Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H15Cl2N2O2P |
Molecular Weight | 261.086 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClCCN(CCCl)P1(=O)NCCCO1
InChI
InChIKey=CMSMOCZEIVJLDB-UHFFFAOYSA-N
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
Molecular Formula | C7H15Cl2N2O2P |
Molecular Weight | 261.086 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Cyclophosphamide (the generic name for Cytoxan, Neosar, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. It is used to treat various types of cancer and some autoimmune disorders. It is a "prodrug"; it is converted in the liver to active forms that have chemotherapeutic activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
|||
Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
|||
Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
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Primary | CYTOXAN Approved UseTo treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date1960 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
31.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1234 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
317 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
247 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
17588 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/ |
600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.93 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/497087/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOPHOSPHAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOPHOSPHAMIDE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
CYCLOPHOSPHAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg/m2 2 times / day multiple, intravenous MTD Dose: 200 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 200 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Other AEs: Bilirubin total increased, Diarrhea... Other AEs: Bilirubin total increased (grade 3, 20%) Sources: Diarrhea (grade 3, 20%) |
300 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 300 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 300 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
DLT: Diarrhea, Lipase increased... Dose limiting toxicities: Diarrhea (grade 3-5, 12%) Sources: Lipase increased (grade 4, 4%) Transaminases increased (grade 3-5, 12%) Nausea and vomiting (grade 3-5, 4%) |
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Sources: |
unhealthy, 26-64 |
DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Sources: Thrombocytopenia (16.7%) Neutropenia (16.7%) |
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Sources: |
unhealthy, 26-64 |
DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 16.7%) Sources: Thrombocytopenia (16.7%) Neutropenia (16.7%) |
2000 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2000 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2000 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 27 - 70 |
DLT: Febrile neutropenia, Thrombocytopenia... Dose limiting toxicities: Febrile neutropenia (33.3%) Sources: Thrombocytopenia (grade 4, 16.7%) |
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, 47-78 |
DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Sources: Thrombocytopenia (grade 4, 16.7%) Constipation (grade 3, 16.7%) |
50 mg 1 times / day multiple, oral MTD Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 47-78 |
|
5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Myelosuppression, Immunosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression Sources: Immunosuppression Bone marrow failure Infection Urinary tract toxicity Toxicity renal Cystitis hemorrhagic Pyelitis Ureteritis Hematuria Cardiotoxicity Myocarditis Myopericarditis Pericardial effusion Arrhythmia (NOS) Congestive heart failure Pulmonary toxicity Pneumonitis Pulmonary fibrosis Pulmonary veno-occlusive disease Respiratory failure Metastases Venoocclusive liver disease Fetal damage |
50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Myelosuppression, Immunosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression Sources: Immunosuppression Bone marrow failure Infection Urinary tract toxicity Toxicity renal Cystitis hemorrhagic Pyelitis Ureteritis Hematuria Cardiotoxicity Myocarditis Myopericarditis Pericardial effusion Arrhythmia (NOS) Congestive heart failure Pulmonary toxicity Pneumonitis Pulmonary fibrosis Pulmonary veno-occlusive disease Respiratory failure Metastases Venoocclusive liver disease Fetal damage |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bilirubin total increased | grade 3, 20% | 200 mg/m2 2 times / day multiple, intravenous MTD Dose: 200 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 200 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Diarrhea | grade 3, 20% | 200 mg/m2 2 times / day multiple, intravenous MTD Dose: 200 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 200 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Diarrhea | grade 3-5, 12% DLT |
300 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 300 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 300 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Transaminases increased | grade 3-5, 12% DLT |
300 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 300 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 300 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Nausea and vomiting | grade 3-5, 4% DLT |
300 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 300 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 300 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Lipase increased | grade 4, 4% DLT |
300 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 300 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 300 mg/m2, 2 times / day Sources: |
unhealthy, 21-72 |
Neutropenia | 16.7% DLT |
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Sources: |
unhealthy, 26-64 |
Thrombocytopenia | 16.7% DLT |
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Sources: |
unhealthy, 26-64 |
Neutropenia | grade 4, 33.3% DLT |
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Sources: |
unhealthy, 26-64 |
Neutropenia | 16.7% DLT |
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Sources: |
unhealthy, 26-64 |
Thrombocytopenia | 16.7% DLT |
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Sources: |
unhealthy, 26-64 |
Neutropenia | grade 4, 16.7% DLT |
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Sources: |
unhealthy, 26-64 |
Febrile neutropenia | 33.3% DLT |
2000 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2000 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2000 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 27 - 70 |
Thrombocytopenia | grade 4, 16.7% DLT |
2000 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2000 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2000 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 27 - 70 |
Constipation | grade 3, 16.7% DLT |
