CHLORAMBUCIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H19Cl2NO2
Molecular Weight	304.212
Optical Activity	NONE
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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf

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 282 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Crosslinking Agent 83

Conditions

Condition	Modality	Highest Phase	Product
Giant follicular lymphoma 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Primary	Approved 8583	LEUKERAN Approved Use LEUKERAN (chlorambucil) is indicated in the treatment of chronic lymphatic (lymphocytic) leukemia, malignant lymphomas including lymphosarcoma, giant follicular lymphoma, and Hodgkin’s disease. It is not curative in any of these disorders but may produce clinically useful palliation. Launch Date 1957
Hodgkin's lymphoma 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Primary	Approved 8583	LEUKERAN Approved Use LEUKERAN (chlorambucil) is indicated in the treatment of chronic lymphatic (lymphocytic) leukemia, malignant lymphomas including lymphosarcoma, giant follicular lymphoma, and Hodgkin’s disease. It is not curative in any of these disorders but may produce clinically useful palliation. Launch Date 1957
Chronic lymphocytic leukemia 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Primary	Approved 8583	LEUKERAN Approved Use LEUKERAN (chlorambucil) is indicated in the treatment of chronic lymphatic (lymphocytic) leukemia, malignant lymphomas including lymphosarcoma, giant follicular lymphoma, and Hodgkin’s disease. It is not curative in any of these disorders but may produce clinically useful palliation. Launch Date 1957
Lymphosarcoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Primary	Approved 8583	LEUKERAN Approved Use LEUKERAN (chlorambucil) is indicated in the treatment of chronic lymphatic (lymphocytic) leukemia, malignant lymphomas including lymphosarcoma, giant follicular lymphoma, and Hodgkin’s disease. It is not curative in any of these disorders but may produce clinically useful palliation. Launch Date 1957

C_max

Value	Dose	Co-administered	Analyte	Population
1.46 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6489421	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORAMBUCIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
259 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6840176	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORAMBUCIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
1.99 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6489421	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORAMBUCIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
380 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6840176	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORAMBUCIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.94 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6489421	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORAMBUCIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/967ed3ff-d99b-41e8-b768-dfb586d3d9a6/spl-doc?hl=chlorambucil			CHLORAMBUCIL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/3065402	healthy, 1.8 Health Status: healthy Age Group: 1.8 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3065402	Disc. AE: Irritability, Myoclonic jerks... AEs leading to discontinuation/dose reduction: Irritability Myoclonic jerks Exaggerated startle response Vomiting Bone marrow depression (mild) Abnormal EEG Sources: https://pubmed.ncbi.nlm.nih.gov/3065402
5 mg/kg single, oral Overdose Dose: 5 mg/kg Route: oral Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/13462782	healthy, 2.5 Health Status: healthy Age Group: 2.5 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13462782	Disc. AE: Convulsive seizure, Comatose... AEs leading to discontinuation/dose reduction: Convulsive seizure Comatose Vomiting Sources: https://pubmed.ncbi.nlm.nih.gov/13462782
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6655776	healthy, 38 Health Status: healthy Age Group: 38 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6655776	Disc. AE: Acute renal failure, Seizures... AEs leading to discontinuation/dose reduction: Acute renal failure Seizures Sources: https://pubmed.ncbi.nlm.nih.gov/6655776
0.2 mg/kg 1 times / day multiple, oral Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Disc. AE: Bone marrow depression, Carcinogenicity... AEs leading to discontinuation/dose reduction: Bone marrow depression Carcinogenicity Infertility Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf
0.2 mg/kg 1 times / day multiple, oral Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Disc. AE: Convulsions, Metastases... AEs leading to discontinuation/dose reduction: Convulsions Metastases Leukemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf
0.2 mg/kg 1 times / day multiple, oral Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf	Disc. AE: Skin rash, Erythema multiforme... AEs leading to discontinuation/dose reduction: Skin rash (rare) Erythema multiforme (rare) Toxic epidermal necrolysis (rare) Stevens-Johnson syndrome (rare) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/010669s032lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28830	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28830
ChemicalBook	CB5270716	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5270716
eMolecules	490279	https://www.emolecules.com/cgi-bin/more?vid=490279
MolPort	MolPort-000-152-694	https://www.molport.com/shop/molecule-link/MolPort-000-152-694
ZINC	ZINC000000001115	http://zinc15.docking.org/substances/ZINC000000001115

