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Details

Stereochemistry ACHIRAL
Molecular Formula C7H15Cl2N2O2P
Molecular Weight 261.0861
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPHOSPHAMIDE ANHYDROUS

SMILES

C1CNP(=O)(N(CCCl)CCCl)OC1

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)

HIDE SMILES / InChI
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

Originator

Curator's Comment:: Cyclophosphamide was developed by Norbert Brock and ASTA (now Baxter Oncology).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Primary
CYTOXAN

Approved Use

To 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 Date

-306806400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1234 μg/L
50 mg 1 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: Imatinib | Bevacizumab
CYCLOPHOSPHAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
17587 μg × h/L
50 mg 1 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: Imatinib | Bevacizumab
CYCLOPHOSPHAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.8 h
50 mg 1 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: Imatinib | Bevacizumab
CYCLOPHOSPHAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
CYCLOPHOSPHAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
Other AEs: Bilirubin total increased, Diarrhea...
Other AEs:
Bilirubin total increased (grade 3, 20%)
Diarrhea (grade 3, 20%)
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
DLT: Diarrhea, Lipase increased...
Dose limiting toxicities:
Diarrhea (grade 3-5, 12%)
Lipase increased (grade 4, 4%)
Transaminases increased (grade 3-5, 12%)
Nausea and vomiting (grade 3-5, 4%)
Sources:
3300 mg/m2 single, intravenous
Highest studied dose
Dose: 3300 mg/m2
Route: intravenous
Route: single
Dose: 3300 mg/m2
Sources:
unhealthy, 26-64
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
DLT: Neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 33.3%)
Thrombocytopenia (16.7%)
Neutropenia (16.7%)
Sources:
2700 mg/m2 single, intravenous
MTD
Dose: 2700 mg/m2
Route: intravenous
Route: single
Dose: 2700 mg/m2
Sources:
unhealthy, 26-64
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
DLT: Neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 16.7%)
Thrombocytopenia (16.7%)
Neutropenia (16.7%)
Sources:
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
Health Status: unhealthy
Age Group: 27 - 70
Sex: F
Sources:
DLT: Febrile neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Febrile neutropenia (33.3%)
Thrombocytopenia (grade 4, 16.7%)
Sources:
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
Health Status: unhealthy
Age Group: 47-78
Sex: M+F
Sources:
DLT: Neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 33.3%)
Thrombocytopenia (grade 4, 16.7%)
Constipation (grade 3, 16.7%)
Sources:
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
Health Status: unhealthy
Age Group: 47-78
Sex: M+F
Sources:
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
Disc. AE: Myelosuppression, Immunosuppression...
AEs leading to
discontinuation/dose reduction:
Myelosuppression
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
Sources:
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Disc. AE: Myelosuppression, Immunosuppression...
AEs leading to
discontinuation/dose reduction:
Myelosuppression
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
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 21-72
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 26-64
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 27 - 70
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 27 - 70
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 47-78
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 47-78
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 47-78
Sex: M+F
Sources:
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Arrhythmia (NOS) Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
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
Cardiotoxicity Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
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
Cystitis hemorrhagic Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Fetal damage Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Hematuria Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Immunosuppression Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Infection Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Metastases Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Myelosuppression Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Myocarditis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Myopericarditis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Pericardial effusion Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Pneumonitis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Pulmonary fibrosis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Pulmonary toxicity Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
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
Pyelitis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Respiratory failure Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Toxicity renal Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
Ureteritis Disc. AE
50 mg/kg multiple, intravenous
Recommended
Dose: 50 mg/kg
Route: intravenous
Route: multiple
Dose: 50 mg/kg
Sources:
unhealthy
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
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
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
weak (co-administration study)
Comment: coadministration with ketoconazole: had small effect on CYCLOPHOSPHAMIDE plasma concentration
Page: 15
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical 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

