Pharmaceutical Chemistry an der Ain Shams University | Karteikarten & Zusammenfassungen

Lernmaterialien für Pharmaceutical chemistry an der Ain Shams University

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TESTE DEIN WISSEN
What’s the difference between 2° amine TCAs & 3°? 
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TESTE DEIN WISSEN
2° amines: selective inhibitors of NET➡️ Less SEs.

3° amines: inhibit both NET & SERT (SERT>NET), have greater anticolenergic, antihestaminic & hypotensive SEs. They have increased cardiotoxicity risk due to the potent inhibition of Na channels. 
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TESTE DEIN WISSEN
What are the targets of corticosteroids (SAIDs) and NSAIDs? 
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TESTE DEIN WISSEN
Corticosteroids ➡️ Phospholipase A2& phospholipase C (preventing the release (de-estrification of phospholipids) of arachidonic 

NSAIDs➡️ Cycloxygenases (endoperoxide synthetases); preventing the conversion of arachidonic acid into cycloendoperoxides. 
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TESTE DEIN WISSEN
Why does the overdose of acetaminophen could cause: fatal hepatic necrosis, renal tubular necrosis & hypoglycemic coma? 
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TESTE DEIN WISSEN
Due to the production of a large amount of NAPQI, which causes the depletion of glutathione that’s required for its detoxification. This leads to the irreversible binding of NAPQI irreversibly to the SH groups of the aas especially in the kidney causing an irreversible protein damage. 
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TESTE DEIN WISSEN
SEs of NSAIDs 
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TESTE DEIN WISSEN
  • Dyspepsia 
  • Ulcers
  • GI bleeding 
  • Renal disorders
  • RF 
  • Tubular necrosis 
  • Analgesic nephropathy
  • Tinnitus& headache 
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TESTE DEIN WISSEN
How do NSAIDs cause gastric damage ? 
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TESTE DEIN WISSEN
Dual insult mechanism: 

Primary insult: 
Because NSAIDs are weak acids, they’re poorly soluble at the gastric pH. 1° insult happens as the insoluble pieces of NSAIDs, lodge in the mucosa, causing a direct tissue damage.

Secondary insult:
Due to the inhibition of COX1 & the consequential inhibition of the cyto-protective PGs. 
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TESTE DEIN WISSEN
What’s the advantage of acetaminophen over aspirin? 
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TESTE DEIN WISSEN
That it can be used in case of salicylates  hypersensitivity. 
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TESTE DEIN WISSEN
What’s the difference between COX1 & COX2, in terms of the physiological function of each? 
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TESTE DEIN WISSEN
 COX1➡️Produce prostaglandins that are cytoprotective; protect the gastric mucosa and renal function. They’re produced during normal cellular activity.

COX2➡️ ~~that have inflammatory effects, and released during inflammation.

Note: selective COX2 inhibitors are cardiotoxic, because it was later found that PGs produced by COX2 have cardio-protective effects.  
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TESTE DEIN WISSEN
How can acetaminophen overdose be managed ? 
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TESTE DEIN WISSEN
By the administration of N-acetyl cysteine, which: 
- Binds to NAPQI and detoxifies it.
- restores the glutathione reserves.
Lösung ausblenden
TESTE DEIN WISSEN
What are the pharmacological effects of salicylates ? 
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TESTE DEIN WISSEN
1. Analgesic& antipyretic 
2. Anti inflammatory 
3. Promote the excretion of Utica acid➡️Used in gouty arthritis.
4. Inhibits platelet aggregation ➡️ Used in the prophylaxis from heart attacks and strokes
5. Might be protective from colon cancer.
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TESTE DEIN WISSEN
How do salicylates inhibit platelet aggregation? 
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TESTE DEIN WISSEN

Salicylates restore the balance, that's often lost in heart patients, between PGI2 that cause vasodilation and decreases platelet aggregation

and TxA2 that causes vasoconstriction and increases platelet aggregation, by binding 

irreversibly to COX enzymes through covalent bonding.

Lösung ausblenden
TESTE DEIN WISSEN
What's the importance of the methyl group at the position 2 in indomethacin? 
Lösung anzeigen
TESTE DEIN WISSEN
It has 2 functions:
1️⃣ It contributes to the pseudo-irriversble inhibition of the COX enzyme as it fits into a hydrophobic pocket at the active site, thus strengthening the interaction with the enzyme as if a covalent bond had been formed. 

