WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 571526
CAS#: 55661-38-6
Description: Nimustine hydrochloride is an antineoplastic agent especially effective against malignant brain tumors. It can help overcome tumor drug resistance, especially in combination with other antineoplastic agents or with radiotherapy for the treatment of various neoplasms.
MedKoo Cat#: 571526
Name: Nimustine hydrochloride
CAS#: 55661-38-6
Chemical Formula: C9H14Cl2N6O2
Exact Mass: 308.0555
Molecular Weight: 309.15
Elemental Analysis: C, 34.97; H, 4.56; Cl, 22.93; N, 27.18; O, 10.35
Synonym: Nimustine hydrochloride; NSC-245,382; NSC245,382; NSC 245,382
IUPAC/Chemical Name: 3-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-1-(2-chloroethyl)-1-nitrosourea hydrochloride
InChi Key: KPMKNHGAPDCYLP-UHFFFAOYSA-N
InChi Code: InChI=1S/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H
SMILES Code: O=C(NCC1=CN=C(C)N=C1N)N(CCCl)N=O.[H]Cl
1: Bekö SL, Urmann D, Lakatos A, Glaubitz C, Schmidt MU. Nimustine hydrochloride: the first crystal structure determination of a 2-chloroethyl-N-nitrosourea hydrochloride derivative by X-ray powder diffraction and solid-state NMR. Acta Crystallogr C. 2012 Mar;68(Pt 3):o144-8. doi: 10.1107/S0108270112005252. Epub 2012 Feb 24. PubMed PMID: 22382550.
2: Sugiyama S, Saito R, Nakamura T, Yamashita Y, Yokosawa M, Sonoda Y, Kumabe T, Watanabe M, Tominaga T. Safety and feasibility of convection-enhanced delivery of nimustine hydrochloride co-infused with free gadolinium for real-time monitoring in the primate brain. Neurol Res. 2012 Jul;34(6):581-7. doi: 10.1179/1743132812Y.0000000050. Epub 2012 Jun 16. PubMed PMID: 22709625.
3: Saito R, Sonoda Y, Kumabe T, Nagamatsu K, Watanabe M, Tominaga T. Regression of recurrent glioblastoma infiltrating the brainstem after convection-enhanced delivery of nimustine hydrochloride. J Neurosurg Pediatr. 2011 May;7(5):522-6. doi: 10.3171/2011.2.PEDS10407. PubMed PMID: 21529193.
4: Shibui S, Narita Y, Mizusawa J, Beppu T, Ogasawara K, Sawamura Y, Kobayashi H, Nishikawa R, Mishima K, Muragaki Y, Maruyama T, Kuratsu J, Nakamura H, Kochi M, Minamida Y, Yamaki T, Kumabe T, Tominaga T, Kayama T, Sakurada K, Nagane M, Kobayashi K, Nakamura H, Ito T, Yazaki T, Sasaki H, Tanaka K, Takahashi H, Asai A, Todo T, Wakabayashi T, Takahashi J, Takano S, Fujimaki T, Sumi M, Miyakita Y, Nakazato Y, Sato A, Fukuda H, Nomura K. Randomized trial of chemoradiotherapy and adjuvant chemotherapy with nimustine (ACNU) versus nimustine plus procarbazine for newly diagnosed anaplastic astrocytoma and glioblastoma (JCOG0305). Cancer Chemother Pharmacol. 2013 Feb;71(2):511-21. doi: 10.1007/s00280-012-2041-5. Epub 2012 Dec 11. PubMed PMID: 23228988.
5: Mizumoto M, Yamamoto T, Ishikawa E, Matsuda M, Takano S, Ishikawa H, Okumura T, Sakurai H, Matsumura A, Tsuboi K. Proton beam therapy with concurrent chemotherapy for glioblastoma multiforme: comparison of nimustine hydrochloride and temozolomide. J Neurooncol. 2016 Oct;130(1):165-170. Epub 2016 Aug 17. PubMed PMID: 27535747.
6: Isobe K, Kobayashi K, Kosaihira S, Kurimoto F, Sakai H, Uchida Y, Nagai Y, Yamaguchi T, Miyanaga A, Ando M, Mori G, Hino M, Gemma A. Phase II study of nimustine hydrochloride (ACNU) plus paclitaxel for refractory small cell lung cancer. Lung Cancer. 2009 Dec;66(3):350-4. doi: 10.1016/j.lungcan.2009.03.003. Epub 2009 Apr 1. PubMed PMID: 19342118.
7: Nitta Y, Ikeya T, Sakakibara A, Tomita Y. Therapy-related myelodysplastic syndrome developed by dacarbazine, nimustine hydrochloride and vincristine sulfate (DAV) therapy for patient with malignant melanoma. J Dermatol. 2011 Feb;38(2):164-8. doi: 10.1111/j.1346-8138.2010.00947.x. Epub 2010 Nov 11. PubMed PMID: 21269313.