PubMed

TitleDatePubMed
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.
1981
N-acetyl-L-cysteine does not affect the pharmacokinetics or myelosuppressive effect of busulfan during conditioning prior to allogeneic stem cell transplantation.
2003 Aug
A mouse-based strategy for cyclophosphamide pharmacogenomic discovery.
2003 Oct
Integrated Population Pharmacokinetic Model of both cyclophosphamide and thiotepa suggesting a mutual drug-drug interaction.
2004 Apr
ABCC2-mediated biliary transport of 4-glutathionylcyclophosphamide and its contribution to elimination of 4-hydroxycyclophosphamide in rat.
2004 Mar
Rational combinations of trastuzumab with chemotherapeutic drugs used in the treatment of breast cancer.
2004 May 19
Diminishing the risk of nonrelapse mortality in hematopoietic stem cell transplantation: Prediction of exposure to the cyclophosphamide metabolite carboxyethylphosphoramide mustard.
2004 Sep
Population pharmacokinetics of cyclophosphamide and its metabolites 4-hydroxycyclophosphamide, 2-dechloroethylcyclophosphamide, and phosphoramide mustard in a high-dose combination with Thiotepa and Carboplatin.
2005 Dec
Accuracy, feasibility, and clinical impact of prospective Bayesian pharmacokinetically guided dosing of cyclophosphamide, thiotepa, and carboplatin in high-dose chemotherapy.
2005 Jan 1
Sparse sampling design for therapeutic drug monitoring of sequentially administered cyclophosphamide, thiotepa, and carboplatin (CTC).
2005 Jun
Effects of co-medicated drugs on cyclophosphamide bioactivation in human liver microsomes.
2005 Mar
Significant induction of cyclophosphamide and thiotepa metabolism by phenytoin.
2005 May
Reduced radiosensitivity and increased CD40 expression in cyclophosphamide-resistant subclones established from human cervical squamous cell carcinoma cells.
2005 Oct
Aprepitant inhibits cyclophosphamide bioactivation and thiotepa metabolism.
2005 Oct
Conservation of in vitro drug resistance patterns in epithelial ovarian carcinoma.
2005 Sep
Real-time dose adjustment of cyclophosphamide in a preparative regimen for hematopoietic cell transplant: a Bayesian pharmacokinetic approach.
2006 Aug 15
Pharmacogenetics of cyclophosphamide in patients with hematological malignancies.
2006 Jan
Neutropenia induced in outbred mice by a simplified low-dose cyclophosphamide regimen: characterization and applicability to diverse experimental models of infectious diseases.
2006 Mar 17
Cyclophosphamide enhances TNF-alpha-induced apoptotic cell death in murine vascular endothelial cell.
2006 Mar 6
Rapid quantitation of cyclophosphamide metabolites in plasma by liquid chromatography-mass spectrometry.
2006 May 1
High exposures to bioactivated cyclophosphamide are related to the occurrence of veno-occlusive disease of the liver following high-dose chemotherapy.
2006 May 8
New approach to the activation of anti-cancer pro-drugs by metalloporphyrin-based cytochrome P450 mimics in all-aqueous biologically relevant system.
2006 Nov
Pharmacokinetics of N-2-chloroethylaziridine, a volatile cytotoxic metabolite of cyclophosphamide, in the rat.
2006 Oct
A mouse model with liver-specific deletion and global suppression of the NADPH-cytochrome P450 reductase gene: characterization and utility for in vivo studies of cyclophosphamide disposition.
2007 Apr
Fluconazole coadministration concurrent with cyclophosphamide conditioning may reduce regimen-related toxicity postmyeloablative hematopoietic cell transplantation.
2007 Jul
Simultaneous quantification of cyclophosphamide and its active metabolite 4-hydroxycyclophosphamide in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (LC-MS/MS).
2007 Jul 1
Genetic polymorphisms of CYP2B6 affect the pharmacokinetics/pharmacodynamics of cyclophosphamide in Japanese cancer patients.
2007 Jun
Mouse mammary tumor virus promoter-containing retroviral promoter conversion vectors for gene-directed enzyme prodrug therapy are functional in vitro and in vivo.
2008
Epstein-Barr virus renders the infected natural killer cell line, NKL resistant to doxorubicin-induced apoptosis.
2008 Dec 2
Combined antitumor effect of cyclophosphamide and bromodeoxyuridine in BDF1 mice bearing L1210 ascites tumors.
2008 Jan
Clonogenic multiple myeloma progenitors, stem cell properties, and drug resistance.
2008 Jan 1
Influence of polymorphisms of drug metabolizing enzymes (CYP2B6, CYP2C9, CYP2C19, CYP3A4, CYP3A5, GSTA1, GSTP1, ALDH1A1 and ALDH3A1) on the pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide.
