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6055-19-2 molecular structure
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2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one

ChemBase ID: 413
Molecular Formular: C7H15Cl2N2O2P
Molecular Mass: 261.085961
Monoisotopic Mass: 260.02481972
SMILES and InChIs

SMILES:
ClCCN(P1(=O)OCCCN1)CCCl
Canonical SMILES:
ClCCN(P1(=O)NCCCO1)CCCl
InChI:
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChIKey:
CMSMOCZEIVJLDB-UHFFFAOYSA-N

Cite this record

CBID:413 http://www.chembase.cn/molecule-413.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one
2-[bis(2-chloroethyl)amino]-1,3,2λ5-oxazaphosphinan-2-one
IUPAC Traditional name
cyclophosphamide
cyclophosphamide, (+-)-
Brand Name
ASTA
Asta B 518
CP
CPA
CTX
CY
Clafen
Claphene
Cyclophosphamid
Cyclophosphamide Monohydrate
Cyclophosphamide Sterile
Cyclophosphamidum
Cyclophosphan
Cyclophosphane
Cyclophosphoramide
Cyclostin
Cyklofosfamid
Cytophosphan
Cytoxan
Cytoxan Lyoph
Endoxan
Endoxan R
Endoxan-Asta
Endoxana
Endoxanal
Endoxane
Enduxan
Genoxal
Hexadrin
Lyophilized Cytoxan
Mitoxan
Neosar
Procytox
Rcra Waste Number U058
Semdoxan
Sendoxan
Senduxan
Zyklophosphamid
Revimmune
Lyophilizedcytoxan
Synonyms
cyclophosphamide
Cyclophosphamide
Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester
Cyclophosphane
Cyclophosphamide monohydrate
Endoxan
Cytoxan
Neosar
Clafen(Cyclophosphamide)
2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one
环磷酰胺 单水合物
CAS Number
6055-19-2
50-18-0
EC Number
200-015-4
MDL Number
MFCD00005978
MFCD00149395
Beilstein Number
8167897
Merck Index
142747
PubChem SID
46505441
160963876
PubChem CID
2907
CHEBI ID
4027
ATC CODE
L01AA01
CHEMBL
88
Chemspider ID
2804
DrugBank ID
DB00531
KEGG ID
D07760
Unique Ingredient Identifier
6UXW23996M
Wikipedia Title
Cyclophosphamide
Medline Plus
a682080

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.076543  H Acceptors
H Donor LogD (pH = 5.5) 0.09654615 
LogD (pH = 7.4) 0.096539564  Log P 0.096547686 
Molar Refractivity 58.4781 cm3 Polarizability 23.373837 Å3
Polar Surface Area 41.57 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.76  LOG S -1.24 
Solubility (Water) 1.51e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Soluble. 1-5 g/100 mL at 23 oC expand Show data source
Melting Point
2°C (35.6°F) expand Show data source
51-53°C expand Show data source
Hydrophobicity(logP)
0.8 expand Show data source
0.803 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
RP6157750 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
UN3464 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
II expand Show data source
Risk Statements
45-46-61-25 expand Show data source
Safety Statements
53-20-36-45-60 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Hazard statements
H301-H340-H350-H360 expand Show data source
GHS Precautionary statements
P281-P301+P310-P321-P308+P313-P405-P501A expand Show data source
Target
DNA/RNA synthesis expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Bioavailability
>75% (oral) expand Show data source
Excretion
Renal expand Show data source
Half Life
3-12 hours expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
>60% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
D (Australia) expand Show data source
D (US) expand Show data source
Purity
95% expand Show data source
97+% expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia
DrugBank - DB00531 external link
Item Information
Drug Groups approved; investigational
Description 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
Humans and other mammals
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]
Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1217 external link
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]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. Pubmed
  • • Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. Pubmed
  • • http://en.wikipedia.org/wiki/Cyclophosphamide
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PATENTS

PATENTS

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