A compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
| Member | Definition | Role |
|---|
| 1,3-dicyanobenzene | | isophthalonitrile |
| 2-(1-piperidinyl)-6-thiophen-2-yl-4-(trifluoromethyl)-3-pyridinecarbonitrile | | 2-(1-piperidinyl)-6-thiophen-2-yl-4-(trifluoromethyl)-3-pyridinecarbonitrile |
| 2-(3,4-dimethoxyphenyl)-5-amino-2-isopropylvaleronitrile | A nitrile that is pentanenitrile substituted by a 3,4-dimethoxyphenyl group at position 2, a methylamino group at position 4 and an isopropyl group at position 2. It is a metabolite of the drug verapamil. | D617 |
| 2-(4-fluorophenyl)-2-[4-[(4-fluorophenyl)-oxomethyl]phenyl]acetonitrile | | 2-(4-fluorophenyl)-2-[4-[(4-fluorophenyl)-oxomethyl]phenyl]acetonitrile |
| 2-(methylamino)-6-thiophen-2-yl-4-(trifluoromethyl)-3-pyridinecarbonitrile | | 2-(methylamino)-6-thiophen-2-yl-4-(trifluoromethyl)-3-pyridinecarbonitrile |
| 2-[(3-oxo-1-cyclohexenyl)amino]benzonitrile | | 2-[(3-oxo-1-cyclohexenyl)amino]benzonitrile |
| 2-[(4-chlorophenyl)methoxy]-6-methoxybenzonitrile | | 2-[(4-chlorophenyl)methoxy]-6-methoxybenzonitrile |
| 2-[3-(diethylamino)propylamino]-4-(methoxymethyl)-6-methyl-3-pyridinecarbonitrile | | 2-[3-(diethylamino)propylamino]-4-(methoxymethyl)-6-methyl-3-pyridinecarbonitrile |
| 2-amino-5-ethyl-4-(2-furanyl)-6-propyl-3-pyridinecarbonitrile | | 2-amino-5-ethyl-4-(2-furanyl)-6-propyl-3-pyridinecarbonitrile |
| 2-cyanophenol | | 2-Cyanophenol |
| 2-hydroxy-3-(5-((morpholin-4-yl)methyl)pyridin-2-yl)-1h-indole-5-carbonitrile | A member of the class of hydroxyindoles that is 1H-indole substituted by hydroxy, 5-(morpholin-4-ylmethyl)pyridin-2-yl, and cyano groups at positions 2, 3 and 5, respectively. It is a potent, brain permeable inhibitor of human GSK3alpha and GSK3beta with Ki of 6.9 nM and 31 nM, respectively. The drug was being developed by AstraZeneca for the treatment of Alzheimer's disease (clinical trial now discontinued). | AZD1080 |
| 2-oxo-4,6-dithiophen-2-yl-1H-pyridine-3-carbonitrile | | 2-oxo-4,6-dithiophen-2-yl-1H-pyridine-3-carbonitrile |
| 2,3-bis(4-hydroxyphenyl)-propionitrile | A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta). | 2,3-bis(4-hydroxyphenyl)propionitrile |
| 2,6-diamino-4-(1-phenylethyl)-4H-thiopyran-3,5-dicarbonitrile | | 2,6-diamino-4-(1-phenylethyl)-4H-thiopyran-3,5-dicarbonitrile |
| 3-[di(propan-2-yl)phosphorylmethyl]benzonitrile | | 3-[di(propan-2-yl)phosphorylmethyl]benzonitrile |
| 3-cyano-4-phenyl-6-(3-bromo-6-hydroxyphenyl)-2-pyridone | A member of the class of pyridones that is 2-pyridone carrying cyano, phenyl and 3-bromo-6-hydroxyphenyl substituents at positions 3, 4 and 6 respectively | 3-cyano-4-phenyl-6-(3-bromo-6-hydroxyphenyl)-2-pyridone |
| 3-cyanopyridine | A nitrile that is pyridine substituted by a cyano group at position 3. | 3-pyridinecarbonitrile |
| 3,4-epithiobutanenitrile | | 2-(thiiran-2-yl)acetonitrile |
| 4-(1H-imidazol-1-ylmethyl)benzonitrile | | 4-(1H-imidazol-1-ylmethyl)benzonitrile |
| 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile | A member of the class of triazoles that is 1-chloro-4-(3-phenylpropyl)benzene substituted at position 3 of the propyl moiety by cyano and 1,2,4-triazol-1-ylmethyl groups. | 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile |
| 4-(methoxymethyl)-6-methyl-2-(2-methylanilino)-3-pyridinecarbonitrile | | 4-(methoxymethyl)-6-methyl-2-(2-methylanilino)-3-pyridinecarbonitrile |
| 4-[(4-chloro-5-dithiazolylidene)amino]benzonitrile | | 4-[(4-chloro-5-dithiazolylidene)amino]benzonitrile |
| 4-[[[4-(2-furanylmethyl)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-3-yl]thio]methyl]benzonitrile | | 4-[[[4-(2-furanylmethyl)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-3-yl]thio]methyl]benzonitrile |
| 4-[4-[2-hydroxy-3-(4-morpholinyl)propoxy]phenyl]benzonitrile | | 4-[4-[2-hydroxy-3-(4-morpholinyl)propoxy]phenyl]benzonitrile |
| 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile | A pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr. It is the active insecticide of the proinsecticide chlorfenapyr. | tralopyril |
