173547-45-0

Basic information

• Product Name: Cyclophosphamide-d4
• Synonyms: Cyclophosphamide-d4;Cyclostin-d4;Cytoxan-d4;Endoxan-d4;Genoxal-d4;Hexadrin-d4;Mitoxan-d4;N,N-Bis(2-chloroethyl)tetrahydro-4,5-d2-2H-1,3,2-oxazaphosphorin-2-amine 2-Oxide
• CAS NO: 173547-45-0
• Molecular Formula: C7H15Cl2N2O2P
• Molecular Weight: 261.085961
• EINECS: 244-379-2
• Product Categories: Intermediates & Fine Chemicals;Isotope Labeled Compounds;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Isotope Labelled Compounds;Isotope Labelled Compounds, Pharmaceuticals, Intermediates & Fine Chemicals, Phosphorylating and Phosphitylating Agents, Phosphorylating and Phosphitylating Agents
• Mol File: 173547-45-0.mol

Chemical Properties

• Melting Point: 41-450C
• Boiling Point: 336.099°C at 760 mmHg
• Flash Point: 157.068°C
• Appearance: /
• Density: 1.355g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: Cyclophosphamide-d4(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclophosphamide-d4(173547-45-0)
• EPA Substance Registry System: Cyclophosphamide-d4(173547-45-0)

Safety Data

• Hazardous Substances Data: 173547-45-0(Hazardous Substances Data)

Usage

Uses

Used in Cancer Chemotherapy:
Cyclophosphamide-d4 is used as a cytotoxic agent for the treatment of various cancers. It is particularly effective in the treatment of solid malignancies such as breast, lung, ovarian, and colorectal cancers. The compound cross-links DNA, causing strand breakage and inducing mutations, which leads to a decrease in aldehyde dehydrogenase 1 (ALDH1) activity and ultimately results in cell death.
Used in Autoimmune Disorder Treatment:
Cyclophosphamide-d4 is also used as an immunosuppressive agent for the treatment of autoimmune disorders. Its alkylating properties help to suppress the immune system, reducing the severity of the disease and improving the patient's quality of life.
Used in Research and Development:
Cyclophosphamide-d4 serves as an internal standard in the quantification of cyclophosphamide by gas chromatography-mass spectrometry (GC-MS) or liquid chromatography-mass spectrometry (LC-MS). This application is crucial for ensuring the accuracy and reliability of cyclophosphamide measurements in various research and diagnostic settings.
Used in Drug Development and Testing:
Due to its cytotoxic properties, Cyclophosphamide-d4 is used in the development and testing of new cancer therapeutics. It helps researchers understand the mechanisms of action and potential side effects of new drugs, ultimately contributing to the development of more effective and safer cancer treatments.
Used in Drug Delivery Systems:
Cyclophosphamide-d4 can be incorporated into drug delivery systems to improve the bioavailability and therapeutic outcomes of cyclophosphamide. Various organic and metallic nanoparticles can be employed as carriers for cyclophosphamide-d4 delivery, aiming to enhance its efficacy against cancer cells and reduce potential side effects.

InChI:InChI=1/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)/i1D2,4D2

Upstream product

• 127-88-8 N,N-di(2-chloroethyl)amidophosphoric acid dichloride 
• 173547-44-9 3-amino-2,2,3,3-tetradeuterio-3-deuteroxypropan-1-ol 

Relevant articles and documents

Synthesis of cyclophosphamide-4,4,5,5-d4

3-Hydroxypropionitrile was subjected to a base-catalyzed exchange reaction in D2O which provided 2,2-dideuterio-3-deuteroxypropionitrile (DOCH2CD2CN) in 70% yield. Reduction of the nitrile with LIAlD4 gave 3-amino-2,2,3,3- tetradeuteriopropan-1-ol (HOCH2CD2CD2NH2) in a crude yield of 71%. Reaction of this intermediate with N,N-bis (2-chloroethyl)phosphoramidic dichloride [Cl2P(O)N(CH2CH2Cl)2] followed by the combination of those chromatography fractions which contained only pure material gave cyclophosphamide-4,4,5,5-d4 as a white oil in 13% yield. A portion of this oil was converted to the monohydrate by the addition of water (1.1 equivalents) and crystallization from ether/petroleum ether (628 yield). For the hydrate, MS analyses gave an average mole percent enrichment (with average deviation over 5 determinations) of 89.1 ± 0.5% d4.