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)
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | LEUKERAN Approved UseLEUKERAN (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 Date1957 |
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| Primary | LEUKERAN Approved UseLEUKERAN (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 Date1957 |
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| Primary | LEUKERAN Approved UseLEUKERAN (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 Date1957 |
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| Primary | LEUKERAN Approved UseLEUKERAN (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 Date1957 |
Cmax
| 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 |
T1/2
| 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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
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: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
Disc. AE: Irritability, Myoclonic jerks... AEs leading to discontinuation/dose reduction: Irritability Sources: Myoclonic jerks Exaggerated startle response Vomiting Bone marrow depression (mild) Abnormal EEG |
5 mg/kg single, oral Overdose Dose: 5 mg/kg Route: oral Route: single Dose: 5 mg/kg Sources: Page: p.239 |
healthy, 2.5 n = 1 Health Status: healthy Age Group: 2.5 Sex: M Population Size: 1 Sources: Page: p.239 |
Disc. AE: Convulsive seizure, Comatose... AEs leading to discontinuation/dose reduction: Convulsive seizure Sources: Page: p.239Comatose Vomiting |
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Co-administed with:: cimetidine, p.o(600 mg; single) Sources: aspirin |
healthy, 38 n = 1 Health Status: healthy Age Group: 38 Sex: M Population Size: 1 Sources: |
Disc. AE: Acute renal failure, Seizures... AEs leading to discontinuation/dose reduction: Acute renal failure Sources: Seizures |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.1 |
Disc. AE: Bone marrow depression, Carcinogenicity... AEs leading to discontinuation/dose reduction: Bone marrow depression Sources: Page: p.1Carcinogenicity Infertility |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.2 |
Disc. AE: Convulsions, Metastases... AEs leading to discontinuation/dose reduction: Convulsions Sources: Page: p.2Metastases Leukemia |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.3 |
Disc. AE: Skin rash, Erythema multiforme... AEs leading to discontinuation/dose reduction: Skin rash (rare) Sources: Page: p.3Erythema multiforme (rare) Toxic epidermal necrolysis (rare) Stevens-Johnson syndrome (rare) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abnormal EEG | Disc. AE | 3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Exaggerated startle response | Disc. AE | 3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Irritability | Disc. AE | 3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Myoclonic jerks | Disc. AE | 3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Vomiting | Disc. AE | 3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Bone marrow depression | mild Disc. AE |
3.2 mg/kg single, oral Overdose Dose: 3.2 mg/kg Route: oral Route: single Dose: 3.2 mg/kg Sources: |
healthy, 1.8 n = 1 Health Status: healthy Age Group: 1.8 Sex: F Population Size: 1 Sources: |
| Comatose | Disc. AE | 5 mg/kg single, oral Overdose Dose: 5 mg/kg Route: oral Route: single Dose: 5 mg/kg Sources: Page: p.239 |
healthy, 2.5 n = 1 Health Status: healthy Age Group: 2.5 Sex: M Population Size: 1 Sources: Page: p.239 |
| Convulsive seizure | Disc. AE | 5 mg/kg single, oral Overdose Dose: 5 mg/kg Route: oral Route: single Dose: 5 mg/kg Sources: Page: p.239 |
healthy, 2.5 n = 1 Health Status: healthy Age Group: 2.5 Sex: M Population Size: 1 Sources: Page: p.239 |
| Vomiting | Disc. AE | 5 mg/kg single, oral Overdose Dose: 5 mg/kg Route: oral Route: single Dose: 5 mg/kg Sources: Page: p.239 |
healthy, 2.5 n = 1 Health Status: healthy Age Group: 2.5 Sex: M Population Size: 1 Sources: Page: p.239 |
| Acute renal failure | Disc. AE | 250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Co-administed with:: cimetidine, p.o(600 mg; single) Sources: aspirin |
healthy, 38 n = 1 Health Status: healthy Age Group: 38 Sex: M Population Size: 1 Sources: |
| Seizures | Disc. AE | 250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Co-administed with:: cimetidine, p.o(600 mg; single) Sources: aspirin |
healthy, 38 n = 1 Health Status: healthy Age Group: 38 Sex: M Population Size: 1 Sources: |
| Bone marrow depression | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.1 |
| Carcinogenicity | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.1 |
| Infertility | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.1 |
| Convulsions | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.2 |
| Leukemia | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.2 |
| Metastases | Disc. AE | 0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.2 |
| Erythema multiforme | rare Disc. AE |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.3 |
| Skin rash | rare Disc. AE |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.3 |
| Stevens-Johnson syndrome | rare Disc. AE |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.3 |
| Toxic epidermal necrolysis | rare Disc. AE |
0.2 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Chronic lymphatic leukemia|Malignant lymphomas Sources: Page: p.3 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
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.
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| Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548207
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NDF-RT |
N0000175558
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NDF-RT |
N0000000236
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NCI_THESAURUS |
C697
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WHO-VATC |
QL01AA02
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WHO-ATC |
L01AA02
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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CHLORAMBUCIL
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SUB06172MIG
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305-03-3
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m3343
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DTXSID7020263
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206-162-0
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1106001
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7143
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CHEMBL515
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3026
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18D0SL7309
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28830
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DB00291
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2708
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603
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3088
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18D0SL7309
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C362
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D002699
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100000081577
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588
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CHLORAMBUCIL
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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. |
ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
