guanidinohydantoin

Description

guanidinohydantoin: structure in first source [MeSH]

5-guanidinohydantoin : An imidazolidine-2,4-dione substituted by a guanidino group at position 5. [CHeBI]

Cross-References

ID Source	ID
PubMed CID	45071972
SCHEMBL ID	2124302
CHEBI ID	142614
MeSH ID	M0441255

Synonyms (13)

Synonym
5-guanidinoimidazolidine-2,4-dione
(2,5-dioxo-4-imidazolidinyl)guanidine
guanidinohydantoin
CHEBI:142614
n-(2,5-dioxoimidazolidin-4-yl)guanidine
5-guanidinohydantoin
104184-01-2
5-(amidinoamino)imidazolidine-2,4-dione
1-(2,5-dioxoimidazolidin-4-yl)guanidine
SCHEMBL2124302
DTXSID70662356
n''-(2,5-dioxoimidazolidin-4-yl)guanidine
5-guanidino-hydantoin

Drug Classes (2)

Class	Description
guanidines	Any organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
imidazolidine-2,4-dione	An imidazolidinone with oxo groups at position 2 and 4.

Pathways (5)

guanidinohydantoin is involved in 5 pathway(s), involving a total of 321 unique proteins and 100 unique compounds

Pathway	Proteins	Compounds
DNA Repair	255	47
Base Excision Repair	35	23
Base-Excision Repair, AP Site Formation	17	16
Depurination	10	7
Cleavage of the damaged purine	4	7

Research

Studies (36)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	13 (36.11)	29.6817
2010's	22 (61.11)	24.3611
2020's	1 (2.78)	2.80

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.78%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	35 (97.22%)	84.16%