PubMed

Title	Date	PubMed
A novel kind of antitumour drugs using sulfonamide as parent compound.	2002-01-05	11755229
Conservative versus immunosuppressive treatment of patients with idiopathic membranous nephropathy.	2002-01	11786104
Sciatica or spinal lymphoma.	2002-01	11779781
A 6-bp deletion in the Crygc gene leading to a nuclear and radial cataract in the mouse.	2002-01	11773036
Efficacy and safety of chlorambucil in intractable noninfectious uveitis: the Massachusetts Eye and Ear Infirmary experience.	2002-01	11772593
Developments in the treatment of uveitis.	2002-01	11772321
Waldenström's macroglobulinemia: clinical course and prognostic factors in 60 patients. Experience from a single hematology unit.	2001-12	11797112
Screening for inhibitory effects of antineoplastic agents on CYP3A4 in human liver microsomes.	2001-12	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.	2001-12	11751423
Waldenström macroglobulinaemia: presenting features and outcome in a series with 217 cases.	2001-12	11736938
Sequence-specific DNA cleavage by dipeptides disubstituted with chlorambucil and 2,6-dimethoxyhydroquinone-3-mercaptoacetic acid.	2001-11-22	11716676
Chronic lymphocytic leukaemia.	2001-11-15	11706875
Characteristic and controlled release of anticancer drug loaded poly (D,L-lactide) microparticles prepared by spray drying technique.	2001-11-07	11695638
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.	2001-11-01	11675354
Giant cell arteritis and renal amyloidosis: report of a case.	2001-11	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.	2001-11	11694402
Prediction of subsequent relapse in children with steroid-sensitive nephrotic syndrome.	2001-11	11685595
Blastic variant of mantle cell lymphoma: a rare but highly aggressive subtype.	2001-11	11681422
Novel bicistronic retroviral vector expressing gamma-glutamylcysteine synthetase and the multidrug resistance protein 1 (MRP1) protects cells from MRP1-effluxed drugs and alkylating agents.	2001-09-20	11560771
Induction of apoptosis by the ADEPT agent ZD2767: comparison with the classical nitrogen mustard chlorambucil and a monofunctional ZD2767 analogue.	2001-09-01	11531265
Lymphoplasmacytic lymphoma/immunocytoma: towards a disease-targeted treatment?	2001-09	11718214
[Vascular purpura in a patient with severe sarcoptic acariasis].	2001-09	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.	2001-09	11552986
A case of Behćet's disease complicated by visceral Leishmaniasis and myelodysplasia: clinical considerations.	2001-09	11532637
Cutaneous necrobiotic xanthogranuloma (NXG)--successfully treated with low dose chlorambucil.	2001-08-30	11525957
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.	2001-08-15	11504743
Stage I and II MALT lymphoma: results of treatment with radiotherapy.	2001-08-01	11483337
Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2'-deoxyguanosine.	2001-08	11511172
A phase II study of sequential combination chemotherapy with cyclophosphamide, prednisone, and 2-chlorodeoxyadenosine in previously untreated patients with chronic lymphocytic leukemia.	2001-08	11480558
A randomized controlled trial to evaluate the role of interferon as initial and maintenance therapy in patients with follicular lymphoma.	2001-07-06	11437398
Genetic damage by bifunctional agents in repair-active pre-meiotic stages of Drosophila males.	2001-07-01	11406175
Bcl-2 antisense oligonucleotides enhance the cytotoxicity of chlorambucil in B-cell chronic lymphocytic leukaemia cells.	2001-07	11699414
Cutaneous xanthomas with concurrent demodicosis and dermatophytosis in a cat.	2001-07	11549045
The effect of optimal treatment on elderly patients with aggressive non-Hodgkin's lymphoma: more patients treated with unaffected response rates.	2001-07	11529466
Granulomatous slack skin: a distinct disorder or a variant of mycosis fungoides?	2001-06-20	11411914
The cell transmembrane pH gradient in tumors enhances cytotoxicity of specific weak acid chemotherapeutics.	2001-06-15	11406545
[Chronic lymphatic leukemia. 3. The concrete case].	2001-06-08	11464816
[Chronic lymphocytic leukemia. 2. Therapy].	2001-06-08	11441667
Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.	2001-06	11585010
[Pneumonia in patients with chronic lymphocytic leukemia. Study of 30 episodes].	2001-05-26	11412696
Synthesis, molecular modelling, and antiproliferative and cytotoxic effects of carbocyclic derivatives of distamycin with chlorambucil moiety.	2001-05	11451534
Hypercalcaemia associated with chronic lymphocytic leukaemia in a Giant Schnauzer.	2001-05	11431998
[Paraneoplastic pemphigus: a pustular form during chronic lymphoid leukemia].	2001-05	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?	2001-05	11378572
Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents.	2001-04	11461761
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
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.	1975-08-07	1138180

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 `Mon Mar 31 17:33:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:31 GMT 2025`
Record UNII	18D0SL7309
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LEUKERAN

Preferred Name

English

CHLORAMBUCIL

Official Name

English

CB-1348

Code

English

CHLORAMBUCIL [JAN]

Common Name

English

CHLORAMBUCIL [EP MONOGRAPH]

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

Chlorambucil [WHO-DD]

Common Name

English

AMBOCHLORIN

Common 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 [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

CHLORAMBUCIL [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548207