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Details

Stereochemistry ACHIRAL
Molecular Formula C5H9Cl2N3O2
Molecular Weight 214.05
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARMUSTINE

SMILES

ClCCNC(=O)N(CCCl)N=O

InChI

InChIKey=DLGOEMSEDOSKAD-UHFFFAOYSA-N
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

HIDE SMILES / InChI

Description

Carmustine is a cancer medication that interferes with the growth and spread of cancer cells in the body. Carmustine is used to treat brain tumors, Hodgkin's disease, multiple myeloma, and non-Hodgkin's lymphoma. Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross-resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Pulmonary toxicity characterized by pulmonary infiltrates and/or fibrosis has been reported to occur from 9 days to 43 months after treatment with BiCNU and related nitrosoureas. A frequent and serious toxicity of BiCNU is delayed myelosuppression. Nausea and vomiting after intravenous administration of BiCNU are noted frequently. Greater myelotoxicity (e.g., leukopenia and neutropenia) has been reported when carmustine was combined with cimetidine.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
57.0 µM [IC50]
1.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BICNU
Primary
BICNU
Primary
BICNU
Primary
BICNU
Primary
BICNU
Secondary
BICNU
Secondary
BICNU

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 μg/mL
600 mg/m² 1 times / day steady-state, intravenous
CARMUSTINE plasma
Homo sapiens
7.8 μM
1000 mg/m² single, intravenous
CARMUSTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
456 μg × min/mL
600 mg/m² 1 times / day steady-state, intravenous
CARMUSTINE plasma
Homo sapiens
538 μM × min
1000 mg/m² single, intravenous
CARMUSTINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18 min
600 mg/m² 1 times / day steady-state, intravenous
CARMUSTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
23%
1000 mg/m² single, intravenous
CARMUSTINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose of BiCNU as a single agent in previously untreated patients is 150 to 200 mg/m2 intravenously every 6 weeks. This may be given as a single dose or divided into daily injections such as 75 to 100 mg/m2 on 2 successive days.
Route of Administration: Other
In Vitro Use Guide
LD50 values for the short term glioma tumour cultures lay in the range 10 - 90 μg/ml for Carmustine.