Pharmaceutical Medicinal Organic Chemistry Flashcards

Flashcards based on the provided lecture notes for Pharmaceutical Medicinal Organic Chemistry, focusing on key concepts, definitions, and examples relevant to the subject.

Which biological field is NOT typically involved in the design, chemical synthesis, and development of pharmaceutical agents?

Human Anatomy

Which disciplines of chemistry are involved in the development of bioactive molecules or drugs?

Medicinal chemistry, Pharmaceutical chemistry, and Organic chemistry

What area of chemistry focuses on synthetic organic chemistry, natural products, and computational chemistry for new therapeutic agents?

Medicinal Chemistry

Who described the therapeutic properties of plants in ancient times?

Ancient Greeks, Romans, China, and India

Which individual was NOT a proponent of 'Materia Medica' during the Middle Ages?

Alexander Fleming

Which of the following is NOT a general anesthetic?

Formalin

Which of the following has a hypnotic activity?

Chloral

Which of the following medicinal drugs is NOT an antiseptic?

Diethyl ether

What is the analgesic constituent of willow bark?

Salicylic acid

Which of the following is NOT a pain killer?

Iodine

Pamaquine, Mepacrine, Chloroquine

antimalarial drugs

Tetratogenic effect, Thalidomide

What term relates to the drug that caused deformity in children when used as a sedative by pregnant women?

QSAR

What framework provides systematic development of drugs based on quantitative structural relationships?

Organic compound

What defines compounds of carbon?

Functional group

What chemical unit is responsible for the characteristic chemical reactions of a compound?

R-OH

What is the general formula for an alcohol?

R-CHO

What is the general formula for an aldehyde?

R-COOH

What is the general formula for a carboxylic acid?

R-COO-R

What is the general formula for an ester?

R-SH

What is the general formula for a thiol?

R-CO-R

What is the general formula for a ketone?

RCONH2

What is the general formula for an amide?

R-NH2

What is the general formula for an amine?

CH3-CH2-O-CH2CH3, used as a solvent

What is the structure and use of Diethyl ether

N2O, mild anesthetic

What is the structure and use of Nitrous oxide

CHCl3, solvent and for organic synthesis

What is the structure and use of Chloroform

C6H5OH, preservative and disinfectant

What is the structure and use of Phenol

C2HCl3O, sedative-hypnotic

What is the structure and use of Chloral (trichloroethanal)

H0C6H4COOH, headache remedy

What is the structure and use of Salicylic acid

C8H9NO2, fever reducer and pain reliever

What is the structure and use of Paracetamol (p-hydroxyacetanilide)

C10H13NO2, analgesic and antipyretic

What is the structure and use of Phenacetin

C17H21NO4, Anesthetic

What is the structure and use of Cocaine

C9H11NO2, numbs the affected area

What is the structure and use of Benzocaine

C15H21N3O, treat malaria

What is the structure and use of Pamaquine

C23H30CIN3O, treat parasitic infections and malaria

What is the structure and use of Mepacrine

Refers to the space arrangement of the atoms or three-dimensional structure of the molecule

What is Stereochemistry?

Any change in stereo-specificity of the drug will affect its pharmacological activity

Why is stereochemistry important in pharmacology?

Optical and Geometric isomerism, Conformational isomerism, Isosterism and bioisosterism

Name the steric factors that influence pharmacological activity

compounds that contain at least one chiral carbon atom or are compounds that differ only in their ability to rotate polarized light.

What are optical isomers?

pairs of molecules for which the three- dimensional arrangement of atoms represents nonsuperimposable mirror images

What are enantiomers?

(S)(-) enantiomer of warfarin and Levo-phenol

What are examples of enantiomers?

cis-trans isomerism

What is geometric isomerism?

different physicochemical properties and pharmacological activity

What is different about geometric isomers?

trans-diethylbestrol and Pentacozine

What is an example of geometric isomerism?

Non-identical space arrangement of atoms in a molecule, resulting from rotation about one or more single bonds

What is conformational isomerism?

Acetylcholine

What id an example of conformational isomerism?

the steric electronic and solubility characteristics of a drug which make it interchangeable with the drugs of the same pharmacologic class

What is isosterism?

Any two ions or molecules having an identical number and arrangement of electrons

What are Isosteres?

functionalgroups which have similar spatial and electronic character, but they retain the activity of the parent.

What is bioisosterism?

It maintains similar biological properties, It resolves biological problems effectively

What is the significance of Bioisosterism in medicinal chemistry?

Loratadine (Claritin) or cetirizine (Zyrtec)

What is the recommended antihistamine for truck drivers to avoid drowsiness?

Carboxyl group

What functional group is present in Zyrtec?

Alcohol group

What functional group is present in Tavist?

Zyrtec

Which medication is better for truck drivers between Zyrtec and Tavist?

Ether, Tertiary amines, Carboxylic acid, Aliphatic hydrocarbons, Halogenated aromatic hydrocarbon, Aromatic hydrocarbon

Name the functional groups

Cetirizine is a second-generation H₁-antagonist

Which drugs are less likely to cause drowisness?

Carboxylic Acid

What is the predominant functional group for Cetirizine

This functional group is hydrophilic and will be predominantly ionized in the plasma and therefore, may limit the extent of absorption across the blood-brain barrier.

Why Cetirizine is less prone to drowsiness

predict the water solubility of Aspirin molecule

What is the empirical method of Lemke?

