Lomustine | CAS#13010-47-4 | MedKoo Biosciences

MedKoo Cat#: 100550 | Name: Lomustine

Description:

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

Lomustine is a nitrosourea with antineoplastic activity. Lomustine alkylates and crosslinks DNA, thereby inhibiting DNA and RNA synthesis. This agent also carbamoylates DNA and proteins, resulting in inhibition of DNA and RNA synthesis and disruption of RNA processing. Lomustine is lipophilic and crosses the blood-brain barrier. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Lomustine

CAS#13010-47-4

Theoretical Analysis

MedKoo Cat#: 100550

Name: Lomustine

CAS#: 13010-47-4

Chemical Formula: C9H16ClN3O2

Exact Mass: 233.0931

Molecular Weight: 233.70

Elemental Analysis: C, 46.26; H, 6.90; Cl, 15.17; N, 17.98; O, 13.69

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 225.00	Ready to ship
2g	USD 350.00	Ready to ship
5g	USD 650.00	Ready to ship
10g	USD 950.00	Ready to ship
20g	USD 1,650.00	Ready to ship

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Synonym

Lomustinume. CeeNU; Belustin; Belustine; Cecenu; Citostal; Lomeblastin; Lucostin; Lucostine; Prava. CCNU. Acronym: CCNU. RB1509; WR139017.

IUPAC/Chemical Name

1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea

InChi Key

GQYIWUVLTXOXAJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)

SMILES Code

O=C(NC1CCCCC1)N(CCCl)N=O

Appearance

Solid powder

Purity

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

Shipping Condition

Shipped under cool temperature as non-hazardous chemical.

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, 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

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R08B14

QC Data

View QC data: current batch, Lot#C9R08B14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lomustine (CCNU; NSC 79037) is a DNA alkylating agent, with antitumor activity

In vitro activity:

To determine MGMT expression in canine lymphoma cells, a cytotoxicity assay was conducted with lomustine and an MGMT inhibitor, O6-benzylguanine (BG), on canine lymphoma cell lines, detecting MGMT activity by a fluorometric oligonucleotide assay. As shown in Figure 1 and Table II, BG inactivation of MGMT activity significantly increased the toxicity of lomustine to CL-1 and Nody-1 cells. Furthermore, MGMT gene expression was also observed in these cell lines with real-time PCR (Figure 3). These results strongly demonstrate that CL-1 and Nody-1 cell lines with MGMT activity are resistant to lomustine toxicity. In contrast, the Ema, GL-1, and UL-1 cell lines did not show a similar resistance to the cytotoxicity caused by lomustine, although real-time PCR detected weak MGMT expression in the UL-1 cells. These results indicate that MGMT strongly influences the sensitivity of canine lymphoma cell lines to lomustine. Furthermore, the IC50 data (Table II) indicated that canine lymphoma cell lines such as CL-1 and Nody-1 that have MGMT activity are resistant to lomustine, whereas cell lines like Ema, GL-1, and UL-1 that have no MGMT activity are sensitive to lomustine. This study has demonstrated that MGMT is strongly correlated with the resistance of canine lymphoma cell lines to the nitrosourea lomustine, as it is with human cells. Furthermore, it has been shown that there are 2 types of lymphoma cells: those that possess MGMT activity and show low sensitivity to lomustine, and others that do not possess MGMT activity and show high sensitivity to lomustine. Can J Vet Res. 2015 Jul; 79(3): 201–209. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4445512/

In vivo activity:

Mice were dosed with either intravenous lomustine Molecular Envelope Technology (MET) nanoparticles (13 mg kg(-1)) or ethanolic lomustine (6.5 mg kg(-1)) and tissues analysed. Efficacy was assessed in an orthotopic U-87 MG glioblastoma model, following intravenous MET lomustine (daily 13 mg kg(-1)) or ethanolic lomustine (daily 1.2 mg kg(-1) - the highest repeated dose possible). Myelosuppression and MET particle macrophage uptake were also investigated. The MET formulation resulted in modest brain targeting (brain/ bone AUC0-4h ratios for MET and ethanolic lomustine = 0.90 and 0.53 respectively and brain/ liver AUC0-4h ratios for MET and ethanolic lomustine = 0.24 and 0.15 respectively). The MET formulation significantly increased mice (U-87 MG tumours) survival times; with MET lomustine, ethanolic lomustine and untreated mean survival times of 33.2, 22.5 and 21.3 days respectively and there were no material treatment-related differences in blood and femoral cell counts. The findings show that lomustine dose intensification with the MET particle system improved the survival of intracranial tumour bearing mice and did not produce significant additional myelosuppressive effects as bone and bone marrow deposition of the drug was reduced with the MET system. Pharm Res. 2016; 33: 1289–1303. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4820487/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	214.51

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 233.70 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. Anand A, Iyer BR, Ponnusamy C, Pandiyan R, Sugumaran A. Design and Development of Lomustine Loaded Chitosan Nanoparticles for Efficient Brain Targeting. Cardiovasc Hematol Agents Med Chem. 2020;18(1):45-54. doi: 10.2174/1871525718666200203112502. PMID: 32013840. 2. Kambayashi S, Minami K, Ogawa Y, Hamaji T, Hwang CC, Igase M, Hiraoka H, Miyama TS, Noguchi S, Baba K, Mizuno T, Okuda M. Expression of O(6)-methylguanine-DNA methyltransferase causes lomustine resistance in canine lymphoma cells. Can J Vet Res. 2015 Jul;79(3):201-9. PMID: 26130852; PMCID: PMC4445512 3. Fisusi FA, Siew A, Chooi KW, Okubanjo O, Garrett N, Lalatsa K, Serrano D, Summers I, Moger J, Stapleton P, Satchi-Fainaro R, Schätzlein AG, Uchegbu IF. Lomustine Nanoparticles Enable Both Bone Marrow Sparing and High Brain Drug Levels - A Strategy for Brain Cancer Treatments. Pharm Res. 2016 May;33(5):1289-303. doi: 10.1007/s11095-016-1872-x. Epub 2016 Feb 22. PMID: 26903051; PMCID: PMC4820487. 4. Stukov AN, Filatova LV, Gershanovich ML, Semiglazova TIu, Tarasenkova AA, Latinova DKh, Vershinina SF, Zargarova NI. [Combined effect of gemcitabine and lomustine in mice with intracranial transplanted lymphosarcoma LIO-1]. Vopr Onkol. 2012;58(3):394-7. Russian. PMID: 22888657.

In vitro protocol:

In vivo protocol:

1. Fisusi FA, Siew A, Chooi KW, Okubanjo O, Garrett N, Lalatsa K, Serrano D, Summers I, Moger J, Stapleton P, Satchi-Fainaro R, Schätzlein AG, Uchegbu IF. Lomustine Nanoparticles Enable Both Bone Marrow Sparing and High Brain Drug Levels - A Strategy for Brain Cancer Treatments. Pharm Res. 2016 May;33(5):1289-303. doi: 10.1007/s11095-016-1872-x. Epub 2016 Feb 22. PMID: 26903051; PMCID: PMC4820487. 2. Stukov AN, Filatova LV, Gershanovich ML, Semiglazova TIu, Tarasenkova AA, Latinova DKh, Vershinina SF, Zargarova NI. [Combined effect of gemcitabine and lomustine in mice with intracranial transplanted lymphosarcoma LIO-1]. Vopr Onkol. 2012;58(3):394-7. Russian. PMID: 22888657.