9-Carboxymethoxymethylguanine

9-Carboxymethoxymethylguanine (CMMG) is a compound which is known as the principal metabolite of the antiviral medication aciclovir (and its prodrug valaciclovir), and has been suggested as the causative agent in the neuropsychiatric side effects sometimes associated with these medications. These are mainly suffered by patients with kidney failure or otherwise decreased kidney function, and can include psychotic reactions, hallucinations, and rarely more complex disorders such as Cotard delusion. Patients suffering these symptoms following aciclovir treatment were found to have much higher levels of CMMG than normal, and since this is the first time Cotard delusion has been linked to a drug as a side effect, this discovery may be useful in the study of Cotard delusion and its treatment.[1][2][3][4][5][6]

9-Carboxymethoxymethylguanine
Identifiers
IUPAC name
  • 2-[(2-Amino-6-oxo-3H-purin-9-yl)methoxy]acetic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC8H9N5O4
Molar mass239.191 g·mol−1
3D model (JSmol)
SMILES
  • C1=NC2=C(N1COCC(=O)O)N=C(NC2=O)N
InChI
  • InChI=1S/C8H9N5O4/c9-8-11-6-5(7(16)12-8)10-2-13(6)3-17-1-4(14)15/h2H,1,3H2,(H,14,15)(H3,9,11,12,16)
  • Key:MICNQLKUSOVNNG-UHFFFAOYSA-N

References
  1. Svensson JO, Barkholt L, Säwe J (March 1997). "Determination of acyclovir and its metabolite 9-carboxymethoxymethylguanine in serum and urine using solid-phase extraction and high-performance liquid chromatography". Journal of Chromatography. B, Biomedical Sciences and Applications. 690 (1–2): 363–6. doi:10.1016/S0378-4347(96)00424-0. PMID 9106067.
  2. Helldén A, Odar-Cederlöf I, Diener P, Barkholt L, Medin C, Svensson JO, et al. (June 2003). "High serum concentrations of the acyclovir main metabolite 9-carboxymethoxymethylguanine in renal failure patients with acyclovir-related neuropsychiatric side effects: an observational study". Nephrology, Dialysis, Transplantation. 18 (6): 1135–41. doi:10.1093/ndt/gfg119. PMID 12748346.
  3. Helldén A, Odar-Cederlöf I, Larsson K, Fehrman-Ekholm I, Lindén T (December 2007). "Death delusion". BMJ. 335 (7633): 1305. doi:10.1136/bmj.39408.393137.BE. PMC 2151143. PMID 18156240.
  4. Ruiz-Roso G, Gomis A, Fernández-Lucas M, Díaz-Domínguez M, Teruel-Briones JL, Quereda C (2012). "Aciclovir and valaciclovir neurotoxicity in patients with renal failure". Nefrologia. 32 (1): 114–5. doi:10.3265/Nefrologia.pre2011.Nov.11247. PMID 22294022.
  5. Lindén, T.; Helldén, A. (2013). "Cotard's syndrome as an adverse effect of acyclovir treatment in renal failure". Journal of the Neurological Sciences. 333: e650. doi:10.1016/j.jns.2013.07.2255. S2CID 54428588.
  6. Saul H (18 October 2013). "Reversing walking corpse syndrome: Cotard's Syndrome trigger found - and it's a household cold sore cream". The Independent.
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