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154-93-8 molecular structure
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1,3-bis(2-chloroethyl)-1-nitrosourea

ChemBase ID: 147
Molecular Formular: C5H9Cl2N3O2
Molecular Mass: 214.04986
Monoisotopic Mass: 213.0071819
SMILES and InChIs

SMILES:
ClCCN(N=O)C(=O)NCCCl
Canonical SMILES:
ClCCNC(=O)N(CCCl)N=O
InChI:
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
InChIKey:
DLGOEMSEDOSKAD-UHFFFAOYSA-N

Cite this record

CBID:147 http://www.chembase.cn/molecule-147.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,3-bis(2-chloroethyl)-1-nitrosourea
1,3-bis(2-chloroethyl)-3-nitrosourea
IUPAC Traditional name
1,3-bis(2-chloroethyl)-1-nitrosourea
carmustine
Brand Name
Becenun
Bi CNU
Carmubris
Gliadel
Gliadel Wafer
Nitrumon
BiCNU
Synonyms
BCNU
Bischlorethylnitrosourea
Bischlorethylnitrosurea
Carmustin
Carmustine
1,3-Bis(2-chloroethyl)-1-nitrosourea
Carmustine
BCNU, N,N’-Bis(2-chloroethyl)-N-nitrosourea, NSC-409962, Becenun, Bicnu,
Becenum
Carmubris
Nitrumon
CAS Number
154-93-8
EC Number
205-838-2
MDL Number
MFCD00057706
PubChem SID
160963610
24278289
46506980
PubChem CID
2578

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.963143  H Acceptors
H Donor LogD (pH = 5.5) 1.0226562 
LogD (pH = 7.4) 1.0226457  Log P 1.0226563 
Molar Refractivity 46.9797 cm3 Polarizability 17.322094 Å3
Polar Surface Area 61.77 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.24  LOG S -2.15 
Solubility (Water) 1.53e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
< 0.1 g/100 mL at 18 °C expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
(Oily liquid to amorphous solid) expand Show data source
Light Yellow to Pale Orange Solid expand Show data source
Melting Point
30 °C(lit.) expand Show data source
30-32°C expand Show data source
Hydrophobicity(logP)
1.5 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
YS2625000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
45-46-60-61-28 expand Show data source
Safety Statements
53-22-36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H350-H360 expand Show data source
GHS Precautionary statements
P201-P264-P301 + P310-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... GSR(2936) expand Show data source
Mechanism of Action
Alkylating agent in cancer chemotherapy expand Show data source
Purity
≥98% expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antineoplastic agent expand Show data source
Used to treat gliomas, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin). expand Show data source
Empirical Formula (Hill Notation)
C5H9Cl2N3O2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank
Sigma Aldrich - C0400 external link
Biochem/physiol Actions
Carmustine is a DNA alkylating agent causing DNA interstrand crosslinks.1 Effective against glioma and other solid tumors.
Toronto Research Chemicals - C183875 external link
An alkylating and carbamoylating nitrosourea compound. It interacts with DNA, RNA and proteins causing DNA interstrand cross linking which is cytotoxic and leads to apoptotic cell death.
DrugBank - DB00262 external link
Item Information
Drug Groups approved
Description A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed)
Indication For the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.
Pharmacology Carmustine is one of the nitrosoureas indicated as palliative therapy as a single agent or in established combination therapy with other approved chemotherapeutic agents in treatment of brain tumors, multiple myeloma, Hodgkin's disease, and non-Hodgkin's lymphomas. 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.
Toxicity The oral LD50s in rat and mouse are 20 mg/kg and 45 mg/kg, respectively. Side effects include leukopenia, thrombocytopenia, nausea. Toxic effects include pulmonary fibrosis (20-0%) and bone marrow toxicity.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic and rapid with active metabolites. Metabolites may persist in the plasma for several days.
Absorption 5 to 28% bioavailability
Half Life 15-30 minutes
Protein Binding 80%
Elimination Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • 10764 (1992)
  • • Johnston, T.P. et al., J. Med. Chem., 1963, 6, 669, (synth)
  • • Loo, T.L. et al., J. Pharm. Sci., 1966, 55, 492, (pharmacol)
  • • Lien, E.J. et al., Spectrosc. Lett., 1972, 5, 293, (pmr)
  • • Thompson, G.R. et al., Toxicol. Appl. Pharmacol., 1972, 21, 405, (tox)
  • • Gombar, C.T. et al., Diss. Abstr. Int., B, 1980, 40, 5223; 5686, (props)
  • • IARC Monog., 1981, 26, 79; Suppl. 6, 116; Suppl. 7, 150, (rev, tox)
  • • Lown, J.W. et al., J.O.C., 1981, 46, 5309, (synth, cmr, N-15 nmr)
  • • Paoletti, R. et al., Am. J. Cardiol., 1983, 52, 21, (rev)
  • • Reed, D.J. et al., Anticancer Drugs: Reactive Metabolism and Drug Interactions, (Ed. Powis, G.) Pergamon Press, 1994, 187, (rev)
  • • Wiencke, J.K. et al., Mutat. Res., 1995, 339, 91, (rev, genotox)
  • • Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 550
  • • Kaba, S.E. et al., Drugs, 1997, 53, 235, (use, rev)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BIF750
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PATENTS

PATENTS

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