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MedKoo Cat#: 206731 | Name: Doranidazole

Description:

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

Doranidazole, also known as PR-000350; PR-350; RP-343; PR-69, is radiosensitizer and potentially for the treatment of non-small cell lung cancer (NSCLC) and pancreatic cancer. PR-350 was an effective hypoxic cell radiosensitizer for a human small cell lung cancer in vivo, in which necrotic change was dominant following irradiation. The magnitude of radiosensitization of tumors by doranidazole is dependent on the oxygenation status of the tumors and that doranidazole may be useful in increasing the response of hypoxic human pancreatic tumor to IORT.

Chemical Structure

Doranidazole
Doranidazole
CAS#161903-10-2

Theoretical Analysis

MedKoo Cat#: 206731

Name: Doranidazole

CAS#: 161903-10-2

Chemical Formula: C8H13N3O6

Exact Mass: 247.0804

Molecular Weight: 247.21

Elemental Analysis: C, 38.87; H, 5.30; N, 17.00; O, 38.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Doranidazole; PR-000350; PR-350; RP-343; PR000350; PR350; RP343; PR-69.
IUPAC/Chemical Name
(2R,3S)-3-((2-nitro-1H-imidazol-1-yl)methoxy)butane-1,2,4-triol
InChi Key
FIITXXIVUIXYMI-RQJHMYQMSA-N
InChi Code
InChI=1S/C8H13N3O6/c12-3-6(14)7(4-13)17-5-10-2-1-9-8(10)11(15)16/h1-2,6-7,12-14H,3-5H2/t6-,7+/m1/s1
SMILES Code
OC[C@@H](O)[C@@H](OCN1C=CN=C1[N+]([O-])=O)CO
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 247.21 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
1: Yasui H, Asanuma T, Kino J, Yamamori T, Meike S, Nagane M, Kubota N, Kuwabara M, Inanami O. The prospective application of a hypoxic radiosensitizer, doranidazole to rat intracranial glioblastoma with blood brain barrier disruption. BMC Cancer. 2013 Mar 8;13:106. doi: 10.1186/1471-2407-13-106. PubMed PMID: 23496909; PubMed Central PMCID: PMC3599813. 2: Murata R, Tsujitani M, Horsman MR. Enhanced local tumour control after single or fractionated radiation treatment using the hypoxic cell radiosensitizer doranidazole. Radiother Oncol. 2008 Jun;87(3):331-8. doi: 10.1016/j.radonc.2008.03.002. Epub 2008 Mar 28. PubMed PMID: 18375007. 3: Karasawa K, Sunamura M, Okamoto A, Nemoto K, Matsuno S, Nishimura Y, Shibamoto Y. Efficacy of novel hypoxic cell sensitiser doranidazole in the treatment of locally advanced pancreatic cancer: long-term results of a placebo-controlled randomised study. Radiother Oncol. 2008 Jun;87(3):326-30. doi: 10.1016/j.radonc.2008.02.007. Epub 2008 Mar 14. PubMed PMID: 18342968. 4: Zhang L, Gong A, Ji J, Wu Y, Zhu X, Lv S, Lv H, Sun X. The radiosensitizing effect of doranidazole on human colorectal cancer cells exposed to high doses of irradiation. BMC Cancer. 2007 Oct 6;7:188. PubMed PMID: 17919337; PubMed Central PMCID: PMC2082041. 5: Nishimura Y, Nakagawa K, Takeda K, Tanaka M, Segawa Y, Tsujino K, Negoro S, Fuwa N, Hida T, Kawahara M, Katakami N, Hirokawa K, Yamamoto N, Fukuoka M, Ariyoshi Y. Phase I/II trial of sequential chemoradiotherapy using a novel hypoxic cell radiosensitizer, doranidazole (PR-350), in patients with locally advanced non-small-cell lung Cancer (WJTOG-0002). Int J Radiat Oncol Biol Phys. 2007 Nov 1;69(3):786-92. Epub 2007 May 23. PubMed PMID: 17512126. 6: Yahiro T, Masui S, Kubota N, Yamada K, Kobayashi A, Kishii K. Effects of hypoxic cell radiosensitizer doranidazole (PR-350) on the radioresponse of murine and human tumor cells in vitro and in vivo. J Radiat Res. 2005 Sep;46(3):363-72. PubMed PMID: 16210793. 