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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
Structure of CYCLOPHOSPHAMIDE ANHYDROUS

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)

HIDE SMILES / InChI

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

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
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

1960
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.8 μg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
317 μg × h/mL
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
7.29 h
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
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
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
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

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: 15.0
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
Remission of active chronic hepatitis after treatment with cyclophosphamide and prednisolone. Report of four cases.
1975 Feb
Phenolization of bladder in treatment of massive intractable hematuria.
1975 Jan
Cyclophosphamide in exacerbations of multiple sclerosis. Therapeutic trial and a strategy for pilot drug studies.
1975 Jun
Cyclophosphamide-induced hemorrhagic cystitis in children with leukemia.
1975 Nov
[Apoptosis of B lymphocytic leukemia induced by anticancer drugs and their cell cycle specificity].
1998 Jan
Thiotepa-associated cardiomyopathy during blood or marrow transplantation: association with the female sex and cardiac risk factors.
1999
[Crescentic glomerulonephritis with anti neutrophil cytoplasmic antibody in children. Cases report].
1999 Aug
Effect of intravesical nitric oxide therapy on cyclophosphamide-induced cystitis.
1999 Dec
Cyclophosphamide cystitis in mice: behavioural characterisation and correlation with bladder inflammation.
1999 Jun
Primary desmoplastic small cell tumor of soft tissues and bone of the hand.
1999 Nov
Low-dose vincristine-associated bilateral vocal cord paralysis.
1999 Oct
Increased expression of growth-associated protein (GAP-43) in lower urinary tract pathways following cyclophosphamide (CYP)-induced cystitis.
1999 Oct 9
Deficits in visceral pain and hyperalgesia of mice with a disruption of the tachykinin NK1 receptor gene.
2000
Overwhelming septic cavernous sinus thrombosis in a woman after combination of high-dose steroid and intravenous cyclophosphamide therapy for lupus nephritis.
2000
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis.
2000 Apr
Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer.
2000 Apr 1
Limits to the "benefits" from our oncologic interventions: a case report.
2000 Aug
Regulation of cyclophosphamide-induced eosinophilia in contact sensitivity: functional roles of interleukin-5-producing CD4(+) lymphocytes.
2000 Aug 1
Hemorrhagic pyelitis, ureteritis, and cystitis secondary to cyclophosphamide: case report and review of the literature.
2000 Feb
Urinary bladder involvement in patients with systemic lupus erythematosus: with review of the literature.
2000 Jan
Changes in urinary bladder neurotrophic factor mRNA and NGF protein following urinary bladder dysfunction.
2000 Jan
Long-term remission in an elderly patient with mantle cell leukemia treated with low-dose cyclophosphamide.
2000 Jan
Effect of Withania somnifera on cyclophosphamide-induced urotoxicity.
2000 Jan 1
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
Studies on the anti-inflammatory and related pharmacological properties of the aqueous extract of Bridelia ferruginea stem bark.
2000 Jul
Ruptured Klebsiella pneumoniae liver abscess after high-dose cyclophosphamide for severe aplastic anemia.
2000 Jul
Paternal exposure to cyclophosphamide alters cell-cell contacts and activation of embryonic transcription in the preimplantation rat embryo.
2000 Jul
Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain.
2000 Jul
[Cyclophosphamide-induced renal pelvic tumor--a case report].
2000 Mar
QT dispersion as a predictor of acute heart failure after high-dose cyclophosphamide.
2000 Mar 4
Dramatic aneurysm regression in polyarteritis nodosa following high dose pulse cyclophosphamide.
2000 May
Up-regulation of pituitary adenylate cyclase-activating polypeptide in urinary bladder pathways after chronic cystitis.
2000 May 8
Hypersensitivity reactions to carboplatin administration are common but not always severe: a 10-year experience.
2001
Doxorubicin and taxane combination regimens for metastatic breast cancer: focus on cardiac effects.
2001 Aug
Serum cardiac troponin I levels and ECG/Echo monitoring in breast cancer patients undergoing high-dose (7 g/m(2)) cyclophosphamide.
2001 Aug
Intraneoplastic polymer-based delivery of cyclophosphamide for intratumoral bioconversion by a replicating oncolytic viral vector.
2001 Feb 1
Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats.
2001 Jul
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
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
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 Mon Mar 31 17:50:44 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:44 GMT 2025
Record UNII
6UXW23996M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPHOSPHAMIDE ANHYDROUS
Common Name English
NSC-26271
Preferred Name 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 Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
NDF-RT N0000000236
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
EPA PESTICIDE CODE 624870
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
NDF-RT N0000175558
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
WHO-ATC L01AA01
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
NCI_THESAURUS C574
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
Code System Code Type Description
HSDB
3047
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
CAS
50-18-0
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
DAILYMED
6UXW23996M
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
FDA UNII
6UXW23996M
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
EVMPD
SUB121739
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
PUBCHEM
2907
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
RXCUI
221085
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
ALTERNATIVE
EVMPD
SUB06859MIG
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
INN
878
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
DRUG BANK
DB00531
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
NSC
26271
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
MERCK INDEX
m4013
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID5020364
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-015-4
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
RXCUI
1545988
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
SMS_ID
100000090277
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
NCI_THESAURUS
C61694
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
CHEBI
4027
Created by admin on Mon Mar 31 17:50:44 GMT 2025 , Edited by admin on Mon Mar 31 17:50:44 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
BINDER->LIGAND
BINDING
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
DEGRADENT -> PARENT
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
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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