| 4-phenyl-3-furoxancarbonitrile | A 1,2,5-oxadiazole substituted by an oxido, cyano and phenyl groups at positions 2, 3 and 4, respectively. It is a vasodilator and inhibitor of platelet aggregation. | 4-phenyl-3-furoxancarbonitrile |
| 4,6-dimethyl-2-[3-(4-morpholinyl)propylamino]-3-pyridinecarbonitrile | | 4,6-dimethyl-2-[3-(4-morpholinyl)propylamino]-3-pyridinecarbonitrile |
| 5-Chloro-2-hydroxy-4,6-dimethylnicotinonitrile | | 5-Chloro-2-hydroxy-4,6-dimethylnicotinonitrile |
| 5-ethyl-4,6-dimethyl-2-sulfanylidene-1H-pyridine-3-carbonitrile | | 5-ethyl-4,6-dimethyl-2-sulfanylidene-1H-pyridine-3-carbonitrile |
| 6-amino-1-(4-chlorophenyl)-2-oxo-4-(1,2,4-triazol-1-ylmethyl)-5-pyrimidinecarbonitrile | | 6-amino-1-(4-chlorophenyl)-2-oxo-4-(1,2,4-triazol-1-ylmethyl)-5-pyrimidinecarbonitrile |
| 6-amino-3-(methoxymethyl)-5-spiro[2H-pyrano[2,3-c]pyrazole-4,4'-thiane]carbonitrile | | 6-amino-3-(methoxymethyl)-5-spiro[2H-pyrano[2,3-c]pyrazole-4,4'-thiane]carbonitrile |
| 6-hydroxy-1-(3-hydroxypropyl)-4-methyl-2-oxo-5-(1-piperidinylmethyl)-3-pyridinecarbonitrile | | 6-hydroxy-1-(3-hydroxypropyl)-4-methyl-2-oxo-5-(1-piperidinylmethyl)-3-pyridinecarbonitrile |
| 6-methyl-2-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile | | 6-methyl-2-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile |
| 6-tert-butyl-2-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile | | 6-tert-butyl-2-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile |
| ag-490 | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoic acid with the amino group of benzylamine. | tyrphostin B42 |
| alectinib | An organic heterotetracyclic compound that is 6,6-dimethyl-5,6-dihydro-11H-benzo[b]carbazol-11-one carrying additional cyano, 4-(morpholin-4-yl)piperidin-1-yl and ethyl substituents at positions 3, 8 and 9 respectively. Used (as the hydrochloride salt) for the treatment of patients with anaplastic lymphoma kinase-positive, metastatic non-small cell lung cancer. | alectinib |
| alogliptin | A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes. | alogliptin |
| alpha-(p-Methoxyphenyl)-2-pyridineacrylonitrile | | alpha-(p-Methoxyphenyl)-2-pyridineacrylonitrile |
| alpha-cyano-4-hydroxycinnamic acid | A monohydroxycinnamic acid that is 4-hydroxycinnamic acid in which the hydrogen alpha- to the carboxy group is replaced by a cyano group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of peptides and oligonucleotides. | alpha-cyano-4-hydroxycinnamic acid |
| alpha(-(cyclopropylcarbonyl)-2-(methyvlsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile) | A beta-diketone and nitrile resulting from the the degradation of the isoxazole ring of isoxaflutole. The active herbicide of the proherbicide isoxaflutole. | 2-cyano-3-cyclopropyl-1-(2-mesyl-4-trifluoromethylphenyl)propan-1,3-dione |
| 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 |
| an2728 | A member of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group. A phosphodiesterase 4 inhibitor that is used for treatment of mild to moderate atopic dermatitis in children and adults. | crisaborole |
| anastrozole | A 1,2,4-triazole compound having a 3,5-bis(2-cyano-2-propyl)benzyl group at the 1-position. | anastrozole |
| AZ3451 | A member of the class of benzimidazoles that is 1H-benzimidazole substituted by (1S)-1-cyclohexylethyl, 6-bromo-1,3-benzodioxol-5-yl, and 4-(cyanoanilino)acyl groups at positions 1, 2 and 5, respectively. It is an allosteric modulator of protease-activated receptor 2 (IC50 = 23 nM) and exhibits anti-osteoarthritis properties. | AZ3451 |
| azoxystrobin | An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture. | azoxystrobin |
| baricitinib | A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine substituted by a 1-[3-(cyanomethyl)-1-(ethanesulfonyl)azetidin-3-yl]-1H-pyrazol-4-yl group at position 5. It is an FDA approved selective Janus Kinase 1 and 2 (JAK1 and JAK2) inhibitor used for the treatment of rheumatoid arthritis. | baricitinib |
| bay 11-7082 | A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells. | (E)-3-tosylacrylonitrile |