2️⃣ a. It keeps the drug molecule in a cis-like confirmation which is more active, where it creates a steric bulk that pushes the chlorobenzoyl moiety to the same side as the methoxybenzo part of indole. 
b. This ensures the non-coplanarity between the aromatic flat surface and the 2 LA, as the H atoms on the phenyl ring clashes with the 7H on the indole repelling the benzoyl moiety out of the plane.
Lösung ausblenden
TESTE DEIN WISSEN
The nomenclature of prostaglandins.
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TESTE DEIN WISSEN
  • PG: denotes the presence of O at C9&11 
  • A letter from A-I: denotes the nature of the O at C9 & C11
  • A number written as a subscript: denotes the number of double bonds 

E.g. PGE2: 2 double bonds➡️ FA precursor with 4 double bonds 
PGG& PGH: cycloendoperoxides➡️ Precursors for PG biosynthesis 
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Q:
What’s the difference between 2° amine TCAs & 3°? 
A:
2° amines: selective inhibitors of NET➡️ Less SEs.

3° amines: inhibit both NET & SERT (SERT>NET), have greater anticolenergic, antihestaminic & hypotensive SEs. They have increased cardiotoxicity risk due to the potent inhibition of Na channels. 
Q:
What are the targets of corticosteroids (SAIDs) and NSAIDs? 
A:
Corticosteroids ➡️ Phospholipase A2& phospholipase C (preventing the release (de-estrification of phospholipids) of arachidonic 

NSAIDs➡️ Cycloxygenases (endoperoxide synthetases); preventing the conversion of arachidonic acid into cycloendoperoxides. 
Q:
Why does the overdose of acetaminophen could cause: fatal hepatic necrosis, renal tubular necrosis & hypoglycemic coma? 
A:
Due to the production of a large amount of NAPQI, which causes the depletion of glutathione that’s required for its detoxification. This leads to the irreversible binding of NAPQI irreversibly to the SH groups of the aas especially in the kidney causing an irreversible protein damage. 
Q:
SEs of NSAIDs 
A:
  • Dyspepsia 
  • Ulcers
  • GI bleeding 
  • Renal disorders
  • RF 
  • Tubular necrosis 
  • Analgesic nephropathy
  • Tinnitus& headache 
Q:
How do NSAIDs cause gastric damage ? 
A:
Dual insult mechanism: 

Primary insult: 
Because NSAIDs are weak acids, they’re poorly soluble at the gastric pH. 1° insult happens as the insoluble pieces of NSAIDs, lodge in the mucosa, causing a direct tissue damage.

Secondary insult:
Due to the inhibition of COX1 & the consequential inhibition of the cyto-protective PGs. 
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Q:
What’s the advantage of acetaminophen over aspirin? 
A:
That it can be used in case of salicylates  hypersensitivity. 
Q:
What’s the difference between COX1 & COX2, in terms of the physiological function of each? 
A:
 COX1➡️Produce prostaglandins that are cytoprotective; protect the gastric mucosa and renal function. They’re produced during normal cellular activity.

COX2➡️ ~~that have inflammatory effects, and released during inflammation.

Note: selective COX2 inhibitors are cardiotoxic, because it was later found that PGs produced by COX2 have cardio-protective effects.  
Q:
How can acetaminophen overdose be managed ? 
A:
By the administration of N-acetyl cysteine, which: 
- Binds to NAPQI and detoxifies it.
- restores the glutathione reserves.
Q:
What are the pharmacological effects of salicylates ? 
A:
1. Analgesic& antipyretic 
2. Anti inflammatory 
3. Promote the excretion of Utica acid➡️Used in gouty arthritis.
4. Inhibits platelet aggregation ➡️ Used in the prophylaxis from heart attacks and strokes
5. Might be protective from colon cancer.
Q:
How do salicylates inhibit platelet aggregation? 
A:

Salicylates restore the balance, that's often lost in heart patients, between PGI2 that cause vasodilation and decreases platelet aggregation

and TxA2 that causes vasoconstriction and increases platelet aggregation, by binding 

irreversibly to COX enzymes through covalent bonding.

Q:
What's the importance of the methyl group at the position 2 in indomethacin? 
A:
It has 2 functions:
1️⃣ It contributes to the pseudo-irriversble inhibition of the COX enzyme as it fits into a hydrophobic pocket at the active site, thus strengthening the interaction with the enzyme as if a covalent bond had been formed. 

2️⃣ a. It keeps the drug molecule in a cis-like confirmation which is more active, where it creates a steric bulk that pushes the chlorobenzoyl moiety to the same side as the methoxybenzo part of indole. 
b. This ensures the non-coplanarity between the aromatic flat surface and the 2 LA, as the H atoms on the phenyl ring clashes with the 7H on the indole repelling the benzoyl moiety out of the plane.
Q:
The nomenclature of prostaglandins.
A:
  • PG: denotes the presence of O at C9&11 
  • A letter from A-I: denotes the nature of the O at C9 & C11
  • A number written as a subscript: denotes the number of double bonds 

E.g. PGE2: 2 double bonds➡️ FA precursor with 4 double bonds 
PGG& PGH: cycloendoperoxides➡️ Precursors for PG biosynthesis 
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