Carmustine

Carmustine

Names
IUPAC name 1,3-Bis(2-chloroethyl)-1-nitrosourea
Other names N,N’-Bis(2-chloroethyl)-N-nitrosourea
Identifiers
CAS Number	154-93-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:3423 Y
ChEMBL	ChEMBL513 Y
ChemSpider	2480 Y
DrugBank	DB00262 Y
ECHA InfoCard	100.005.309
EC Number	205-838-2
KEGG	D00254 N
MeSH	Carmustine
PubChem	2578
RTECS number	YS2625000
UNII	U68WG3173Y Y
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 ClCCNC(=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
ATC code	L01AD01 (WHO)
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H300, H350, H360
GHS precautionary statements	P301+310, P308+313
EU classification (DSD)	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	Noxytiolin 1,1,3,3-Tetramethylguanidine Metformin Allantoic acid Buformin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Carmustine (bis-chloroethylnitrosourea, BCNU, BiCNU) is a medication used mainly for chemotherapy and sometimes for immunosuppression before organ transplantation. It is a nitrogen mustard β-chloro-nitrosourea compound used as an alkylating agent. 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 and now by Emcure Pharmaceuticals. In India it is sold under various brand names, including Consium.

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.