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C0253

Sigma-Aldrich

Chlorambucil

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Synonym(s):
4-(4-[Bis(2-chloroethyl)amino]phenyl)butyric acid, 4-[Bis(2-chloroethyl)amino]benzenebutyric acid
Empirical Formula (Hill Notation):
C14H19Cl2NO2
CAS Number:
Molecular Weight:
304.21
Beilstein:
999011
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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)

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This Item
C0768C1100000Y0001298
Chlorambucil

Sigma-Aldrich

C0253

Chlorambucil

Chlorambucil European Pharmacopoeia (EP) Reference Standard

C1100000

Chlorambucil

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

Gene Information

human ... CYP2D6(1565)

Gene Information

human ... ALDH1A1(216), ALDH1B1(219)

Gene Information

-

Gene Information

-

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

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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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.

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