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)
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 |
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3342460
Curator's Comment: Data in rats only. Chlorambucil is ionized at physiological pH and thus minimally enters brain, with a brain/plasma concentration of only 0.02.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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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 |
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 |
healthy, 2.5 |
Disc. AE: Convulsive seizure, Comatose... AEs leading to discontinuation/dose reduction: Convulsive seizure Sources: Comatose Vomiting |
250 mg single, oral Overdose |
healthy, 38 |
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 Recommended Dose: 0.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.2 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Bone marrow depression, Carcinogenicity... AEs leading to discontinuation/dose reduction: Bone marrow depression Sources: Carcinogenicity Infertility |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Convulsions, Metastases... AEs leading to discontinuation/dose reduction: Convulsions Sources: Metastases Leukemia |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Skin rash, Erythema multiforme... AEs leading to discontinuation/dose reduction: Skin rash (rare) Sources: Erythema 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 |
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 |
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 |
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 |
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 |
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 |
Comatose | Disc. AE | 5 mg/kg single, oral Overdose |
healthy, 2.5 |
Convulsive seizure | Disc. AE | 5 mg/kg single, oral Overdose |
healthy, 2.5 |
Vomiting | Disc. AE | 5 mg/kg single, oral Overdose |
healthy, 2.5 |
Acute renal failure | Disc. AE | 250 mg single, oral Overdose |
healthy, 38 |
Seizures | Disc. AE | 250 mg single, oral Overdose |
healthy, 38 |
Bone marrow depression | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Carcinogenicity | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Infertility | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Convulsions | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Leukemia | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Metastases | Disc. AE | 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: |
unhealthy Health Status: unhealthy Sources: |
Erythema multiforme | rare Disc. AE |
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: |
unhealthy Health Status: unhealthy Sources: |
Skin rash | rare Disc. AE |
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: |
unhealthy Health Status: unhealthy Sources: |
Stevens-Johnson syndrome | rare Disc. AE |
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: |
unhealthy Health Status: unhealthy Sources: |
Toxic epidermal necrolysis | rare Disc. AE |
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: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of membranous nephropathy. | 2001 |
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A systematic overview of chemotherapy effects in B-cell chronic lymphocytic leukaemia. | 2001 |
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Achieving optimal outcomes in chronic lymphocytic leukaemia. | 2001 |
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[Treatment of uveitis with immunosuppressives: antimetabolites and alkylating agents]. | 2001 |
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Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents. | 2001 Apr |
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Decreased cytotoxicity and increased antimitotic activity of a proline analogue of chlorambucil as a prodrug susceptible to the action of fibroblast's prolidase. | 2001 Apr |
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[Renal involvement in Waldenstroms macroglobulinemia. Case report and review of the literature]. | 2001 Apr |
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[Treatment of polycythemia vera]. | 2001 Apr 6 |
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Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2'-deoxyguanosine. | 2001 Aug |
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A phase II study of sequential combination chemotherapy with cyclophosphamide, prednisone, and 2-chlorodeoxyadenosine in previously untreated patients with chronic lymphocytic leukemia. | 2001 Aug |
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Stage I and II MALT lymphoma: results of treatment with radiotherapy. | 2001 Aug 1 |
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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 |
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Waldenström's macroglobulinemia: clinical course and prognostic factors in 60 patients. Experience from a single hematology unit. | 2001 Dec |
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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 |
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[Acute cholestatic hepatitis due to chlorambucil]. | 2001 Feb |
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New aspects on the pathogenesis, diagnostic procedures, and therapeutic management of chronic lymphocytic leukemia. | 2001 Jan |
|
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 |
|
UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism. | 2001 Jun |
|
[Chronic lymphatic leukemia. 3. The concrete case]. | 2001 Jun 8 |
|
[Chronic lymphocytic leukemia. 2. Therapy]. | 2001 Jun 8 |
|
Acquired Factor VIII autoantibody: four cases demonstrating the heterogenous nature of this condition and problems involved in diagnosis and treatment. | 2001 Mar |
|
A meta-analysis of cytotoxic treatment for frequently relapsing nephrotic syndrome in children. | 2001 Mar |
|
Treatment of elderly patients with intermediate- and high-grade non-Hodgkin's lymphoma: a retrospective population-based study. | 2001 Mar |
|
Hypercalcaemia associated with chronic lymphocytic leukaemia in a Giant Schnauzer. | 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 |
|
Treatment of myelopathy in Sjögren syndrome with a combination of prednisone and cyclophosphamide. | 2001 May |
|
Induction of mutant lymphocytes in cyclophosphamide- and chlorambucil-treated patients. | 2001 May |
|
ChlVPP alternating with PABlOE is superior to PABlOE alone in the initial treatment of advanced Hodgkin's disease: results of a British National Lymphoma Investigation/Central Lymphoma Group randomized controlled trial. | 2001 May 18 |
|
2-[N1-2-pyrimidyl-aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate: a potent antitumor agent. | 2001 May 7 |
|
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 |
|
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 |
|
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1739612
Curator's Comment: Chronic lymphocytic leukaemia cells were treated
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
Edited
Mon Mar 31 17:33:31 GMT 2025
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admin
on
Mon Mar 31 17:33:31 GMT 2025
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Record UNII |
18D0SL7309
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Record Status |
Validated (UNII)
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Record Version |
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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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Code System | Code | Type | Description | ||
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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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18D0SL7309
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2708
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603
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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. |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Has antineoplastic activity
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
A white or almost white, crystalline or slightly granular powder.
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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