| bay 11-7085 | A sulfone that is benzene substituted by [(E)-2-cyanoethenyl]sulfonyl and tert-butyl groups at position 1 and 4, respectively. It is an irreversible inhibitor of IkappaB-alpha phosphorylation in cells (IC50 = 10 muM) and prevents the activation of NF-kappaB. | BAY11-7085 |
| benzonitrile | A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group. | benzonitrile |
| benzyl cyanide | A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a phenyl group. | phenylacetonitrile |
| bezitramide | | bezitramide |
| bicalutamide | A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group. | N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide |
| bms 214662 | A member of the class of benzodiazepines that is 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine substituted by (1H-imidazol-5-yl)methyl, benzyl, (thiophen-2-yl)sulfonyl, and cyano groups at positions 1, 3R, 4 and 7, respectively. It is a potent inhibitor of farnesyltransferase (IC50 = 1.35nM) which was under clinical development for the treatment of solid tumors. | BMS-214662 |
| bms 477118 | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes. | saxagliptin |
| bosutinib | An aminoquinoline that is 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline bearing additional cyano and methoxy substituents at positions 3 and 6 respectively. | bosutinib |
| carbonyl cyanide m-chlorophenyl hydrazone | A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death. | CCCP |
| carbonyl cyanide p-trifluoromethoxyphenylhydrazone | A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group. | carbonyl cyanide p-trifluoromethoxyphenylhydrazone |
| chlorfenapyr | A member of the class of pyrroles that is 4-bromo-1H-pyrrole-3-carbonitrile which is substituted at positions 1, 2 and 5 by ethoxymethyl, p-chlorophenyl and trifluoromethyl groups, respectively. A proinsecticide used for termite control and crop protection against several insects and mite pests. | chlorfenapyr |
| chloroacetonitrile | | Chloroacetonitrile |
| cimaterol | | 2-amino-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzonitrile |
| 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 |
| citalopram | A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group. | 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile |
| closantel | An aromatic amide resulting from the formal condensation of the carboxy group of 3,5-diiodosalicylic acid with the amino group of aniline substituted at positions 2, 4, and 5 by methyl, (4-chlorophenyl)(cyano)methyl, and methyl groups respectively. | N-{5-chloro-4-[(4-chlorophenyl)(cyano)methyl]-2-methylphenyl}-2-hydroxy-3,5-diiodobenzamide |
| crotononitrile | | crotononitrile |
| cyanamide | A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group. | cyanamide |
| cyanophenphos | | Cyanofenphos |
| cyanopyrazine | | cyanopyrazine |
| cyantraniliprole | A carboxamide that is chlorantraniliprole in which the chlorine atom attached to the phenyl ring has been replaced by a cyano group. A ryanodine receptor agonist, it is used as insecticide for the control of whitefly, thrips, aphids, fruitflies, and fruit worms in crops such as onions, potatoes and tomatoes. It is highly toxic to honeybees. | cyantraniliprole |
| cyazofamid | A member of the class of imidazoles carrying dimethylsulfamyl, cyano, chloro and 4-tolyl substituents at positions 1, 2, 4 and 5 respectively. A fungicide used mainly for controlling Oomycete and Plasmodiophora diseases on potatoes and tomatoes. It is a skin and eye irritant and is moderately toxic to birds, most aquatic organisms, honeybees and earthworms. | cyazofamid |
| cyc 682 | A nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML). | sapacitabine |
| cyenopyrafen | A member of the class of pyrazoles that is ethene in which the hydrogens at position 1 have been replaced by p-tert-butylphenyl and cyano groups, while the hydrogens at position 2 have been replaced by pivaloyloxy and 1,3,4-trimethylpyrazol-5-yl groups (the E isomer). A proacaricide (by hydrolysis of the pivalate ester linkage to give the corresponding enol), it was formerly used for the control of mites in fruit, vegetables and tea. | cyenopyrafen |
