CHLORAMBUCIL

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 Search

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 250	Crosslinking Agent 73	Lymphoma, Follicular

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia, Lymphocytic, Chronic, B-Cell 37	Primary	DNA	Approved 7883	LEUKERAN
Lymphoma, Non-Hodgkin 45	Primary	DNA	Approved 7883	LEUKERAN
Hodgkin Disease 28	Primary	DNA	Approved 7883	LEUKERAN
Lymphoma, Follicular 5	Primary	DNA	Approved 7883	LEUKERAN
Indolent lymphoma 1			Approved (off-label) 8
Ovarian cancer 1			Approved (off-label) 8

PubMed

Title	Date	PubMed
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.	1975 Aug 7	1138180
Non-corticosteroid treatment for nephrotic syndrome in children.	2001	11687155
Treatment of membranous nephropathy.	2001	11509678
A systematic overview of chemotherapy effects in B-cell chronic lymphocytic leukaemia.	2001	11441934
Potential new therapeutic options in Behçet's syndrome.	2001	11437673
Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents.	2001 Apr	11461761
Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2'-deoxyguanosine.	2001 Aug	11511172
A phase II study of sequential combination chemotherapy with cyclophosphamide, prednisone, and 2-chlorodeoxyadenosine in previously untreated patients with chronic lymphocytic leukemia.	2001 Aug	11480558
Stage I and II MALT lymphoma: results of treatment with radiotherapy.	2001 Aug 1	11483337
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	11504743
Waldenström's macroglobulinemia: clinical course and prognostic factors in 60 patients. Experience from a single hematology unit.	2001 Dec	11797112
Screening for inhibitory effects of antineoplastic agents on CYP3A4 in human liver microsomes.	2001 Dec	11770832
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	11751423
Waldenström macroglobulinaemia: presenting features and outcome in a series with 217 cases.	2001 Dec	11736938
Granulomatous slack skin: a distinct disorder or a variant of mycosis fungoides?	2001 Jan-Feb	11411914
Bcl-2 antisense oligonucleotides enhance the cytotoxicity of chlorambucil in B-cell chronic lymphocytic leukaemia cells.	2001 Jul	11699414
Cutaneous xanthomas with concurrent demodicosis and dermatophytosis in a cat.	2001 Jul	11549045
The effect of optimal treatment on elderly patients with aggressive non-Hodgkin's lymphoma: more patients treated with unaffected response rates.	2001 Jul	11529466
Genetic damage by bifunctional agents in repair-active pre-meiotic stages of Drosophila males.	2001 Jul 1	11406175
A randomized controlled trial to evaluate the role of interferon as initial and maintenance therapy in patients with follicular lymphoma.	2001 Jul 6	11437398
Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.	2001 Jun	11585010
The cell transmembrane pH gradient in tumors enhances cytotoxicity of specific weak acid chemotherapeutics.	2001 Jun 15	11406545
[Chronic lymphatic leukemia. 3. The concrete case].	2001 Jun 8	11464816
[Chronic lymphocytic leukemia. 2. Therapy].	2001 Jun 8	11441667
Synthesis, molecular modelling, and antiproliferative and cytotoxic effects of carbocyclic derivatives of distamycin with chlorambucil moiety.	2001 May	11451534
Hypercalcaemia associated with chronic lymphocytic leukaemia in a Giant Schnauzer.	2001 May	11431998
[Paraneoplastic pemphigus: a pustular form during chronic lymphoid leukemia].	2001 May	11427801
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	11378572
[Pneumonia in patients with chronic lymphocytic leukemia. Study of 30 episodes].	2001 May 26	11412696
Giant cell arteritis and renal amyloidosis: report of a case.	2001 Nov	11758014
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	11694402
Prediction of subsequent relapse in children with steroid-sensitive nephrotic syndrome.	2001 Nov	11685595
Blastic variant of mantle cell lymphoma: a rare but highly aggressive subtype.	2001 Nov	11681422
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	11675354
A novel kind of antitumour drugs using sulfonamide as parent compound.	2001 Nov-Dec	11755229
Sequence-specific DNA cleavage by dipeptides disubstituted with chlorambucil and 2,6-dimethoxyhydroquinone-3-mercaptoacetic acid.	2001 Nov-Dec	11716676
Characteristic and controlled release of anticancer drug loaded poly (D,L-lactide) microparticles prepared by spray drying technique.	2001 Nov-Dec	11695638
Lymphoplasmacytic lymphoma/immunocytoma: towards a disease-targeted treatment?	2001 Sep	11718214
[Vascular purpura in a patient with severe sarcoptic acariasis].	2001 Sep	11590343
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	11552986
A case of Behćet's disease complicated by visceral Leishmaniasis and myelodysplasia: clinical considerations.	2001 Sep	11532637
Induction of apoptosis by the ADEPT agent ZD2767: comparison with the classical nitrogen mustard chlorambucil and a monofunctional ZD2767 analogue.	2001 Sep 1	11531265
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	11560771
Chronic lymphocytic leukaemia.	2001 Sep-Oct	11706875
Cutaneous necrobiotic xanthogranuloma (NXG)--successfully treated with low dose chlorambucil.	2001 Sep-Oct	11525957
Conservative versus immunosuppressive treatment of patients with idiopathic membranous nephropathy.	2002 Jan	11786104
Sciatica or spinal lymphoma.	2002 Jan	11779781
A 6-bp deletion in the Crygc gene leading to a nuclear and radial cataract in the mouse.	2002 Jan	11773036
Efficacy and safety of chlorambucil in intractable noninfectious uveitis: the Massachusetts Eye and Ear Infirmary experience.	2002 Jan	11772593
Developments in the treatment of uveitis.	2002 Jan	11772321

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

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Name

Type

Language

CHLORAMBUCIL

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