Chemistry:9-Carboxymethoxymethylguanine

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Short description: Chemical compound
9-Carboxymethoxymethylguanine
9-Carboxymethoxymethylguanine Structure.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC8H9N5O4
Molar mass239.191 g·mol−1
3D model (JSmol)

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]

References

  1. "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): 363–366. March 1997. doi:10.1016/S0378-4347(96)00424-0. PMID 9106067. 
  2. "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): 1135–1141. June 2003. doi:10.1093/ndt/gfg119. PMID 12748346. 
  3. "Death delusion". BMJ 335 (7633): 1305. December 2007. doi:10.1136/bmj.39408.393137.BE. PMID 18156240. 
  4. "Aciclovir and valaciclovir neurotoxicity in patients with renal failure". Nefrologia 32 (1): 114–115. 2012. doi:10.3265/Nefrologia.pre2011.Nov.11247. PMID 22294022. 
  5. "Cotard's syndrome as an adverse effect of acyclovir treatment in renal failure". Journal of the Neurological Sciences 333: e650. 2013. doi:10.1016/j.jns.2013.07.2255. 
  6. Saul, Heather (18 October 2013). "Reversing walking corpse syndrome: Cotard's Syndrome trigger found - and it's a household cold sore cream.". The Independent. https://www.independent.co.uk/news/science/reversing-walking-corpse-syndrome-cotards-syndrome-trigger-found--and-its-a-household-cold-sore-cream-8888670.html.