| cyflumetofen | A nitrile that is acetonitrile in which the methyl hydrogens have been replaced by o-trifluoromethylbenzoyl, p-tert-butylphenyl, and (2-methoxyethoxy)carbonyl groups. | 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate |
| cyfluthrin | A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile. | cyfluthrin |
| cyhalothrin | A carboxylic ester obtained by formal condensation between 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. | cyhalothrin |
| cypermethrin | A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile. | cypermethrin |
| d 888 | A nitrile that acts as an L-type calcium channel blocker. | devapamil |
| dactolisib | An imidazoquinoline that is 3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinoline substituted at position 1 by a 4-(1-cyanoisopropyl)phenyl group and at position 8 by a quinolin-3-yl group. A dual PI3K/mTOR inhibitor used in cancer treatment. | dactolisib |
| decamethrin | A cyclopropanecarboxylate ester obtained by formal condensation between 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. It is the active insecticide of the proinsecticide tralomethrin. | deltamethrin |
| delgocitinib | A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine substituted by a (3S,4R)-1-(cyanoacetyl)-3-methyl-1,6-diazaspiro[3.4]octan-6-yl group at position 4. It is a pan-Janus kinase (JAK) inhibitor and is approved for treatment of atopic dermatitis (AD) in Japan. | delgocitinib |
| dhurrin | A beta-D-glucoside consisting of (S)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. | (S)-4-hydroxymandelonitrile beta-D-glucoside |
| dichlobanil | A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide. | 2,6-dichlorobenzonitrile |
| diclazuril | | 2-(4-chlorophenyl)-2-[2,6-dichloro-4-(3,5-dioxo-1,2,4-triazin-2-yl)phenyl]acetonitrile |
| 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 |
| difenoxin | A piperidinemonocarboxylic acid that is 4-phenylpiperidine-4-carboxylic acid in which the hydrogen attached to the nitrogen atom is substituted by a 3-cyano-3,3-diphenylpropyl group. | difenoxin |
| diphenoxylate | A piperidinecarboxylate ester that is the ethyl ester of difenoxin. | diphenoxylate |
| ekb 569 | | pelitinib |
| enbucrilate | | enbucrilate |
| entacapone | A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group. | entacapone |
| ethaboxam | A member of the class of aromatic amides obtained by formal condensation of the carboxy group of 4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxylic acid with the amino group of amino(2-thienyl)acetonitrile. | N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide |
| febuxostat | A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. It is an orally-active, potent, and selective xanthine oxidase inhibitor used for the treatment of chronic hyperuricaemia in patients with gout. | febuxostat |
| fenpiclonil | A member of the class of pyrroles carrying cyano and 2,3-dichlorophenyl substituents at positions 3 and 4 respectively. A fungicide used mainly to control seed-borne pathogens in cereal crops. | fenpiclonil |
| finafloxacin | A quinolone that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted at positions 1, 6, 7 and 8 by cyclopropyl, fluoro, hexahydropyrrolo[3,4-b][1,4]oxazin-6-yl and cyano groups respectively; an antibiotic used for treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. | finafloxacin |
| fipronil | A member of the class of pyrazoles that is 1H-pyrazole that is substituted at positions 1, 3, 4, and 5 by 2,6-dichloro-4-(trifluoromethyl)phenyl, cyano, (trifluoromethyl)sulfinyl, and amino groups, respectively. | 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile |
| fipronil sulfone | A member of the class of pyrazoles that is 1H-pyrazole that is substituted at positions 1, 3, 4, and 5 by 2,6-dichloro-4-(trifluoromethyl)phenyl, cyano, (trifluoromethyl)sulfonyl, and amino groups, respectively. It is a metabolite of the agrochemical fipronil. | fipronil-sulfone |
