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C0400

Sigma-Aldrich

Carmustine

≥98%

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Synonym(s):
1,3-Bis(2-chloroethyl)-1-nitrosourea, BCNU
Empirical Formula (Hill Notation):
C5H9Cl2N3O2
CAS Number:
Molecular Weight:
214.05
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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This Item
1096724Y0002128239785
Carmustine ≥98%

Sigma-Aldrich

C0400

Carmustine

Carmustine United States Pharmacopeia (USP) Reference Standard

USP

1096724

Carmustine

Carmustine European Pharmacopoeia (EP) Reference Standard

Y0002128

Carmustine

form

(Oily liquid to amorphous solid)

form

(Oily liquid to amorphous solid)

form

(Oily liquid to amorphous solid)

form

solid

solubility

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

solubility

-

solubility

-

solubility

water: 30 mg/mL

originator

Bristol-Myers Squibb

originator

-

originator

-

originator

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

100

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

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Mapping the human kinome in response to DNA damage
Owusu M, et al.
Testing, 26(3), 555-563 (2019)
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)
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

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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