Substance	Classes	Roles	Relationship Strength
agmatine	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite	low
gamma-guanidinobutyric acid	guanidines; monocarboxylic acid; zwitterion	fungal metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	low
creatine	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical	low
5-(n,n-hexamethylene)amiloride	aromatic amine; azepanes; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines	antineoplastic agent; apoptosis inducer; odorant receptor antagonist; sodium channel blocker	low
ethylisopropylamiloride	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker	low
pimagedine	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor	low
apraclonidine	dichlorobenzene; guanidines; imidazolines	alpha-adrenergic agonist; antiglaucoma drug; beta-adrenergic agonist; diagnostic agent; ophthalmology drug	low
arcaine	guanidines		low
bethanidine	guanidines	adrenergic antagonist; antihypertensive agent	low
camostat	benzoate ester; carboxylic ester; diester; guanidines; tertiary carboxamide	anti-inflammatory agent; anticoronaviral agent; antifibrinolytic drug; antihypertensive agent; antineoplastic agent; antiviral agent; serine protease inhibitor	low
cimetidine	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor	low
epinastine	benzazepine; guanidines	anti-allergic agent; H1-receptor antagonist; histamine antagonist; ophthalmology drug	low
famotidine	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor	low
guanethidine	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent	low
guanidine	carboxamidine; guanidines; one-carbon compound		low
guazatine	aliphatic nitrogen antifungal agent; guanidines; secondary amino compound	antifungal agrochemical	low
metformin	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic	low
nafamostat	benzoic acids; guanidines		low
(n-(p-cyanophenyl)-n'-(diphenylmethyl)guanidine)acetic acid	glycine derivative; guanidines	epitope; sweetening agent	low
phenyl biguanide	guanidines	central nervous system drug	low
biguanides	guanidines		low
diphenylguanidine	guanidines	allergen	low
dicyandiamido	guanidines; nitrile	curing agent; explosive; fertilizer; flame retardant; nitrification inhibitor	low
methylguanidine	guanidines	EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite; uremic toxin	low
galegine	guanidines		low
amiloride	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker	low
guanazodine	guanidines		low
guanadrel	guanidines; spiroketal	adrenergic antagonist; antihypertensive agent	low
zanamivir	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor	low
propamidine	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug	low
hexamidine	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug	low
synthalin a	guanidines	hepatotoxic agent; hypoglycemic agent; nephrotoxin	low
guanidinopropionic acid	guanidines; zwitterion	hypoglycemic agent	low
guanidinoethane sulfonate	guanidines; organosulfonic acid; zwitterion		low
hydroxyguanidine	guanidines; one-carbon compound	antineoplastic agent; antiviral agent	low
nopaline	amino acid opine; D-glutamic acid derivative; guanidines; L-arginine derivative; secondary amino compound; tricarboxylic acid		low
benzamil	guanidines; pyrazines		low
octopine	amino acid opine; amino dicarboxylic acid; D-alpha-amino acid zwitterion; D-arginine derivative; guanidines; secondary amino compound	animal metabolite; xenobiotic metabolite	low
3',4'-dichlorobenzamil	guanidines; pyrazines		low
acetylphenylalanyl-prolyl-boroarginine	acetamides; C-terminal boronic acid peptide; guanidines	anticoagulant; EC 3.4.21.5 (thrombin) inhibitor	low
n,n-dimethylarginine	dimethylarginine; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor	low
e 64	dicarboxylic acid monoamide; epoxy monocarboxylic acid; guanidines; L-leucine derivative; zwitterion	antimalarial; antiparasitic agent; protease inhibitor	low
omega-n-methylarginine	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid		low
argininehydroxamic acid	guanidines; hydroxamic acid; L-arginine derivative		low
bcx 1812	3-hydroxy monocarboxylic acid; acetamides; cyclopentanols; guanidines	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor	low
4-guanidinobenzoate	benzoic acids; guanidines		low
aminopotentidine	aromatic ether; benzamides; guanidines; nitrile; piperidines; substituted aniline	H2-receptor antagonist	low
symmetric dimethylarginine	amino acid zwitterion; dimethylarginine; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor	low
delta-n-methylarginine	guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid		low
nitroarginine	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid		low
argininamide	amino acid amide; guanidines; L-arginine derivative		low
n(1)-guanyl-1,7-diaminoheptane	guanidines; primary amino compound	antineoplastic agent; EC 2.5.1.46 (deoxyhypusine synthase) inhibitor	low
tosylarginine methyl ester	guanidines; L-arginine ester; methyl ester; sulfonamide		low
N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide	D-leucine derivative; dichlorobenzene; furoic acid; glycine derivative; guanidines; pyrazolylpiperidine		low
l803087	benzenes; fluoroindole; guanidines; L-arginine derivative; methyl ester; phenylindole; secondary carboxamide	somatostatin receptor agonist	low
mitoguazone	guanidines; hydrazone	antineoplastic agent; apoptosis inducer; EC 4.1.1.50 (adenosylmethionine decarboxylase) inhibitor	low
famotidine	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor	low
gabexate methanesulfonate	benzoate ester; guanidines; methanesulfonate salt		low
betrixaban	benzamides; guanidines; monochloropyridine; monomethoxybenzene; secondary carboxamide	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor	low
