Nimustine hydrochloride

For research use only. Not for therapeutic Use.

  • CAT Number: I014525
  • CAS Number: 55661-38-6
  • Molecular Formula: C9H14Cl2N6O2
  • Molecular Weight: 309.15
  • Purity: ≥95%
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Nimustine Hydrochloride(Cat No.:I014525)is a nitrosourea-class alkylating agent used in chemotherapy for treating brain tumors, malignant lymphomas, and other cancers. It works by crosslinking DNA strands and inhibiting DNA synthesis, leading to apoptosis in rapidly dividing cancer cells. Nimustine’s ability to penetrate the blood-brain barrier makes it particularly effective for central nervous system malignancies. It is also used in research to study DNA damage mechanisms and the development of chemoresistance. Nimustine Hydrochloride remains an essential tool in advancing cancer treatment and understanding alkylating agent pharmacodynamics.


Catalog Number I014525
CAS Number 55661-38-6
Synonyms

CS 439 HCl; CS439 HCl; CS-439 HCl; CS-439; CS439; CS 439;Urea, N’-((4-amino-2-methyl-5-pyrimidinyl)methyl)-N-(2-chloroethyl)-N-nitroso-, monohydrochloride (9CI)

Molecular Formula C9H14Cl2N6O2
Purity ≥95%
Target Apoptosis
Solubility Soluble in DMSO
Storage 2–8 °C
IUPAC Name 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-1-(2-chloroethyl)-1-nitrosourea;hydrochloride
InChI 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
InChIKey KPMKNHGAPDCYLP-UHFFFAOYSA-N
SMILES CC1=NC=C(C(=N1)N)CNC(=O)N(CCCl)N=O.Cl
Reference

</br>1: 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.</br>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.</br>3: 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.</br>4: 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.</br>5: 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.</br>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.</br>7: 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.</br>8: 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.</br>9: 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.</br>10: 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.</br>11: Kono K, Takahashi JA, Ueba T, Mori H, Hashimoto N, Fukumoto M. Effects of combination chemotherapy with biscoclaurine-derived alkaloid (Cepharanthine) and nimustine hydrochloride on malignant glioma cell lines. J Neurooncol. 2002 Jan;56(2):101-8. PubMed PMID: 11995810.</br>12: 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.</br>13: Beppu T, Yoshida Y, Arai H, Wada T, Suzuki M, Ogawa A, Hakozaki S, Kubo N. A phase II study of nimustine hydrochloride, cisplatin, and etoposide combination chemotherapy for supratentorial malignant gliomas. J Neurooncol. 2000 Sep;49(3):213-8. PubMed PMID: 11212900.</br>14: 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.</br>15: 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.</br>16: 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.</br>17: 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.</br>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.</br>19: Miyagawa S, Kirby ML. Pathogenesis of persistent truncus arteriosus induced by nimustine hydrochloride in chick embryos. Teratology. 1989 Mar;39(3):287-94. PubMed PMID: 2727936.</br>20: 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.</br></br>

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