9-carboxymethoxymethylguanine profile

9-carboxymethoxymethylguanine: metabolite of acyclovir [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	135508007
CHEMBL ID	1256485
CHEBI ID	180454
SCHEMBL ID	22799102
MeSH ID	M0108502

Synonym
unii-n28227w35c
n28227w35c ,
acetic acid, ((2-amino-1,6-dihydro-6-oxo-9h-purin-9-yl)methoxy)-
80685-22-9
9-carboxymethoxymethylguanine
CHEBI:180454
2-[(2-amino-6-oxo-1h-purin-9-yl)methoxy]acetic acid
cmmg
CHEMBL1256485
9-[(carboxymethoxy)methyl]-guanine
DTXSID40230501
acetic acid, 2-((2-amino-1,6-dihydro-6-oxo-9h-purin-9-yl)methoxy)-
carboxy-acyclovir
AKOS030255078
2-[(2-amino-6-oxo-6,9-dihydro-1h-purin-9-yl)methoxy]acetic acid
Q15405288
2-((2-amino-6-oxo-1h-purin-9(6h)-yl)methoxy)acetic acid
SCHEMBL22799102
CS-0136963
HY-137181
AKOS040758357

Excerpt	Reference
" Serious neurological adverse side effects have occurred during ACV treatment in patients with renal failure, but the cause of the symptoms remains unknown."	( High serum concentrations of the acyclovir main metabolite 9-carboxymethoxymethylguanine in renal failure patients with acyclovir-related neuropsychiatric side effects: an observational study. Barkholt, L; Diener, P; Helldén, A; Medin, C; Odar-Cederlöf, I; Säwe, J; Ståhle, L; Svensson, JO, 2003)

Excerpt	Reference
" Indwelling intrathecal catheters allowed serial CSF sampling throughout the dosing interval."	( Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function. Haas, DW; Johnson, B; Luther, JM; Nicotera, J; Smith, JP; Weller, S, 2010)
" Evaluation of CSF:serum albumin ratios, renal function and CSF concentrations of aciclovir and CMMG may all contribute to the optimization of aciclovir dosing and avoidance of AINS."	( An unexpectedly high occurrence of aciclovir-induced neuropsychiatric symptoms in patients treated for herpesvirus CNS infection: a prospective observational study. Grahn, A; Helldén, A; Lindström, J; Lycke, J; Studahl, M, 2019)

Class	Description
oxopurine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (18)

Assay ID	Title	Year	Journal	Article
AID521956	Ratio of Cmax in human CSF to Cmax in human plasma with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521935	Tmax in human CSF with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521915	Drug level in human CSF with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521941	AUC (0 to 12 hrs) in human CSF with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521932	Cmax in human systemic circulation with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521909	Drug level in human plasma with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521938	AUC (0 to 6 hrs) in human systemic circulation with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521936	Tmax in human systemic circulation with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521934	Tmax in human systemic circulation with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521937	Tmax in human CSF with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521931	Cmax in human CSF with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521933	Cmax in human CSF with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521939	AUC (0 to 6 hrs) in human CSF with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521906	Drug level in human plasma with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521930	Cmax in human systemic circulation with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521912	Drug level in human CSF with normal renal function assessed as CMMG level at 2000 mg, po every 6 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521940	AUC (0 to 12 hrs) in human systemic circulation with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
AID521957	Ratio of Cmax in human CSF to Cmax in human plasma with chronic kidney disease assessed as CMMG level at 1500 mg, po every 12 hrs measured after fifth dose by LC/MS	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (5.88)	18.7374
1990's	1 (5.88)	18.2507
2000's	6 (35.29)	29.6817
2010's	4 (23.53)	24.3611
2020's	5 (29.41)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (5.56%)	6.00%
Case Studies	5 (27.78%)	4.05%
Observational	1 (5.56%)	0.25%
Other	11 (61.11%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.31	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.95	4	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.31	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	4.12	15	2-aminopurines; oxopurine	antimetabolite; antiviral drug
guanine [no description available]	5.29	16	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ganciclovir [no description available]	7.41	1	2-aminopurines; oxopurine	antiinfective agent; antiviral drug
valacyclovir Valacyclovir: A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.	4.25	5	L-valyl ester	antiviral drug
penciclovir penciclovir : A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration.	7.54	2	2-aminopurines; propane-1,3-diols	antiviral drug

Condition	Relationship Strength	Studies
Chronic Illness [description not available]	2.05	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.05	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.42	2
Bladder Neck Obstruction [description not available]	2.41	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.41	1
Brain Disorders [description not available]	3.74	2
Altered Level of Consciousness [description not available]	2.6	1
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	3.74	2
Behavior Disorders [description not available]	2.74	3
Central Nervous System Disease [description not available]	2.21	1
B Virus Infection [description not available]	2.21	1
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	2.74	3
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	2.21	1
Acute Kidney Failure [description not available]	3.23	1
Shingles [description not available]	3.67	3
Herpes Zoster An acute infectious, usually self-limited, disease believed to represent activation of latent varicella-zoster virus (HERPESVIRUS 3, HUMAN) in those who have been rendered partially immune after a previous attack of CHICKENPOX. It involves the SENSORY GANGLIA and their areas of innervation and is characterized by severe neuralgic pain along the distribution of the affected nerve and crops of clustered vesicles over the area. (From Dorland, 27th ed)	3.67	3
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	3.23	1
Encephalopathy, Toxic [description not available]	2.95	4
Chronic Kidney Failure [description not available]	2.72	3
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	2.72	3
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.43	2
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.01	1
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.01	1
Delirium of Mixed Origin [description not available]	2.03	1
Hallucination of Body Sensation [description not available]	2.03	1
Delirium A disorder characterized by CONFUSION; inattentiveness; disorientation; ILLUSIONS; HALLUCINATIONS; agitation; and in some instances autonomic nervous system overactivity. It may result from toxic/metabolic conditions or structural brain lesions. (From Adams et al., Principles of Neurology, 6th ed, pp411-2)	2.03	1
Hallucinations Subjectively experienced sensations in the absence of an appropriate stimulus, but which are regarded by the individual as real. They may be of organic origin or associated with MENTAL DISORDERS.	2.03	1

9-carboxymethoxymethylguanine

Description

Cross-References

Synonyms (21)

Toxicity

Dosage Studied

Drug Classes (1)

Bioassays (18)

Research

Studies (17)

Study Types

9-carboxymethoxymethylguanine

Description

Cross-References

Synonyms (21)

Toxicity

Dosage Studied

Drug Classes (1)

Bioassays (18)

Research

Studies (17)

Study Types

Related Drugs (8)

Related Conditions (27)