massadine	alkaloid; guanidines; organobromine compound; pyrrolecarboxamide	animal metabolite; EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor; marine metabolite	low
batzelladine a	alkaloid; carboxylic ester; guanidines; organic heterotricyclic compound; pyrrolopyrimidine; triazaacenaphthylene	anti-HIV-1 agent; metabolite	low
vanchrobactin	catechols; dipeptide; guanidines; monocarboxylic acid; primary alcohol; triol	bacterial metabolite; marine metabolite; siderophore	low
decarbamylsaxitoxin	alkaloid; guanidines; ketone hydrate; paralytic shellfish toxin; primary alcohol; pyrrolopurine	bacterial metabolite; marine metabolite; neurotoxin; toxin; xenobiotic	low
dibromophakellin	alkaloid; guanidines; organobromine compound	alpha-adrenergic agonist; animal metabolite; marine metabolite	low
hordatine a	aromatic ether; benzofurans; dicarboxylic acid diamide; guanidines; phenols	adrenergic antagonist; metabolite	low
crambescidin 800	alkaloid; carboxylic ester; guanidines; monocarboxylic acid amide; organic heteropentacyclic compound; primary amino compound; secondary alcohol; spiro compound	anti-HIV-1 agent; anti-HSV-1 agent; antimalarial; marine metabolite	low
saxitoxin	alkaloid; carbamate ester; guanidines; ketone hydrate; paralytic shellfish toxin; pyrrolopurine	cyanotoxin; marine metabolite; neurotoxin; sodium channel blocker; toxin	low
callipeltin a	cyclodepsipeptide; guanidines; lactone; oligopeptide; phenols	anti-HIV-1 agent; antifungal agent; metabolite	low
phleomycin d1	bi-1,3-thiazole; chelate-forming peptide; disaccharide derivative; glycopeptide; guanidines	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; bacterial metabolite	low
phenylamil	guanidines; pyrazines		low
tegaserod	carboxamidine; guanidines; hydrazines; indoles	gastrointestinal drug; serotonergic agonist	low
allantoin	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary	low
hydantoin-5-propionic acid	imidazolidine-2,4-dione; monocarboxylic acid	metabolite; mouse metabolite	low
phenytoin	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent	low
dantrolene	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist	low
ethotoin	imidazolidine-2,4-dione	anticonvulsant	low
mephenytoin	imidazolidine-2,4-dione	anticonvulsant	low
5,5-dimethylhydantoin	imidazolidine-2,4-dione		low
hydantoins	imidazolidine-2,4-dione		low
hydroxyphenytoin	imidazolidine-2,4-dione; phenols	metabolite	low
chlordantoin	imidazolidine-2,4-dione		low
iprodione	benzenes; dichlorophenyl dicarboximide fungicide; imidazole fungicide; imidazolidine-2,4-dione; ureas	antifungal agrochemical; nematicide	low
fosphenytoin	imidazolidine-2,4-dione		low
diazolidinylurea	imidazolidine-2,4-dione		low
5-methylhydantoin	imidazolidine-2,4-dione		low
1-methylhydantoin	imidazolidine-2,4-dione	bacterial metabolite	low
1-aminohydantoin	imidazolidine-2,4-dione		low
ethylphenylhydantoin	imidazolidine-2,4-dione		low
alloxanic acid	imidazolidine-2,4-dione		low
(S)-Mephenytoin	imidazolidine-2,4-dione		low
bw 245c	imidazolidine-2,4-dione; monocarboxylic acid; secondary alcohol		low
4-hydroxymephenytoin	imidazolidine-2,4-dione		low
bw a868c	imidazolidine-2,4-dione		low
5-(3,4-dihydroxy-1,5-cyclohexadien-1-yl)-5-phenylhydantoin	imidazolidine-2,4-dione		low
3-[2-hydroxy-3-(4-morpholinyl)propyl]-5,5-dimethylimidazolidine-2,4-dione	imidazolidine-2,4-dione		low
2-(2,5-dioxo-4,4-dipropyl-1-imidazolidinyl)-N-(3-methoxyphenyl)acetamide	imidazolidine-2,4-dione		low
4-[(2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)methyl]benzoic acid methyl ester	imidazolidine-2,4-dione		low
2-(2,5-dioxo-4-imidazolidinyl)-N-(1-naphthalenyl)acetamide	imidazolidine-2,4-dione		low
3-[2-[4-(4-chlorophenyl)sulfonyl-1-piperazinyl]-2-oxoethyl]-5-(2-methylpropyl)imidazolidine-2,4-dione	imidazolidine-2,4-dione		low
2-[[2-(4-ethyl-4-methyl-2,5-dioxo-1-imidazolidinyl)-1-oxoethyl]amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide	imidazolidine-2,4-dione		low
5-methyl-3-[2-(4-morpholinyl)-2-oxoethyl]-5-phenylimidazolidine-2,4-dione	imidazolidine-2,4-dione		low
N-(3-cyanophenyl)-2-(4-ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)acetamide	imidazolidine-2,4-dione		low
2-[4-[4-(difluoromethoxy)phenyl]-4-methyl-2,5-dioxo-1-imidazolidinyl]acetic acid ethyl ester	imidazolidine-2,4-dione		low
2-(4-butyl-4-methyl-2,5-dioxo-1-imidazolidinyl)-N-[4-(4-morpholinylsulfonyl)phenyl]acetamide	imidazolidine-2,4-dione		low
N-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]-2-[4-methyl-4-(4-methylphenyl)-2,5-dioxo-1-imidazolidinyl]acetamide	imidazolidine-2,4-dione		low
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[4-methyl-2,5-dioxo-4-(2-phenylethyl)-1-imidazolidinyl]acetamide	imidazolidine-2,4-dione		low
N-[3-(1-azepanylsulfonyl)phenyl]-2-[4-(1H-indol-3-ylmethyl)-2,5-dioxo-1-imidazolidinyl]acetamide	imidazolidine-2,4-dione		low
2-[4-(4-methoxyphenyl)-4-methyl-2,5-dioxo-1-imidazolidinyl]-N-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]acetamide	imidazolidine-2,4-dione		low
2-(2',5'-dioxo-1'-spiro[3,4-dihydro-2H-1-benzopyran-4,4'-imidazolidine]yl)-N-[4-[ethyl(propan-2-yl)amino]phenyl]acetamide	imidazolidine-2,4-dione		low
nitrofurantoin	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent	low
azimilide	imidazolidine-2,4-dione		low
nifurtoinol	hydrazone; imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent	low
5-hydroxydantrolene	imidazolidine-2,4-dione		low
N-(4-ethoxyphenyl)-2-[4-[2-(methylthio)ethyl]-2,5-dioxo-1-imidazolidinyl]acetamide	imidazolidine-2,4-dione		low
(5S,5aR,8aS,8bR)-7-tert-butyl-5-(4-methoxyphenyl)-8b-methyl-2-(3-methylphenyl)-5a,8a-dihydro-5H-pyrrolo[1,2]pyrrolo[4,5-a]imidazole-1,3,6,8-tetrone	imidazolidine-2,4-dione		low

