Structures ‫من ملفات التجميعات‬

1. Jan page 4

2. Jan page 5 and 6

2-keto: long t1/2, less withdrawal symptoms.

3-hydroxy: intermediate t1/2, more withdrawal symptoms and preferred in the elderly (LOT: Lora,Oxa,Tema).

Triazolo: short t1/2, more withdrawal symptoms.

Diazepam: CH3 at C-1, no OH at C-3.

Nordiazepam: CH3 is removed by N-demethylation. Nordiazepam, Temazepam, Oxazepam

Temazepam: CH3 at C-1 and OH at C-3. are all the active metabolites of Diazepam.

Oxazepam: Only OH at C-3. (Oxa=OH)

 3. Jan page 7

Loratadine is a prodrug metabolized to Desloratadine the active metabolite.

Terfenadine is a prodrug, metabolized to Fexofenadine the active metabolite.

Terfenadine has 3 CH3, one of them will be carboxylated (C=OH) upon metabolism.

Terfenadine is cardiotoxic and not used anymore, but its metabolite Fexofenadine is not.

Hydroxyzine is a prodrug and first-generation antihistamine metabolized to the second-generation active drug
Cetirizine. It is oxidized to Cetirizine. ‫ما عليكم بالرسم كله شوفوا اللي عليه خط بس‬

4. Jan page 32

Pyridine ring
 5. Jan page 32

Non-sedating antihistamines Loratadine, Desloratadine, and Fexofenadine have 4 cycles, except Cetirizine with 3
cycles but C=O at the end (see structures on the previous page).

Sedating antihistamines have 3 cycles or less, Diphenhydramine, Chlorpheniramine, Promethazine, and

Hydroxyzine.

Chlorpheniramine Diphenhydramine Promethazine Hydroxyzine

6. Jan page 47

Ladostigil is a novel (new) neuroprotective.

This drug combines the mechanisms of action of Rivastigmine and Rasagiline into a single drug.

Rivastigmine is reversible acetylcholinesterase used in Alzheimer's disease and Rasagiline is an irreversible

monoamine oxidase B inhibitor used in Parkinson's disease.

7. Jan page 50

The pharmacophore of fluoroquinolones is 3-carboxy-4-pyridone.

Gemifloxacin
 8. Jan page 50

Histamine is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group.

9. Jan page 50

Modification in Diclofenac structure to avoid metabolic activation and hepatocyte toxicity.

10. Jan page 50

Convert NSRI to SNRI by demethylation of the side chain tertiary amino group to yield a secondary amino group.

11. Jan page 53

Tricyclic antidepressants are photosensitive. Most one cause photosensitivity is Imipramine.

.‫ فروقات بسيطة فقط‬،‫كلها متشابهة زي الفيل‬

Imipramine Clomipramine Amitriptyline

 12. Jan page 53

This methyl group increase selectivity to COX-1 receptors.

13. Jan page 53

The chemical structure of methacholine is identical to acetylcholine but with a methyl group on the beta carbon
(hence being called acetyl-β-methylcholine), this β-methyl group provides selectivity towards muscarinic receptors
as compared to nicotinic receptors.

Methachloine Acetylcholine

14. Jan page 53

Indomethacin

15. Jan page 54

Natural statins can be obtained from fungi. Lovastatin is mainly produced by Aspergillus terreus strains, and
Mevastatin by Penicillium citrinum. Statins are also present in Red yeast rice extract.

Mevastatin is considered the first statin drug, but it was never marketed. The first statin drug available to the general
public was Lovastatin, which is a prodrug.

Only difference

Mevastatin Lovastatin
 16. Jan page 62

Fluphenazine has a piperazine ring which increases potency to D2 receptors and lead decreased anticholinergic
activity, sedation, and hypotension.

Piperazine ring

17. Jan page 64

Erythromycin structure.

18. Jan page 65

Valacyclovir is a prodrug converted to acyclovir the active form. Valacyclovir was developed to increase the oral
absorption and plasma levels of acyclovir.

19. Jan page 71

Morphine to Hydromorphone by adding ketone group at C-6, which will increase analgesic activity (potency).
 20. Jan page 72

Maybe the ester group or 4-Phenylpiperidine is responsible for the short-duration action of Pethidine.

‫ماني متأكد من الجواب‬

4-Phenylpiperidine, by simplification or drug dissection method.

21. Jan page 79

Methicillin structure.

Beta-lactam ring

22. Jan page 79

‫في ملف يزيد‬

Oseltamivir is a prodrug converted to its active form by ester hydrolysis.

23. Jan page 79

Quinine (antimalarial) structure. Quinidine (antiarrhythmic) is an isomer.

