Carmustine (98%) | CAS#154-93-8 | alkylating agent

MedKoo Cat#: 100962 | Name: Carmustine (98%)

Description:

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

Carmustine is antineoplastic nitrosourea. Carmustine alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis. This agent also carbamoylates proteins, including DNA repair enzymes, resulting in an enhanced cytotoxic effect. Carmustine is highly lipophilic and crosses the blood-brain barrier readily.

Chemical Structure

Carmustine (98%)

CAS#154-93-8

Theoretical Analysis

MedKoo Cat#: 100962

Name: Carmustine (98%)

CAS#: 154-93-8

Chemical Formula: C5H9Cl2N3O2

Exact Mass: 213.0072

Molecular Weight: 214.05

Elemental Analysis: C, 28.06; H, 4.24; Cl, 33.12; N, 19.63; O, 14.95

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 450.00	Ready to ship
2g	USD 750.00	Ready to ship
5g	USD 1,650.00	Ready to ship

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Related CAS #

No Data

Synonym

NCI-C04773; Nitrumon; NSC 409962; NSC-409962; SK 27702; SRI 1720; DTI 015;; FDA 0345; BCNU Becenum; Bi CNU; BiCNU; Carmustine;

IUPAC/Chemical Name

1,3-bis(2-chloroethyl)-1-nitrosourea

InChi Key

DLGOEMSEDOSKAD-UHFFFAOYSA-N

InChi Code

InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

SMILES Code

O=C(NCCCl)N(CCCl)N=O

Appearance

Light yellow solid (low temperature)

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under cool temperature as poison and hazardous chemical .

Storage Condition

Dry, dark at -20 oC

Solubility

Soluble in DMSO

Shelf Life

>3 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

29241900

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#BBC80622

QC Data

View QC data: current batch, Lot#BBC80622

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Carmustine is an antitumor chemotherapeutic agent, which works by akylating DNA and RNA

In vitro activity:

Bis-chloroethylnitrosourea (BCNU or carmustine) was identified as an effective amyloid beta (Aβ) reducing compound. To quantify Aβ levels, Chinese hamster ovary (CHO) cells stably expressing amyloid precursor protein 751WT (APP751WT) called 7WD10 cells were exposed to different concentrations of BCNU for 48 hours and the conditioned media were collected. BCNU decreased normalized levels of Aβ starting from 5 μM by 39% (P < 0.05), 10 μM by 51% (P < 0.01) and 20 μM by 63% (P < 0.01) in CHO cells compared to a control group treated with butyl amine, a structural derivative of BCNU. Interestingly, soluble amyloid precursor protein α (sAPPα) levels were increased to 167% (P < 0.01) at 0.5 μM, 186% (P < 0.05) at 1 μM, 204% (P < 0.01) at 5 μM and 152% (P < 0.05) at 10 μM compared to untreated cells. The effects of 12 structural derivatives of BCNU were also tested on Aβ levels, but none of them were as potent as BCNU. BCNU treatment at 5 μM led to an accumulation of immature APP at the cell surface resulting in an increased ratio of surface to total APP by 184% for immature APP, but no change in mature APP. It is also remarkable that BCNU reduced Aβ generation independent of secretases which were not altered up to 40 μM. Interestingly, levels of transforming growth factor beta (TGFβ) were increased at 5 μM (43%, P < 0.05), 10 μM (73%, P < 0.01) and 20 μM (92%, P < 0.001). In conclusion, BCNU reduces Aβ generation and plaque burden at non-toxic concentrations possibly through altered intracellular trafficking and processing of APP. Taken together these data provided unequivocal evidence that BCNU is a potent secretase-sparing anti-Aβ drug. Reference: BMC Med. 2013 Mar 26;11:81. https://pubmed.ncbi.nlm.nih.gov/23531149/

In vivo activity:

