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911 Reactions Block 3 Flashcards

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15863654960Hi you're doing great and everything is going to be fine0
15863654961Ether1
15863735680Epoxide2
15863741509Acetal3
15863751072Thioester4
15863752887Sulfoxide5
15863755051Sulfone6
15863757957N-oxide7
15863759379Nitrile8
15863763163Carboxamides9
15863767077Carboxy ester10
15863771224Phase 1 Metabolism PurposeTo introduce functional groups needed for phase 2 processing11
15863785742Phase 2 Metabolism PurposeTo increase hydrophilicity of drugs / metabolites to promote excretion12
15863797750When would something be protonated?pH < pKa13
15863800875When would something be deprotonated?pH > pKa14
15863810513General CYP reaction1. NADPH 2. Reductase 3. CYP 4. O215
15863858370Privileged Positions1. Benzylic carbon 2. Allylic carbon 3. Carbon alpha to carbonyl 4. Carbon alpha to heteroatom 5. Aryl carbon 6. Carbon-carbon double bonds 7. Nitrogen-center 8. Sulfur-center16
15863872230Benzylic carbon17
15863875621Allylic carbon18
15863891150Carbon alpha to carbonyl19
15863895023Carbon alpha to heteroatom20
15863926205Aryl carbonCarbon ortho/para to EDG21
158639411422 general steps of CYP oxidation reaction1. Insertion of an oxygen atom 2. Fragmentation of a drug22
15863946435Enantiomersisomers that are mirror images of each other23
15863950608Diastereomersstereoisomers that are not mirror images24
15863957940Racemic mixtureA mixture that contains equal amounts of the (+) and (-) enantiomers. Racemic mixtures are not optically active.25
15864005890What oxidation reactions can CYPs complete?Hydroxylation of alkanes oxidation of primary alcohols oxidation of secondary alcohols hydroxylation of arenes oxidation of alkanes and alkenes oxidation of nitrogen compounds oxidation of sulfur compounds26
15864045427CYP hydroxylation of alkanesAlkane —> alcohol27
15864067844CYP oxidation of primary alcoholsPrimary alcohol —> aldehyde —> carboxylic acid28
15864078998CYP hydroxylation of arenesArenes —> phenol (ortho/para to EDGs)29
15864090815Common EDGsNH2 OH OCH3 C6H530
15864107000CYP oxidation of alkanes and alkenesAlkane —> alkene —> epoxide31
15864110103CYP oxidation of tertiary aminesTertiary amines —> N-oxide32
15864254390CYP oxidation of secondary aminesSecondary amine —> N-hydroxlamines33
15864285268N-hydroxylamines34
15864290021CYP oxidation of primary aminesPrimary amine —> nitroso compounds (toxic)35
15864306059CYP oxidation of sulfideSulfide —> sulfoxide36
15864309552CYP oxidation of sulfoxideSulfoxide —> sulfone37
15864316790What are the different oxidation-fragmentation reactions?Dehalogenation Deamination Dealkylation Dehydrogenation38
15864343275CYP dehalogenation of primary alkyl halidePrimary alkyl halide —> aldehyde39
15864347915CYP dehalogenation of secondary alkyl halideSecondary alkyl halide —> ketone40
15864355203Do tertiary alkyl halides under CYP oxidation?No41
15864357762CYP oxidation of dihalidesDihalide —> acid halide (toxic)42
15864379657CYP deamination of primary aminePrimary amine —> aldehyde43
15864383330CYP deamination of secondary amineSecondary amine —> ketone44
15864389751CYP dealkylationLoss of an alkyl group Hemiacetyl intermediate products: alcohol and aldehyde (biproduct)45
15864406867CYP dehydrogenationLoss of 2 H+ Products: quinone and pyridines (toxic)46
158644230614 most important CYPsCYP3A4/5/7 CYP2D6 CYP2C9 CYP1A/1/247
158644703004 CYPs most susceptible to SNPsCYP3A4/5/7 CYP2D6 CYP2C9 CYP1A/1/248
15864496285FMOs reactionsOxidize drugs with nitrogen, sulfur, and phosphorous groups49
15864506346FMO N-oxidationNitrogen oxidation50
15864509120FMO S-oxidationSulfur oxidation51
15864512896What do FMOs rely on?FAD-OOH52
15864513621FAD-OOH53
15864548504What is the predominant FMO?FMO354
15864559093FMO Thioether oxidationThioether —> sulfoxides and sulfones55
15864608903PeroxidasesTheir job is to catalyze metabolic reactions that release Hydrogen Peroxide (H2O2) which is toxic to cells.56
15864637368Peroxidase exampleCatalase57
15864645862Alcohol dehydrogenase (ADH) reactionsOxidize primary alcohols oxidize secondary alcohols reduce carbonyl groups58