| flonicamid | A pyridinecarboxamide that is nicotinamide substituted by a trifluoromethyl group at position 4 and a cyanomethyl group at the carbamoyl nitrogen atom. | flonicamid |
| fludioxonil | A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria. | fludioxonil |
| fluvalinate | | fluvalinate |
| Girgensonine | | Girgensonine |
| glasdegib | A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a (2R,4S)-4-{[(4-cyanophenyl)carbamoyl]amino}-1-methylpiperidin-2-yl group at position 2. It is a hedgehog signalling pathway inhibitor that acts by binding to Smoothened (SMO) receptors and blocking signal transduction (IC50 = 5 nM). It is used in combination with low-dose cytarabine, for the treatment of newly-diagnosed acute myeloid leukemia (AML) in adult patients (aged >= 75 years), or who have medical conditions that prevent the use of standard chemotherapy. | glasdegib |
| GS-441524 | A C-nucleoside analog that is (2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile substituted by a 4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl group at position 2. It is the active metabolite of remdesivir and exhibits a broad range of inhibitory activity against various RNA viruses including HCV, parainfluenza and SARS-CoV. | GS-441524 |
| GS-443902 | An organic triphosphate that is GS-441524 in which the 5'-hydroxy group has been replaced by a triphosphate group. It is the active metabolite of remdesivir. | GS-443902 |
| hki 272 | A quinoline compound having a cyano group at the 3-position, a 3-chloro-4-(2-pyridylmethoxy)anilino group at the 4-position, a 4-dimethylamino-trans-but-2-enoylamido group at the 6-position, and an ethoxy group at the 7-position. | neratinib |
| iFSP1 | A member of the class of pyridobenzimidazoles that is pyrido[1,2-a]benzimidazole substituted by amino, cyano, 4-methylphenyl, and cyano groups at positions 1, 2, 3 and 4, respectively. It is a potent inhibitor of ferroptosis suppressor protein 1 (FSP1) with EC50 of 103 nM. It induces ferroptosis in GPX4 knockout cells that overexpress FSP1. | iFSP1 |
| incb-018424 | A pyrazole substituted at position 1 by a 2-cyano-1-cyclopentylethyl group and at position 3 by a pyrrolo[2,3-d]pyrimidin-4-yl group. Used as the phosphate salt for the treatment of patients with intermediate or high-risk myelofibrosis, including primary myelofibrosis, post-polycythemia vera myelofibrosis and post-essential thrombocythemia myelofibrosis. | ruxolitinib |
| indole-3-acetonitrile | A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group. | indole-3-acetonitrile |
| ioxynil | A nitrile that is benzonitrile substituted by a hydroxy group at position 4 and iodo groups at positions 3 and 5. | ioxynil |
| isavuconazole | A 1,3-thiazole that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,5-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively. It is an antifungal drug used for the treatment of invasive aspergillosis and invasive mucormycosis. | isavuconazole |
| l 778,123 | A member of the class of imidazoles that is 1H-imidazole substituted by (4-cyanophenyl)methyl and [4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl groups at positions 1 and 5, respectively. It is a dual inhibitor of FPTase and GGPTase-I. | L-778,123 (free base) |
| letrozole | | letrozole |
| lfm a13 | An enamide obtained by formal condensation of the carboxy group of (2Z)-2-cyano-3-hydroxybut-2-enoic acid with the amino group of 2,5-dibromoaniline. It is a dual-function inhibitor of Bruton's tyrosine kinase (BTK) and Polo-like kinases (PLK) that exhibits anticancer properties. | LFM-A13 |
| mdv 3100 | A benzamide obtained by formal condensation of the carboxy group of 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl}-2-fluorobenzoic acid with methylamine. Used for the treatment of of metastatic castration-resistant prostate cancer. | enzalutamide |
| mesoxalonitrile | | oxomalononitrile |
