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Details

Stereochemistry RACEMIC
Molecular Formula C7H15Cl2N2O2P
Molecular Weight 261.086
Optical Activity ( + / - )
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPHOSPHAMIDE ANHYDROUS

SMILES

ClCCN(CCCl)P1(=O)NCCCO1

InChI

InChIKey=CMSMOCZEIVJLDB-UHFFFAOYSA-N
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)

HIDE SMILES / InChI

Description

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

PubMed

PubMed

TitleDatePubMed
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.
1981
The chemistry, toxicology, and identification in rat and human urine of 4-hydroxy-5-phenyl-1,3-oxazaperhydroin-2-one: a reactive metabolite in felbamate bioactivation.
2001 Aug
Does neurokinin-1-receptor antagonist aprepitant diminish the efficacy of cyclophosphamide-based chemotherapy?
2009 Nov
Cyclophosphamide-metabolizing enzyme polymorphisms and survival outcomes after adjuvant chemotherapy for node-positive breast cancer: a retrospective cohort study.
2010
Transplacental transfer of anthracyclines, vinblastine, and 4-hydroxy-cyclophosphamide in a baboon model.
2010 Dec
VEGFR2 heterogeneity and response to anti-angiogenic low dose metronomic cyclophosphamide treatment.
2010 Dec 15
Fludarabine-based myeloablative regimen as pretransplant conditioning therapy in adult acute leukemia/myelodysplastic syndrome: comparison with oral or intravenous busulfan with cyclophosphamide.
2010 Jun
Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide.
2010 Mar 16
In vitro investigation into the potential of a mistletoe extract to alleviate adverse effects of cyclophosphamide.
2010 May-Jun
Adenoviral delivery of pan-caspase inhibitor p35 enhances bystander killing by P450 gene-directed enzyme prodrug therapy using cyclophosphamide+.
2010 Sep 13
A day and night difference in the response of the hepatic transcriptome to cyclophosphamide treatment.
2015 Feb
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
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
NDF-RT N0000000236
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
EPA PESTICIDE CODE 624870
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
NDF-RT N0000175558
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
WHO-ATC L01AA01
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
Code System Code Type Description
HSDB
50-18-0
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
CAS
50-18-0
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
EVMPD
SUB121739
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
PUBCHEM
2907
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY SWITZERF
RXCUI
221085
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
ALTERNATIVE
EVMPD
SUB06859MIG
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
INN
878
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
DRUG BANK
DB00531
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
MERCK INDEX
M4013
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY Merck Index
EPA CompTox
50-18-0
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-015-4
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
RXCUI
1545988
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY
NCI_THESAURUS
C61694
Created by admin on Tue Mar 06 10:46:29 UTC 2018 , Edited by admin on Tue Mar 06 10:46:29 UTC 2018
PRIMARY