To verify whether decreased amyloidogenic processing of APP by BCNU observed in cell cultures is translated in vivo into decreased plaque burden, mice overexpressing APP with Swedish mutation and PS1 with ΔE9 deletion were used as a robust mouse model for Aβ plaques (APdE9) as these mice develop a modest amount of amyloid plaques as early as six months of age. Overall plaque burden was calculated as the ratio of 'the area occupied by plaques to the total region area', which was clearly decreased by about 81% (P < 0.01) in BCNU-treated mice compared to saline-treated mice (Figure 5A, B and.5C). A representative histology section for saline- or BCNU-treated mice is shown in Figure5A and 5B at comparable brain levels. The total plaque numbers were reduced only by 26% (Figure 5D, P < 0.05). However, when the plaques were counted based on their size, those plaques which measured more than 1.0 square micron decreased by 39% (Figure 5E,5E, P < 0.05) and those measuring above 3.0 square microns decreased by 41% (Figure5F, P < 0.05) in the BCNU-treated mice compared to the saline-treated mice. Highly decreased plaque burden and a modest reduction in plaque numbers in BCNU-treated mice indicates that BCNU decreases the severity of plaques by reducing larger plaques. Exposure of BCNU even just for two months resulted in a 75% reduction in the levels of Aβ40 (Figure 6B), which correlates well with the amount of reduction in amyloid plaques. Thus, BCNU-induced changes in APP metabolites observed in cell cultures were confirmed in vivo in the mouse brains. BMC Med. 2013; 11: 81. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3655051/

	Solvent	mg/mL	mM
Solubility
	DMSO	35.0	163.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 214.05 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. Thamilselvan V, Menon M, Thamilselvan S. Carmustine enhances the anticancer activity of selenite in androgen-independent prostate cancer cells. Cancer Manag Res. 2012;4:383-95. doi: 10.2147/CMAR.S38022. Epub 2012 Nov 9. PMID: 23204869; PMCID: PMC3508550. 2. Hayes CD, Dey D, Palavicini JP, Wang H, Patkar KA, Minond D, Nefzi A, Lakshmana MK. Striking reduction of amyloid plaque burden in an Alzheimer's mouse model after chronic administration of carmustine. BMC Med. 2013 Mar 26;11:81. doi: 10.1186/17417015-11-81. PMID: 23531149; PMCID: PMC3655051. 3. Jones AL, Millar JL, Millar BC, Powell B, Selby P, Winkley A, Lakhani S, Gore ME, McElwain TJ. Enhanced anti-tumour activity of carmustine (BCNU) with tumour necrosis factor in vitro and in vivo. Br J Cancer. 1990 Nov;62(5):776-80. doi: 10.1038/bjc.1990.378. PMID: 2245169; PMCID: PMC1971510.

In vitro protocol:

In vivo protocol:

1. Jones AL, Millar JL, Millar BC, Powell B, Selby P, Winkley A, Lakhani S, Gore ME, McElwain TJ. Enhanced anti-tumour activity of carmustine (BCNU) with tumour necrosis factor in vitro and in vivo. Br J Cancer. 1990 Nov;62(5):776-80. doi: 10.1038/bjc.1990.378. PMID: 2245169; PMCID: PMC1971510. 2. Hayes CD, Dey D, Palavicini JP, Wang H, Patkar KA, Minond D, Nefzi A, Lakshmana MK. Striking reduction of amyloid plaque burden in an Alzheimer's mouse model after chronic administration of carmustine. BMC Med. 2013 Mar 26;11:81. doi: 10.1186/17417015-11-81. PMID: 23531149; PMCID: PMC3655051

