• Phenothiazine structure and asked about mechanism of action?

Ans: Anti dopamine

• Which is used for hypothyroidism treatment?

Ans: Thyroxine (Levothyroxine)

Note: The name was given with the structure

• H2 blockers, gave structures and asked which preserve potency and efficacy?

Ans: Famotidine (Thiazole moiety)

Thiazole

• Ranitidine, what is the pharmacophore?

Ans: Furan

Furan
• Patient takes diazepam what is the antidote? (wants the structure of Flumazenil)

• What to give for heroin overdose? (wants the structure of Naloxone)

• Metabolized by?

AmpHotericin B

Ans: Hydrolysis
• Gave 4 structures and asked which is quinine structure?

Quinine
Quinine

• Which is dihydropyridine structure?

Note: choose any that contains this

• Which is used for absence seizure or which is Ethosuximide structure?

• What type of bond? Which one is salicylic acid structure?

Ans: Covalent bond

Aspirin (Acetylsalicylic acid)

• What type of bond?

Ans: Hydrogen bond

Acetaminophen (Paracetamol)

• Another question about Acetaminophen, what is its pharmacophore?

Ans: Benzene ring and Carbonyl group

• Steroids structures and asked which one is given oral?

Ans:

Betamethasone
Note: Careful their structures are similar, but drug names
might be given.

• Structure amphetamine metabolism? (Gave the reaction and asked for the enzyme)
-MAO
-MFO

Note: Both these options are wrong the correct answer may be CYP2D6

The reactions below just to have an idea, maybe they came like that?!

Amphetamine
• Structure DOC for GAD (generalized anxiety disorder)?
-Alprazolam (correct)
-Lorazepam
-Diazepam

Alprazolam

• Structure two estrogen and asked what they are?

Ans: Hormones
• Structure what to avoid with penicillin allergy?
Note: Avoid any one with beta lactam ring

• Structure what is the benefit of extra benzene in ACEI?

Ans: The extra group will bind to the origin strongly

Note: This image just to give you an idea

• Structure Erythromycin?
• Which of the following is the reason why Erythromycin is sensitive to acidic pH?

Ans: Ketal fomation between hydroxyl group (6 and 12) and ketone at position 9 (Ketal ketone)
• Structure least dominant of Histamine?
Note: The one with the more positive charges (+)

Add thilido and NSAIDs one affect GIT and the other heart

• Which NSAID have more cardiotoxicity? (Safest for GIT, from non COX-2, Ibuprofen)

Ans: Celecoxib
• Which NSAID is safe for people with heart issues? (Naproxen or Diclofenac)

• Which anticancer is more cardio-toxic? (Doxorubicin)

• Which of the following is the bioisoster for Roplvacaine?

Ans: Levobupvicaine
 ‫*شامل فقط للشرح في مقطع الفيديو‬
https://youtu.be/DJtWjfgoBb0
MEDICINAL CHEMISTRY ZAITONAH STRUCTURES - SAME FILE ORGANIZED IN TABLES
1) Codiene & - Codiene to morphine
morphine Oxidation
O-demethylation
- Morphine to codeine:
Methylation
Reduction
- What region in codeine
makes it used as
antitussive?
Lack of 14 beta- OH
2) Aspirin - What makes aspirin works
as antiplatelet?
Acetyl group bind covalently
to COX1 receptor
- What is the type of acetyl
group bond makes it
connected to cox1 receptor?
Covalent bond***

3) Quinine & - Quinine: used in malaria (R-

quinidine confiugation)***
- Quinidine: used in arrhythmia
(S configuarion)***
-

4) Oseltamivir - To remember the structure:

look for BIRD
- Conversion:
- From oseltamivir phosphate
to oseltamivir carboxylate by:
Ester hydrolysis
- Type of metabolism:
hydrolysis
5) Phospholipid - Head: hydrophilic
- To remember easily:

- Tail: Hydrophobic

6) BZD - 7C cycle*** "Z7" + 2 N

- How to decrease the
duration of BZD?
Add polar function to C3
Will increase excretion and
thereby decreases duration
of action
7) Dihydropyridine - Structure of DHP
- Know what is DHP CCB

8) Clozapine - Structure may came without

name and asks you what is
the side effect of this
structure?
Agranulocytosis monitor
CBC
To remember the
structure:
- Cl Chloride at the end
- oza "BZD 7 cycle"
- Pine: N at the structure

9) Barbiturates - Structure - The more the branching the more the lipophilicity the
- Short duration** shorter duration of action

10) NSAIDs

11) Fondaparinux Type of the structure?

