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AAI: Chemistry > Histamine > Flashcards

Histamine Flashcards

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1
Q

Examples of first generation anti-histamines

A

Diphenhydramine

Chlorphenamine

Promethazine

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2
Q

Examples of second generation anti-histamines

A

Loratidine

Cetirizine

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3
Q

Examples of third generation anti-histamines

A

Levocetirizine

Fexofenadine

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4
Q

Side effects of first + second generation anti-histamines

A

Drowsiness

Effects can last for 24h + more for first gen.

Less of an issue in second gen.

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5
Q

Biological origin of histamine

A

Decarboxylation of L-histidine

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6
Q

Which nitrogen in histamine is protonated at pH 7

A

Aliphatic nitrogen (not in the ring)

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7
Q

Function of H1 receptor

A

Hayfever treatment (loratidine)

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8
Q

Function of H2 receptor

A

Stomach ulcer treatment (cimetidine)

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9
Q

Function of H3 receptor

A

Brain function

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10
Q

Function of H4 receptor

A

Regulation of immune system

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11
Q

SN1 nucleophilic substitutions

A
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12
Q

SN2 nucleophilic substitution

A
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13
Q

Structure activity relationship of first generation anti-histamines

A
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14
Q

What generation anti-histamine is promethazine?

A

First generation

Causes drowsiness - prescribed for insomnia

To treat for hayfever, often with decongestant

H1 - antagonist, some affinity for alpha1- adrenoceptor

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15
Q

What nucleophilic substitution is used?

Synthesis of Promethazine

A
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16
Q

What type of molecular properties cause drugs to pass through blood-brain barrier?

A

Neutral, oily molecules with high log P

17
Q

What generation anti-histamine is Cetirizine?

A

2nd generation

Selective H1 - receptor inverse agonist

Formulated as racemate

18
Q

Does cetrizine cause drowsiness?

A

No - hardly crosses BBB

19
Q

Which form of cetirizine is more active?

A

L-cetirizine

20
Q

Synthesis of Cetirizine

A
21
Q

Name a 3rd generation anti-histamine

A

Levocetirizine

(an enantio-pure version of cetirizine as its more specific)

22
Q

What are 3rd generation anti-histamines thought to have?

A

Fewer side effects

23
Q

What are 3rd generation anti-histamines derived from

A

2nd generation anti-histamine (enantio-pure/metabolised versions)

3rd gens. are more specific so cause less side effects

AAI: Chemistry (3 decks)

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