of significant tumor growth suppression. Reference: J Radiat Res. 2011;52(2):208-14. https://academic.oup.com/jrr/article/52/2/208/991880

Preparing Stock Solutions

The following data is based on the product molecular weight 214.18 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
Formulation protocol:
1. Petray PB, Morilla MJ, Corral RS, Romero EL. In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. Mem Inst Oswaldo Cruz. 2004 Mar;99(2):233-5. doi: 10.1590/s0074-02762004000200021. Epub 2004 Jun 24. PMID: 15250482. 2. Abe C, Uto Y, Nakae T, Shinmoto Y, Sano K, Nakata H, Teraoka M, Endo Y, Maezawa H, Masunaga S, Nakata E, Hori H. Evaluation of the in vivo radiosensitizing activity of etanidazole using tumor-bearing chick embryo. J Radiat Res. 2011;52(2):208-14. doi: 10.1269/jrr.10122. PMID: 21436611.
In vitro protocol:
1. Petray PB, Morilla MJ, Corral RS, Romero EL. In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. Mem Inst Oswaldo Cruz. 2004 Mar;99(2):233-5. doi: 10.1590/s0074-02762004000200021. Epub 2004 Jun 24. PMID: 15250482.
In vivo protocol:
1. Abe C, Uto Y, Nakae T, Shinmoto Y, Sano K, Nakata H, Teraoka M, Endo Y, Maezawa H, Masunaga S, Nakata E, Hori H. Evaluation of the in vivo radiosensitizing activity of etanidazole using tumor-bearing chick embryo. J Radiat Res. 2011;52(2):208-14. doi: 10.1269/jrr.10122. PMID: 21436611.
1: Hurwitz SJ, Coleman CN, Riese N, Loeffler JS, Alexander E 3rd, Buswell L, Neben TY, Shargel L, Kramer RA. Distribution of etanidazole into human brain tumors: implications for treating high grade gliomas. Int J Radiat Oncol Biol Phys. 1992;22(3):573-6. doi: 10.1016/0360-3016(92)90879-m. PMID: 1531216. 2: Abe C, Uto Y, Nakae T, Shinmoto Y, Sano K, Nakata H, Teraoka M, Endo Y, Maezawa H, Masunaga S, Nakata E, Hori H. Evaluation of the in vivo radiosensitizing activity of etanidazole using tumor-bearing chick embryo. J Radiat Res. 2011;52(2):208-14. doi: 10.1269/jrr.10122. PMID: 21436611. 3: Teicher BA, Herman TS, Holden SA. Effect of pH, oxygenation, and temperature on the cytotoxicity and radiosensitization by etanidazole. Int J Radiat Oncol Biol Phys. 1991 Apr;20(4):723-31. doi: 10.1016/0360-3016(91)90015-v. PMID: 1825994. 4: Jin C, Bai L, Wu H, Tian F, Guo G. Radiosensitization of paclitaxel, etanidazole and paclitaxel+etanidazole nanoparticles on hypoxic human tumor cells in vitro. Biomaterials. 2007 Sep;28(25):3724-30. doi: 10.1016/j.biomaterials.2007.04.032. Epub 2007 May 3. PMID: 17509678. 5: Shulman LN, Buswell L, Goodman H, Muto M, Berkowitz R, Teicher B, Kusumoto T, Hurwitz SJ, Kalish LA, Coleman CN. Phase I pharmacokinetic study of the hypoxic cell sensitizer etanidazole with carboplatin and cyclophosphamide in the treatment of advanced ovarian cancer. Int J Radiat Oncol Biol Phys. 1994 Jun 15;29(3):545-8. doi: 10.1016/0360-3016(94)90453-7. PMID: 8005814. 6: Evans SM, LaCreta F, Helfand S, VanWinkle T, Curran WJ Jr, Brown DQ, Hanks G. Technique, pharmacokinetics, toxicity, and efficacy of intratumoral etanidazole and radiotherapy for treatment of spontaneous feline oral squamous cell carcinoma. Int J Radiat Oncol Biol Phys. 1991 Apr;20(4):703-8. doi: 10.1016/0360-3016(91)90012-s. PMID: 1825993. 7: Wang FJ, Wang CH. Sustained release of etanidazole from spray dried microspheres prepared by non-halogenated solvents. J Control Release. 2002 Jun 17;81(3):263-80. doi: 10.1016/s0168-3659(02)00066-4. PMID: 12044566. 