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PAI > Chemistry 1 > Flashcards

Chemistry 1 Flashcards

Need to finish lecture 4 plus SAR

1
Q

What are opium alkaloids?

A
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2
Q

Examples of opium alkaloid drugs

A
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3
Q

What type of analgesics are opium alkaloids?

A

Centrally acting analgesics

Strong Narcotic effect

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4
Q

Opium alkaloids have a strong ______ effect?

What does it mean?

A
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5
Q

How many opioid compounds have been approved?

A

>50

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6
Q

Clinical use of opioids

A

Mainly used for their analgesic properties in the management of acute + chronic pain

  • Moderate - severe pain e.g. fentanyl
  • Cough e.g. codeine
  • Diarrhoea e.g. loperamide
  • Opioid dependance e.g. methadone
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7
Q

Name ADRs of opioids

A
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8
Q

Describe the problem of opioid use

A

Tolerance leads to physical dependance, which leads to addiction

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9
Q

How is codeine converted to morphine?

A
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10
Q

Name the 3 major subtypes of opiate receptor

A
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11
Q

Which opiate receptor is common?

A

Mu-opioid receptor

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12
Q

Delta agonist function

A
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13
Q

Mu1 agonist function

A

Supraspinal analgesia + physical dependance

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14
Q

Mu2 agonist function

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15
Q

Kappa agonist function

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16
Q

Agonist function of nociceptor

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17
Q

Name the body’s natural painkillers + where they are produced

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18
Q

Name the 6 stages of narcotic analgesic development

A
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19
Q

Shape + no. of rings in morphine structure

A
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20
Q

How do we test analgesics?

A

In vivo (in living organism)

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21
Q

Why does in vivo analgesia decrease?

A
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22
Q

What prohibits CNS receptor access?

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23
Q

How comes heroin can enter CNS easier than morphine?

A
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24
Q

How many chiral centres does Morphine have?

A
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25
Q

Why is morphine’s enantiomer completely inactive?

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26
Q

What is epimerisation?

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27
Q

What is pharmacophore?

A
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28
Q

Draw common metabolic reactions of morphine

A
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29
Q

What functional group does Mu-receptor agonist have and how is it dealkylated?

A

Mu-receptor have an N-methyl group which is dealkylated by CYP3A4

30
Q

Why are non-metabolites limited therapeutically?

A
31
Q

Why do some patients not respond to codeine-based analgesics?

A
32
Q

Phase 2: What do phenols conjugate with?

What type of patients have those conjugates found in their urine + are they active?

A

Phenols conjugate with either glucuronic acid or sulfate

Both conjugates found in urine of patients taking multicyclic opioids

Mainly inactive

33
Q

Phase 2 conjugation impacts on _______

A
34
Q

What has a higher potency than morphine + by how much?

A
35
Q

What is a drawback of M6G?

A
36
Q

What are the 4 strategies for morphine analogue development?

A
37
Q

What is vary substituents?

A
38
Q

Describe molecular structure

  • What is the easiest position to add substituents?
  • What does semi-synthesis require?
    *
A
39
Q

Draw synthesis of N-alkylated morphine analogues

A
40
Q

Functionalisation of 2ndary amine using alkyl halides leads to a range of N-alkylmorphines

What alkyl morphines cause:

  • increase in antagonism?
  • 0 activity?
  • agonists?
  • 14x activity of morphine?
A
41
Q

How was Naloxone produced?

What is the clinical use of Naloxone?

A
42
Q

In simplification, _____ complexity causes ________ of synthesis

A
43
Q

Which 5 rings in the morphine skeleton has no activity if it is removed?

A

E

44
Q

Name structure if:

  • D is removed?
  • C + D is removed?
  • B, C + D is removed?
  • B, C, D + E is removed?

All of the rings above have been removed but which one has a rapid onset of analgesic action but short onset?

A
45
Q

Which levorphanol isomer has little/no activity?

A

(+) isomer

46
Q

If we want to extend morphine, what do we add to form a:

  • antagonist?
  • increase activity?
A

Antagonist = allyl on N

Increase activity = phenethyl

47
Q

Which simplified morphine analogue causes higher toxicity than morphine?

A
48
Q

Example of a 4-phenylpiperidine + describe clinical use

A
49
Q

Name a successful piperidine derivative + explain why it is good

A

Fentanyl

100x > potent than morphine

Lacks OH in phenol but still lipophilic

50
Q

Which methadone isomer is active?

A
51
Q

Where is methadone’s chiral centre?

A
52
Q

What is the clinical use of methadone?

A
53
Q

Why is methadone marketed in its racemic form?

A
54
Q

What is the clinical use of methadone’s S(+) isomer + how does this lead to its serious side effects?

A
55
Q

Methadone has a prolonged duration of action.

Why is this?

A
56
Q

How is methadone administrated?

A

Orally or Injection

57
Q

A patient has difficulty swallowing orally.

How can they be administered methadone?

A

Swish + spit

Patients who struggle swallowing oral dosage forms use methadone with alkalinising agent to increase saliva pH from 6.4 - 8.5

If solution is held in mouth for 2 and a half minutes, buccal absorption of 85% is achieved

58
Q

What opioid receptor does tramadol use?

A
59
Q

Who cannot take tramadol + why?

A
60
Q

What racemic isomer form is tramadol marketed + why?

A

Racemic mixture of Cis-Isomers

(1R, 2R) enantiomer > 30x potent than (1S, 2S)

Racemic formulation displays tolerability

61
Q

Describe tramadol metabolism

A

O-demethylated via CYP2D6 metabolism to more potent opioid (200 fold increase)

62
Q

How are oripavines made?

A
63
Q

What are conformational restrictions?

A
64
Q

What is the diers-alders reaction?

A

Concerted cycloaddition reaction between diene + dienophile to form 6-membered ring containing double bond

65
Q

How are oripavines formed?

A
66
Q

Examples of oripavines

A
67
Q

How was buprenorphine made?

A
68
Q

How is buprenorphine formulated?

A
69
Q

Difference between Etorphine + Morphine

A
70
Q

Clinical use of Etorphine

A

PAI (17 decks)

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