9 carbon atoms

What is the total number of carbons in the aspirin molecule?

ester group and the carboxylic acid group

functional groups contribute to its solubilizing potential

Water Insoluble

Aspirin solubility

10mg/mL @ 37 degree Celsius 0.33g/100mL at h20 in room temperature

What is the soly of Aspirin?

HO

What is a logical primary metabolite of a phase I reaction for norepinephrine?

hydrolysis by amidase enzymes and oxidative N-dealkylation

What metabolic pathways might occur with Atenolol (Tenormin)?

The agent has a very short t1/2 because of its susceptibility of hydrolysis by esterases, The agent should not be "pushed" in an iv line that is supplying a drug to a patient that is buffered with bicarbonate

What is true about Esmolol (Brevibloc)

Phase I and Phase II

What are the phases of drug metabolism?

Functionalization

Phase I

Conjugation

Phase II

Azo Reduction, Nitro Reduction, Hydrolysis, Oxidation, Reduction

What are examples of Phase I drug?

Glucoronidation, Sulfate Conjugation, Glycine /Glutamine Conjugation, GSH/mercapturic Acid Conju., Acetylation, methylation

What are examples of Phase II drug?

Barbiturates, amphetamines, phenylbu- tazone, phenytoin, Morphine, caffeine, theophylline, Codeine, Acetaminophen, nicotine, methaqualone

Examples of phase I drug-metabolizing reactions

Acetaminophen, morphine, diazepam, sulfathiazole, digoxin, digitoxin

Glucuronidation

Sulfonamides, isoniazid, clonazepam, mescaline, dapsone

Acetylation

Antiseptics are compounds that kill(bactericidal) or prevent the growth (bacteriostatic) of microorganisms when applied to living tissues.

what is the definition of an antiseptic?

As the carbon chain becomes more branched in alcohols,their antimicrobial activitytypically decreases.

What happens to the antimicrobial activity of alcohols as the carbon chain becomes more branched?

The bond thatassociates iodinewithpolyvinyl pyrrolidone up) in PVP-iodine complexes is primarily a weak van der Waals interaction or a interaction, where the iodine molecules are held within the polymer matrixthrough non-covalentforces.

What kind of bond associates iodine with polyvinylpyrrolidone in PVP–iodine?

The mostactive agentforthe clinical treatmentoftuberculosisis typically a combination therapy involving multiple amgs. Commonly used digs inclus psoniazid, rifampicin, pyrazinamide, and etambutol.

What is the most active agent for the clinical treatment of tuberculosis?

Dihydrofoldreductase (DHFR) in bacteria plays a crical role insynthesizing tetrahydrofolate (THE), whichis essential for the production ofpurines thymidylate, and certainamino acids.

What is the function of dihydrofolate reductase in bacteria?

bacteria that have developed resistance to multiple antibiotics, making them challenging to treat effectively.

What are multidrug-resistant bacteria?

These are bacteria that have developed resistance to multiple antibiotics, making them challenging to treat effectively.

Why are multidrug-resistant bacteria of concern to medicine?

promoting appropriate antibiotic use through patient education and counseling, emphasizing the importance of completing prescribed antibiotic courses and not sharing or saving antibiotics

How can a pharmacy student and future pharmacist contribute in minimizing the emergence of antimicrobial-resistance (AMR)?

extrapyramidal symptoms(such as tremor), weight gain, sedation, and hyperprolactinemia.

What are the adverse effects of risperidone?

CYP2D6 enzyme family

What CYP enzyme family metabolizes risperidone and paroxetine?

paliperidone.

What is the active metabolite of risperidone?

paroxetine inhibits the CYP2D6 enzyme, leading to increased serum levels of risperidone and its active metabolite paliperidone.

What happens to the serum levels of each drug if risperidone and paroxetine are given together?

Yes, there may be a need to reduce the dose of risperidone due to the increased serum levels when co-administered with paroxetine, to avoid potential adverse effects or toxicity.

Is there a need to reduce the dose of the other drug? Why?

Conduct a thorough and mechanistic SAR analysis of the three therapeutic options in the case, Apply the chemical understanding gained from the SAR analysis to this patient’s specific needs to make a therapeutic recommendation.

Which of the three therapeutic choices would you recommend?

Stereochemistry

What is the space arrangement of the atoms or three-dimensional structure of the molecule?

Stereochemistry

What can change in stereo-specificity effect in pharmacological activity in?

(S)(-) enantiomer of warfarin is 5 times more potent as an oral anticoagulant than the (R)(-) enantiomer

Example of Optical isomerism

trans-diethylbestrol has same potency as estradiol, whereas cis-diethylbestrol is only one fourteenth as active (only 7% of the estrogenic activity)

Example of Geometric Isomerism

trans conformation: binds to muscarinic receptor

Example of Acetylcholine

Bioisoterism

synthesis of structural analogues of a lead compound by substitution of an atom or a group of atoms in the parent compound for another with similar electronic and steric characteristics

Carboxyl group characteristics

might make it harder for the drug to cross this barrier, reducing the likelihood of causing drowsiness.

Alcohol group characteristics

potentially make it easier for the drug to cross the blood-brain barrier, increasing the risk of drowsiness.

Hydrophobic functional group

both cetirizine and clemastine contain several hydrophobic functional groups that would facilitate their crossing the blood-brain barrier.

CYP450-independent

Amine oxidation and Dehydrogenation

Hydrolyses

Procaine, succinylcholine, aspirin, clofibrate, Procainamide, lidocaine, indomethacin

Antiseptics

compounds that kill (bactericidal) or prevent the growth (bacteriostatic) of microorganisms when applied to living tissues.