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Details

Stereochemistry ACHIRAL
Molecular Formula C14H19Cl2NO2
Molecular Weight 304.212
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORAMBUCIL

SMILES

OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl

InChI

InChIKey=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)

HIDE SMILES / InChI

Description

Chlorambucil is a bifunctional 12 alkylating agent of the nitrogen mustard type that has been found active against selected human 13 neoplastic diseases. Chlorambucil alkylates and cross-links DNA during all phases of the cell cycle, inducing DNA damage via three different methods of covalent adduct generation with double-helical DNA. Bone marrow suppression (anemia, neutropenia, thrombocytopenia) is the most commonly occurring side effect of chlorambucil. There are no known drug/drug interactions with chlorambucil.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Chlorambucil-induced acute hepatic failure in a patient with membranous nephropathy.
2000 Aug
Coexpression of rat glutathione S-transferase A3 and human cytidine deaminase by a bicistronic retroviral vector confers in vitro resistance to nitrogen mustards and cytosine arabinoside in murine fibroblasts.
2000 May
Expression and prognostic significance of IAP-family genes in human cancers and myeloid leukemias.
2000 May
Non-corticosteroid treatment for nephrotic syndrome in children.
2001
A systematic overview of chemotherapy effects in B-cell chronic lymphocytic leukaemia.
2001
[Treatment of uveitis with immunosuppressives: antimetabolites and alkylating agents].
2001
Severe bone marrow failure associated with the use of alternating steroid with chlorambucil in lupus membranous nephropathy in Chinese.
2001
Pulmonary mucosa-associated lymphoid tissue lymphoma in a patient with common variable immunodeficiency syndrome.
2001
Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents.
2001 Apr
Decreased cytotoxicity and increased antimitotic activity of a proline analogue of chlorambucil as a prodrug susceptible to the action of fibroblast's prolidase.
2001 Apr
Treatment of Behçet's disease--an update.
2001 Apr
DNA minor groove alkylating agents.
2001 Apr
Fludarabine for chronic lymphocytic leukemia.
2001 Apr 12
Fludarabine for chronic lymphocytic leukemia.
2001 Apr 12
Fludarabine for chronic lymphocytic leukemia.
2001 Apr 12
Stage I and II MALT lymphoma: results of treatment with radiotherapy.
2001 Aug 1
Impact of therapy With chlorambucil, fludarabine, or fludarabine plus chlorambucil on infections in patients with chronic lymphocytic leukemia: Intergroup Study Cancer and Leukemia Group B 9011.
2001 Aug 15
Waldenström's macroglobulinemia: clinical course and prognostic factors in 60 patients. Experience from a single hematology unit.
2001 Dec
Screening for inhibitory effects of antineoplastic agents on CYP3A4 in human liver microsomes.
2001 Dec
[Bendamustine, vincristine, prednisolone (BOP) in therapy of advanced low-grade non-Hodgkin lymphoma]].
2001 Feb 23
Granulomatous slack skin: a distinct disorder or a variant of mycosis fungoides?
2001 Jan-Feb
Bcl-2 antisense oligonucleotides enhance the cytotoxicity of chlorambucil in B-cell chronic lymphocytic leukaemia cells.
2001 Jul
Genetic damage by bifunctional agents in repair-active pre-meiotic stages of Drosophila males.
2001 Jul 1
UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism.
2001 Jun
Chlorambucil/prednisone-induced seizures in a patient with non-Hodgkin's lymphoma.
2001 Jun
Acquired Factor VIII autoantibody: four cases demonstrating the heterogenous nature of this condition and problems involved in diagnosis and treatment.
2001 Mar
A meta-analysis of cytotoxic treatment for frequently relapsing nephrotic syndrome in children.
2001 Mar
Treatment of elderly patients with intermediate- and high-grade non-Hodgkin's lymphoma: a retrospective population-based study.
2001 Mar
Immunosuppressive and cytotoxic drugs in the treatment of rheumatic skin disorders.
2001 Mar
Chlorambucil drug resistance in chronic lymphocytic leukemia: the emerging role of DNA repair.
2001 Mar
Primary low-grade B cell non-Hodgkin's lymphoma of MALT type simultaneously arising in the colon and in the lung: report of a case.
2001 Mar
Use of methotrexate in the management of sight-threatening uveitis.
2001 Mar
Lung cancer after Hodgkin's disease: a nested case-control study of the relation to treatment.
2001 Mar 15
Synthesis and antitumor activity of novel paclitaxel-chlorambucil hybrids.
2001 Mar 26
Synthesis, molecular modelling, and antiproliferative and cytotoxic effects of carbocyclic derivatives of distamycin with chlorambucil moiety.
2001 May
Hypercalcaemia associated with chronic lymphocytic leukaemia in a Giant Schnauzer.
2001 May
Treatment of myelopathy in Sjögren syndrome with a combination of prednisone and cyclophosphamide.
2001 May
Novel treatment strategies in chronic lymphocytic leukemia.
2001 May
ChlVPP alternating with PABlOE is superior to PABlOE alone in the initial treatment of advanced Hodgkin's disease: results of a British National Lymphoma Investigation/Central Lymphoma Group randomized controlled trial.
2001 May 18
[Pneumonia in patients with chronic lymphocytic leukemia. Study of 30 episodes].
2001 May 26
Response to fludarabine in B-cell chronic lymphocytic leukemia patients previously treated with chlorambucil as up-front therapy and a CHOP-like regimen as second line therapy.
2001 Nov
Prediction of subsequent relapse in children with steroid-sensitive nephrotic syndrome.
2001 Nov
Blastic variant of mantle cell lymphoma: a rare but highly aggressive subtype.
2001 Nov
Caspase 8 activation independent of Fas (CD95/APO-1) signaling may mediate killing of B-chronic lymphocytic leukemia cells by cytotoxic drugs or gamma radiation.
2001 Nov 1
Characteristic and controlled release of anticancer drug loaded poly (D,L-lactide) microparticles prepared by spray drying technique.
2001 Nov-Dec
Autologous plasma activates Akt/protein kinase B and enhances basal survival and resistance to DNA damage-induced apoptosis in B-chronic lymphocytic leukaemia cells.
2001 Sep
A case of Behćet's disease complicated by visceral Leishmaniasis and myelodysplasia: clinical considerations.
2001 Sep
Conservative versus immunosuppressive treatment of patients with idiopathic membranous nephropathy.
2002 Jan
A 6-bp deletion in the Crygc gene leading to a nuclear and radial cataract in the mouse.
2002 Jan
Developments in the treatment of uveitis.
2002 Jan
Patents

