Cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
| Member | Definition | Role |
|---|
| 1-azakenpaullone | An organic heterotetracyclic compound that is 7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indole substituted at positions 6 and 9 by oxo and bromo groups respectively. | 1-azakenpaullone |
| 2-hydroxy-1,4-benzoxazin-3-one | A benzoxazine bearing hydroxy and oxo substituents at positions 2 and 3 respectively. | HBOA |
| apixaban | A pyrazolopyridine that is 7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide substituted at position 1 by a 4-methoxyphenyl group and at position 6 by a 4-(2-oxopiperidin-1-yl)phenyl group. It is used for the prevention and treatment of thromboembolic diseases. | apixaban |
| benazepril | A benzazepine that is benazeprilat in which the carboxy group of the 2-amino-4-phenylbutanoic acid moiety has been converted to the corresponding ethyl ester. It is used (generally as its hydrochloride salt) as a prodrug for the angiotensin-converting enzyme inhibitor benazeprilat in the treatment of hypertension and heart failure. | benazepril |
| benazeprilat | A benzazepine that is 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-pro-S hydrogen is replaced by the amino group of (2S)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug benazepril in the treatment of hypertension and heart failure. | benazeprilat |
| chaetominine | An organic heterotetracyclic compound that consists of 4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione substituted by a hydroxy group at position 5, a methyl group at position 2 and a 4-oxoquinazolin-3(4H)-yl group at position 4 (the 2S,4R,5aS,9cS stereoisomer). It is a cytotoxic alkaloid isolated from the endophytic fungus Chaetomium. | chaetominine |
| chlormezanone | A 1,3-thiazine that is 1,3-thiazinan-4-one S,S-dioxide in which a hydrogen at position 2 is substituted by a 4-chlorophenyl group and the hydrogen attached to the nitrogen is substituted by methyl. A non-benzodiazepine muscle relaxant, it was used in the management of anxiety and in the treatment of muscle spasms until being discontinued worldwide by its manufacturer in 1996, due to rare but serious cutaneous reactions. | chlormezanone |
| cilostazol | A lactam that is 3,4-dihydroquinolin-2(1H)-one in which the hydrogen at position 6 is substituted by a 4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy group. | cilostazol |
| creatinine | A lactam obtained by formal cyclocondensation of creatine. It is a metabolite of creatine. | creatinine |
| cytisine | An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking. | cytisine |
| cytochalasin b | An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments. | cytochalasin B |
| cytotrienin a | A 21-membered macrocyclic lactam which contains three conjugated double bonds as part of the ring system. It acts as an apoptosis inducer in human leukemia HL-60 cells and is isolated from Streptomyces sp. | cytotrienin A |
| dilacor xr | A lactam that is 2,3-dihydro-1,5-benzothiazepin-4(5H)-one in which positions 2 and 3 are substituted by 4-methoxyphenyl and acetoxy, respectively, while the hydrogen attached to the nitrogen is substituted by a 2-(dimethylamino)ethyl group. | 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate |
| grazoprevir | An azamacrocyclic compound that is a hepatitis C protease inhibitor used in combination with elbasvir (under the brand name Zepatier) for treatment of chronic HCV genotypes 1 or 4 infection in adults. | grazoprevir |
| herbimycin | A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects. | herbimycin |
| ixabepilone | A macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. | ixabepilone |
| lactacystin | L-Cysteine substituted at nitrogen by an acetyl group and at sulfur by a substituted-lactam carbonyl group. | lactacystin |
| ly 411575 | A dibenzoazepine that is 5,7-dihydro-6H-dibenzo[b,d]azepin-6-one which is substituted at the 7 pro-S position by the C-terminal carboxamide nitrogen of N(2)-[(2S)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-L-alaninamide. It is a potent, cell permeable and selective gamma-secretase inhibitor. It has been tested as a possible treatment for Alzheimer's disease and shows promise for its potential to counteract severe hearing loss. | LY-411575 |
| mycotrienin i | | Ansatrienin A |
| N-[(4-chlorophenyl)methyl]-2-[(2R,6S)-5,12-dioxo-2-phenyl-1-oxa-4-azacyclododec-8-en-6-yl]acetamide | | N-[(4-chlorophenyl)methyl]-2-[(2R,6S)-5,12-dioxo-2-phenyl-1-oxa-4-azacyclododec-8-en-6-yl]acetamide |
| n-methylpyrrolidone | A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group. | N-methylpyrrolidin-2-one |
| nsc 664704 | An indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta). | kenpaullone |
| palustrine | | Palustrine |
| paullone | An indolobenzazepine that is 5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine carrying an oxo substituent at position 6. | paullone |
| pf 1163a | A macrolide antibiotic that is 4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione substituted by a 4-(2-hydroxyethoxy)benzyl group at position 3 and a (2R)-2-hydroxypentyl group at position 13 (the 3S,10R,13S stereoisomer). It is isolated from Penicillium sp.PF1163 and exhibits antifungal activity against the pathogenic fungal strain Candida albicans TIMM1768. | PF 1163A |
| pf 1163b | A macrolide antibiotic that is 4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione substituted by a 4-(2-hydroxyethoxy)benzyl group at position 3 and a pentyl group at position 13 (the 3S,10R,13S stereoisomer). It is isolated from Penicillium sp.PF1163 and exhibits antifungal activity against the pathogenic fungal strain Candida albicans TIMM1768. | PF 1163B |
| phenanthridone | A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity. | phenanthridone |
| pseurotin | A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively. | pseurotin A |
| rifamycin sv | A member of the class of rifamycins that exhibits antibiotic and antitubercular properties. | rifamycin SV |
| rifaximin | A semisynthetic member of the class of rifamycins and non-systemic gastrointestinal site-specific broad spectrum antibiotic. Used in the treatment of traveller's diarrhoea, hepatic encephalopathy and irritable bowel syndrome. | rifaximin |
| rivaroxaban | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-chlorothiophene-2-carboxylic acid with the amino group of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. An anticoagulant used for prophylaxis of venous thromboembolism in patients with knee or hip replacement surgery. | rivaroxaban |
| ro 4929097 | A member of the class of dibenzoazepines that is the amide formed from formal condensation of the carboxy group of 2,2-dimethyl-3-oxo-3-[(2,2,3,3,3-pentafluoropropyl)amino]propanoic acid with the amino group of (7S)-7-amino-5,7-dihydrodibenzo[b,d]azepin-6-one. | RO4929097 |
| simeprevir | | simeprevir |
| streptogramin a | A macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms including methicillin-resistant Staphylococcus aureus. | pristinamycin IIA |
| tentoxin | | tentoxin |
| thiocillin | | Thiocillin |
| tmc-95a | A 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. It includes a R-hydroxy group at position 11 and a (3-methyl-2-oxopentanoyl)amino group at position at position 18 with a S-methyl group. It acts as a proteasome inhibitor and is obtained from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample. | TMC-95A |
| tmc-95b | A 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. A stereoisomer of TMC-95A, it has a [(3R)-3-methyl-2-oxopentanoyl]amino group at position 18. It acts as a proteasome inhibitor and is isolated from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample. | TMC-95B |
| umirolimus | | Umirolimus |
| vicenistatin | | Vicenistatin |
| zotarolimus | | zotarolimus |