1: Frankiewicz A, Saduś-Wojciechowska M, Najda J, Czerw T, Mendrek W, Sobczyk-Kruszelnicka M, Soska K, Ociepa M, Hołowiecki J, Giebel S. Comparable safety profile of BeEAM (bendamustine, etoposide, cytarabine, melphalan) and BEAM (carmustine, etoposide, cytarabine, melphalan) as conditioning before autologous haematopoietic cell transplantation. Contemp Oncol (Pozn). 2018;22(2):113-117. doi: 10.5114/wo.2018.77046. Epub 2018 Jun 30. PubMed PMID: 30150889; PubMed Central PMCID: PMC6103227. 2: Kim YJ, Kim WS, Choi YH, Cheon JE, Choi JY, Kang HJ, Park JE, Ryu YJ, Kim IO. Radiologic evaluation of pulmonary injury following carmustine- and cyclophosphamide-based preparative regimen for autologous peripheral blood stem cell transplantation in children. Pediatr Radiol. 2018 Aug 18. doi: 10.1007/s00247-018-4223-8. [Epub ahead of print] PubMed PMID: 30121852. 3: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500930/ PubMed PMID: 29999989. 4: Asano K, Kurose A, Kamataki A, Kato N, Ogawa K, Katayama K, Kakuta K, Fumoto T, Ohkuma H. Importance and accuracy of intraoperative frozen section diagnosis of the resection margin for effective carmustine wafer implantation. Brain Tumor Pathol. 2018 Jul;35(3):131-140. doi: 10.1007/s10014-018-0320-5. Epub 2018 Jun 14. PubMed PMID: 29948295. 5: Rubino S, Bach MD, Schober AL, Lambert IH, Mongin AA. Downregulation of Leucine-Rich Repeat-Containing 8A Limits Proliferation and Increases Sensitivity of Glioblastoma to Temozolomide and Carmustine. Front Oncol. 2018 May 7;8:142. doi: 10.3389/fonc.2018.00142. eCollection 2018. PubMed PMID: 29868469; PubMed Central PMCID: PMC5949383. 6: Sippl C, Ketter R, Bohr L, Kim YJ, List M, Oertel J, Urbschat S. MiRNA-181d Expression Significantly Affects Treatment Responses to Carmustine Wafer Implantation. Neurosurgery. 2018 May 26. doi: 10.1093/neuros/nyy214. [Epub ahead of print] PubMed PMID: 29846701. 7: Kumabe T, Shibahara I, Saito R. [Results for Treatment of Newly-Diagnosed Glioblastoma Using Carmustine Wafers(Gliadel(®))]. No Shinkei Geka. 2018 May;46(5):367-376. doi: 10.11477/mf.1436203736. Japanese. PubMed PMID: 29794312. 8: Lin KI, Lin CC, Kuo SM, Lai JC, Wang YQ, You HL, Hsu ML, Chen CH, Shiu LY. Carnosic acid impedes cell growth and enhances anticancer effects of carmustine and lomustine in melanoma. Biosci Rep. 2018 Jul 2;38(4). pii: BSR20180005. doi: 10.1042/BSR20180005. Print 2018 Aug 31. PubMed PMID: 29789400; PubMed Central PMCID: PMC6028752. 9: Grangeon L, Ferracci FX, Fetter D, Maltete D, Langlois O, Gilard V. How safe are carmustine wafers? Rev Neurol (Paris). 2018 May;174(5):346-351. doi: 10.1016/j.neurol.2017.09.011. Epub 2018 Apr 25. PubMed PMID: 29703443. 10: Akiyama Y, Kimura Y, Enatsu R, Mikami T, Wanibuchi M, Mikuni N. Advantages and Disadvantages of Combined Chemotherapy with Carmustine Wafer and Bevacizumab in Patients with Newly Diagnosed Glioblastoma: A Single-Institutional Experience. World Neurosurg. 2018 May;113:e508-e514. doi: 10.1016/j.wneu.2018.02.070. Epub 2018 Feb 21. PubMed PMID: 29476996. 11: Ius T, Cesselli D, Isola M, Toniato G, Pauletto G, Sciacca G, Fabbro S, Pegolo E, Rizzato S, Beltrami AP, di Loreto C, Skrap M. Combining Clinical and Molecular Data to Predict the Benefits of Carmustine Wafers in Newly Diagnosed High-Grade Gliomas. Curr Treat Options Neurol. 2018 Feb 23;20(2):3. doi: 10.1007/s11940-018-0489-2. Review. PubMed PMID: 29476361. 