| milrinone | A member of the class of bipyridines that is 2-pyridone which is substituted at positions 3, 5, and 6 by cyano, pyrid-4-yl, and methyl groups, respectively. It is used (particularly intravenously, as the lactate) for the short-term management of severe heart failure. | milrinone |
| monepantel | A secondary carboxamide resulting from the formal condensation of the carboxy group of p-[(trifluoromethyl)sulfanyl]benzoic acid with the amino group of (2S)-2-amino-3-hydroxy-2-methylpropanenitrile in which the hydroxy group has been converted to the corresponding 5-cyano-2-(trifluoromethyl)phenyl ether. A broad-spectrum nematicide, it is used to control gastrointestinal roundworms in sheep and goats. | monepantel |
| N-(3-cyanophenyl)-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxamide | A member of the class of biphenyls that is the amide obtained by formal condensation of the carboxy group of 2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)[1,1'-biphenyl]-4-carboxylic acid with the amino group of 3-cyanoaniline. | N-(3-cyanophenyl)-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxamide |
| n-(cyanomethyl)-4-(2-((4-(4-morpholinyl)phenyl)amino)-4-pyrimidinyl)benzamide | A benzamide obtained by formal condensation of the carboxy group of 4-{2-[4-(morpholin-4-yl)anilino]pyrimidin-4-yl}benzoic acid with the primary amino group of aminoacetonitrile. It is an ATP-competitive JAK1/JAK2 inhibitor with IC50 of 11 nM and 18 nM, respectively. Used for the treatment of patients with intermediate- or high-risk myelofibrosis. | momelotinib |
| nafadotride | A naphthalenecarboxamide resulting from the formal condensation of the carboxylic acid group of 4-cyano-1-methoxynaphthalene-2-carboxylic acid with the primary amino group of 1-(1-butylpyrrolidin-2-yl]methanamine. It is a highly potent, competitive, preferential dopamine D3 receptor antagonist, centrally active upon systemic administration. | nafadotride |
| nilvadipine | | Nilvadipine |
| nirmatrelvir | An azabicyclohexane that is (1R,5S)-3-azabicyclo[3.1.0]hexane substituted by {(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}aminoacyl, 3-methyl-N-(trifluoroacetyl)-L-valinamide, methyl and methyl groups at positions 2S, 3, 6 and 6, respectively. It is the first orally administered inhibitor of SARS-CoV-2 main protease developed by Pfizer and used in combination with ritonavir for the treatment of COVID-19. | nirmatrelvir |
| norverapamil | A secondary amino compound that is 3,4-dimethoxyphenylethylamine in which one of the hydrogens attached to the nitrogen has been replaced by a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group. | 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile |
| or 1259 | | levosimendan |
| perampanel | A member of the class of bipyridines that is 2,3'-bipyridin-6'-one substituted at positions 1' and 5' by phenyl and 2-cyanophenyl groups respectively. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy. | perampanel |
| periciazine | A member of the class of phenothiazines that is 10H-phenothiazine substituted by a 3-(4-hydroxypiperidin-1-yl)propyl group at the nitrogen atom and a carbonitrile group at position 2. Periciazine is a first generation antipsychotic. | periciazine |
| pf-06463922 | A cyclic ether that is 16,17-dihydro-2H-8,4-(metheno)pyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecin-15(10H)-one substituted by methyl groups at positions 2 and 10R, and by cyano, amino and fluoro groups at positions 3, 7 and 12 respectively. It is a small molecule inhibitor of ALK and ROS1 kinase developed by Pfizer for the treatment of ALK-positive non-small cell lung cancer. | lorlatinib |
| pirinitramide | | piritramide |
| prizes | A carboxamidine that is acetamidine in which the amino hydrogens are substituted by a (6-chloropyridin-3-yl)methyl and a methyl group while the hydrogen attached to the imino nitrogen is replaced by a cyano group. | acetamiprid |
| ravuconazole | A member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4) | ravuconazole |
| ricinine | | ricinine |
| rilpivirine | An aminopyrimidine that is pyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 4-cyanophenyl and 4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl groups respectively. Used for treatment of HIV. | rilpivirine |