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	2000's	2010's
adenine	2	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2013	2017	9.0	low	0	2
allantoin	2	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary	2016	2018	7.0	low	0	2
cytosine	1	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2013	2013	11.0	low	0	1
purine	1	purine		2020	2020	4.0	low	0	1
lysine	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite	2013	2013	11.0	low	0	1
valine	1	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	2010	2010	14.0	low	1	0
2-aminopurine	1	2-aminopurines; nucleobase analogue	antimetabolite	2013	2013	11.0	low	0	1
hydantoins	36	imidazolidine-2,4-dione		2001	2020	13.0	high	18	18
azomycin	1	C-nitro compound; imidazoles	antitubercular agent	2017	2017	7.0	low	0	1
2'-deoxy-5'-adenosine monophosphate	1	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-monophosphate	fundamental metabolite	2010	2010	14.0	low	1	0
chromates	1	chromium oxoanion; divalent inorganic anion	oxidising agent	2010	2010	14.0	low	1	0
chlorine	1	diatomic chlorine; gas molecular entity	bleaching agent	2018	2018	6.0	low	0	1
2,6-diaminopurine	1	2,6-diaminopurines; primary amino compound	antineoplastic agent	2013	2013	11.0	low	0	1
4,6-diamino-5-n-formamidopyrimidine	1	aminopyrimidine; formamidopyrimidine		2010	2010	14.0	low	1	0
peroxynitrous acid	2	nitrogen oxoacid		2005	2013	15.0	low	1	1
singlet oxygen	3	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient	2003	2018	12.7	low	1	2
oxazolone	2			2005	2015	14.0	low	1	1
oligonucleotides	1			2005	2005	19.0	low	1	0
spiroiminodihydantoin	25	azaspiro compound	mutagen	2001	2020	14.3	high	16	9
8-oxodeoxyguanosine triphosphate	1	purine 2'-deoxyribonucleoside 5'-triphosphate	mutagen	2011	2011	13.0	low	0	1
deoxyguanosine	5	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2005	2015	14.0	low	2	3
2'-deoxyguanosine 5'-phosphate	1	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite	2010	2010	14.0	low	1	0
deoxyguanosine triphosphate	1	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-triphosphate	Arabidopsis thaliana metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite	2016	2016	8.0	low	0	1
guanosine triphosphate	1	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor	2011	2011	13.0	low	0	1
guanine	18	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2001	2020	13.1	medium	8	10
guanosine	25	guanosines; purines D-ribonucleoside	fundamental metabolite	2001	2020	14.3	medium	16	9
9-methylguanine	1			2018	2018	6.0	low	0	1
8-hydroxyguanosine	1	purine nucleoside		2005	2005	19.0	low	1	0
8-hydroxyguanine	10	oxopurine		2001	2017	13.7	low	4	6
8-hydroxy-2'-deoxyguanosine	3	guanosines	biomarker	2005	2013	14.0	low	1	2
8-hydroxyguanosine triphosphate	1			2011	2011	13.0	low	0	1
5-guanidino-4-nitroimidazole	1			2017	2017	7.0	medium	0	1

Condition	Indicated	Studies	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
Breast Cancer	0	1	2005	2005	19.0	high	0	0	0	1	0	0
Breast Neoplasms	0	1	2005	2005	19.0	high	0	0	0	1	0	0

Dosage (2)

Article	Year
Comparative analysis of four oxidized guanine lesions from reactions of DNA with peroxynitrite, singlet oxygen, and γ-radiation. Chemical research in toxicology, , Feb-18, Volume: 26, Issue:2	2013
Quantitation of four guanine oxidation products from reaction of DNA with varying doses of peroxynitrite. Chemical research in toxicology, , Volume: 18, Issue:12	2005