CYCLOPHOSPHAMIDE ANHYDROUS

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 Search

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

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 232 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Crosslinking Agent 76

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 8043	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 145 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 54 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 29 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 8043	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 8043	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 411 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 8043	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 8043	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 8043	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 8043	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 8043	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 8043	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 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8043	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 74 substrate 1601 inducer 707	activator 20 inducer 355

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B6 501

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1648	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	no
CYP2A6 659	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 884	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 884	inducer 1440 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588594/	yes
CYP2C18 11	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C19 1392	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C9 1648	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 1772	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	yes
CYP3A5 122	activator 202 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 1772	activator 202 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 1601	substrate 3113 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
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
Thiotepa-associated cardiomyopathy during blood or marrow transplantation: association with the female sex and cardiac risk factors.	1999	10534063
[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
[Cyclophosphamide-induced bladder cancer in a patient with Wegener granuromatosis].	1999 Jan	10067308
Increase of hematopoietic responses by triple or single helical conformer of an antitumor (1-->3)-beta-D-glucan preparation, Sonifilan, in cyclophosphamide-induced leukopenic mice.	1999 Jan	10052129
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.	1999 Jul	10457124
Cyclophosphamide cystitis in mice: behavioural characterisation and correlation with bladder inflammation.	1999 Jun	10700343
Prevention of cyclophosphamide-induced hemorrhagic cystitis by glucose-mannose binding plant lectins.	1999 Jun	10332487
Characterization of a human cell clone expressing cytochrome P450 for safe use in human somatic cell therapy.	1999 Jun 30	10415877
Evaluation of uroprotective efficacy of amifostine against cyclophosphamide induced hemorrhagic cystitis.	1999 Mar	10100560
Effect of dexamethasone on cyclophosphamide-induced cystitis in rats: lack of relation with bradykinin B1 receptor-mediated motor responses.	1999 Mar 12	10204687
Thiotepa, busulfan and cyclophosphamide as a preparative regimen for allogeneic transplantation for advanced chronic myelogenous leukemia.	1999 May	10373061
Chlorambucil-induced postclosure exencephaly and axial skeletal abnormalities in rat fetuses.	1999 May-Jun	10378468
Pharmacological and histopathological study of cyclophosphamide-induced hemorrhagic cystitis - comparison of the effects of dexamethasone and Mesna.	1999 Oct	10510257
Cyclophosphamide-associated uroepithelial toxicity.	1999 Oct 5	10507982
Increased expression of growth-associated protein (GAP-43) in lower urinary tract pathways following cyclophosphamide (CYP)-induced cystitis.	1999 Oct 9	10536274
Apparent cyclophosphamide (cytoxan) embryopathy: a distinct phenotype?	1999 Sep 17	10482872
Long-term results of an intensive regimen: VEBEP plus involved-field radiotherapy in advanced Hodgkin's disease.	1999 Sep-Oct	10526668
Overwhelming septic cavernous sinus thrombosis in a woman after combination of high-dose steroid and intravenous cyclophosphamide therapy for lupus nephritis.	2000	10713653
Cyclophosphamide inhibits the development of diabetes in the diabetes-prone BB rat.	2000 Aug	10990075
Limits to the "benefits" from our oncologic interventions: a case report.	2000 Aug	10926815
Regulation of cyclophosphamide-induced eosinophilia in contact sensitivity: functional roles of interleukin-5-producing CD4(+) lymphocytes.	2000 Aug 1	11006010
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.	2000 Dec 15	11135211
Changes in urinary bladder neurotrophic factor mRNA and NGF protein following urinary bladder dysfunction.	2000 Jan	10683293
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	10607705
Ruptured Klebsiella pneumoniae liver abscess after high-dose cyclophosphamide for severe aplastic anemia.	2000 Jul	10861821
Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/P450-reductase-based cancer gene therapy.	2000 Jul 15	10919648
[Cyclophosphamide-induced renal pelvic tumor--a case report].	2000 Mar	10806575
QT dispersion as a predictor of acute heart failure after high-dose cyclophosphamide.	2000 Mar 4	10711930
[Assessment of cardiotoxicity of high dose cyclophosphamide with electrocardiographic, echocardiographic, and troponin I monitoring in patients with breast tumors].	2000 Nov	11109196
Report of severe neurotoxicity with cyclophosphamide.	2000 Nov-Dec	11132226
Cytochrome P-450 2C9 sensitizes human prostate tumor cells to cyclophosphamide via a bystander effect.	2000 Oct	10991840
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.	2000 Sep	11020424
Individualizing high-dose oral busulfan: prospective dose adjustment in a pediatric population undergoing allogeneic stem cell transplantation for advanced hematologic malignancies.	2000 Sep	11019834
Hypersensitivity reactions to carboplatin administration are common but not always severe: a 10-year experience.	2001	11528251
Doxorubicin and taxane combination regimens for metastatic breast cancer: focus on cardiac effects.	2001 Aug	11552226
Serum cardiac troponin I levels and ECG/Echo monitoring in breast cancer patients undergoing high-dose (7 g/m(2)) cyclophosphamide.	2001 Aug	11535996
Azathioprine-induced destructive cholangitis.	2001 Feb	11232733
Intraneoplastic polymer-based delivery of cyclophosphamide for intratumoral bioconversion by a replicating oncolytic viral vector.	2001 Feb 1	11221871
Erythropoietin restores the anemia-induced reduction in cyclophosphamide cytotoxicity in rat tumors.	2001 Feb 15	11245434
What is proper treatment for Wegener granulomatosis?	2001 Jul 23	11485512
Leiomyosarcoma of the bladder fourteen years after cyclophosphamide therapy for retinoblastoma.	2001 Jun	11487082
Transitional cell carcinoma of the urinary bladder following exposure to cyclophosphamide in childhood.	2001 Jun	11475121
Alterations in neuropeptide expression in lumbosacral bladder pathways following chronic cystitis.	2001 Mar	11312054
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with Streptococcus pneumoniae.	2001 May	11545565
Protective effect of berberine on cyclophosphamide-induced haemorrhagic cystitis in rats.	2001 May	11393582
Dominant role of intercellular adhesion molecule-1 in the pathogenesis of autoimmune diabetes in non-obese diabetic mice.	2001 Sep	11591119
Prevention of further cyclophosphamide induced hemorrhagic cystitis by hyperbaric oxygen and mesna in guinea pigs.	2001 Sep	11490309

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 `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

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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