| s 8932 | A carboxylic ester resulting from the formal condensation of the carboxy group of N-[(S)-{[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(phenoxy)phosphoryl]-L-alanine with the hydroxy group of 2-ethylbutan-1-ol. A broad-spectrum antiviral prodrug with potent in vitro antiviral activity against a diverse panel of RNA viruses such as Ebola virus, MERS-CoV and SARS-CoV. It is currently in Phase III clinical trials for the treatment of Covid-19 in adults. | remdesivir |
| SL-327 | A nitrile that is acrylonitrile in which the hydrogen attached to the same carbon as the cyano group has been replaced by an o-(trifluoromethyl)phenyl group, while the remaining hydrogens of the ethenyl group have been replaced by amino and (4-aminophenyl)sulfanyl groups. The configuration of the double bond is not specified. It is an inhibitor of MEK1 and MEK2. | SL-327 |
| su 1498 | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]prop-2-enoic acid with the amino group of 3-phenylpropylamine. | SU1498 |
| sulfoxaflor | A member of the class of pyridines that is 5-ethyl-2-trifluoromethylpyridine in which the ethyl group is substituted at position 1 by an N-cyano-S-methylsulfonimidoyl group. The insecticide sulfoxalor is a mixture of the four possible stereoisomers arising from the two tetrahedral stereocentres. | [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide |
| systhane | A nitrile that is hexanenitrile substituted at the 2-position by p-chlorophenyl and (1,2,4-triazol-1-yl)methyl groups. | 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile |
| tak-632 | A member of the class of benzothiazoles that is 1,3-benzothiazole substituted by (cyclopropanecarbonyl)amino, 4-fluoro-3-{2-[3-(trifluoromethyl)phenyl]acetamido}phenoxy, and cyano groups at positions 2, 6 and 7, respectively. It is a potent pan-RAF inhibitor with IC50 of 1.4, 2.4 and 8.3 nM for CRAF, BRAF(V600E), BRAF(WT), respectively. | TAK-632 |
| taxiphyllin | A beta-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. | (R)-4-hydroxymandelonitrile beta-D-glucoside |
| teriflunomide | An enamide obtained by formal condensation of the carboxy group of (2Z)-2-cyano-3-hydroxybut-2-enoic acid with the anilino group of 4-(trifluoromethyl)aniline. Used for the treatment of relapsing forms of multiple sclerosis and rheumatoid arthritis. | teriflunomide |
| tetracyanoquinodimethane | A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups. | tetracyanoquinodimethane |
| thiacloprid | A nitrile that is cyanamide in which the hydrogens are replaced by a 1,3-thiazolidin-2-ylidene group which in turn is substituted by a (6-chloropyridin-3-yl)methyl group at the ring nitrogen. | thiacloprid |
| tofacitinib | A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely active rheumatoid arthritis. | tofacitinib |
| toyocamycin | An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group. | toyocamycin |
| trelagliptin | | trelagliptin |
| trilostane | An epoxy steroid that is 3,17beta-dihydroxy-5alpha-androst-2-ene-2-carbonitrile in which the oxygen of the epoxy group is joined to the 4alpha and 5 alpha positions. | trilostane |
| tyrphostin ag825 | An organic sulfide that consists of 1,3-benzothiazole-2-thiol in which the hydrogen attached to the sulfur atom is replaced by a 5-[(1E)-3-amino-2-cyano-3-oxoprop-1-en-1-yl]-2-hydroxy-3-methoxybenzyl group. It acts as an epidermal growth factor receptor antagonist. | tyrphostin AG 825 |
| verapamil | A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group. | 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile |
| vilazodone | A 1-benzofuran that is 5-(piperazin-1-yl}-1-benzofuran-2-carboxamide having a (5-cyanoindol-3-yl)butyl group attached at position N-4 on the piperazine ring. Used for the treatment of major depressive disorder. | vilazodone |
| zaleplon | A pyrazolo[1,5-a]pyrimidine having a nitrile group at position 3 and a 3-(N-ethylacetamido)phenyl substituent at the 7-position. | zaleplon |