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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

Molecular Formula C14H19Cl2NO2
Molecular Weight 304.212
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.
1975 Aug 7
Non-corticosteroid treatment for nephrotic syndrome in children.
2001
Treatment of membranous nephropathy.
2001
A systematic overview of chemotherapy effects in B-cell chronic lymphocytic leukaemia.
2001
Potential new therapeutic options in Behçet's syndrome.
2001
Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents.
2001 Apr
Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2'-deoxyguanosine.
2001 Aug
A phase II study of sequential combination chemotherapy with cyclophosphamide, prednisone, and 2-chlorodeoxyadenosine in previously untreated patients with chronic lymphocytic leukemia.
2001 Aug
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
The Chinese hamster FANCG/XRCC9 mutant NM3 fails to express the monoubiquitinated form of the FANCD2 protein, is hypersensitive to a range of DNA damaging agents and exhibits a normal level of spontaneous sister chromatid exchange.
2001 Dec
Waldenström macroglobulinaemia: presenting features and outcome in a series with 217 cases.
2001 Dec
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
Cutaneous xanthomas with concurrent demodicosis and dermatophytosis in a cat.
2001 Jul
The effect of optimal treatment on elderly patients with aggressive non-Hodgkin's lymphoma: more patients treated with unaffected response rates.
2001 Jul
Genetic damage by bifunctional agents in repair-active pre-meiotic stages of Drosophila males.
2001 Jul 1
A randomized controlled trial to evaluate the role of interferon as initial and maintenance therapy in patients with follicular lymphoma.
2001 Jul 6
Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.
2001 Jun
The cell transmembrane pH gradient in tumors enhances cytotoxicity of specific weak acid chemotherapeutics.
2001 Jun 15
[Chronic lymphatic leukemia. 3. The concrete case].
2001 Jun 8
[Chronic lymphocytic leukemia. 2. Therapy].
2001 Jun 8
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
[Paraneoplastic pemphigus: a pustular form during chronic lymphoid leukemia].
2001 May
Does intensive treatment with high dose chlorambucil and prednisone as first line and cladribine as second line influence the survival of the patients with chronic lymphocytic leukemia?
2001 May
[Pneumonia in patients with chronic lymphocytic leukemia. Study of 30 episodes].
2001 May 26
Giant cell arteritis and renal amyloidosis: report of a case.
2001 Nov
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
A novel kind of antitumour drugs using sulfonamide as parent compound.
2001 Nov-Dec
Sequence-specific DNA cleavage by dipeptides disubstituted with chlorambucil and 2,6-dimethoxyhydroquinone-3-mercaptoacetic acid.
2001 Nov-Dec
Characteristic and controlled release of anticancer drug loaded poly (D,L-lactide) microparticles prepared by spray drying technique.
2001 Nov-Dec
Lymphoplasmacytic lymphoma/immunocytoma: towards a disease-targeted treatment?
2001 Sep
[Vascular purpura in a patient with severe sarcoptic acariasis].
2001 Sep
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
Induction of apoptosis by the ADEPT agent ZD2767: comparison with the classical nitrogen mustard chlorambucil and a monofunctional ZD2767 analogue.
2001 Sep 1
Novel bicistronic retroviral vector expressing gamma-glutamylcysteine synthetase and the multidrug resistance protein 1 (MRP1) protects cells from MRP1-effluxed drugs and alkylating agents.
2001 Sep 20
Chronic lymphocytic leukaemia.
2001 Sep-Oct
Cutaneous necrobiotic xanthogranuloma (NXG)--successfully treated with low dose chlorambucil.
2001 Sep-Oct
Conservative versus immunosuppressive treatment of patients with idiopathic membranous nephropathy.
2002 Jan
Sciatica or spinal lymphoma.
2002 Jan
A 6-bp deletion in the Crygc gene leading to a nuclear and radial cataract in the mouse.
2002 Jan
Efficacy and safety of chlorambucil in intractable noninfectious uveitis: the Massachusetts Eye and Ear Infirmary experience.
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:40:46 UTC 2019
Edited
by admin
on Tue Oct 22 00:40:46 UTC 2019
Record UNII
18D0SL7309
Record Status Validated (UNII)
Record Version
  • Download
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.
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Has antineoplastic activity
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
A white or almost white, crystalline or slightly granular powder.
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC