Carmustine

Title: Carmustine
CAS Registry Number: 154-93-8
CAS Name: N,N¢-Bis(2-chloroethyl)-N-nitrosourea
Additional Names: BCNU
Manufacturers' Codes: NSC-409962
Trademarks: Becenun (BMS); Bicnu (BMS); Carmubris (BMS)
Molecular Formula: C5H9Cl2N3O2
Molecular Weight: 214.05
Percent Composition: C 28.06%, H 4.24%, Cl 33.13%, N 19.63%, O 14.95%
Literature References: Chloroethylnitrosourea derivative with antitumor activity. Similar to chlorozotocin, lomustine, nimustine, ranimustine, q.q.v. Synthesis: Johnston et al., J. Med. Chem. 6, 669 (1963). Properties: Loo et al., J. Pharm. Sci. 55, 492 (1966). Decompn studies as related to antileukemic activity: Montgomery et al., J. Med. Chem. 10, 668 (1967). Antifungal action: Hunt, Pittilo, Antimicrob. Agents Chemother. 1965, 710. Toxicology studies: Thompson, Larson, Toxicol. Appl. Pharmacol. 21, 405 (1972). Review of pulmonary toxicity: A. C. Smith, Pharmacol. Ther. 41, 443-460 (1989).
Properties: Light yellow powder that melts to an oily liquid; mp 30-32°. Both powder and liquid are stable. Dec rapidly in acid and in soln above pH 7. Most stable in petroleum ether or aqueous soln at pH 4. Non-ionized at pH 7 with consequent high lipid solubility. Sol in water up to 4 mg/ml and in 50% ethanol up to 150 mg/ml: DeVita et al., Cancer Res. 25, 1876 (1965). LD50 in mice (mg/kg): 19-25 orally, 26 i.p., 24 s.c.; in rats (mg/kg): 30-34 orally (Thompson, Larson).
Melting point: mp 30-32°
Toxicity data: LD50 in mice (mg/kg): 19-25 orally, 26 i.p., 24 s.c.; in rats (mg/kg): 30-34 orally (Thompson, Larson)
CAUTION: This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-53.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrosoureas.
Carnauba Wax Carnegine Carnidazole Carnitine Carotol

Carmustine
Skeletal formula of carmustine
Ball-and-stick model of carmustine molecule
Identifiers
CAS number 154-93-8 YesY
PubChem 2578
ChemSpider 2480 YesY
UNII U68WG3173Y YesY
EC number 205-838-2
UN number 2811
DrugBank DB00262
KEGG D00254 N
MeSH Carmustine
ChEBI CHEBI:3423 YesY
ChEMBL CHEMBL513 YesY
RTECS number YS2625000
ATC code L01AD01
Jmol-3D images
Properties
Molecular 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
Bioavailability 5–28%
Routes of
administration
  • Intravenous
  • Intralesional
Metabolism Hepatic
Elimination
half-life
15–30 min
Protein binding 80%
Excretion
  • Renal
  • Respiratory
Legal status


Prescription only

Pregnancy
category
D(US)
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
GHS hazard statements H300, H350, H360
GHS precautionary statements P301+310, P308+313
EU classification Very Toxic T+
R-phrases R45, R46, R60, R61, R28
S-phrases S22, S36/37/39, S45
LD50 20 mg kg−1 (oral, rat)
Related compounds
Related ureas Dimethylurea
Related compounds
  • Noxytiolin
  • 1,1,3,3-Tetramethylguanidine
  • Metformin
  • Allantoic acid
  • Buformin
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Carmustine or BCNU (bis-chloroethylnitrosourea) 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 is marketed under the name BiCNU by Bristol-Myers Squibb. In India, carmustine is marketed under the name Carustine by Curacell Biotech.