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Options (Choose One) - Medicinal chemistry

Grade 12IBChemistry

Review the key concepts, formulae, and examples before starting your quiz.

🔑Concepts

The Therapeutic Index (TITI) measures a drug's relative safety. For humans, TI=TD50ED50TI = \frac{TD_{50}}{ED_{50}}, where TD50TD_{50} is the toxic dose for 50%50\% of the population and ED50ED_{50} is the minimum effective dose for 50%50\% of the population.

Bioavailability is the fraction of the administered dosage that reaches the target part of the human body. Factors affecting it include method of administration, solubility (hydrophobicity/hydrophilicity), and functional groups.

Aspirin (acetylsalicylic acid) is synthesized by reacting salicylic acid with ethanoic anhydride: C7H6O3+C4H6O3C9H8O4+C2H4O2C_7H_6O_3 + C_4H_6O_3 \rightarrow C_9H_8O_4 + C_2H_4O_2. Recrystallization is used for purification.

Penicillins contain a beta-lactam ring (a four-membered ring including a nitrogen atom). It works by irreversibly inhibiting the transpeptidase enzyme, preventing bacterial cell wall synthesis.

Strong analgesics (opiates) like morphine, codeine, and diamorphine (heroin) work by binding to opioid receptors in the brain, blocking pain signals. Diamorphine is more potent than morphine as it is less polar, allowing it to cross the blood-brain barrier more easily.

Stomach pH regulation involves antacids like Mg(OH)2Mg(OH)_2 or Al(OH)3Al(OH)_3 which neutralize excess HClHCl. H2H_2-receptor antagonists (e.g., ranitidine) and Proton Pump Inhibitors (e.g., omeprazole) reduce the production of stomach acid.

Antiviral drugs like Oseltamivir (Tamiflu) and Zanamivir (Relenza) work as neuraminidase inhibitors, preventing the virus from escaping the host cell to infect others.

Taxol is a chiral drug used in cancer treatment. Its synthesis requires a chiral auxiliary, which is a chiral molecule that binds to the starting material to force the reaction to follow a specific stereochemical path, producing only the desired enantiomer.

Nuclear Medicine uses radioisotopes. Technetium-99m99m (99mTc^{99m}Tc) is commonly used in medical imaging due to its short half-life (t1/26t_{1/2} \approx 6 hours) and emission of low-energy gamma (γ\gamma) radiation.

📐Formulae

TI=LD50ED50 (Animal studies)TI = \frac{LD_{50}}{ED_{50}} \text{ (Animal studies)}

TI=TD50ED50 (Human studies)TI = \frac{TD_{50}}{ED_{50}} \text{ (Human studies)}

pH=pKa+log10([A][HA])pH = pK_a + \log_{10}\left(\frac{[A^-]}{[HA]}\right)

N(t)=N0eλtN(t) = N_0 e^{-\lambda t}

λ=ln2t1/2\lambda = \frac{\ln 2}{t_{1/2}}

💡Examples

Problem 1:

A patient produces 0.500.50 dm3dm^3 of gastric juice with a concentration of HClHCl of 0.0200.020 moldm3mol\,dm^{-3}. Calculate the mass of magnesium hydroxide, Mg(OH)2Mg(OH)_2, required to neutralize this acid.

Solution:

Mass = 0.290.29 gg

Explanation:

First, calculate moles of HClHCl: n=c×V=0.020×0.50=0.010n = c \times V = 0.020 \times 0.50 = 0.010 molmol. The neutralization equation is Mg(OH)2+2HClMgCl2+2H2OMg(OH)_2 + 2HCl \rightarrow MgCl_2 + 2H_2O. Molar ratio of Mg(OH)2:HClMg(OH)_2 : HCl is 1:21:2. Moles of Mg(OH)2=0.0102=0.0050Mg(OH)_2 = \frac{0.010}{2} = 0.0050 molmol. Molar mass of Mg(OH)258.32Mg(OH)_2 \approx 58.32 gmol1g\,mol^{-1}. Mass =0.0050×58.32=0.2916= 0.0050 \times 58.32 = 0.2916 gg.

Problem 2:

Contrast the structures of morphine and diamorphine (heroin) to explain why diamorphine is more potent.

Solution:

Morphine has two hydroxyl (OH-OH) groups; diamorphine has two ester (OCOCH3-OCOCH_3) groups.

Explanation:

The hydroxyl groups in morphine are polar, making it less soluble in lipids. The ester groups in diamorphine are less polar, making it more lipid-soluble. This allows diamorphine to cross the non-polar blood-brain barrier more efficiently and reach the opioid receptors in higher concentrations.

Medicinal chemistry - Revision Notes & Key Formulas | IB Grade 12 Chemistry