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, 47-78 |
Thrombocytopenia | grade 4, 16.7% DLT |
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, 47-78 |
Neutropenia | grade 4, 33.3% DLT |
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, 47-78 |
Arrhythmia (NOS) | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Bone marrow failure | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Cardiotoxicity | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Congestive heart failure | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Cystitis hemorrhagic | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Fetal damage | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hematuria | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Immunosuppression | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Infection | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Metastases | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Myelosuppression | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Myocarditis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Myopericarditis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pericardial effusion | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pneumonitis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary fibrosis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary toxicity | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary veno-occlusive disease | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Pyelitis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Respiratory failure | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Toxicity renal | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Ureteritis | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Urinary tract toxicity | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Venoocclusive liver disease | Disc. AE | 5 mg/kg 1 times / day multiple, oral Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Arrhythmia (NOS) | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Bone marrow failure | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Cardiotoxicity | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Congestive heart failure | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Cystitis hemorrhagic | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Fetal damage | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Hematuria | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Immunosuppression | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Infection | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Metastases | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Myelosuppression | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Myocarditis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Myopericarditis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pericardial effusion | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pneumonitis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary fibrosis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary toxicity | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary veno-occlusive disease | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Pyelitis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Respiratory failure | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Toxicity renal | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Ureteritis | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Urinary tract toxicity | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Venoocclusive liver disease | Disc. AE | 50 mg/kg multiple, intravenous Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (co-administration study) Comment: coadministration with ketoconazole: caused a KTZ dose-dependent decrease in main parameters of DECP (Cmax, Tmax, and AUC0–∞) and provided magnitude exposure of DECP (more than a 50% AUC decrease) as a consequence of CYP3A inhibition |
PubMed
Title | Date | PubMed |
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Carcinoma of the urinary bladder in patients receiving cyclophosphamide. | 1975 Aug 7 |
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Remission of active chronic hepatitis after treatment with cyclophosphamide and prednisolone. Report of four cases. | 1975 Feb |
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Phenolization of bladder in treatment of massive intractable hematuria. | 1975 Jan |
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Cyclophosphamide in exacerbations of multiple sclerosis. Therapeutic trial and a strategy for pilot drug studies. | 1975 Jun |
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Cyclophosphamide-induced hemorrhagic cystitis in children with leukemia. | 1975 Nov |
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[Apoptosis of B lymphocytic leukemia induced by anticancer drugs and their cell cycle specificity]. | 1998 Jan |
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Thiotepa-associated cardiomyopathy during blood or marrow transplantation: association with the female sex and cardiac risk factors. | 1999 |
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[Crescentic glomerulonephritis with anti neutrophil cytoplasmic antibody in children. Cases report]. | 1999 Aug |
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Effect of intravesical nitric oxide therapy on cyclophosphamide-induced cystitis. | 1999 Dec |
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Cyclophosphamide cystitis in mice: behavioural characterisation and correlation with bladder inflammation. | 1999 Jun |
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Primary desmoplastic small cell tumor of soft tissues and bone of the hand. | 1999 Nov |
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Low-dose vincristine-associated bilateral vocal cord paralysis. | 1999 Oct |
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Increased expression of growth-associated protein (GAP-43) in lower urinary tract pathways following cyclophosphamide (CYP)-induced cystitis. | 1999 Oct 9 |
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Deficits in visceral pain and hyperalgesia of mice with a disruption of the tachykinin NK1 receptor gene. | 2000 |
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Overwhelming septic cavernous sinus thrombosis in a woman after combination of high-dose steroid and intravenous cyclophosphamide therapy for lupus nephritis. | 2000 |
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Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis. | 2000 Apr |
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Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer. | 2000 Apr 1 |
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Limits to the "benefits" from our oncologic interventions: a case report. | 2000 Aug |
