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Cyclophosphamide monohydrate - 97%, high purity , DNA inhibitor, CAS No.6055-19-2, DNA inhibitor
Basic Description
Synonyms
2-(Bis(2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide hydrate | CCG-40013 | Cyclophosphamide hydrate | Cyclophosphamide monohydrate, ISOPAC(R) | NSC-756711 | HY-17420A | Revimmune | s2057 | Tox21_110100_1 | C06933 | CAS-6055-19-2 | D00287 | DTXCID604
Specifications & Purity
≥97%
Storage Temp
Store at 2-8°C,Argon charged
Shipped In
Wet ice
This product requires cold chain shipping. Ground and other economy services are not available.
Action Type
INHIBITOR
Mechanism of action
DNA inhibitor
Product Description
Cyclophosphamide monohydrate is an alkylating, cytotoxic agent experimentally shown to crosslink DNA, causing strand breakage and inducing mutations. It is also believed to possess immunosuppressive properties. Cyclophosphamide Monohydrate inhibits ALDH1 (aldehyde dehydrogenase 1) through its degradation product acrolein, as well as induces apoptosis in the rat thymus via the Fas/Fas ligand pathway.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Organic nitrogen compounds
Class
Organonitrogen compounds
Subclass
Nitrogen mustard compounds
Intermediate Tree Nodes
Not available
Direct Parent
Nitrogen mustard compounds
Alternative Parents
Phosphoric monoester diamides Oxazaphosphinanes Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organochlorides Organic oxides Hydrocarbon derivatives Alkyl chlorides
Molecular Framework
Aliphatic heteromonocyclic compounds
Substituents
Nitrogen mustard - Phosphoric monoester diamide - Organic phosphoric acid derivative - Oxazaphosphinane - Organic phosphoric acid amide - Oxacycle - Organoheterocyclic compound - Azacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organochloride - Organopnictogen compound - Organohalogen compound - Organic oxygen compound - Alkyl chloride - Alkyl halide - Aliphatic heteromonocyclic compound
Description
This compound belongs to the class of organic compounds known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
External Descriptors
hydrate
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
Pubchem Sid
504753081
Pubchem Sid Url
https://pubchem.ncbi.nlm.nih.gov/substance/504753081
IUPAC Name
N,N-bis(2-chloroethyl)-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine;hydrate
INCHI
InChI=1S/C7H15Cl2N2O2P.H2O/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14;/h1-7H2,(H,10,12);1H2
InChIKey
PWOQRKCAHTVFLB-UHFFFAOYSA-N
Smiles
C1CNP(=O)(OC1)N(CCCl)CCCl.O
Isomeric SMILES
C1CNP(=O)(OC1)N(CCCl)CCCl.O
WGK Germany
3
RTECS
RP6157750
Alternate CAS
6055-19-2,50-18-0 (Parent)
PubChem CID
22420
UN Number
2811
Packing Group
I
MeSH Entry Terms
(+,-)-2-(bis(2-Chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-Oxide Monohydrate;B 518;B-518;B518;Cyclophosphamide;Cyclophosphamide Anhydrous;Cyclophosphamide Monohydrate;Cyclophosphamide, (R)-Isomer;Cyclophosphamide, (S)-Isomer;Cyclophosphane;Cy
Molecular Weight
279.1
Beilstein
4678992
Reaxy-Rn
8167897
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Solubility
Soluble in water (30 mg/ml), ethanol (slightly soluble), benzene (slightly soluble), ethylene glycol (slightly soluble), carbon tetrachloride (slightly soluble), dioxane (slightly soluble), ether (sparingly soluble), acetone (sparingly soluble), alcohol,
Sensitivity
Heat, Light, Air sensitive.
Flash Point(°F)
235.4 °F
Flash Point(°C)
113 °C
Boil Point(°C)
110°C
Melt Point(°C)
49-53°C
Molecular Weight
279.100 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Exact Mass
278.035 Da
Monoisotopic Mass
278.035 Da
Topological Polar Surface Area
42.600 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
212.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
2
Citations of This Product
1.
