Carmustine
| Names | |
|---|---|
| IUPAC name
1,3-Bis(2-chloroethyl)-1-nitrosourea[1]
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| Other names
N,N'-Bis(2-chloroethyl)-N-nitrosourea, bis-chloroethylnitrosourea, BCNU
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| KEGG | |
| MeSH | Carmustine |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2811 |
CompTox Dashboard (EPA)
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| Properties | |
| 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 | |
| L01AD01 (WHO) | |
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| License data | |
| Legal status | |
| Hazards | |
| GHS labelling: | |
| GHS06: Toxic GHS08: Health hazard | |
| Danger | |
| H300, H350, H360 | |
| P301+P310, P308+P313 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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20 mg kg−1 (oral, rat) |
| Related compounds | |
Related ureas
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1,3-Dimethylurea |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Clinical data | |
|---|---|
| Trade names | BiCNU, Gliadel |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682060 |
| License data |
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| Drug class | Antineoplastic agents |
| Identifiers | |
| E number | {{#property:P628}} |
| CompTox Dashboard (EPA) |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
Carmustine, sold under the brand name BiCNU among others, is a medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro-nitrosourea compound used as an alkylating agent.[6]
Description
[edit | edit source]Carmustine is an orange-yellow solid medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro-nitrosourea compound.[7]
Mechanism of action
[edit | edit source]As an alkylating agent, carmustine can form interstrand crosslinks in DNA, which prevents DNA replication and DNA transcription.[8]
Uses
[edit | edit source]Carmustine is used as an alkylating agent to treat several types of brain cancer including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma, and lymphoma (Hodgkin's and non-Hodgkin).
Carmustine is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such as O6-benzylguanine. The AGT-inhibitors increase the efficacy of carmustine 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.[9] Use under this protocol, usually with fludarabine and melphalan, was developed by oncologists at the University of Texas MD Anderson Cancer Center.[citation needed]
Implants
[edit | edit source]In the treatment of brain tumours, the U.S. Food and Drug Administration (FDA) approved biodegradable discs infused with carmustine (Gliadel).[10] 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.[11]
Production
[edit | edit source]Carmustine for injection was marketed under the name BiCNU by Bristol-Myers Squibb[12] and now[when?] by Emcure 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]
See also
[edit | edit source]References
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External links
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