2008 Jun
Targeting Bcl-2 family members with the BH3 mimetic AT-101 markedly enhances the therapeutic effects of chemotherapeutic agents in in vitro and in vivo models of B-cell lymphoma.
2008 Jun 1
Low-dose metronomic cyclophosphamide treatment mediates ischemia-dependent K-ras mutation in colorectal carcinoma xenografts.
2008 Jun 12
Colorectal cancer stem cells are enriched in xenogeneic tumors following chemotherapy.
2008 Jun 18
Pharmacokinetics of cyclophosphamide and thiotepa in a conventional fractionated high-dose regimen compared with a novel simplified unfractionated regimen.
2009 Feb
Carbamazepine induces bioactivation of cyclophosphamide and thiotepa.
2009 Feb
Population pharmacokinetics of cyclophosphamide and metabolites in children with neuroblastoma: a report from the Children's Oncology Group.
2009 Jan
Altered cyclophosphamide and thiotepa pharmacokinetics in a patient with moderate renal insufficiency.
2009 Jan
Dominant effect of antiangiogenesis in combination therapy involving cyclophosphamide and axitinib.
2009 Jan 15
Does neurokinin-1-receptor antagonist aprepitant diminish the efficacy of cyclophosphamide-based chemotherapy?
2009 Nov
Cyclophosphamide-metabolizing enzyme polymorphisms and survival outcomes after adjuvant chemotherapy for node-positive breast cancer: a retrospective cohort study.
2010
Transplacental transfer of anthracyclines, vinblastine, and 4-hydroxy-cyclophosphamide in a baboon model.
2010 Dec
VEGFR2 heterogeneity and response to anti-angiogenic low dose metronomic cyclophosphamide treatment.
2010 Dec 15
Fludarabine-based myeloablative regimen as pretransplant conditioning therapy in adult acute leukemia/myelodysplastic syndrome: comparison with oral or intravenous busulfan with cyclophosphamide.
2010 Jun
Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide.
2010 Mar 16
In vitro investigation into the potential of a mistletoe extract to alleviate adverse effects of cyclophosphamide.
2010 May-Jun
Adenoviral delivery of pan-caspase inhibitor p35 enhances bystander killing by P450 gene-directed enzyme prodrug therapy using cyclophosphamide+.
2010 Sep 13
A day and night difference in the response of the hepatic transcriptome to cyclophosphamide treatment.
2015 Feb
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
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
Name Type Language
CYCLOPHOSPHAMIDE ANHYDROUS
Common Name English
NSC-26271
Code English
ANHYDROUS CYCLOPHOSPHAMIDE
Common Name English
(+/-)-2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORINE 2-OXIDE
Systematic Name English
2H-1,3,2-OXAZAPHOSPHORIN-2-AMINE, N,N-BIS(2-CHLOROETHYL)TETRAHYDRO-, 2-OXIDE
Systematic Name English
CYCLOPHOSPHAMIDE [HSDB]
Common Name English
CYCLOPHOSPHAMIDE [WHO-DD]
Common Name English
CYCLOPHOSPHAMIDE LYOPHILIZED
Common Name English
CYCLOPHOSPHAMIDE ANHYDROUS [MI]
Common Name English
CYCLOPHOSPHAMIDE [INN]
Common Name English
CYCLOPHOSPHAMIDE, ANHYDROUS
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
NDF-RT N0000000236
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
EPA PESTICIDE CODE 624870
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
NDF-RT N0000175558
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
WHO-ATC L01AA01
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
NCI_THESAURUS C574
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
Code System Code Type Description
HSDB
3047
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
CAS
50-18-0
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
FDA UNII
6UXW23996M
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
EVMPD
SUB121739
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
PUBCHEM
2907
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
RXCUI
221085
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
ALTERNATIVE
EVMPD
SUB06859MIG
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
INN
878
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
DRUG BANK
DB00531
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
MERCK INDEX
M4013
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY Merck Index
EPA CompTox
50-18-0
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-015-4
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
RXCUI
1545988
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY
NCI_THESAURUS
C61694
Created by admin on Sat Jun 26 14:54:06 UTC 2021 , Edited by admin on Sat Jun 26 14:54:06 UTC 2021
PRIMARY