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C0253

Chlorambucil

Name: Chlorambucil
Brand: SIGMA

DNA alkylating agent, powder

Synonym(s):

4-(4-[Bis(2-chloroethyl)amino]phenyl)butyric acid, 4-[Bis(2-chloroethyl)amino]benzenebutyric acid

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₁₉Cl₂NO₂

CAS Number:

305-03-3

Molecular Weight:

304.21

NACRES:

NA.77

PubChem Substance ID:

24278287

UNSPSC Code:

12352200

EC Number:

206-162-0

MDL number:

MFCD00021783

Beilstein/REAXYS Number:

999011

Form:

powder

Quality level:

200

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Properties

Product Name

Chlorambucil,

form

powder

Quality Level

200

storage temp.

2-8°C

SMILES string

OC(=O)CCCc1ccc(cc1)N(CCCl)CCCl

InChI

1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)

InChI key

JCKYGMPEJWAADB-UHFFFAOYSA-N

Gene Information

human ... CYP2D6(1565)

Description

Application

Chlorambucil has been used:

as an alkylating/chemotherapeutic agent to study its anti-inflammatory effects on amyloidogenesis in mice
as a positive control to determine the cytotoxicity in murine leukemic monocyte macrophages
as an adenine-specific DNA-alkylating reagent in the construction of multifunctional conjugate (8950A-Chb(Cl/OH) for mutation-specific DNA alkylation in HeLa S3 cells

Biochem/physiol Actions

Chlorambucil is a nitrogen mustard alkylating agent that acts as an anti-cancer drug. Chlorambucil binds to membranes, RNA, DNA, and proteins. It exhibits anti-inflammatory and anti-tumor activity by DNA cross-linking. Chlorambucil shows therapeutic effects against chronic lymphocytic leukemia (CLL) via a p53-dependent mechanism.

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pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H315,H319,H335,H350

pcodes

P201 - P202 - P261 - P301 + P310 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Articles

DNA Damage and Repair

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.

DNA-Dependent protein kinase activity correlates with clinical and in vitro sensitivity of chronic lymphocytic leukemia lymphocytes to nitrogen mustards.

C Muller et al.

Blood, 92(7), 2213-2219 (1998-09-25)

The objective of this study is to investigate the role of DNA-dependent protein kinase (DNA-PK) in the chronic lymphocytic leukemia (CLL) lymphocyte response to nitrogen mustard therapy. DNA-PK is a nuclear serine/threonine kinase that functions in DNA double-strand break repair

Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs.

Palle J Pedersen et al.

Journal of medicinal chemistry, 52(10), 3408-3415 (2009-05-01)

The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability

A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer.

Shrabani Barman et al.

Angewandte Chemie (International ed. in English), 55(13), 4194-4198 (2016-02-27)

Among the well-known phototriggers, the p-hydroxyphenacyl (pHP) group has consistently enabled the very fast, efficient, and high-conversion release of active molecules. Despite this unique behavior, the pHP group has been ignored as a delivery agent, particularly in the area of

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Global Trade Item Number

SKU	GTIN
C0253-10G	04061833450321
C0253-1G	04061826690017