8: Miyagawa S, Ando M, Takao A. Cardiovascular anomalies produced by nimustine hydrochloride in the rat fetus. Teratology. 1988 Dec;38(6):553-8. PubMed PMID: 3238611.
9: Takata Y, Hayashi S, Ohno T, Dekio S. Paralytic ileus associated with a combination of dacarbazine-nimustine hydrochloride-vincristine chemotherapy. J Dermatol. 1997 Oct;24(10):682-3. PubMed PMID: 9375471.
10: Yamazaki N, Yamamoto A, Wada T, Ishikawa M. Dacarbazine, nimustine hydrochloride, cisplatin and tamoxifen combination chemotherapy for advanced malignant melanoma. J Dermatol. 1999 Aug;26(8):489-93. PubMed PMID: 10487002.
11: Joss RA, Siegenthaler P, Ludwig C, Alberto P, Castiglione MM, Cavalli F. Phase II trial of nimustine (ACNU; 3-[4-amino-2-methyl-5-pyrimidinyl) methyl]-1-(2-chloroethyl)-1-nitrosourea hydrochloride) in patients with small cell carcinoma of the lung after failure on combination chemotherapy. Invest New Drugs. 1986;4(2):175-9. PubMed PMID: 3015827.
12: Watanabe T, Katayama Y, Yoshino A, Fukaya C, Yamamoto T. Human interferon beta, nimustine hydrochloride, and radiation therapy in the treatment of newly diagnosed malignant astrocytomas. J Neurooncol. 2005 Mar;72(1):57-62. PubMed PMID: 15803376.
13: Zhang R, Saito R, Mano Y, Kanamori M, Sonoda Y, Kumabe T, Tominaga T. Concentration rather than dose defines the local brain toxicity of agents that are effectively distributed by convection-enhanced delivery. J Neurosci Methods. 2014 Jan 30;222:131-7. doi: 10.1016/j.jneumeth.2013.11.004. Epub 2013 Nov 20. PubMed PMID: 24269253.
14: Beppu T, Kamada K, Nakamura R, Oikawa H, Takeda M, Fukuda T, Arai H, Ogasawara K, Ogawa A. A phase II study of radiotherapy after hyperbaric oxygenation combined with interferon-beta and nimustine hydrochloride to treat supratentorial malignant gliomas. J Neurooncol. 2003 Jan;61(2):161-70. PubMed PMID: 12622455.
15: Mizushima Y, Kashii T, Nakagawa K, Monno S, Yano S. Effects of granulocyte colony-stimulating factor, interleukin-1 alpha, and interleukin-6 on prolonged myelosuppression induced by nimustine hydrochloride in rats. J Immunother (1991). 1992 Aug;12(2):98-104. PubMed PMID: 1380297.
16: Izaki S, Goto H, Okuda K, Matsuda M, Watanabe Y, Fujioka K, Hanzawa N, Sumita H, Takahashi H, Goto S, Kai S, Sekiguchi H, Funabiki T, Sasaki H, Ikuta K, Yokota S. Long-term follow-up of busulfan, etoposide, and nimustine hydrochloride (ACNU) or melphalan as conditioning regimens for childhood acute leukemia and lymphoma. Int J Hematol. 2007 Oct;86(3):253-60. PubMed PMID: 17988993.
17: Anda T, Shabani HK, Tsunoda K, Tokunaga Y, Kaminogo M, Shibata S, Hayashi T, Iseki M. Relationship between expression of O6-methylguanine-DNA methyltransferase, glutathione-S-transferase pi in glioblastoma and the survival of the patients treated with nimustine hydrochloride: an immunohistochemical analysis. Neurol Res. 2003 Apr;25(3):241-8. PubMed PMID: 12739231.
18: Tatsuhara T, Tabuchi F, Yamane M, Hori T. Rapid and simple method for the determination of nimustine hydrochloride in human blood and brain by high-performance liquid chromatography. J Chromatogr. 1990 Apr 6;526(2):507-14. PubMed PMID: 2361989.
19: Tanaka M, Shibui S, Nomura K, Nakanishi Y. Radiotherapy combined with nimustine hydrochloride and etoposide for malignant gliomas: results of a pilot study. Jpn J Clin Oncol. 2001 Jun;31(6):246-50. PubMed PMID: 11463801.
20: Goseki N, Endo M. Thiol depletion and chemosensitization on nimustine hydrochloride by methionine-depleting total parenteral nutrition. Tohoku J Exp Med. 1990 Jul;161(3):227-39. PubMed PMID: 2123363.
