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 229 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Crosslinking Agent 76	Chronic lymphocytic leukemia Hodgkin’s disease, lymphocytic lymphoma (nodular or diffuse) Multiple myeloma Neuroblastoma Breast cancer Adenocarcinoma of the ovary Mycosis fungoides Retinoblastoma Acute lymphoblastic leukemia Acute myelogenous and monocytic leukemia Chronic granulocytic leukemia Burkitt’s lymphoma Hodgkin’s disease histiocytic lymphoma Hodgkin’s disease mixed-cell type lymphoma

Conditions

Condition	Modality	Targets	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	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Multiple myeloma 145 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Chronic lymphocytic leukemia 54 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Mycosis fungoides 29 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Neuroblastoma 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Adenocarcinoma of the ovary 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Retinoblastoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Breast cancer 411 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Minimal change nephrotic syndrome 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary		Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Hodgkin’s disease mixed-cell type lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Hodgkin’s disease histiocytic lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Burkitt’s lymphoma 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Chronic granulocytic leukemia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Acute myelogenous and monocytic leukemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000
Acute lymphoblastic leukemia 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	DNA	Approved 7997	CYTOXAN Approved Use To treat Hodgkin’s disease, lymphocytic lymphoma, mixed-cell type lymphoma, histiocytic lymphoma, Burkitt’s lymphoma; multiple myeloma, leukemias, mycosis fungoides, neuroblastoma, adenocarcinoma of ovary, retinoblastoma, breast carcinoma and minimal Change Nephrotic Syndrome in Pediatric Patients. Launch Date -306806400000

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 Sources: https://pubmed.ncbi.nlm.nih.gov/24440659	unhealthy, 21-72 Health Status: unhealthy Age Group: 21-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24440659	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
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: https://pubmed.ncbi.nlm.nih.gov/24440659	unhealthy, 21-72 Health Status: unhealthy Age Group: 21-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24440659	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
3300 mg/m2 single, intravenous Highest studied dose Dose: 3300 mg/m2 Route: intravenous Route: single Dose: 3300 mg/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/8558227	unhealthy, 26-64 Health Status: unhealthy Age Group: 26-64 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8558227	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
2700 mg/m2 single, intravenous MTD Dose: 2700 mg/m2 Route: intravenous Route: single Dose: 2700 mg/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/8558227	unhealthy, 26-64 Health Status: unhealthy Age Group: 26-64 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8558227	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
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: https://pubmed.ncbi.nlm.nih.gov/9296218	unhealthy, 27 - 70 Health Status: unhealthy Age Group: 27 - 70 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9296218	DLT: Febrile neutropenia, Thrombocytopenia... Dose limiting toxicities: Febrile neutropenia (33.3%) Thrombocytopenia (grade 4, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/9296218
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: https://pubmed.ncbi.nlm.nih.gov/19117344	unhealthy, 47-78 Health Status: unhealthy Age Group: 47-78 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19117344	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
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: https://pubmed.ncbi.nlm.nih.gov/19117344	unhealthy, 47-78 Health Status: unhealthy Age Group: 47-78 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19117344	Sources: https://pubmed.ncbi.nlm.nih.gov/19117344
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	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
50 mg/kg multiple, intravenous 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 55 substrate 1470 inducer 657	activator 20 inducer 343

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B6 486

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1362	inducer 1333 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	no
CYP2A6 625	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP2B6 845	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP2B6 845	inducer 1333 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588594/	yes
CYP2C18 9	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP2C19 1277	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP2C9 1362	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP3A4 1462	inducer 1333 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	yes
CYP3A5 119	activator 171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15	yes
CYP3A4 1462	activator 171 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	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

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1470	substrate 2752 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/

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM61903308
BOC Sciences	61903-30-8
Chemspace	CSC009998569
Chemspace	CSC043619834
Compound Cloud	99735
Enamine	BBV-45114560
Enamine	BBV-78465774
MuseChem	R008788
Toronto Research Chemicals	H926301
Toronto Research Chemicals	H941675
ZINC	ZINC000000897095	http://zinc15.docking.org/substances/ZINC000000897095
ZINC	ZINC000000897102	http://zinc15.docking.org/substances/ZINC000000897102
ZINC	ZINC000000897103	http://zinc15.docking.org/substances/ZINC000000897103
ZINC	ZINC000100051348	http://zinc15.docking.org/substances/ZINC000100051348
eMolecules	300441040
eMolecules	31588563
eMolecules	76746294