Xiaoling Guo, Jinlian Li, Jiwen Cui, Yuhua Wang, Hongfu Gao, Sue Hao, Dongmei Wu.
(2015)
Sensitive Detection of MCF-7 Cells Based on Poly Calcein Modified Electrode and Its Applied in Cytotoxicity Assay. International Journal of Electrochemical Science,
10
(6732).
2.
Yi Xiao, Haomin Yi, Jingzhi Zhu, Suhua Chen, Guofang Wang, Yilong Liao, Yuanyuan Lei, Liyin Chen, Xingcai Zhang, Fangfu Ye.
(2023)
Evaluation of DNA adduct damage using G-quadruplex-based DNAzyme. Bioactive Materials,
23
(45).
3.
Yaowei Guo, Jin Liu, Qinglin Tang, Cuicui Li, Yanying Zhang, Yao Wang, Yanxin Wang, Yupeng Bi, Christopher D. Snow, Matt J. Kipper, Laurence A. Belfiore, Jianguo Tang.
(2022)
Lanthanide (Eu3+/Tb3+)-Loaded γ-Cyclodextrin Nano-Aggregates for Smart Sensing of the Anticancer Drug Irinotecan. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,
23
(12):
(6597).
4.
Kai-Yuan Huang, Hong-Xing He, Shao-Bin He, Xiang-Ping Zhang, Hua-Ping Peng, Zhen Lin, Hao-Hua Deng, Xing-Hua Xia, Wei Chen.
(2019)
Gold nanocluster-based fluorescence turn-off probe for sensing of doxorubicin by photoinduced electron transfer. SENSORS AND ACTUATORS B-CHEMICAL,
296
(126656).
5.
Deng Hao-Hua, Huang Kai-Yuan, Zhuang Qiong-Qiong, Zhuang Quan-Quan, Peng Hua-Ping, Liu Yin-Huan, Xia Xing-Hua, Chen Wei.
(2018)
Preparation of strongly fluorescent water-soluble dithiothreitol modified gold nanoclusters coated with carboxychitosan, and their application to fluorometric determination of the immunosuppressive 6-mercaptopurine. MICROCHIMICA ACTA,
185
(8):
(1-8).
6.
Jianyong Li, Xiaojun Kong, Xiwang Li, Yajun Yang, Jiyu Zhang.
(2013)
Genotoxic evaluation of aspirin eugenol ester using the Ames test and the mouse bone marrow micronucleus assay. FOOD AND CHEMICAL TOXICOLOGY,
62
(805).
7.
Hang Ruan, Yuwen Zhong, Huining Ding, Zehui He, Jiaqi Li, Meng Long, Zhi Wang, Qing Xia, Teng Guo, Chunyun Zhu, Tao Yang, Nianping Feng, Yongtai Zhang.
(2024)
Dual-continuous microneedle patch integrating transdermal delivery of pH-sensitive licorzinc MOFs and Zn2+ hydrogel sensors for treating alopecia areata. CHEMICAL ENGINEERING JOURNAL,
499
(155961).
8.
Fengyi Du, Lixia Xu, Haoran Wang, Mengke Lu, Qinxin Wang, Xiaonan Qiu, Baoding Chen, Miaomiao Zhang.
(2025)
Fe-Doped Carbon Dots-Incorporated In Situ Hydrogel for Near Infrared-Triggered Cascading Photothermal/Thermodynamic Therapy to Boost Cancer Immunity Cycle. BIOMACROMOLECULES,
9.
Tang Xudong, Shang Yangyang, Yang Hong, Song Yalan, Li Shan, Qin Yusi, Song Jingyi, Chen Kang, Liu Yang, Zhang Dinglin, Chen Lei.
(2024)
Targeted delivery of Fc-fused PD-L1 for effective management of acute and chronic colitis. Nature Communications,
15
(1):
(1-18).
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9 Citations
H2121237