Penta
Name of the drug?
Fondaparinux
12) Statins Lovastatin prodrug and natural
statin
***

13) Bond C2H2 Triple bond

C2H4 double bond
C2H6 single bond
14) Beta-lactams - Pt with an allergy from
penicillin what should be the
alternative?
*choose any structure that
DON T CONTAIN the beta-
lactam ring*

15) Tricyclic - What antidepressant causes

antidepressents photosensitivity?
- Answer: structures of TCA
- Which TCA undergo photo-
oxidation when exposed to
light?
Clomipramine
16) Ethosuximide Which one of the following
can be used in absence
seizure?
- What is the name of this
structure?

17) Celecoxib - COX2 inhibitor:

- their major problems are
cardiac-related

18) Vitamin D

19) Warfarin - What is the type of

metabolism?
Phase-2 conjugation**
- Warfarin structure:
3 rings are closed and one
open

20) Epinephrine - Epinephrine to

phenylephrine?
By removing on OH group
Increases the selectivity of
alpha one
Used as nasal decongestant

21) Antihistamines - Case about a patient that

needs to take histamine and
he will drive
Choose 2nd generation
antihistamines as they
DON'T CROSS THE BBB

- Loratadine:

BBB can be used

22) Amphotericin B - Structure of amphotericin B
and asks you what is the
metabolism?
Hydrolysis

23) Acetaminophen - Types of bond?

H bond

24) Floroquinolone - To increase or decrease the

spectrum position 7
- What is the
pharmacophore?

25) Zidovudine - Structure of Zidovudine and

asks you what is the
functional group
responsible for the antiviral
activity?
Azide group****

- Zidovudine: HIV drug can be

used during pregnancy

26) Thalidomide - Type of isomer?

Enantiomer***
R-enantiomer sleep
inducer
S-enantiomer
teratogenic
27) Histamine 2 - What is the least dominant
tautomer of histamine at
physiological pH?
Least dominant: 2 positive
ions on N & NH3
Most dominant: 1 positive
ion on NH3

28) NSRI - Changes from NSRI to

SNRIs?
- Demethylation of side chain
tertiary amino group to yield a
secondary amino group

29) Glibenclamide - Asks you what is the

(glyburide) pharmacophore of
glyburide? *****
- Benzensulphonyl urea

30) Erythromycin - Which of the following is the

reason why erythromycin is
sensitive to pH?
- Ketal formation between
hydroxyl group (6 and 12) and
ketone at position 9

31) Ropivacaine - Which of the following is the

bioisoster for
ropivacaine?***
Levobupvicaine

32) PPI - Which of the following

metabolic reactions can
occur at the pointed arrow
on the structure?
Oxidation
33) Miscellaneous - Which of the following
medications contains
moiety?
- The structure you find in it the
triazole structure choose it

34) Cephalosporins
 of Reaction on if dtz Removed
na.me
or dealkylation
ro demethylation 0

ifRemovebecomemorphinewhichtpotency

ifsaligiico.ci

2oHoCHs

which make aspin in

work as antiplatelet
 when quinine is configured

Malaria optical
isomer

cancer
antiarrythmia

active oseltamivir

Eep sa

1004
p
phospholipid structure
 B2b How to 1 duration

add polar function to C

3
Apolarity
detection
duration

Barbiturates
Dihydropyridine CCB

Iii
leaf effect on IG

MCMinhibitor
e

aspirin
 natured C i
prodry statin
or

say

is

g s
G
 r

Basie
n

CzHz 4 2 1 2 6 C valence ee 4
0244 4 2 41 re H h I
CzH6 Cu z C6xD He
04 6
Cole
f
Edt H
Hp
p ETH
t C C H ti H GH
triplebond doublebond H
single
8 atom DJ six
C347F

d's

rrn
 Cefn Ceelo
cefta

d d
Iniperen aretronam
Which antidepressants cause photosensitivity
TCA
‫ مو شرط لكن التفرع شرط‬N‫ال‬
TCA agents
I lg
If
night

