Carmustine

Carmustine

Names
IUPAC name 1,3-Bis(2-chloroethyl)-1-nitrosourea[1]
Other names N,N’-Bis(2-chloroethyl)-N-nitroso-urea
Identifiers
ATC code	L01AD01
CAS Registry Number	154-93-8 Y
ChEBI	CHEBI:3423 Y
ChEMBL	ChEMBL513 Y
ChemSpider	2480 Y
DrugBank	DB00262 Y
EC number	205-838-2
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
Jmol-3D images	Image
KEGG	D00254 N
MeSH	Carmustine
PubChem	2578
RTECS number	YS2625000
SMILES ClCCNC(=O)N(CCCl)N=O
UNII	U68WG3173Y Y
UN number	2811
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	US: D (Evidence of risk)
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H300, H350, H360
GHS precautionary statements	P301+310, P308+313
EU classification	T+
R-phrases	R45, R46, R60, R61, R28
S-phrases	S22, S36/37/39, S45
LD50 (Median lethal 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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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 .

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

• Lomustine
• Semustine

References

External links

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