U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C7H15Cl2N2O2P
Molecular Weight 261.0861
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

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
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.
1975 Aug 7
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.
1981
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.
2000 Dec 15
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.
2000 May
Fatal haemorrhagic myocarditis secondary to cyclophosphamide therapy.
2000 Oct
Doxorubicin and taxane combination regimens for metastatic breast cancer: focus on cardiac effects.
2001 Aug
Transient posterior encephalopathy induced by chemotherapy in children.
2001 Feb
Azathioprine-induced destructive cholangitis.
2001 Feb
Cyclophosphamide-induced hemorrhagic cystitis in rats that underwent colocystoplasty: experimental study.
2001 Feb
Intraneoplastic polymer-based delivery of cyclophosphamide for intratumoral bioconversion by a replicating oncolytic viral vector.
2001 Feb 1
Erythropoietin restores the anemia-induced reduction in cyclophosphamide cytotoxicity in rat tumors.
2001 Feb 15
Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats.
2001 Jul
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
Treatment based on a combination of the CYP2B1/cyclophosphamide system and p53 delivery enhances tumour regression in human pancreatic cancer.
2001 Mar
Alterations in neuropeptide expression in lumbosacral bladder pathways following chronic cystitis.
2001 Mar
Nitric oxide synthases and cyclophosphamide-induced cystitis in rats.
2001 Mar
Hematopoietic stem cell transplantation for high-risk adult patients with severe aplastic anemia; reduction of graft failure by enhancing stem cell dose.
2001 Mar
Reduced cardiotoxicity and preserved antitumor efficacy of liposome-encapsulated doxorubicin and cyclophosphamide compared with conventional doxorubicin and cyclophosphamide in a randomized, multicenter trial of metastatic breast cancer.
2001 Mar 1
Use of chemotherapy plus a monoclonal antibody against HER2 for metastatic breast cancer that overexpresses HER2.
2001 Mar 15
Expression of inducible nitric oxide synthase in primary culture of rat bladder smooth muscle cells by plasma from cyclophosphamide-treated rats.
2001 Mar 23
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
Cyclophosphamide, doxorubicin, and paclitaxel enhance the antitumor immune response of granulocyte/macrophage-colony stimulating factor-secreting whole-cell vaccines in HER-2/neu tolerized mice.
2001 May 1
Stem cell toxicity of oxazaphosphorine metabolites in comparison to their antileukemic activity.
2002 Apr 1
Aldehyde-dehydrogenase gene-transduced hematopoietic cell line K562 overcomes the cytoxicity of cyclophosphamide in vitro.
2002 Jun
DNA-dependent protein kinase in leukaemia cells and correlation with drug sensitivity.
2002 May-Jun
Relationship between irreversible alopecia and exposure to cyclophosphamide, thiotepa and carboplatin (CTC) in high-dose chemotherapy.
2002 Nov
N-acetyl-L-cysteine does not affect the pharmacokinetics or myelosuppressive effect of busulfan during conditioning prior to allogeneic stem cell transplantation.
2003 Aug
Alteration of pharmacokinetics of cyclophosphamide and suppression of the cytochrome p450 genes by ciprofloxacin.
2003 Feb
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
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
High exposures to bioactivated cyclophosphamide are related to the occurrence of veno-occlusive disease of the liver following high-dose chemotherapy.
2006 May 8
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
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
Population pharmacokinetics of cyclophosphamide and metabolites in children with neuroblastoma: a report from the Children's Oncology Group.
2009 Jan
Does neurokinin-1-receptor antagonist aprepitant diminish the efficacy of cyclophosphamide-based chemotherapy?
2009 Nov
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
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:54:05 UTC 2021
Edited
by admin
on Sat Jun 26 14:54:05 UTC 2021
Record UNII
6UXW23996M
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
DEGRADENT -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION