NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one
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2-[bis(2-chloroethyl)amino]-1,3,2λ5-oxazaphosphinan-2-one
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IUPAC Traditional name
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cyclophosphamide
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cyclophosphamide, (+-)-
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Brand Name
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ASTA
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Asta B 518
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CP
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CPA
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CTX
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CY
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Clafen
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Claphene
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Cyclophosphamid
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Cyclophosphamide Monohydrate
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Cyclophosphamide Sterile
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Cyclophosphamidum
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Cyclophosphan
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Cyclophosphane
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Cyclophosphoramide
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Cyclostin
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Cyklofosfamid
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Cytophosphan
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Cytoxan
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Cytoxan Lyoph
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Endoxan
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Endoxan R
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Endoxan-Asta
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Endoxana
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Endoxanal
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Endoxane
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Enduxan
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Genoxal
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Hexadrin
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Lyophilized Cytoxan
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Mitoxan
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Neosar
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Procytox
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Rcra Waste Number U058
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Semdoxan
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Sendoxan
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Senduxan
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Zyklophosphamid
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Revimmune
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Lyophilizedcytoxan
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Synonyms
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cyclophosphamide
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Cyclophosphamide
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Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester
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Cyclophosphane
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Cyclophosphamide monohydrate
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Endoxan
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Cytoxan
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Neosar
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Clafen(Cyclophosphamide)
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2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one
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环磷酰胺 单水合物
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CAS Number
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EC Number
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MDL Number
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MFCD00149395
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MFCD00005978
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Beilstein Number
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Merck Index
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PubChem SID
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PubChem CID
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CHEBI ID
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ATC CODE
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CHEMBL
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Chemspider ID
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DrugBank ID
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KEGG ID
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Unique Ingredient Identifier
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Wikipedia Title
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Medline Plus
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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12.076543
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H Acceptors
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2
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H Donor
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1
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LogD (pH = 5.5)
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0.09654615
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LogD (pH = 7.4)
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0.096539564
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Log P
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0.096547686
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Molar Refractivity
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58.4781 cm3
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Polarizability
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23.373837 Å3
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Polar Surface Area
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41.57 Å2
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Rotatable Bonds
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5
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Lipinski's Rule of Five
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true
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Log P
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0.76
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LOG S
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-1.24
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Solubility (Water)
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1.51e+01 g/l
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DETAILS
DETAILS
DrugBank
Selleck Chemicals
Wikipedia
DrugBank -
DB00531
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Item |
Information |
Drug Groups
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approved; investigational |
Description
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Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the liver to form the active aldophosphamide. It has been used in the treatment of lymphoma and leukemia. Its side effect, alopecia, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer. [PubChem] |
Indication |
For management of malignant lymphomas, multiple myeloma,leukemias, mycosis fungoides (advanced disease), neuroblastoma (disseminated disease), adenocarcinoma of the ovary, retinoblastoma and carcinoma of the breast |
Pharmacology |
Cyclophosphamide is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death. |
Toxicity |
infection, myelosuppression, and cardiac toxicity |
Affected Organisms |
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Humans and other mammals |
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Biotransformation |
hepatic |
Absorption |
90-100% |
Half Life |
3-12 hours |
Protein Binding |
>60% |
Elimination |
It is eliminated primarily in the form of metabolites, but from 5% to 25% of the dose is excreted in urine as unchanged drug. |
References |
• |
Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7.
[Pubmed]
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• |
Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7.
[Pubmed]
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External Links |
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Selleck Chemicals -
S1217
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Research Area: Cancer Biological Activity: Cyclophosphamide is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities. In the liver, cyclophosphamide is converted to the active metabolites aldophosphamide and phosphoramide mustard, which bind to DNA, thereby inhibiting DNA replication and initiating cell death. [1]Cyclophosphamide is given as a treatment for many types of cancer, among them lymphomas, ovary, breast, and bladder; and chronic lymphocytic leukaemia. [2]This agent inhibited cell proliferation of NCI-H727 with IC50 at 9.3 nM. [3] |
PATENTS
PATENTS
PubChem Patent
Google Patent