7: Hamasu T, Inanami O, Tsujitani M, Yokoyama K, Takahashi E, Kashiwakura I, Kuwabara M. Post-irradiation hypoxic incubation of X-irradiated MOLT-4 cells reduces apoptotic cell death by changing the intracellular redox state and modulating SAPK/JNK pathways. Apoptosis. 2005 May;10(3):557-67. PubMed PMID: 15909118. 8: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jan-Feb;27(1):49-77. PubMed PMID: 15834459. 9: Shibamoto Y, Sugie C, Ito M, Ogino H. The Japanese experiences with hypoxia-targeting pharmacoradiotherapy: from hypoxic cell sensitisers to radiation-activated prodrugs. Expert Opin Pharmacother. 2004 Dec;5(12):2459-67. Review. PubMed PMID: 15571464. 10: Sunamura M, Karasawa K, Okamoto A, Ogata Y, Nemoto K, Hosotani R, Nishimura Y, Matsui K, Matsuno S; PR-350 study group. Phase III trial of radiosensitizer PR-350 combined with intraoperative radiotherapy for the treatment of locally advanced pancreatic cancer. Pancreas. 2004 Apr;28(3):330-4. PubMed PMID: 15084982. 11: Aoki M, Furusawa Y, Shibamoto Y, Kobayashi A, Tsujitani M. Effect of a hypoxic cell sensitizer doranidazole on the radiation-induced apoptosis of mouse L5178Y lymphoma cells. J Radiat Res. 2002 Jun;43(2):161-6. PubMed PMID: 12238330. 12: Kuwabara M, Iida Y, Inanami O, Sawamura S, Yokoyama K, Tsujitani M. Radiation-chemical properties of the hypoxic cell radiosensitizer doranidazole (PR-350). J Radiat Res. 2002 Mar;43(1):77-88. PubMed PMID: 12056332. 13: Mizumoto K, Qian LW, Zhang L, Nagai E, Kura S, Tanaka M. A nitroimidazole derivative, PR-350, enhances the killing of pancreatic cancer cells exposed to high-dose irradiation under hypoxia. J Radiat Res. 2002 Mar;43(1):43-51. PubMed PMID: 12056329. 14: Watanabe M, Tateishi T, Takezawa N, Tanaka M, Kumai T, Nakaya S, Kobayashi S. Effects of PR-350, a newly developed radiosensitizer, on dihydropyrimidine dehydrogenase activity and 5-fluorouracil pharmacokinetics. Cancer Chemother Pharmacol. 2001 Mar;47(3):250-4. PubMed PMID: 11320669. 15: Nemoto K, Shibamoto Y, Ohmagari J, Baba Y, Ebe K, Ariga H, Takai Y, Ouchi A, Sasai K, Shinozaki M, Tsujitani M, Sakaguchi M, Yamada S, Sakamoto K. Phase Ia study of a hypoxic cell sensitizer doranidazole (PR-350) in combination with conventional radiotherapy. Anticancer Drugs. 2001 Jan;12(1):1-6. PubMed PMID: 11272282. 16: Shibamoto Y, Kubota T, Kishii K, Tsujitani M. Radiosensitivity of human pancreatic cancer cells in vitro and in vivo, and the effect of a new hypoxic cell sensitizer, doranidazole. Radiother Oncol. 2000 Aug;56(2):265-70. PubMed PMID: 10927148. 17: Suzuki Y, Hasegawa M, Hayakawa K, Mitsuhashi N, Niibe H. In vivo study of radiosensitizing effect of hypoxic cell radiosensitizer PR-350 on a human small cell lung cancer. Anticancer Res. 1999 Sep-Oct;19(5B):3993-4000. PubMed PMID: 10628343. 18: Matsuoka H, Shibamoto Y, Kubota T, Tsujitani M, Majima T. In vivo efficacy and pharmacokinetics of a new hypoxic cell radiosensitizer doranidazole in SUIT-2 human pancreatic cancer xenografted in mouse pancreas. Oncol Rep. 2000 Jan-Feb;7(1):23-6. PubMed PMID: 10601585. 19: Shibamoto Y. [Contribution of radiation biology to the development of radiation therapy]. Gan To Kagaku Ryoho. 1999 Aug;26(9):1242-7. Review. Japanese. PubMed PMID: 10478175. 20: Hirokawa K, Nakajima T, Tsumura M, Nishita T, Yamada R, Onoyama Y. Pharmacokinetics and radiosensitizing effect of PR-350. Radiat Med. 1997 Jan-Feb;15(1):45-9. PubMed PMID: 9134584.