CYCLOPHOSPHAMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H15Cl2N2O2P.H2O
Molecular Weight	279.101
Optical Activity	( + / - )
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.ClCCN(CCCl)P1(=O)NCCCO1

InChI

InChIKey=PWOQRKCAHTVFLB-UHFFFAOYSA-N

InChI=1S/C7H15Cl2N2O2P.H2O/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14;/h1-7H2,(H,10,12);1H2

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.myelomabeacon.com/resources/2008/10/15/cyclophosphamide/

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 247 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Crosslinking Agent 80

Conditions

Condition	Modality	Highest Phase	Product
Hodgkin’s disease, lymphocytic lymphoma (nodular or diffuse) 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Multiple myeloma 159 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Chronic lymphocytic leukemia 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Mycosis fungoides 30 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Neuroblastoma 25 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Adenocarcinoma of the ovary 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Retinoblastoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Breast cancer 431 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Minimal change nephrotic syndrome 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Hodgkin’s disease mixed-cell type lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Hodgkin’s disease histiocytic lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Burkitt’s lymphoma 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Chronic granulocytic leukemia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Acute myelogenous and monocytic leukemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11
Acute lymphoblastic leukemia 27 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8360	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 -3.06806391E11

C_max

Value	Dose	Co-administered	Analyte	Population
1234 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: Imatinib \| Bevacizumab	Imatinib \| Bevacizumab	CYCLOPHOSPHAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
17587 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: Imatinib \| Bevacizumab	Imatinib \| Bevacizumab	CYCLOPHOSPHAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: Imatinib \| Bevacizumab	Imatinib \| Bevacizumab	CYCLOPHOSPHAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/0e1cb955-99c8-4fe5-89d1-399c8e52174e/spl-doc?hl=cyclophosphamide			CYCLOPHOSPHAMIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg/m2 2 times / day multiple, intravenous MTD Dose: 200 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 200 mg/m2, 2 times / day Co-administed with:: Clofarabine, i.v(40 mg/m(2) daily × 3 days) Sources: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16	unhealthy, 21-72 n = 5 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 21-72 Sex: M+F Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16	Other AEs: Bilirubin total increased, Diarrhea... Other AEs: Bilirubin total increased (grade 3, 20%) Diarrhea (grade 3, 20%) Sources: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16
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 Co-administed with:: Clofarabine, i.v(40 mg/m(2) daily × 3 days) Sources: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16	unhealthy, 21-72 n = 25 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 21-72 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16	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: https://pubmed.ncbi.nlm.nih.gov/24440659 Page: p.5, 16
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Co-administed with:: paclitaxel, i.v(160 mg/m2) Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98	unhealthy, 26-64 n = 6 Health Status: unhealthy Condition: Breast cancer Age Group: 26-64 Sex: F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Thrombocytopenia (16.7%) Neutropenia (16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Co-administed with:: paclitaxel, i.v(160 mg/m2) Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98	unhealthy, 26-64 n = 6 Health Status: unhealthy Condition: Breast cancer Age Group: 26-64 Sex: F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 16.7%) Thrombocytopenia (16.7%) Neutropenia (16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/8558227 Page: p.98
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 Co-administed with:: paclitaxel, i.v(200 mg/m2, once in 3 weeks, 5 cycles) Sources: https://pubmed.ncbi.nlm.nih.gov/9296218 Page: p.658	unhealthy, 27 - 70 n = 6 Health Status: unhealthy Condition: Breast cancer Age Group: 27 - 70 Sex: F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/9296218 Page: p.658	DLT: Febrile neutropenia, Thrombocytopenia... Dose limiting toxicities: Febrile neutropenia (33.3%) Thrombocytopenia (grade 4, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/9296218 Page: p.658
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 Co-administed with:: paclitaxel, i.v(175 mg/m(2) (Day 1), 6 cycles) Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519	unhealthy, 47-78 n = 6 Health Status: unhealthy Condition: Urothelial bladder cancer Age Group: 47-78 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Thrombocytopenia (grade 4, 16.7%) Constipation (grade 3, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519
50 mg 1 times / day multiple, oral MTD Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Co-administed with:: paclitaxel, i.v(175 mg/m(2) (Day 1), 12 cycles) Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519	unhealthy, 47-78 n = 6 Health Status: unhealthy Condition: Urothelial bladder cancer Age Group: 47-78 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519	Sources: https://pubmed.ncbi.nlm.nih.gov/19117344 Page: p.519
5 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1
50 mg/kg multiple, intravenous (total\|max) Recommended Dose: 50 mg/kg Route: intravenous Route: multiple Dose: 50 mg/kg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf Page: p.1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 77 substrate 1709 inducer 768	activator 21 inducer 383

