FIMMRA functional groups (11-14, week 6)

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18 Terms

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Carboxylic acid

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

both
acidic
forms a salt in basic solution
phase 1: stable
phase 2: glucouronidation

<ul><li><p>both</p></li><li><p>acidic</p></li><li><p>forms a salt in basic solution</p></li><li><p>phase 1: stable</p></li><li><p>phase 2: glucouronidation</p></li></ul><p></p>

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Ester

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA
neutral
hydrolysis in basic solution
phase 1: hydrolysis (hydrolase)
phase 2: stable

<ul><li><p>HBA</p></li><li><p>neutral</p></li><li><p>hydrolysis in basic solution</p></li><li><p>phase 1: hydrolysis (hydrolase)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Amides

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

primary and secondary = both; tertiary = HBA
neutral
stable
phase 1: hydrolysis (hydrolase)
phase 2: stable

<ul><li><p>primary and secondary = both; tertiary = HBA</p></li><li><p>neutral</p></li><li><p>stable</p></li><li><p>phase 1: hydrolysis (hydrolase)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Carbonate

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA
neutral
unstable in acid
phase 1: hydrolysis (hydrolase)
phase 2: stable

<ul><li><p>HBA</p></li><li><p>neutral</p></li><li><p>unstable in acid</p></li><li><p>phase 1: hydrolysis (hydrolase)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Carbamate

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
neutral
unstable in acid
phase 1: hydrolysis (hydrolase)
phase 2: stable

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>neutral</p></li><li><p>unstable in acid</p></li><li><p>phase 1: hydrolysis (hydrolase)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Urea

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
neutral
stable
phase 1: hydrolysis
phase 2: stable

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>neutral</p></li><li><p>stable</p></li><li><p>phase 1: hydrolysis</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Amidine

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
basic
generally stable; can form salt in acid
stable

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>basic</p></li><li><p>generally stable; can form salt in acid</p></li><li><p>stable</p></li></ul><p></p>

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Guanidine

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
basic
generally stable; can form salt in acid
stable

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Sulfonamide

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

(on nitrogen) primary and secondary = both; tertiary = HBA
neutral
stable
stable

<ul><li><p>(on nitrogen) primary and secondary = both; tertiary = HBA</p></li><li><p>neutral</p></li><li><p>stable</p></li><li><p>stable</p></li></ul><p></p>

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Sulfonic acids

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

both
acidic
generally stable; salt formation in base
stable

<ul><li><p>both</p></li><li><p>acidic</p></li><li><p>generally stable; salt formation in base</p></li><li><p>stable</p></li></ul><p></p>

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Nitro

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA
neutral
stable
phase 1: reduction to an amine (NH₂)
phase 2: stable

<ul><li><p>HBA</p></li><li><p>neutral</p></li><li><p>stable</p></li><li><p>phase 1: reduction to an amine (NH<sub>2</sub>)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Nitrate

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA
neutral
unstable in acidic or basic conditions
phase 1: hydrolysis (-OH + HNO₂)
phase 2: stable

<ul><li><p>HBA</p></li><li><p>neutral</p></li><li><p>unstable in acidic or basic conditions</p></li><li><p>phase 1: hydrolysis (-OH + HNO<sub>2</sub>)</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Nitrite (draw what it looks like)

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Oxime

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

Both
neutral
unstable in acid
stable
POTENTAL FOR E AND Z ISOMERS

<ul><li><p>Both</p></li><li><p>neutral</p></li><li><p>unstable in acid</p></li><li><p>stable</p></li><li><p>POTENTAL FOR E AND Z ISOMERS</p></li></ul><p></p>

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Alkyloxime

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA
neutral
unstable in acid
stable
POTENTIAL FOR E AND Z ISOMERS

<ul><li><p>HBA</p></li><li><p>neutral</p></li><li><p>unstable in acid</p></li><li><p>stable</p></li><li><p>POTENTIAL FOR E AND Z ISOMERS</p></li></ul><p></p>

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Hydrazone

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
basic
unstable in acid
phase 1: hydrolysis
phase 2: stable

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>basic</p></li><li><p>unstable in acid</p></li><li><p>phase 1: hydrolysis</p></li><li><p>phase 2: stable</p></li></ul><p></p>

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Hydrazine

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
basic
stable
stable
phase 1: stable
phase 2: acylation

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>basic</p></li><li><p>stable</p></li><li><p>stable</p></li><li><p>phase 1: stable</p></li><li><p>phase 2: acylation</p></li></ul><p></p>

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Hydrazide

HBA or HBD
pH
in vitro
in vivo (phase 1 and phase 2)

HBA (HBD if containing NH)
basic
stable
phase 1: hydrolysis (to carboxylic acid?)
phase 2: acylation

<ul><li><p>HBA (HBD if containing NH)</p></li><li><p>basic</p></li><li><p>stable</p></li><li><p>phase 1: hydrolysis (to carboxylic acid?)</p></li><li><p>phase 2: acylation</p></li></ul><p></p>

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