Quinine Quinidine
 24. Jan page 79

‫في ملف يزيد‬

SAR of quinolones. The pharmacophore is 3-carboxy-4-pyridone. (see question 7).

F at C-6 increases lipophilicity.

Piperazine ring increases gram-negative activity.

25. Jan page 79

Epinephrine is converted to Phenylephrine by removing one OH group. This will increase alpha 1 selectivity.

26. Jan page 80

D-galactose and D-mannose are diastereomers. But D-glucose and D-mannose are epimers.
 27. Jan page 87

‫هذا يجي السؤال كذا‬

At which pH the drug will be more volatile?

‫تختار أقل رقم عشان في عالقة عكسية بين البي اتش والفوالتيلتي حق أي دواء‬
The total quantity of volatile compounds increased significantly as the pH decreased.

28. Jan page 87

‫سؤال شاطح بس نضيفه هنا عشان فيه رسمة‬

29. Jan page 88 and 89

Quinine structure see question 23.

Amitriptyline question 11.

Amphotericin B Hydrolysis ‫من النوت‬

Which TCA is more photosensitive question 11.

 30. Jan page 103

Part responsible for antipseudomonal activity is carboxyl group (COOH). ‫ذا اللي لقيته في النت ماني متأكد مرة‬

31. Jan page 103

Natural Tetracyclines have a tertiary hydroxyl group (OH) at C-6 which undergo Acid-catalyzed dehydration involving
the C-5a hydrogen and the resulting product is C5a,6-anhydrotetracycline which is much deeper in color than
Tetracycline and is biologically inactive.

CH3 H3C CH3

H3C
N CH3 N
HO CH3
H H
H OH OH

NH2 NH2

OH OH
OH O OH O O OH OH O O O

Tetracycline 5a,6-anhydrotetracycline

inactive ‫ يصير‬،‫ وينضاف في الحلقة دبل بوند‬OH ‫تروح ال‬

32. Jan page 108

Oseltamivir structure question 22.

BDZ metabolites question 1 and 2.

 33. Jan page 112

Sulfa allergy is due to SO2 in structure.

34. Jan page 112

BDZ questions 1 and 2.

Thalidomide ‫يزيد‬

Morphine and Codeine

If OH is added= Increases analgesic activity and decreases antitussive activity (becomes Morphine).

If CH3 is added= Decreases analgesic activity and increases antitussive activity (becomes Codeine).
 ‫هذا السؤال يقول في دواء جديد اسمه سيكوستيقمين مشتق من ريفاستيقمين ‪ Rivastigmine‬دواء الزهايمر‪ ،‬ويقول إن الدواء الجديد فيه‬
‫‪ amphetamine‬ف ايش تشوف كونك كـ صيدلي في ال ‪ Pharmacy and Therapeutic Committee‬هل ندخله في الفورملري حق المستشفى أو‬
‫ال؟‬
‫الجواب ال ما ندخله عشان موجود فيه امفيتامين وهذا دواء مخدر يسبب إدمان‬

‫الستركشرات اللي في ملف يزيد كلها‬

Have chlore atom, which is Clomipramine.
Tri= 3

Azole= Nitrogen
‫أكثر واحد فيه شحنات موجبة يكون ‪least dominant‬‬
END
 ‫ملف فبراير‬
1. Feb page 10 and 11

Zidovudine structure, the part responsible for activity is N3.

Which of the following is used for absence seizure?

Ethosuximde

Which drug has the shortest duration of action?

Thiopental

Which part of Ranitidine is responsible for activity?

Furan ring
What is the prodrug of Acyclovir?

Valacyclovir

‫ في ملف يناير‬18 ‫نفس سؤال‬

2. Feb page 20

Erythromycin see question 17.

Ropivacaine=Levobupivacaine, page 13

Ciprofloxacin=piperazine ring increase gram negative activity, question 24.

Carbenicillin antipseudomonal activity is due to COOH, question 30.

Amphetamine reactions: oxidative deamination, aliphatic hydroxylation, aromatic hydroxylation

TCA structures in question 11.

Quinine structure question 23.

 3. Feb page 26

Which statin is prodrug? Lovastatin, question 15 Jan.

Indomethacin question 14 Jan.

Which is a second-generation H1 (not H2) antagonist? Acrivastine

See question 5.

BDZ see question 2 first page.

Nalidixic acid pharmacophore is 3-carboxy-4-pyridone, question 7

The addition of F group structure leads to what? Increased lipophilicity, see question 24

Rivastigmine and psychostigmine see page 12.

4. Feb page 35

Erythromycin structure

5. Feb page 39

TCA selectivity differs by the amine group whether it is secondary or tertiary.

Secondary: Selective to NE.

Tertiary: Non-selective to NE and 5-HT.

See question 11 about TCA structures.