9-Carboxymethoxymethylguanine

9-Carboxymethoxymethylguanine
Identifiers
	IUPAC name 2-[(2-Amino-6-oxo-3H-purin-9-yl)methoxy]acetic acid;
CAS Number	80685-22-9 ;
PubChem CID	133521;
ChemSpider	117782;
CompTox Dashboard (EPA)	DTXSID40230501 ;
Chemical and physical data
Formula	C8H9N5O4
Molar mass	239.19 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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;

9-Carboxymethoxymethylguanine (CMMG) is a compound which is known as the principal metabolite of the antiviral drug acyclovir (and its prodrug valacyclovir), and has been suggested as the causative agent in the neuropsychiatric side effects sometimes associated with these drugs. These are mainly suffered by patients with renal 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 acyclovir 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

Svensson, J. O.; Barkholt, L.; Säwe, J. (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. 690 (1–2): 363–366. doi:10.1016/S0378-4347(96)00424-0. PMID 9106067.
Helldén, A.; Odar-Cederlof, I.; Diener, P.; Barkholt, L.; Medin, C.; Svensson, J. O.; Sawe, J.; Stahle, L. (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): 1135–1141. doi:10.1093/ndt/gfg119. PMID 12748346.
Hellden, A.; Odar-Cederlöf, I.; Larsson, K.; Fehrman-Ekholm, I.; Lindén, T. (2007). "Death delusion". BMJ. 335 (7633): 1305. doi:10.1136/bmj.39408.393137.BE. PMC 2151143. PMID 18156240.
Ruiz-Roso, G.; Gomis, A.; Fernández-Lucas, M.; Díaz-Domínguez, M.; Teruel-Briones, J. L.; Quereda, C. (2012). "Acyclovir and valacyclovir neurotoxicity in patients with renal failure". Nefrologia. 32 (1): 114–115. doi:10.3265/Nefrologia.pre2011.Nov.11247. PMID 22294022.
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.
Reversing walking corpse syndrome: Cotard's Syndrome trigger found - and it's a household cold sore cream. The Independent, Friday 18 October 2013

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[1] Svensson, J. O.; Barkholt, L.; Säwe, J. (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. 690 (1–2): 363–366. doi:10.1016/S0378-4347(96)00424-0. PMID 9106067.

[2] Helldén, A.; Odar-Cederlof, I.; Diener, P.; Barkholt, L.; Medin, C.; Svensson, J. O.; Sawe, J.; Stahle, L. (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): 1135–1141. doi:10.1093/ndt/gfg119. PMID 12748346.

[3] Hellden, A.; Odar-Cederlöf, I.; Larsson, K.; Fehrman-Ekholm, I.; Lindén, T. (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, J. L.; Quereda, C. (2012). "Acyclovir and valacyclovir neurotoxicity in patients with renal failure". Nefrologia. 32 (1): 114–115. 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.

[6] Reversing walking corpse syndrome: Cotard's Syndrome trigger found - and it's a household cold sore cream. The Independent, Friday 18 October 2013