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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
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 282	Crosslinking Agent 83

Conditions

Condition	Modality	Highest Phase	Product
Giant follicular lymphoma 1	Primary	Approved 8,583	LEUKERAN
Hodgkin's lymphoma 33	Primary	Approved 8,583	LEUKERAN
Chronic lymphocytic leukemia 59	Primary	Approved 8,583	LEUKERAN
Lymphosarcoma 3	Primary	Approved 8,583	LEUKERAN

C_max

Value	Dose	Co-administered	Analyte	Population
1.46 μg/mL	40 mg single, oral		CHLORAMBUCIL plasma	Homo sapiens
259 ng/mL	10 mg single, oral		CHLORAMBUCIL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1.99 μg × h/mL	40 mg single, oral		CHLORAMBUCIL plasma	Homo sapiens
380 ng × h/mL	10 mg single, oral		CHLORAMBUCIL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.94 h	40 mg single, oral		CHLORAMBUCIL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%			CHLORAMBUCIL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3.2 mg/kg single, oral Overdose	healthy, 1.8	Disc. AE: Irritability, Myoclonic jerks...
5 mg/kg single, oral Overdose	healthy, 2.5	Disc. AE: Convulsive seizure, Comatose...
250 mg single, oral Overdose	healthy, 38	Disc. AE: Acute renal failure, Seizures...
0.2 mg/kg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Bone marrow depression, Carcinogenicity...
0.2 mg/kg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Convulsions, Metastases...

Showing 1 to 5 of 6 entries

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AEs

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AE	Significance	Dose	Population
Abnormal EEG	Disc. AE	3.2 mg/kg single, oral Overdose	healthy, 1.8
Exaggerated startle response	Disc. AE	3.2 mg/kg single, oral Overdose	healthy, 1.8
Irritability	Disc. AE	3.2 mg/kg single, oral Overdose	healthy, 1.8
Myoclonic jerks	Disc. AE	3.2 mg/kg single, oral Overdose	healthy, 1.8
Vomiting	Disc. AE	3.2 mg/kg single, oral Overdose	healthy, 1.8

Showing 1 to 5 of 21 entries

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Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 5 entries

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PubMed

Show entries

Title	Date	PubMed
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.	1975 Aug 7	1138180
Chlorambucil-induced seizure in a patient with nephrotic syndrome.	1999	10450047
Chlorambucil induction of HsRad51 in B-cell chronic lymphocytic leukemia.	1999 Aug	10473103
Chlorambucil-induced inappropriate antidiuresis in a man with chronic lymphocytic leukemia.	1999 Jan	10037268
Mechanisms of mutation induction in germ cells of the mouse as assessed by the specific locus test.	1999 Jul 16	10517996

Showing 1 to 5 of 36 entries

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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.