173547-45-0 Usage
Description
Cyclophosphamide-d4 contains four deuterium atoms. It is intended for use as an internal standard for the quantification of cyclophosphamide by GC- or LC-MS. Cyclophosphamide is a nitrogen mustard alkylating agent used in the treatment of cancers and autoimmune disorders. In cells with low levels of aldehyde dehydrogenase, cyclophosphamide acts as a prodrug and is metabolized to the active compound phosphoramide mustard, which crosslinks with DNA and causes cell death.
Chemical Properties
White to Off-White Solid
Uses
Cyclophosphamide-d4 is a cytotoxic nitrogen mustard derivative widely used in cancer chemotherapy. Cyclophosphamide-d4 cross-links DNA, causes strand breakage, and induces mutations. Its clinical activity is associated with a decrease in aldehyde dehydrogenase 1 (ALDH1) activity. This substance is listed as a known human carcinogen.
Check Digit Verification of cas no
The CAS Registry Mumber 173547-45-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,3,5,4 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 173547-45:
(8*1)+(7*7)+(6*3)+(5*5)+(4*4)+(3*7)+(2*4)+(1*5)=150
150 % 10 = 0
So 173547-45-0 is a valid CAS Registry Number.
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
173547-45-0Relevant articles and documents
Synthesis of cyclophosphamide-4,4,5,5-d4
Walsh,Shulman-Roskes,Anderson,Chang,Ludeman
, p. 1193 - 1198 (2007/10/03)
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.