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B6 538

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1803	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	no
CYP2A6 736	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 985	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 985	inducer 1542 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588594/	yes
CYP2C18 13	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C19 1537	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C9 1803	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 1909	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	yes
CYP3A5 130	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 1909	activator 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814316/ Page: 15.0	yes	weak (co-administration study) Comment: coadministration with ketoconazole: had small effect on CYCLOPHOSPHAMIDE plasma concentration Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814316/ Page: 15.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1709	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814316/	yes	DECP 3	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 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814316/

PubMed

Title	Date	PubMed
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.	1975 Aug 7	1138180
Remission of active chronic hepatitis after treatment with cyclophosphamide and prednisolone. Report of four cases.	1975 Feb	1144250
Phenolization of bladder in treatment of massive intractable hematuria.	1975 Jan	1054198
[Crescentic glomerulonephritis with anti neutrophil cytoplasmic antibody in children. Cases report].	1999 Aug	10752259
Effect of intravesical nitric oxide therapy on cyclophosphamide-induced cystitis.	1999 Dec	10569621
The uroprotection of mesna on cyclophosphamide cystitis in rats. Its consequences on behaviour and brain activities.	1999 Jun	10457601
Primary desmoplastic small cell tumor of soft tissues and bone of the hand.	1999 Nov	10555010
Low-dose vincristine-associated bilateral vocal cord paralysis.	1999 Oct	10578547
Pharmacological and molecular evidence for kinin B1 receptor expression in urinary bladder of cyclophosphamide-treated rats.	1999 Sep	10498854
Apparent cyclophosphamide (cytoxan) embryopathy: a distinct phenotype?	1999 Sep 17	10482872
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis.	2000 Apr	10749792
Limits to the "benefits" from our oncologic interventions: a case report.	2000 Aug	10926815
Hemorrhagic pyelitis, ureteritis, and cystitis secondary to cyclophosphamide: case report and review of the literature.	2000 Feb	10637075
Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/P450-reductase-based cancer gene therapy.	2000 Jul 15	10919648
Cyclophosphamide and water retention: mechanism revisited.	2000 Jun	10905395
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.	2000 May	11180191
[Assessment of cardiotoxicity of high dose cyclophosphamide with electrocardiographic, echocardiographic, and troponin I monitoring in patients with breast tumors].	2000 Nov	11109196
Cytochrome P-450 2C9 sensitizes human prostate tumor cells to cyclophosphamide via a bystander effect.	2000 Oct	10991840
Myopericarditis caused by cyclophosphamide used to mobilize peripheral blood stem cells in a myeloma patient with renal failure.	2000 Sep	11041571
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.	2000 Sep	11020424
A rapid assay for mitochondrial DNA damage and respiratory chain inhibition in the yeast Saccharomyces cerevisiae.	2001	11746749
[Improvement of combination chemotherapy tolerance of human umbilical cord blood CD(34)(+) cells transducted with double drug resistance genes by a bicistronic retroviral vector].	2001 Apr	11877073
Doxorubicin and taxane combination regimens for metastatic breast cancer: focus on cardiac effects.	2001 Aug	11552226
Transient posterior encephalopathy induced by chemotherapy in children.	2001 Feb	11275465
Cyclophosphamide-induced hemorrhagic cystitis in rats that underwent colocystoplasty: experimental study.	2001 Feb	11176454
Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats.	2001 Jul	11435893
What is proper treatment for Wegener granulomatosis?	2001 Jul 23	11485512
Transitional cell carcinoma of the urinary bladder following exposure to cyclophosphamide in childhood.	2001 Jun	11475121
Nitric oxide synthases and cyclophosphamide-induced cystitis in rats.	2001 Mar	11284451
Expression of inducible nitric oxide synthase in primary culture of rat bladder smooth muscle cells by plasma from cyclophosphamide-treated rats.	2001 Mar 23	11282106
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	11325840
Prevention of further cyclophosphamide induced hemorrhagic cystitis by hyperbaric oxygen and mesna in guinea pigs.	2001 Sep	11490309
Simple method based on fluorescent detection for the determination of 4-hydroxycyclophosphamide in plasma.	2002 Jun	12021633
The in vitro effect of Viscum album (VA) extract on DNA repair of peripheral blood mononuclear cells (PBMC) in cancer patients.	2002 Mar	11933116
DNA-dependent protein kinase in leukaemia cells and correlation with drug sensitivity.	2002 May-Jun	12168870
N-acetyl-L-cysteine does not affect the pharmacokinetics or myelosuppressive effect of busulfan during conditioning prior to allogeneic stem cell transplantation.	2003 Aug	12900770
Bioactivation of cyclophosphamide: the role of polymorphic CYP2C enzymes.	2003 Jun	12684728
Simultaneous quantification of cyclophosphamide, 4-hydroxycyclophosphamide, N,N',N"-triethylenethiophosphoramide (thiotepa) and N,N',N"-triethylenephosphoramide (tepa) in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2004 Mar	15039933
ABCC2-mediated biliary transport of 4-glutathionylcyclophosphamide and its contribution to elimination of 4-hydroxycyclophosphamide in rat.	2004 Mar	14617693
Rational combinations of trastuzumab with chemotherapeutic drugs used in the treatment of breast cancer.	2004 May 19	15150302
Diminishing the risk of nonrelapse mortality in hematopoietic stem cell transplantation: Prediction of exposure to the cyclophosphamide metabolite carboxyethylphosphoramide mustard.	2004 Sep	15371987
Accuracy, feasibility, and clinical impact of prospective Bayesian pharmacokinetically guided dosing of cyclophosphamide, thiotepa, and carboplatin in high-dose chemotherapy.	2005 Jan 1	15671556
Sparse sampling design for therapeutic drug monitoring of sequentially administered cyclophosphamide, thiotepa, and carboplatin (CTC).	2005 Jun	15905813
Effects of co-medicated drugs on cyclophosphamide bioactivation in human liver microsomes.	2005 Mar	15711186
Significant induction of cyclophosphamide and thiotepa metabolism by phenytoin.	2005 May	15685452
Aprepitant inhibits cyclophosphamide bioactivation and thiotepa metabolism.	2005 Oct	15838656
High exposures to bioactivated cyclophosphamide are related to the occurrence of veno-occlusive disease of the liver following high-dose chemotherapy.	2006 May 8	16622453
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	17218484
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	17485255
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	18496131