15864675563ADH Primary alcohol oxidationPrimary alcohol —> aldehyde59
15864702446ADH secondary alcohol oxidationSecondary alcohol —> ketone60
15864716666ADH carbonyl reductionKetone —> secondary alcohol aldehyde —> primary alcohol61
15864722664When would ADH need NAD+?When oxidizing an alcohol62
15864724957When would ADH need NADH?When reducing a carbonyl63
15864733409Is ADH reversible?Yes - the only one that is64
15864737644Aldehyde dehydrogenase (ALDH) reactionAldehyde —> carboxylic acid65
15864776051What is ALDH dependent on?NAD+66
15864819420Aldehyde oxidase (AO) reactions1. Oxidizes aldehydes 2. Oxidized nitrogen-containing heterocycles67
15864824442AO aldehyde oxidationAldehyde + H2O + O2—> carboxylic acid + H2O268
15864838168AO nitrogen-containing heterocyclic oxidationOxidation occurs at alpha carbon to N69
15864859004What does AO depend on?O2 and H2O70
15864862527Xanthine oxidase (XO) reactionHypoxanthine + H2O + O2—> xanthine + H2O2—> Uric acid + H2O271
15864881625What does XO depend on?H2O and O272
15864885613How does AO differ from ALDH?With AO, electrons are transferred to an oxygen With ALDH, electrons are transferred to NAD+73
15864897091MAOs reactionsOxidation of amines (primary, secondary, and tertiary)74
15864907270What is MAOs dependent on?FAD75
15864921103MAO primary amine oxidationPrimary amine —> imine —(ox. deamination)—> aldehyde76
15864958461Imine77
15864969142Oxidative deaminationImine —> aldehyde78
15864976565Flavin-based reductases (FR)Reduce drugs and metabolites by handing the electron directly to the drug or molecule79
15864984807What are FRs dependent on?NADPH80
15864987082Carbonyl reductases (CR) reactionCarbonyl —> alcohol81
15864999683What is CR dependent on?NADPH82
15865004378How do ADH and CR differ?ADH is reversible and CR is not83
15865007068Azo reductases (AR) reactionN=N —> hydrazine —> anilines84
15865045101Aniline85
15865048155Hydrazine86
15865056757What does AZ requireNADPH or NADH87
15865060171Nitro reductases (NR) reactionNitro group(NO2) —> N=O —> amine (NH2)88
15865084203What does NR require?NADPH or NADH89
15865088895Carboxyesterases (CE) reactionCarboxylic ester —> alcohol and carboxylate90
15865118405Phase 2 conjugation reactionsGlucuronidation Sulfination Glutathione Acetylation Amino Acid91
15865132403Glucuronidation enzymeUGT92
15865134669UGT reactionAttaches a glucuronate to drugs and metabolites93
15865136348Glucuronate94
15865146939Do UGTs have a broad or narrow specificity?Broad95
15865155421What is the most important phase 2 enzyme?UGT96
15865160316Functional groups UGTs act on?Alcohols thiols amines carboxylic acids carboxamides97
15865179783O-glucuronidationAdds glucuronate to alcohol or carboxylic acid98
15865185988N-glucuronidationAdds glucuronate to amines99
15865199516S-glucuronidationAdds glucuronate to thiol100
15865201544C-glucuronidationAdds glucuronate to hydrocarbon group101
15865220837Are UGTs present at birth?No102
15865239466Sulfation EnzymeSTs103
15865248132STs reactionAdds SO3 onto drugs and metabolites104
15865259382What functional groups do STs work on?Aromatic alcohols, primary and secondary alcohols, aryl amines, and N-hydroxyamines105
15865265296In what people are STs favorable?Children106
15865269990Glutathione structure107
15865281489Glutathione (GSH) reactionAdds glutathione to toxic drugs and metabolites to make them mercapturic acids108
15865286770FavismReduced level of NADPH affects glutathione levels and leaves RBCs vulnerable to oxidizing agents109
15865313212Acetylation enzymeNATs110
15865313213What do NATs require?Acetyl-CoA111
15865318415What do STs require?An activated form of sulfate (PAPs)112
15865329129What do UGTs require?UDP-Glucuronate113
15865332635NATs reactionAdds an acetyl group to N-H bonds114
15865352478Acetyl group115
15865359553Amino acid conjugation enzymeNACTs116
15865361326NACTs reactionCouple a CoA-activated drug/metabolite to an amino acid117
15865367696Which amino acid is typically conjugated to drugs / metabolites by NACTs ?Gly118
15865371411Toxic metabolitesIminoquinones epoxides acid chlorides nitroso compounds119
15865378547Nitroso compound120
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