Carmustine

Carmustine

Names
IUPAC name 1,3-Bis(2-chloroethyl)-1-nitrosourea
Other names N,N’-Bis(2-chloroethyl)-N-nitroso-urea
Identifiers
CAS Number	154-93-8 Y
ChEBI	CHEBI:3423 Y
ChEMBL	ChEMBL513 Y
ChemSpider	2480 Y
DrugBank	DB00262 Y
EC Number	205-838-2
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
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).
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Infobox references

Carmustine (bis-chloroethylnitrosourea, BCNU, BiCNU) is a medication used mainly for chemotherapy and sometimes for immunosuppression before transplant. 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 .

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). They are implanted under the skull during a surgery called a craniotomy. 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.

See also

• Lomustine
• Semustine

External links

• MedlinePlus DrugInfo medmaster-a682060
• BiCNU package insert, U.S.
• Idis press release for EU