12: Khorram R, Raissi H, Morsali A, Shahabi M. The computational study of the γ-Fe(2)O(3) nanoparticle as Carmustine drug delivery system: DFT approach. J Biomol Struct Dyn. 2018 Feb 2:1-11. doi: 10.1080/07391102.2018.1429312. [Epub ahead of print] PubMed PMID: 29381124. 13: Yamamuro S, Hanashima Y, Yoshimura S, Aoki H, Kamiya K, Takamine Y, Negishi H, Yoshino A. Glioblastoma fed by middle meningeal artery and displaying cyst formation soon after repeated implantation of carmustine wafers: A case report. Mol Clin Oncol. 2017 Dec;7(6):953-956. doi: 10.3892/mco.2017.1455. Epub 2017 Oct 17. PubMed PMID: 29285355; PubMed Central PMCID: PMC5740916. 14: Wang GB, Liu JH, Hu J, Xue K. MiR-21 enhanced glioma cells resistance to carmustine via decreasing Spry2 expression. Eur Rev Med Pharmacol Sci. 2017 Nov;21(22):5065-5071. doi: 10.26355/eurrev_201711_13819. PubMed PMID: 29228450. 15: Ghiciuc CM, Strat AL, Ochiuz L, Lupusoru CE, Ignat M, Vasile A, Grigorovici A, Stoleriu I, Solcan C. Inhibition of bcl-2 and cox-2 Protein Expression after Local Application of a New Carmustine-Loaded Clinoptilolite-Based Delivery System in a Chemically Induced Skin Cancer Model in Mice. Molecules. 2017 Nov 20;22(11). pii: E2014. doi: 10.3390/molecules22112014. PubMed PMID: 29156646. 16: Roux A, Caire F, Guyotat J, Menei P, Metellus P, Pallud J; Neuro-Oncology Club of the French Neurosurgical Society. Carmustine wafer implantation for high-grade gliomas: Evidence-based safety efficacy and practical recommendations from the Neuro-oncology Club of the French Society of Neurosurgery. Neurochirurgie. 2017 Dec;63(6):433-443. doi: 10.1016/j.neuchi.2017.07.003. Epub 2017 Nov 6. Review. PubMed PMID: 29122306. 17: Joffe E, Rosenberg D, Rozovski U, Perry C, Kirgner I, Trestman S, Gur O, Aviv F, Sarid N, Kolomansky A, Gepstein L, Herishanu Y, Naparstek E. Replacing carmustine by thiotepa and cyclophosphamide for autologous stem cell transplantation in Hodgkin's and non-Hodgkin's B-cell lymphoma. Bone Marrow Transplant. 2018 Jan;53(1):29-33. doi: 10.1038/bmt.2017.205. Epub 2017 Oct 16. PubMed PMID: 29035395. 18: Doishita S, Shimono T, Yoneda T, Yamada E, Tsukamoto T, Takemori D, Kimura D, Tatekawa H, Sakamoto S, Miki Y. In vitro Study of Serial Changes to Carmustine Wafers (Gliadel) with MR Imaging and Computed Tomography. Magn Reson Med Sci. 2018 Jan 10;17(1):58-66. doi: 10.2463/mrms.mp.2017-0035. Epub 2017 Sep 4. PubMed PMID: 28867760; PubMed Central PMCID: PMC5760234. 19: Roux A, Peeters S, Zanello M, Bou Nassif R, Abi Lahoud G, Dezamis E, Parraga E, Lechapt-Zalcmann E, Dhermain F, Dumont S, Louvel G, Chretien F, Sauvageon X, Devaux B, Oppenheim C, Pallud J. Extent of resection and Carmustine wafer implantation safely improve survival in patients with a newly diagnosed glioblastoma: a single center experience of the current practice. J Neurooncol. 2017 Oct;135(1):83-92. doi: 10.1007/s11060-017-2551-4. Epub 2017 Jul 1. PubMed PMID: 28669011. 20: Sonoda Y, Shibahara I, Matsuda KI, Saito R, Kawataki T, Oda M, Sato Y, Sadahiro H, Nomura S, Sasajima T, Beppu T, Kanamori M, Sakurada K, Kumabe T, Tominaga T, Kinouchi H, Shimizu H, Ogasawara K, Suzuki M. Opening the ventricle during surgery diminishes survival among patients with newly diagnosed glioblastoma treated with carmustine wafers: a multi-center retrospective study. J Neurooncol. 2017 Aug;134(1):83-88. doi: 10.1007/s11060-017-2488-7. Epub 2017 May 22. PubMed PMID: 28534151.