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.
| Member | Definition | Role |
|---|
| (n-(p-cyanophenyl)-n'-(diphenylmethyl)guanidine)acetic acid | A trisubstituted guanidine, carrying 4-cyanophenyl, diphenylmethyl and carboxymethyl substituents, which is known to act as a highly potent sweetening agent. | [N-(4-cyanophenyl)-N'-(diphenylmethyl)guanidine]acetic acid |
| 3',4'-dichlorobenzamil | | 3,5-diamino-N-[amino-[(3,4-dichlorophenyl)methylimino]methyl]-6-chloro-2-pyrazinecarboxamide |
| 4-guanidinobenzoate | Benzoic acid substituted at the para position by a guanidino group. | 4-guanidinobenzoic acid |
| 5-(n,n-hexamethylene)amiloride | A member of the class of pyrazines that is amiloride in which the two amino hydrogens at position N-5 are replaced by a hexamethylene moiety, resulting in the formation of an azepane ring. | 5-(N,N-hexamethylene)amiloride |
| acetylphenylalanyl-prolyl-boroarginine | A C-terminal boronic acid petide that is N-acetyl-D-phenylalanyl-L-prolyl-L-arginine in which the C-termnal carboxy group has been replaced by a borono (-B(OH)2) group. A thrombin (Factor IIa) inhibitor, thereby acting as an anticoagulant. | Ac-(D)Phe-Pro-boroArg-OH |
| agmatine | | agmatine |
| amiloride | A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid. | amiloride |
| aminopotentidine | A benzamide obtained by formal condensation of the carboxy group of 4-aminobenzoic acid with the primary amino group of 1-(2-aminoethyl)-2-cyano-3-{3-[3-(piperidin-1-ylmethyl)phenoxy]propyl}guanidine. | aminopotentidine |
| apraclonidine | An imidazoline that is 2-amino 4,5-dihydro-1H-imidazoline in which one of the exocyclic amino hydrogens has been replaced by a 4-amino-2,6-dichlorophenyl group. | apraclonidine |
| arcaine | A guanidine derivative consisting of butane having guanidino groups at the 1- and 4-positions. | 1,4-diguanidinobutane |
| argininamide | An amino acid amide resulting from the formal condensation of the carboxy group of L-arginine with ammonia. | L-arginine amide |
| argininehydroxamic acid | An arginine derivative obtained by formal condensation of the carboxy group of L-arginine with the amino group of hydroxylamine. | L-arginine hydroxamate |
| batzelladine a | A carboxylic ester obtained by the formal condensation of (2aS,3S,4R,7R,8aS)-4-methyl-7-nonyl-2,2a,3,4,6,7,8,8a-octahydro-1H-5,6,8b-triazaacenaphthylene-3-carboxylic acid with the hydroxy group of 4-carbamimidamidobutyl (3R)-3-(9-hydroxynonyl)-1-imino-1,2,3,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-4-carboxylate. Isolated from a bright red Caribbean sponge, Batzella, it has potential anti-HIV activity. | batzelladine A |
| bcx 1812 | A member of the class of guanidines that is used (as its trihydrate) for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days. | peramivir |
| benzamil | | Benzamil |
| bethanidine | | bethanidine |
| betrixaban | A secondary carboxamide obtained by formal condensation of the carboxy group of 4-(N,N-dimethylcarbamimidoyl)benzoic acid with the amino group of 2-amino-N-(5-chloropyridin-2-yl)-5-methoxybenzamide. A synthetic anticoagulant compound that targets activated factor Xa in the coagulation cascade. | betrixaban |
| biguanides | | biguanide |
| callipeltin a | A 10-membered cyclodepsipeptide containing four amino acids in the L- configuration, Ala, Leu, Thr (2 residues); one (Arg) in the D-configuration; two N-methyl amino acids, N-MeAla and N-MeGln; a methoxy tyrosine, a 3, 4-dimethyl-L-glutamine, and a 4-amino-7-guanidino-2,3 dihydroxypentanoic acid (AGDHE), formally derived from L-Arg. It is obtained from the shallow water sponge Callipelta and has been found to show activity against HIV virus. | callipeltin A |
| camostat | A benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients. | camostat |
| cimetidine | A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach. | cimetidine |
| crambescidin 800 | An organic heteropentacyclic guanidine alkaloid isolated from the marine sponge Crambe crambe and Batzella. It exhibits anti-HIV-1 and anti-HSV-1 activity. | crambescidin 800 |
| creatine | A glycine derivative having methyl and amidino groups attached to the nitrogen. | creatine zwitterion; creatine |