8: Marcus KJ, Dutton SC, Barnes P, Coleman CN, Pomeroy SL, Goumnerova L, Billett AL, Kieran M, Tarbell NJ. A phase I trial of etanidazole and hyperfractionated radiotherapy in children with diffuse brainstem glioma. Int J Radiat Oncol Biol Phys. 2003 Apr 1;55(5):1182-5. doi: 10.1016/s0360-3016(02)04391-2. PMID: 12654425. 9: Stone HB, Hirst VK, Cribbs R, Luu YH, Brown JM. A comparison of radiosensitization by etanidazole and pimonidazole in mouse tumors. Int J Radiat Oncol Biol Phys. 1991 May;20(5):987-95. doi: 10.1016/0360-3016(91)90195-a. PMID: 1827089. 10: Inanami O, Sugihara K, Okui T, Hayashi M, Tsujitani M, Kuwabara M. Hypoxia and etanidazole alter radiation-induced apoptosis in HL60 cells but not in MOLT-4 cells. Int J Radiat Biol. 2002 Apr;78(4):267-74. doi: 10.1080/09553000110105695. PMID: 12020438. 11: Morilla MJ, Montanari J, Frank F, Malchiodi E, Corral R, Petray P, Romero EL. Etanidazole in pH-sensitive liposomes: design, characterization and in vitro/in vivo anti-Trypanosoma cruzi activity. J Control Release. 2005 Apr 18;103(3):599-607. doi: 10.1016/j.jconrel.2004.12.012. PMID: 15820407. 12: Shulman LN, Buswell L, Kalish LA, Coleman CN. Use of the hypoxic cell sensitizer etanidazole (SR-2508) with intravenous melphalan and prednisone in the treatment of multiple myeloma: a pharmacokinetic study. Int J Radiat Oncol Biol Phys. 1994 Jun 15;29(3):541-3. doi: 10.1016/0360-3016(94)90452-9. PMID: 8005813. 13: Wang FJ, Wang CH. Etanidazole-loaded microspheres fabricated by spray-drying different poly(lactide/glycolide) polymers: effects on microsphere properties. J Biomater Sci Polym Ed. 2003;14(2):157-83. doi: 10.1163/156856203321142597. PMID: 12661666. 14: O'Dwyer PJ, LaCreta FP. Pharmacology and clinical investigation of SR-2508 (etanidazole). Cancer Treat Res. 1991;58:45-63. doi: 10.1007/978-1-4615-3876-9_3. PMID: 1683785. 15: Aguilera TA, Giaccia AJ. The end of the hypoxic EPOch. Int J Radiat Oncol Biol Phys. 2015 Apr 1;91(5):895-7. doi: 10.1016/j.ijrobp.2015.01.041. PMID: 25832683. 16: Tharmalingham H, Hoskin P. Clinical trials targeting hypoxia. Br J Radiol. 2019 Jan;92(1093):20170966. doi: 10.1259/bjr.20170966. Epub 2018 Jul 6. PMID: 29979089; PMCID: PMC6435072. 17: Eschwège F, Sancho-Garnier H, Chassagne D, Brisgand D, Guerra M, Malaise EP, Bey P, Busutti L, Cionini L, N'Guyen T, Romanini A, Chavaudra J, Hill C. Results of a European randomized trial of Etanidazole combined with radiotherapy in head and neck carcinomas. Int J Radiat Oncol Biol Phys. 1997 Sep 1;39(2):275-81. doi: 10.1016/s0360-3016(97)00327-1. PMID: 9308928. 18: Buswell L, Recht A, Clark J, Ravikumar T, Busse PM, Coleman CN. Combined- modality therapy of esophageal cancer with radiotherapy, etanidazole, and cisplatin-fluorouracil, with or without surgery: neurotoxicity, other toxicities and outcome. Int J Radiat Oncol Biol Phys. 1994 Jun 15;29(3):535-40. doi: 10.1016/0360-3016(94)90451-0. PMID: 8005812. 19: Bornstein BA, Herman TS, Hansen JL, Buswell L, Zouranjian PS, Fraser SM, Teicher BA, Svensson GK, Coleman CN. Pilot study of local hyperthermia, radiation therapy, etanidazole, and cisplatin for advanced superficial tumours. Int J Hyperthermia. 1995 Jul-Aug;11(4):489-99. doi: 10.3109/02656739509022484. PMID: 7594803. 20: Teicher BA, Herman TS, Holden SA, Jones SM. Addition of misonidazole, etanidazole, or hyperthermia to treatment with fluosol-DA/carbogen/radiation. J Natl Cancer Inst. 1989 Jun 21;81(12):929-34. doi: 10.1093/jnci/81.12.929. PMID: 2525198.