Patents

Sample Use Guides

In Vivo Use Guide

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

from 20 to 160 ug/ml

Substance Class	Chemical Created by `admin` on `Thu Jul 06 23:14:59 UTC 2023` Edited by `admin` on `Thu Jul 06 23:14:59 UTC 2023`
Record UNII	8N3DW7272P
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CYCLOPHOSPHAMIDE

Official Name

English

(±)-2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORINE 2-OXIDE MONOHYDRATE

Systematic Name

English

CYCLOBLASTIN

Brand Name

English

CYCLOPHOSPHAMIDE [MI]

Common Name

English

CYCLOPHOSPHAMIDE [WHO-IP]

Common Name

English

NSC-756711

Code

English

PROCYTOX

Brand Name

English

REVIMMUNE

Brand Name

English

CYCLOPHOSPHAMIDE [EP MONOGRAPH]

Common Name

English

NEOSAR

Brand Name

English

CYCLOPHOSPHAMIDUM [WHO-IP LATIN]

Common Name

English

CYTOXAN

Brand Name

English

ENDOXAN

Brand Name

English

CICLOFOSFAMIDE

Common Name

English

CYCLOPHOSPHAMIDE [USP-RS]

Common Name

English

B-518

Code

English

CYTOPHOSPHANE

Common Name

English

CYCLOPHOSPHAMIDE [USP MONOGRAPH]

Common Name

English

CYCLOPHOSPHANUM [WHO-IP]

Common Name

English

ENDOXAN MONOHYDRATE

Common Name

English

CYTOPHOSPHAN

Brand Name

English

CYCLOPHOSPHAMIDE [VANDF]

Common Name

English

2H-1,3,2-OXAZAPHOSPHORIN-2-AMINE, N,N-BIS(2-CHLOROETHYL)TETRAHYDRO-, 2-OXIDE, MONOHYDRATE, (±)-

Common Name

English

Cyclophosphamide monohydrate [WHO-DD]

Common Name

English

CYCLOSTIN

Brand Name

English

CYCLOPHOSPHAMIDE [ORANGE BOOK]

Common Name

English

CYCLOPHOSPHAMIDE HYDRATE [JAN]

Common Name

English

CYCLOPHOSPHAMIDE MONOHYDRATE

Common Name

English

CYCLOPHOSPHAMIDE [IARC]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

343611