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C0400

Sigma-Aldrich

Carmustine

≥98% (TLC), oily liquid to amorphous solid, DNA alkylating agent

Synonym(s):

1,3-Bis(2-chloroethyl)-1-nitrosourea, BCNU

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About This Item

Empirical Formula (Hill Notation):
C5H9Cl2N3O2
CAS Number:
154-93-8
Molecular Weight:
214.05
EC Number:
205-838-2
MDL number:
MFCD00057706
UNSPSC Code:
12352200
PubChem Substance ID:
24278289
NACRES:
NA.77

product name

Carmustine, ≥98%

Quality Level

200

Assay

≥98%

form

(Oily liquid to amorphous solid)

mp

30 °C (lit.)

solubility

ethanol: 19.60-20.40 mg/mL, clear, pale yellow to yellow

originator

Bristol-Myers Squibb

storage temp.

−20°C

SMILES string

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

InChI

1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

InChI key

DLGOEMSEDOSKAD-UHFFFAOYSA-N

Gene Information

human ... GSR(2936)

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General description

Carmustine is a mustard gas related β-chloro-nitrosourea compound, which is used in chemotherapy. It inhibits DNA replication and DNA transcription.

Application

Carmustine has been used to select transduced cells expressing MGMTP140K, a foamy virus vector. It has also been used in fluorescence-activated cell sorting (FACS) assay, to test the response of cell lines to carmustine.

Biochem/physiol Actions

Carmustine is a DNA alkylating agent causing DNA interstrand crosslinks. Effective against glioma and other solid tumors.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H350,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 2 Oral - Carc. 1B - Repr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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W Stahl et al.
Chemical research in toxicology, 5(1), 106-109 (1992-01-01)
S-[(2-Chloroethyl)carbamoyl]glutathione (SCCG), a compound formed during the decomposition of BCNU in the presence of GSH, induces DNA damage in a human lymphoblastoid cell line. This GSH conjugate was shown by direct fast atom bombardment mass spectrometric analysis to transfer an
Shuqiang Yuan et al.
Stem cells (Dayton, Ohio), 31(1), 23-34 (2012-11-08)
Development of effective therapeutic strategies to eliminate cancer stem cells, which play a major role in drug resistance and disease recurrence, is critical to improve cancer treatment outcomes. Our study showed that glioblastoma stem cells (GSCs) exhibited low mitochondrial respiration
16th Int?l. Sympos. High Voltage Eng (2016)
Inês F Antunes et al.
Molecular pharmaceutics, 9(11), 3277-3285 (2012-09-27)
Extracellular β-glucuronidase (β-GUS) in tumors has been investigated as a target enzyme for prodrug therapy. However, despite encouraging preclinical results, animal studies also indicate that the success of prodrug therapy might be limited by the insufficient prodrug-converting enzyme activity, especially
Foamy viral vector integration sites in SCID-repopulating cells after MGMTP140K-mediated in vivo selection
Olszko ME, et al
Gene Therapy, 22(7), 591-591 (2015)
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