| decarbamylsaxitoxin | A pyrrolopurine that is 2,6-diiminodecahydropyrrolo[1,2-c]purine carrying an additional hydroxymethyl substituent at position 4 as well as two hydroxy substituents at position 10. A toxin that is isolated from marine dinoflagellates and cyanobacteria and is known to cause paralytic shellfish poisoning. | decarbamoylsaxitoxin |
| delta-n-methylarginine | A non-proteinogenic L-alpha-amino acid that is L-arginine substituted by a methyl group at N(5)-position. | N(5)-methyl-L-arginine |
| dibromophakellin | An alkaloid isolated from the marine sponge Phakellia flabellata and Acanthella costata. It acts as an alpha2B adrenoceptor agonist. | (-)-dibromophakellin |
| dicyandiamido | A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a cyano group. It is used in the manufacture of fertilizers, pharmaceuticals, explosives, oil well drilling muds, and dyestuffs. | cyanoguanidine |
| diphenylguanidine | Guanidine carrying a phenyl substituent on each of the two amino groups. It is used as an accelerator in the rubber industry. | 1,3-diphenylguanidine |
| e 64 | | E64 zwitterion; E64 |
| epinastine | A benzazepine that is 6,11-dihydro-5H-dibenzo[b,e]azepine in which the azepine ring is fused to the e side of 4,5-dihydro-1H-imidazol-2-amine. | epinastine |
| ethylisopropylamiloride | A member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group. | ethylisopropylamiloride |
| famotidine | | famotidine |
| famotidine | | famotidine |
| gabexate methanesulfonate | | gabexate methanesulfonate |
| galegine | | Galegine |
| gamma-guanidinobutyric acid | The 4-guanidino derivative of butanoic acid. | 4-guanidinobutanoic acid zwitterion; 4-guanidinobutanoic acid; 4-guanidinobutyric acid |
| gamma-guanidinobutyric acid | A monocarboxylic acid that is butanoic acid substituted by a guanidino group at position 4. | 4-guanidinobutanoic acid zwitterion; 4-guanidinobutanoic acid; 4-guanidinobutyric acid |
| guanadrel | A spiroketal resulting from the formal condensation of the keto group of cyclohexanone with the hydroxy groups of 1-(2,3-dihydroxypropyl)guanidine. A postganglionic adrenergic blocking agent formerly used (generally as the sulfate salt) for the management of hypertension, it has been largely superseded by other drugs less likely to cause orthostatic hypotension (dizzy spells on standing up or stretching). | guanadrel |
| guanazodine | | guanazodine |
| guanethidine | A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group. | guanethidine |
| guanidine | An aminocarboxamidine, the parent compound of the guanidines. | guanidine |
| guanidinoethane sulfonate | The N-amidino derivative of taurine. | taurocyamine zwitterion; taurocyamine |
| guanidinohydantoin | An imidazolidine-2,4-dione substituted by a guanidino group at position 5. | 5-guanidinohydantoin |
| guanidinopropionic acid | A guanidine compound bearing an N-(2-carboxyethyl) substituent. It is a creatine analogue that has been found to decreases plasma glucose levels | 3-guanidinopropanoic acid zwitterion; 3-guanidinopropanoic acid |
| guazatine | A member of the class of guanidines that is dioctylamine in which a hydrogen from each of the terminal methyl groups is replaced by a guanidino group. Once used as a fungicidal seed dressing, it is no longer approved for use in the European Union. | iminoctadine |
| hexamidine | A polyether that is the bis(4-guanidinophenyl) ether of hexane-1,6-diol. | hexamidine |
| hordatine a | A member of the calss of benzofurans that is a homodimer of para-coumarylagmatine where a hydroxy group of one molecule has reacted across the other molecule's ethene double bond to combine the two molecules and form a furan ring. | hordatine A |
| hydroxyguanidine | A member of the class of guanidines that is guanidine in which one of the hydrogens attached to the nitrogen at position 1 is substituted by a hydroxy group. | N-hydroxyguanidine |
| l803087 | A fluoroindole that is 1H-indole substituted by phenyl, 4-{[(2S)-5-carbamimidamido-1-methoxy-1-oxopentan-2-yl]amino}-4-oxobutyl, fluoro and fluoro groups at positions 2, 3, 5 and 7, respectively. It is a selective nonpeptidic agonist of the somatostatin subtype-4 (SST4) receptor with Ki of 0.7 nM. | L-803087 |
