Nimustine hydrochloride | CAS# | Antineoplastic

MedKoo Cat#: 571526 | Name: Nimustine

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Description:

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

Nimustine 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.

Chemical Structure

Nimustine

CAS#42471-28-3

Theoretical Analysis

MedKoo Cat#: 571526

Name: Nimustine

CAS#: 42471-28-3

Chemical Formula: C9H13ClN6O2

Exact Mass: 272.0789

Molecular Weight: 272.69

Elemental Analysis: C, 39.64; H, 4.81; Cl, 13.00; N, 30.82; O, 11.73

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 350.00	2 Weeks
1g	USD 950.00	2 Weeks

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Synonym

Nimustine; NSC-245,382; NSC245,382; NSC 245,382

IUPAC/Chemical Name

3-((4-amino-2-methylpyrimidin-5-yl)methyl)-1-(2-chloroethyl)-1-nitrosourea

InChi Key

VFEDRRNHLBGPNN-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H13ClN6O2/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)

SMILES Code

O=C(NCC1=CN=C(C)N=C1N)N(CCCl)N=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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nimustine is an antineoplastic agent especially effective against malignant brain tumors.

In vitro activity:

Resting L1210 cells were treated with nimustine (ACNU), a bifunctional alkylating anticancer agent, for 2 h in a nutrient-depleted medium. The cells treated with ACNU were functioning normally in all the cell functions examined but were completely devoid of proliferating capacity. These results suggest the possibility that ACNU might impair the proliferative capacity of the resting cell population inside a solid tumor without causing such impairment to the cells of normal organs and tissues composed of intrinsically non-proliferative cells. Reference: Biol Pharm Bull. 1998 Apr;21(4):414-7. https://pubmed.ncbi.nlm.nih.gov/9586585/

In vivo activity:

The myelorestorative effects of granulocyte colony-stimulating factor (G-CSF), interleukin-1 alpha (IL-1 alpha) and interleukin-6 (IL-6) were studied in F-344 rats which had been treated with cyclophosphamide (CY), carboplatin (CBDCA), or nimustine hydrochloride (ACNU). Animals treated with ACNU had prolonged myelosuppression. In rats which received multiple doses of ACNU, G-CSF treatment exhibited a beneficial effect on WBC, HB, and PLT levels, the most prominent on the HB value. Reference: J Immunother (1991). 1992 Aug;12(2):98-104. https://pubmed.ncbi.nlm.nih.gov/1380297/

Preparing Stock Solutions

The following data is based on the product molecular weight 272.69 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.

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. Kondo N, Takahashi A, Mori E, Noda T, Zdzienicka MZ, Thompson LH, Helleday T, Suzuki M, Kinashi Y, Masunaga S, Ono K, Hasegawa M, Ohnishi T. FANCD1/BRCA2 plays predominant role in the repair of DNA damage induced by ACNU or TMZ. PLoS One. 2011 May 9;6(5):e19659. doi: 10.1371/journal.pone.0019659. Erratum in: PLoS One. 2011;6(6). doi:10.1371/annotation/c6be24d1-bc23-43b4-ae01-b86dad174069. PMID: 21573016; PMCID: PMC3090409. 2. Noda Y, Hayatsu H, Kawazoe Y. Effects of treatment with nimustine (ACNU), a bifunctional alkylating anticancer agent, on cultured resting L1210 cells. Biol Pharm Bull. 1998 Apr;21(4):414-7. doi: 10.1248/bpb.21.414. PMID: 9586585. 3. 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. doi: 10.1097/00002371-199208000-00004. PMID: 1380297. 4. Miyagawa S, Ando M, Takao A. Cardiovascular anomalies produced by nimustine hydrochloride in the rat fetus. Teratology. 1988 Dec;38(6):553-8. doi: 10.1002/tera.1420380602. PMID: 3238611.

In vitro protocol:

In vivo protocol:

1. 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. doi: 10.1097/00002371-199208000-00004. PMID: 1380297. 2. Miyagawa S, Ando M, Takao A. Cardiovascular anomalies produced by nimustine hydrochloride in the rat fetus. Teratology. 1988 Dec;38(6):553-8. doi: 10.1002/tera.1420380602. PMID: 3238611.

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.