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 | |
| Names | |
|---|---|
| IUPAC name 1,3-Bis(2-chloroethyl)-1-nitrosourea[1] | |
| Other names N,N'-Bis(2-chloroethyl)-N-nitrosourea, bis-chloroethylnitrosourea, BCNU | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
|
| ECHA InfoCard | 100.005.309 |
| EC Number |
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| KEGG |
|
| MeSH | Carmustine |
| RTECS number |
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| UNII | |
| UN number | 2811 |
| |
| |
| Properties | |
| C5H9Cl2N3O2 | |
| Molar mass | 214.05 g·mol−1 |
| Appearance | Orange crystals |
| Odor | Odourless |
| Melting point | 30 °C (86 °F; 303 K) |
| logP | 1.375 |
| Acidity (pKa) | 10.194 |
| Basicity (pKb) | 3.803 |
| Pharmacology | |
| L01AD01 (WHO) | |
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| License data | |
| Legal status | |
| Hazards | |
| GHS labelling: | |
  | |
| Danger | |
| H300,H350,H360 | |
| P301+P310,P308+P313 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
| Clinical data | |
|---|---|
| Trade names | BiCNU, Gliadel |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682060 |
| License data | |
| Drug class | Antineoplastic agents |
| Identifiers | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.005.309 |
Carmustine, sold under the brand nameBiCNU among others, is amedication used mainly forchemotherapy. It is anitrogen mustard β-chloro-nitrosourea compound used as analkylating agent.[6]
Carmustine is an orange-yellow solidmedication used mainly forchemotherapy. It is anitrogen mustard β-chloro-nitrosourea compound.[7]
As analkylating agent, carmustine can form interstrand crosslinks inDNA, which prevents DNA replication and DNA transcription.[8]
Carmustine is used as analkylating agent to treat several types ofbrain cancer includingglioma,glioblastoma multiforme,medulloblastoma andastrocytoma,multiple myeloma, andlymphoma (Hodgkin's andnon-Hodgkin).
Carmustine is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such asO6-benzylguanine. The AGT-inhibitors increase the efficacy of carmustine by inhibiting thedirect reversal pathway of DNA repair, which will prevent formation of theinterstrand crosslink between the N1 ofguanine and the N3 ofcytosine.
It is also used as part of a chemotherapeutic protocol in preparation for hematologicalstem cell transplantation, a type ofbone marrow transplant, in order to reduce the white blood cell count in the recipient.[9] Use under this protocol, usually withfludarabine andmelphalan, was developed by oncologists at theUniversity of Texas MD Anderson Cancer Center.[citation needed]
In the treatment ofbrain tumours, the U.S.Food and Drug Administration (FDA) approvedbiodegradable discs infused with carmustine (Gliadel).[10] They are implanted under the skull during a surgery called acraniotomy. 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.[11]
Carmustine for injection was marketed under the name BiCNU by Bristol-Myers Squibb[12] and now[when?] byEmcure Pharmaceuticals.[13] In India it is sold under various brand names, including Consium.[citation needed]. The product is available as a generic version with other manufacturers offering the product licensed in the US and EU markets.[citation needed]
