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Merck

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

Key Documents

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Product Name

Chlorambucil,

InChI key

JCKYGMPEJWAADB-UHFFFAOYSA-N

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)

SMILES string

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

form

powder

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... CYP2D6(1565)

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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.

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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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
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
Qingyao Shou et al.
Journal of natural products, 76(7), 1384-1387 (2013-07-16)
Two novel alkaloids (parvifloranines A and B), possessing an unusual 11-carbon skeleton linked with amino acids, were isolated from Geijera parviflora, an endemic Australian Rutaceae. Their structures were elucidated by extensive spectroscopic measurements including 2D NMR analyses. Parvifloranine A was
Shmuel Shtrasburg et al.
Autoimmunity reviews, 12(1), 18-21 (2012-08-11)
The mainstay of AA amyloidosis prevention and treatment is suppression of inflammation. In the present study we have tried to determine the efficacy of a variety of anti-inflammatory agents at suppressing AA amyloidosis in a mouse model of the disease.
Emanuele Zucca et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(5), 565-572 (2013-01-09)
Apart from localized gastric disease, there is no consensus on standard initial treatment of mucosa-associated lymphoid tissue lymphoma. The IELSG-19 study (Randomized Trial of Chlorambucil Versus Chlorambucil Plus Rituximab Versus Rituximab in MALT Lymphoma) was launched to compare chlorambucil alone
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