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Regulation of cyclophosphamide-induced eosinophilia in contact sensitivity: functional roles of interleukin-5-producing CD4(+) lymphocytes. | 2000 Aug 1 |
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Hemorrhagic pyelitis, ureteritis, and cystitis secondary to cyclophosphamide: case report and review of the literature. | 2000 Feb |
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Urinary bladder involvement in patients with systemic lupus erythematosus: with review of the literature. | 2000 Jan |
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Changes in urinary bladder neurotrophic factor mRNA and NGF protein following urinary bladder dysfunction. | 2000 Jan |
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Long-term remission in an elderly patient with mantle cell leukemia treated with low-dose cyclophosphamide. | 2000 Jan |
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Effect of Withania somnifera on cyclophosphamide-induced urotoxicity. | 2000 Jan 1 |
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Nitric oxide-producing CD11b(+)Ly-6G(Gr-1)(+)CD31(ER-MP12)(+) cells in the spleen of cyclophosphamide-treated mice: implications for T-cell responses in immunosuppressed mice. | 2000 Jan 1 |
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Studies on the anti-inflammatory and related pharmacological properties of the aqueous extract of Bridelia ferruginea stem bark. | 2000 Jul |
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Ruptured Klebsiella pneumoniae liver abscess after high-dose cyclophosphamide for severe aplastic anemia. | 2000 Jul |
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Paternal exposure to cyclophosphamide alters cell-cell contacts and activation of embryonic transcription in the preimplantation rat embryo. | 2000 Jul |
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Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain. | 2000 Jul |
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[Cyclophosphamide-induced renal pelvic tumor--a case report]. | 2000 Mar |
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QT dispersion as a predictor of acute heart failure after high-dose cyclophosphamide. | 2000 Mar 4 |
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Dramatic aneurysm regression in polyarteritis nodosa following high dose pulse cyclophosphamide. | 2000 May |
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Up-regulation of pituitary adenylate cyclase-activating polypeptide in urinary bladder pathways after chronic cystitis. | 2000 May 8 |
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Hypersensitivity reactions to carboplatin administration are common but not always severe: a 10-year experience. | 2001 |
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Doxorubicin and taxane combination regimens for metastatic breast cancer: focus on cardiac effects. | 2001 Aug |
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Serum cardiac troponin I levels and ECG/Echo monitoring in breast cancer patients undergoing high-dose (7 g/m(2)) cyclophosphamide. | 2001 Aug |
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Intraneoplastic polymer-based delivery of cyclophosphamide for intratumoral bioconversion by a replicating oncolytic viral vector. | 2001 Feb 1 |
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Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats. | 2001 Jul |
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Bladder carcinoma associated with cyclophosphamide therapy for ovarian cancer occurring with a latency of 20 years. | 2001 Jul |
|
What is proper treatment for Wegener granulomatosis? | 2001 Jul 23 |
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Leiomyosarcoma of the bladder fourteen years after cyclophosphamide therapy for retinoblastoma. | 2001 Jun |
|
Transitional cell carcinoma of the urinary bladder following exposure to cyclophosphamide in childhood. | 2001 Jun |
|
Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology. | 2001 Jun |
|
Frequent, moderate-dose cyclophosphamide administration improves the efficacy of cytochrome P-450/cytochrome P-450 reductase-based cancer gene therapy. | 2001 Jun 1 |
|
High-dose paclitaxel in combination with doxorubicin, cyclophosphamide and peripheral blood progenitor cell rescue in patients with high-risk primary and responding metastatic breast carcinoma: toxicity profile, relationship to paclitaxel pharmacokinetics and short-term outcome. | 2001 Jun 15 |
|
Nitric oxide synthases and cyclophosphamide-induced cystitis in rats. | 2001 Mar |
|
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with Streptococcus pneumoniae. | 2001 May |
|
Protective effect of berberine on cyclophosphamide-induced haemorrhagic cystitis in rats. | 2001 May |
|
Dominant role of intercellular adhesion molecule-1 in the pathogenesis of autoimmune diabetes in non-obese diabetic mice. | 2001 Sep |
|
Prevention of further cyclophosphamide induced hemorrhagic cystitis by hyperbaric oxygen and mesna in guinea pigs. | 2001 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Cyclophosphamide can also be administered orally (1 mg per kg per day to 5 mg per kg per day) in malignant diseases.
40-50 mg per kg in divided doses over 2 to 5 days in malignant diseases and 2 mg per kg daily for 8 to 12 weeks in minimal change nephrotic sindrome
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6600859
Curator's Comment: Cyclophosphamide was tested for its ability to inhibit human lymphocyte proliferation and to modulate lymphocyte response to mitogens in vitro. At higher concentrations (20 to 160 ug/ml), the drug had a suppressive effect with a maximum suppression of 99%.
from 20 to 160 ug/ml
Substance Class |
Chemical
Created
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6UXW23996M
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NCI_THESAURUS |
C697
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NDF-RT |
N0000000236
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EPA PESTICIDE CODE |
624870
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NDF-RT |
N0000175558
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WHO-ATC |
L01AA01
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NCI_THESAURUS |
C574
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3047
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50-18-0
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6UXW23996M
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m4013
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED |
URINE
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BINDER->LIGAND |
BINDING
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SOLVATE->ANHYDROUS |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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DEGRADENT -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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