Carmustine

Carmustine

Carmustine
Skeletal formula of carmustine
Ball-and-stick model of carmustine molecule
Names
IUPAC name
1,3-Bis(2-chloroethyl)-1-nitrosourea[1]
Other names
N,N’-Bis(2-chloroethyl)-N-nitroso-urea
Identifiers
 Y
ATC code L01
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
DrugBank  Y
EC number 205-838-2
Jmol-3D images Image
KEGG  N
MeSH
PubChem
RTECS number YS2625000
UNII  Y
UN number 2811
Properties
C5H9Cl2N3O2
Molar mass 214.05 g·mol−1
Appearance Orange crystals
Odor Odourless
Melting point 30 °C (86 °F; 303 K)
log P 1.375
Acidity (pKa) 10.194
Basicity (pKb) 3.803
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H300, H350, H360
P301+310, P308+313
Very Toxic T+
R-phrases R45, R46, R60, R61, R28
S-phrases S22, S36/37/39, S45
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
20 mg kg−1 (oral, rat)
Related compounds
Related ureas
Dimethylurea
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Carmustine (bis-chloroethylnitrosourea, BCNU, BiCNU) is a mustard gas-related β-chloro-nitrosourea compound used as an alkylating agent in chemotherapy. As a dialkylating agent, BCNU is able to form interstrand crosslinks in DNA, which prevents DNA replication and DNA transcription.

It has the appearance of an orange-yellow solid.

Carmustine for injection was earlier marketed under the name BiCNU by Bristol-Myers Squibb[2] and now by Emcure Pharmaceuticals.[3] In India it is sold under various brand names including Consium .

Contents

  • Uses 1
  • Implants 2
  • See also 3
  • References 4
  • External links 5

Uses

It is used in the treatment of several types of brain cancer (including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma), multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin). BCNU is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such as O6-benzylguanine. The AGT-inhibitors increase the efficacy of BCNU by inhibiting the direct reversal pathway of DNA repair, which will prevent formation of the interstrand crosslink between the N1 of guanine and the N3 of cytosine.

It is also used as part of a chemotherapeutic protocol in preparation for hematological stem cell transplantation, a type of bone marrow transplant, in order to reduce the white blood cell count in the recipient (patient). Use under this protocol, usually with Fludarabine and Melphalan, was coined by oncologists at the University of Texas MD Anderson Cancer Center.

Implants

In the treatment of brain tumours, the U.S. Food and Drug Administration (FDA) approved biodegradable discs infused with carmustine (Gliadel).[4] They are implanted under the skull during a surgery called a craniotomy.[5] The disc allows for controlled release of carmustine in the extracellular fluid of the brain, thus eliminating the need for the encapsulated drug to cross the blood-brain barrier.[6]

See also

References

  1. ^ "Carmustine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 11 April 2012. 
  2. ^ http://www.bms.com/news/features/2012/Pages/CompanyStatementonBiCNU.aspx
  3. ^ Emcure Press release
  4. ^ Ewend MG, Brem S, Gilbert M; et al. (June 2007). "Treatment of single brain metastasis with resection, intracavity carmustine polymer wafers, and radiation therapy is safe and provides excellent local control". Clin. Cancer Res. 13 (12): 3637–41.  
  5. ^ http://www.cancerbackup.org.uk/Treatments/Chemotherapy/Individualdrugs/Gliadelimplants
  6. ^ http://www.hopkinsmedicine.org/hmn/W05/feature3.cfm

External links