Carmustine (99.5%)
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MedKoo CAT#: 100141

CAS#: 154-93-8

Description: 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

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Carmustine (99.5%)
CAS# 154-93-8

Theoretical Analysis

MedKoo Cat#: 100141
Name: Carmustine (99.5%)
CAS#: 154-93-8
Chemical Formula: C5H9Cl2N3O2
Exact Mass: 213.00718
Molecular Weight: 214.05
Elemental Analysis: C, 28.06; H, 4.24; Cl, 33.13; N, 19.63; O, 14.95

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same day
200.0mg USD 250.0 Same day
500.0mg USD 450.0 Same day
1.0g USD 750.0 Same day
2.0g USD 950.0 Same day
5.0g USD 1850.0 Same day
10.0g USD 3250.0 Same day
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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

Purity: >99.5% (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, not in water

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: 29241900

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.0 163.51

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.

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

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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.



Additional Information

 
BiCNU® (carmustine for injection) is one of the nitrosoureas used in the treatment of certain neoplastic diseases. It is 1,3-bis (2-chloroethyl)-1-nitrosourea. It is sterile lyophilized pale yellow flakes or congealed mass with a molecular weight of 214.06. It is highly soluble in alcohol and lipids, and poorly soluble in water. BiCNU is administered by intravenous infusion after reconstitution as recommended.  BiCNU is available in 100 mg single dose vials of lyophilized material. Sterile diluent for constitution of BiCNU is co-packaged with the active drug product for use in constitution of the lyophile. The diluent is supplied in an ampule containing 3 mL of Dehydrated Alcohol Injection, USP.
 
Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross-resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Intravenously administered carmustine is rapidly degraded, with no intact drug detectable after 15 minutes. However, in studies with 14C-labeled drug, prolonged levels of the isotope were detected in the plasma and tissue, probably representing radioactive fragments of the parent compound. It is thought that the antineoplastic and toxic activities of carmustine may be due to metabolites. Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2. The fate of the remainder is undetermined. Because of the high lipid solubility and the relative lack of ionization at physiological pH, carmustine crosses the blood-brain barrier quite effectively. Levels of radioactivity in the CSF are ≥50% of those measured concurrently in plasma.