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C0253

Chlorambucil

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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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)

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

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7266V
WXBF4436V
WXBF3026V
BCCH8961
BCCG4515

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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
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
Daniel Catovsky et al.
Clinical lymphoma, myeloma & leukemia, 11 Suppl 1, S2-S6 (2011-11-09)
Although chlorambucil has been used in the management of chronic lymphocytic leukemia (CLL) for 55 years, the optimal dose and treatment duration have not been established. We summarized data from 4 UK randomized CLL trials over the past 30 years
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Global Trade Item Number

SKUGTIN
C0253-1G04061826690017
C0253-10G04061833450321