CYCLOPHOSPHAMIDE ANHYDROUS

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 Search

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

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 282 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Crosslinking Agent 83

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 8583	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
Multiple myeloma 159 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Chronic lymphocytic leukemia 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Mycosis fungoides 31 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Neuroblastoma 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Adenocarcinoma of the ovary 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Retinoblastoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Breast cancer 432 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Minimal change nephrotic syndrome 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Hodgkin’s disease mixed-cell type lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Hodgkin’s disease histiocytic lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Burkitt’s lymphoma 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Chronic granulocytic leukemia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Acute myelogenous and monocytic leukemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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
Acute lymphoblastic leukemia 27 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf	Primary	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
30.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN	DOXORUBICIN	CYCLOPHOSPHAMIDE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1234 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	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

Value	Dose	Co-administered	Analyte	Population
317 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN	DOXORUBICIN	CYCLOPHOSPHAMIDE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
17588 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22245954/	600 mg/m² single, intravenous dose: 600 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN	DOXORUBICIN	CYCLOPHOSPHAMIDE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.93 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/497087/	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022191	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

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 150 substrate 1946 inducer 1087	activator 23 inducer 440

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B6 669

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 2497	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	no
CYP2A6 911	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 1160	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2B6 1160	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588594/	yes
CYP2C18 13	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C19 2141	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP2C9 2497	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12739762/	yes
CYP3A5 201	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012141s090,012142s112lbl.pdf#page=15 Page: 15.0	yes
CYP3A4 2633	activator 342 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 1946	substrate 4014 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
Cyclophosphamide in exacerbations of multiple sclerosis. Therapeutic trial and a strategy for pilot drug studies.	1975 Jun	1097604
Cyclophosphamide-induced hemorrhagic cystitis in children with leukemia.	1975 Nov	1059500
[Apoptosis of B lymphocytic leukemia induced by anticancer drugs and their cell cycle specificity].	1998 Jan	10921050
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 cystitis in mice: behavioural characterisation and correlation with bladder inflammation.	1999 Jun	10700343
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
Increased expression of growth-associated protein (GAP-43) in lower urinary tract pathways following cyclophosphamide (CYP)-induced cystitis.	1999 Oct 9	10536274
Deficits in visceral pain and hyperalgesia of mice with a disruption of the tachykinin NK1 receptor gene.	2000	10854767
Overwhelming septic cavernous sinus thrombosis in a woman after combination of high-dose steroid and intravenous cyclophosphamide therapy for lupus nephritis.	2000	10713653
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis.	2000 Apr	10749792
Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer.	2000 Apr 1	10766175
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
Hemorrhagic pyelitis, ureteritis, and cystitis secondary to cyclophosphamide: case report and review of the literature.	2000 Feb	10637075
Urinary bladder involvement in patients with systemic lupus erythematosus: with review of the literature.	2000 Jan	10714091
Changes in urinary bladder neurotrophic factor mRNA and NGF protein following urinary bladder dysfunction.	2000 Jan	10683293
Long-term remission in an elderly patient with mantle cell leukemia treated with low-dose cyclophosphamide.	2000 Jan	10602166
Effect of Withania somnifera on cyclophosphamide-induced urotoxicity.	2000 Jan 1	10680587
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
Studies on the anti-inflammatory and related pharmacological properties of the aqueous extract of Bridelia ferruginea stem bark.	2000 Jul	10904158
Ruptured Klebsiella pneumoniae liver abscess after high-dose cyclophosphamide for severe aplastic anemia.	2000 Jul	10861821
Paternal exposure to cyclophosphamide alters cell-cell contacts and activation of embryonic transcription in the preimplantation rat embryo.	2000 Jul	10859244
Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain.	2000 Jul	10840460
[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
Dramatic aneurysm regression in polyarteritis nodosa following high dose pulse cyclophosphamide.	2000 May	10813312
Up-regulation of pituitary adenylate cyclase-activating polypeptide in urinary bladder pathways after chronic cystitis.	2000 May 8	10754506
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
Intraneoplastic polymer-based delivery of cyclophosphamide for intratumoral bioconversion by a replicating oncolytic viral vector.	2001 Feb 1	11221871
Involvement of hypogastric and pelvic nerves for conveying cystitis induced nociception in conscious rats.	2001 Jul	11435893
Bladder carcinoma associated with cyclophosphamide therapy for ovarian cancer occurring with a latency of 20 years.	2001 Jul	11426986
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
Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology.	2001 Jun	11377097
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
Nitric oxide synthases and cyclophosphamide-induced cystitis in rats.	2001 Mar	11284451
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 `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)`
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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