PubMed

Title	Date	PubMed
Carcinoma of the urinary bladder in patients receiving cyclophosphamide.	1975 Aug 7	1138180
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.	1981	6792207
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
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.	2000 May	11180191
Fatal haemorrhagic myocarditis secondary to cyclophosphamide therapy.	2000 Oct	11271907
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
Azathioprine-induced destructive cholangitis.	2001 Feb	11232733
Cyclophosphamide-induced hemorrhagic cystitis in rats that underwent colocystoplasty: experimental study.	2001 Feb	11176454
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
Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats.	2001 Jul	11435893
Frequent, moderate-dose cyclophosphamide administration improves the efficacy of cytochrome P-450/cytochrome P-450 reductase-based cancer gene therapy.	2001 Jun 1	11389073
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	11401310
Treatment based on a combination of the CYP2B1/cyclophosphamide system and p53 delivery enhances tumour regression in human pancreatic cancer.	2001 Mar	11332152
Alterations in neuropeptide expression in lumbosacral bladder pathways following chronic cystitis.	2001 Mar	11312054
Nitric oxide synthases and cyclophosphamide-induced cystitis in rats.	2001 Mar	11284451
Hematopoietic stem cell transplantation for high-risk adult patients with severe aplastic anemia; reduction of graft failure by enhancing stem cell dose.	2001 Mar	11255278
Reduced cardiotoxicity and preserved antitumor efficacy of liposome-encapsulated doxorubicin and cyclophosphamide compared with conventional doxorubicin and cyclophosphamide in a randomized, multicenter trial of metastatic breast cancer.	2001 Mar 1	11230490
Use of chemotherapy plus a monoclonal antibody against HER2 for metastatic breast cancer that overexpresses HER2.	2001 Mar 15	11248153
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
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
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
Stem cell toxicity of oxazaphosphorine metabolites in comparison to their antileukemic activity.	2002 Apr 1	11960610
Aldehyde-dehydrogenase gene-transduced hematopoietic cell line K562 overcomes the cytoxicity of cyclophosphamide in vitro.	2002 Jun	12513786
DNA-dependent protein kinase in leukaemia cells and correlation with drug sensitivity.	2002 May-Jun	12168870
Relationship between irreversible alopecia and exposure to cyclophosphamide, thiotepa and carboplatin (CTC) in high-dose chemotherapy.	2002 Nov	12407434
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
Alteration of pharmacokinetics of cyclophosphamide and suppression of the cytochrome p450 genes by ciprofloxacin.	2003 Feb	12621481
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
Reduced radiosensitivity and increased CD40 expression in cyclophosphamide-resistant subclones established from human cervical squamous cell carcinoma cells.	2005 Oct	16142355
Aprepitant inhibits cyclophosphamide bioactivation and thiotepa metabolism.	2005 Oct	15838656
Conservation of in vitro drug resistance patterns in epithelial ovarian carcinoma.	2005 Sep	16000215
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
Pharmacokinetics of N-2-chloroethylaziridine, a volatile cytotoxic metabolite of cyclophosphamide, in the rat.	2006 Oct	16470409
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
Fluconazole coadministration concurrent with cyclophosphamide conditioning may reduce regimen-related toxicity postmyeloablative hematopoietic cell transplantation.	2007 Jul	17580253
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
Low-dose metronomic cyclophosphamide treatment mediates ischemia-dependent K-ras mutation in colorectal carcinoma xenografts.	2008 Jun 12	18223682
Colorectal cancer stem cells are enriched in xenogeneic tumors following chemotherapy.	2008 Jun 18	18560594
Pharmacokinetics of cyclophosphamide and thiotepa in a conventional fractionated high-dose regimen compared with a novel simplified unfractionated regimen.	2009 Feb	19155964
Population pharmacokinetics of cyclophosphamide and metabolites in children with neuroblastoma: a report from the Children's Oncology Group.	2009 Jan	18927240
Does neurokinin-1-receptor antagonist aprepitant diminish the efficacy of cyclophosphamide-based chemotherapy?	2009 Nov	20512296
VEGFR2 heterogeneity and response to anti-angiogenic low dose metronomic cyclophosphamide treatment.	2010 Dec 15	21159176
Fludarabine-based myeloablative regimen as pretransplant conditioning therapy in adult acute leukemia/myelodysplastic syndrome: comparison with oral or intravenous busulfan with cyclophosphamide.	2010 Jun	21120188
Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide.	2010 Mar 16	20179710
In vitro investigation into the potential of a mistletoe extract to alleviate adverse effects of cyclophosphamide.	2010 May-Jun	20486623
A day and night difference in the response of the hepatic transcriptome to cyclophosphamide treatment.	2015 Feb	24819615

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