| massadine | An alkaloid isolated from Stylissa massa. | massadine |
| metformin | A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1. | metformin |
| methylguanidine | A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group. | methylguanidine |
| mitoguazone | A hydrazone obtained by formal condensation of the two carbonyl groups of methylglyoxal with the primary amino groups of two molecules of aminoguanidine. | mitoguazone |
| n,n-dimethylarginine | A L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group. | N(omega),N(omega)-dimethyl-L-arginine |
| n(1)-guanyl-1,7-diaminoheptane | A member of the class of guanidines in which the imino hydrogen of guanidine itself has been replaced by a 7-aminoheptyl group. It is an inhibitor of deoxyhypusine synthase activity (GO:0034038). | 2-(7-aminoheptyl)guanidine |
| 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 | A leucine derivative obtained by fpormal condensation of the secondary amino group of 5-({2,3-dichloro-4-[1-methyl-5-(piperidin-4-yl)-1H-pyrazol-3-yl]phenoxy}methyl)-2-furoic acid and the carboxy group of N-amidino-L-leucylglycine | 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 |
| nafamostat | | nafamostat |
| nitroarginine | An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group. | N(gamma)-nitro-L-arginine |
| nopaline | An amino acid opine resulting from the formal reductive condensation of the amino group of L-arginine with the keto group of 2-oxopentanedioic acid. | D-nopaline |
| octopine | The (1R)-1-carboxyethyl derivative of L-arginine. It is a metabolite released by plant tumours. | D-octopine dizwitterion; D-octopine |
| omega-n-methylarginine | A L-arginine derivative with a N(omega)-methyl substituent. | (2S)-2-amino-5-[[amino(methylimino)methyl]amino]pentanoic acid; N(omega)-methyl-L-arginine zwitterion; N(omega)-methyl-L-arginine |
| omega-n-methylarginine | The zwitterion obtained from N(omega)-methyl-L-arginine by transfer of a proton from the carboxylic acid group to the alpha-amino group. | (2S)-2-amino-5-[[amino(methylimino)methyl]amino]pentanoic acid; N(omega)-methyl-L-arginine zwitterion; N(omega)-methyl-L-arginine |
| phenyl biguanide | A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a phenyl group. | phenyl biguanide |
| phenylamil | | Phenylamil |
| phleomycin d1 | A glycopeptide originally isolated from the bacterium Streptomyces verticillus which contains a (4'R)-4',5'-dihydro-2,4'-bi-1,3-thiazole-2',4-diyl moiety with a a 4-guanidylbutylaminocarbonyl group attached to the 4-position of the terminal thiazole ring. Like all phleomycins, phleomycin D1 can form complexes with redox-active metals such as Co, Cu, and Fe. | phleomycin D1 |
| pimagedine | A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide. | aminoguanidine |
| propamidine | A polyether that is the bis(4-guanidinophenyl) ether of propane-1,3-diol. Used (as its isethionate salt) for the treatment of minor eye or eyelid infections, such as conjunctivitis and blepharitis. | propamidine |
| saxitoxin | An alkaloid isolated from the marine dinoflagellates and cyanobacteria that causes paralytic shellfish poisoning. | saxitoxin |
| symmetric dimethylarginine | A L-arginine derivative having two methyl groups at the N(omega)- and N'(omega)-positions | N(omega),N'(omega)-dimethyl-L-arginine zwitterion; N(omega),N'(omega)-dimethyl-L-arginine |
| synthalin a | A member of the class of guanidines that is decane having guanidino groups at the 1- and 10-positions. | synthalin A |
| tegaserod | | tegaserod |
| tosylarginine methyl ester | An L-arginine ester that is methyl L-argininate in which one of the hydrogens attached to the alpha-nitrogen is substituted by a tosyl group. | TAMe |
| vanchrobactin | A catechol-type natural product that is composed of 2,3-dihydroxybenzoic acid, D-arginine and L-serine joined in sequence by peptide linkages. It is a siderophore synthesized by the bacterial fish pathogen Vibrio anguillarum. | vanchrobactin |
| zanamivir | | zanamivir |