Etanidazole monohydrate

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MedKoo CAT#: 126331

CAS#: 182323-12-2 (hydrate)

Description: 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

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Etanidazole monohydrate
CAS# 182323-12-2 (hydrate)
Instruction

Theoretical Analysis

MedKoo Cat#: 126331
Name: Etanidazole monohydrate
CAS#: 182323-12-2 (hydrate)
Chemical Formula: C7H12N4O5
Exact Mass: 232.08
Molecular Weight: 232.196
Elemental Analysis: C, 36.21; H, 5.21; N, 24.13; O, 34.45

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 182323-12-2 (hydrate)   22668-01-5 (free base)  

Synonym: Etanidazole monohydrate; Etanidazole; SR2508; SR 2508; SR-2508

IUPAC/Chemical Name: N-(2-hydroxyethyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide hydrate

InChi Key: VLPRXIRKJZLPHS-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H10N4O4.H2O/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);1H2

SMILES Code: C1=CN(C(=N1)[N+](=O)[O-])CC(=O)NCCO.O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 232.20 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:
In vitro protocol:
In vivo protocol:

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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.


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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.