Sample Use Guides

In Vivo Use Guide
0.1 to 0.2 mg/kg body weight daily for 3 to 6 weeks
Route of Administration: Oral
In Vitro Use Guide
The inhibition of 3H-thymidine incorporation into the DNA of mitogen-stimulated lymphocytes from patients with chronic lymphocytic leukaemia by chlorambucil was measured in vitro. For the lymphocytes from the untreated patients the mean ID50 was 3.1 ug/ml.
Name Type Language
CHLORAMBUCIL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
CB-1348
Code English
CHLORAMBUCIL [USP]
Common Name English
CHLORAMBUCIL [JAN]
Common Name English
CHLORAMBUCIL [WHO-DD]
Common Name English
CHLORAMBUCIL [IARC]
Common Name English
4-(P-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRIC ACID
Common Name English
CHLORAMBUCILUM [WHO-IP LATIN]
Common Name English
AMBOCHLORIN
Common Name English
LEUKERAN
Brand Name English
NSC-3088
Code English
CHLORAMBUCIL [VANDF]
Common Name English
ECLORIL
Common Name English
BENZENEBUTANOIC ACID, 4-(BIS(2-CHLOROETHYL)AMINO)-
Common Name English
LYMPHOLYSIN
Common Name English
CHLORAMBUCIL [MART.]
Common Name English
CHLORAMBUCIL [HSDB]
Common Name English
CHLORAMBUCIL [EP]
Common Name English
CHLORAMBUCIL [WHO-IP]
Common Name English
NCI-3088
Code English
CHLORAMBUCIL [USP-RS]
Common Name English
CHLORAMBUCIL [INN]
Common Name English
CHLORAMBUCIL [ORANGE BOOK]
Common Name English
CHLORAMBUCIL [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX 189
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
NDF-RT N0000175558
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
NDF-RT N0000000236
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
NCI_THESAURUS C697
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
WHO-VATC QL01AA02
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
WHO-ATC L01AA02
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
Code System Code Type Description
WIKIPEDIA
CHLORAMBUCIL
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
EVMPD
SUB06172MIG
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
CAS
305-03-3
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
MERCK INDEX
M3343
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY Merck Index
EPA CompTox
305-03-3
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-162-0
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
IUPHAR
7143
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
ChEMBL
CHEMBL515
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
HSDB
305-03-3
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
DRUG BANK
DB00291
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
RXCUI
2346
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY RxNorm
PUBCHEM
2708
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
INN
603
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
NCI_THESAURUS
C362
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
MESH
D002699
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLORAMBUCIL
Created by admin on Tue Oct 22 00:40:46 UTC 2019 , Edited by admin on Tue Oct 22 00:40:46 UTC 2019
PRIMARY Description: A white or almost white, crystalline or slightly granular powder. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS and acetone R. Category: Cytotoxic drug. Storage: Chlorambucil should be kept in a well-closed container, protected from light. Additional information: CAUTION: Chlorambucil must be handled with care, avoiding contact with the skin and inhalation of airborne particles. Definition: Chlorambucil contains not less than 98.0% and not more than 101.0% of C14H19Cl2NO2, calculated with reference to the anhydrous substance.