O
g
t

C THIlNo2
2,5-Pyrrolidinedione, 3-ethyl-3-methyl

db

active form of uit D

 3Ring open
Ring

407 methyl
. ‫مابينوا مكتوب تحته اسم او‬

alphy Bet awwbetaverylittle

9

a
 ‫ركب بس تحسبًا للي يبغى‬E‫كان كاتب اسم ا‬
2nd antihistamine
R 25 of
pro Ing

R
R R

Iotafidine

‫بس عشان عيونكم تتعود عالفرق‬

Ri Rr r
Rr p Rl
Rr Dz

R Hep R
Rr Rr
‫ركبات افهمو الفكرة فقط‬E‫ماهي ا‬

Break ester from the remaining

give acid alcohol

ZoH I
CooH

I 0

alcohol
zaH
ped
I alcohol
acid

1
Ester
‫مو فاهمة ايش يبغوا بالضبط ‪ ..‬في اختبار وحدة ‪ ١٦‬فبراير ماجاها لكن في ‪ ٣‬جاهم من قبل زي ‪ ١٢‬فبراير وكدا‬
‫ً‬
‫اص‪e‬‬ ‫خليكم عارف‪ g‬شكله‬

‫اعتقد انو يجيب مركبات كثير ويقول الفارماكوفور ‪quinolones‬‬

‫وتختاروا ا‪E‬ركب اللي جوته دي الحلقت‪ g‬بزحمتها ا‪.‬ساسية‬

‫‪6CR S‬‬
‫‪be‬‬ ‫‪only‬‬
‫‪Ine‬‬

‫‪cook‬‬
‫‪acid‬‬

‫‪X‬‬ ‫‪halogen gpCig‬‬

‫‪f‬‬
‫‪etc‬‬
‫مدري لو هيكون يلخبط او ‪.‬‬

‫‪4 I‬‬

‫‪nine O cold‬‬
‫‪0 hes‬‬ ‫‪fo‬‬ ‫‪0‬‬
‫مش قاعدة و‪ .‬لها صحة بس ممكن نفتكرها كدا‬
‫‪O‬‬ ‫وفي دي ا‪E‬ركبات بس‬
‫‪one‬‬ ‫‪c‬‬

‫‪u‬‬
 ‫اللي حاب زيادة وهيزعل لو ماحل هذي ممكن توصلك ‪l‬جابة‬

‫‪d‬‬ ‫‪d‬‬ ‫‪b‬‬

‫‪r‬‬
‫‪r‬‬ ‫‪p‬‬ ‫‪e‬‬ ‫‪e‬‬ ‫‪r‬‬

‫‪d‬‬ ‫‪d‬‬ ‫‪d‬‬ ‫‪f‬‬ ‫‪d‬‬

‫‪hexaneWAM‬‬ ‫‪over decor‬‬
‫‪butane‬‬ ‫‪afar‬‬

‫ميثان( و )إيثان( بنات عم تزوج بهما رجل يدعى‬

‫)بروبان( وأسكنهم في )بيوتان( ورزق منهما )بنتان(‬
‫أسماهم )هكسان( و) هبتان( ثم تقدم لهما رجل‪ g‬هما‬
‫)أوكتان( و)نونان( وكان مهرهما عباره عن)ديكان(‬

‫دعواتكم ‪..‬‬
‫‪RubaMah‬‬
 SAIF ALGHAMDI
!‫توكلت على ا‬

Tetracycline

Tetracycline
(1,2,3,4,4a,5,5a,6,6a,11,11a,12,12a-Dodecahydronaphthacene)

Quinolone

Beta Lactam

Sulfonamide

Azole

Quinidine

Salicylic acid

Paracetamol

Morphine
Zidovudine
 paracetamol

a
Increase gram negative activity

i think
 Structure

Benzodiazepines

Barbiturates

Quinidine

Convert codeine to morphine by ( give structure of two drug)

demethylation
(aspirin structure) then ask which SAR related to its antiplatelet activity

Which one is double bonds structure ?

Structure of quinine?

Methacholine structure

dihydropyridine structure ?
Structere of Oseltamvire

structure of phospholipids
hydrophilic head and hydrophibic tail
 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.