Carmustine

Carmustine
Names
IUPAC name
1,3-Bis(2-chloroethyl)-1-nitrosourea[1]
Other names
N,N'-Bis(2-chloroethyl)-N-nitrosourea, bis-chloroethylnitrosourea, BCNU
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.309
EC Number
  • 205-838-2
KEGG
MeSH Carmustine
PubChem CID
RTECS number
  • YS2625000
UNII
UN number 2811
InChI
  • InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11) Y
    Key: DLGOEMSEDOSKAD-UHFFFAOYSA-N Y
SMILES
  • C(CCl)NC(=O)N(CCCl)N=O
Properties
Chemical formula
 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
Pharmacology
L01AD01 (WHO)
  • AU: D
License data
Legal status
Hazards
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H300, H350, H360
Precautionary statements
 P301+P310, P308+P313
Lethal dose or concentration (LD, LC):
20 mg kg−1 (oral, rat)
Related compounds
Related ureas
 1,3-Dimethylurea
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
Carmustine
Clinical data
Trade namesBiCNU, Gliadel
AHFS/Drugs.comMonograph
MedlinePlusa682060
License data
Drug classAntineoplastic agents
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard100.005.309

Carmustine, sold under the brand name BiCNU among others, is a medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro-nitrosourea compound used as an alkylating agent.[6]

  1. ^ CID 2578 from PubChem
  2. ^ "Carmustine 100mg Powder and solvent for Solution for Infusion - Summary of Product Characteristics (SmPC)". (emc). 24 March 2020.
  3. ^ "Gliadel 7.7mg Implant - Summary of Product Characteristics (SmPC)". (emc). 15 June 2020.
  4. ^ "Bicnu- carmustine kit". DailyMed. Retrieved 27 February 2021.
  5. ^ "Gliadel- carmustine wafer". DailyMed. Retrieved 27 February 2021.
  6. ^ Silverman RB, Holladay MW (January 2014). "Chapter 6 - DNA-Interactive Agents". In Silverman RB, Holladay MW (eds.). The Organic Chemistry of Drug Design and Drug Action (Third ed.). Boston: Academic Press. pp. 275–331. doi:10.1016/b978-0-12-382030-3.00006-4. ISBN 978-0-12-382030-3.
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