Medicinal Chemistry IB SL Chemistry

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60 Terms

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Drug
Something that causes a physiological change in the body
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Medicine
Something used to treat or prevent diseases
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Medicine and Drugs must do one of the following…
* alter incoming sensory sensations
* alter a person’s mood or emotions
* alter the physiological state of the body, including consciousness and coordination
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Therapeutic effect
beneficial effect of a medicine
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What are the 3 parenteral methods of administration?
* intramuscular - into muscle
* subcutaneous - directly under the skin
* intravenous - bloodstream(most rapid effect)
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bioavailability
fraction of administered dosage of a drug that enters the bloodstream and have an active effect
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What factors affect bioavailability?
* method of drug administration
* polarity of drug
* type of function groups in drug
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True or False? Intravenous administration has a bioavailability of 100%
True
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True or False? Oral doses need to be 3 times stronger than an intravenous dose
False. They must be 4 times stronger
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What are the best type of molecules to be administered, in terms of solubility
One that is largely hydrophobic but still has some solubility
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Which functional groups are able to form hydrogen bonds easily?
* carboxyl
* hydroxyl
* amine
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Which functional groups enhance lipid solubility(non-polar)?
Ones that lack the ability to ionize or form hydrogen bonds

* phenyl group(benzene ring)
* hydrocarbon chain
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How is the solubility of aspirin increased?
It reacts with NaOH
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True or False? Ionic salts increase solubility
True
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Therapeutic window
Measure of safety of a drug. A wide window means a wide margin between toxic and safe doses
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Therapeutic Index(TI) for humans
TI = TD(50)/ED(50)

* TD(50) - median toxic dose
* ED(50) - median effective dose
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What are the main stages of drug development?
* drug is synthesized
* Drug is tested on animals to find lethal dose
* Drug is tested on humans in a double blind experiment
* Unwanted side effects and tolerance must be determined
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How can you test the purity of aspirin?
Can be determined by melting points and IR spectrum
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True or False? More impurities means higher a melting point
False. More impurities means a lower melting point
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Analgesic
painkiller

* aspirin
* ibuprofen
* paracetamol
* morphine
* codeine
* dimorphine
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How does aspirin block the sensation of pain?
It blocks the action of enzymes that produce prostaglandins, which are involved in the transmission of pain impulses to the brain
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Anticogulant
prevents blood from clotting
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What are 5 common methods of drug administration?
* oral
* polar, water-soluble
* intravenous
* unstable or poorly soluble
* transdermal(skin patch or ointment)
* non-polar, lipid-soluble
* rectal
* unstable in gastric acid
* inhalation
* volatile
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Antibiotics
Drugs that kill or inhibit the growth of bacteria

* penicillin
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What is a beta-lactam ring?
A box shaped structure found in penicillin consists of three carbons and a nitrogen to make the base. One of the carbons in double bonded to an oxygen
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What doe beta-lactam antibiotics do?
They interfere with cell wall formation in bacteria by inhibiting the enzymes responsible for creating cross-links in the cell wall
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Antibiotic resistance
Bacteria that resists the effects of an antibiotic
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What are the causes of antibiotic resistance?
* overprescription of antibiotics for basic illnesses
* patients don’t complete their course of antibiotics
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How are antibiotics released into the environment?
* antibiotics are given to healthy farm animals
* Improper disposal by hospitals or companies
* excreted by human urine
* pharmaceutical waste
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Opiates
Natural analgesics derived from opium. Bind to opioid receptors in the brain and block transmissions of pain impulses.

* morphine
* codine
* dimorphine
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What are the advantages and disadvantages of strong analgesics/opiates?
Advantages:

* provide relief for pain
* wide therapeutic window
* improve quality of life
* reduce anxiety

\
Disadvantages:
* euphoria and lack of self-control
* regular usage can lead to addiction, dependence, and withdraw
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Blood-brain barrier
Tightly packed cell restricting passage of substances from bloodstream to brain that is largely composed of lipids
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How is dimorphine created from morphine?
morphine + ethanoic acid →dimorphine + water
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algmates
type of antacids that prevents acid from rising in the esophagus
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Proton pump inhibitor
inhibits the secretion of H+ ions into gastric juice. Stomach acid inhibitor that can last up to three days.

* omeprazole
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H2 Receptor antagonists(H2 blockers)
stomach acid inhibitor that blocks histamine receptors in acid-producing cells in the stomach

* ranitidine
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Virus
submicroscopic organism that replicates inside living cells of other organisms. Consist of a protein coat and nucleic acid
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Bacteria
small single cell microorganisms that are self reproducing, living, and contain various cell organelles. They are larger than viruses
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Why are viruses harder to target with drugs than bacteria?
* they lack a cell structure
* they lack subunits that can be targeted by antivirals
* they mutate quicker
* they must be targeted at a genetic level
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True or False? Antibiotics are effective against bacteria but ineffective against viruses
True
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How do antiviral drugs work?
* alter a cell’s genetic material
* block enzyme activity
* bind to cellular receptors targeted by viruses
* prevent release of viruses
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What are some examples of antiviral drugs for the common flu?
* oseltamivir(oral)
* zanamivir(inhalation)
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Why is HIV hard to treat?
* mutates rapidly
* has host cells to replicate


* drugs that treat HIV may harm the host cell
* high price of anti-viral drugs
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What are Socio-Cultural factors that affect AIDS?
* condom use
* ignorance and misinformation
* stigmas
* prostitution
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What are the three levels that nuclear waste is classified into?
* Low-Level waste(LLW)
* produces weak radiation for a short time
* Intermediate-Level Waste(ILW)
* produces strong radiation for a short time
* High-Level Waste(HLW)
* produces strong radiation for a long time
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What levels of radiation are typically found in medical settings?
* Low-Level and Intermediate-Level
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What are examples of low-level waste?
* gowns
* protective clothing
* shoe covers
* tissues
* needles
* mops
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How do you dispose Low-level waste?
Store in shielded containers until the isotopes have decayed, then dispose of as non-radioactive waste
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What are some examples of Intermediate-level waste?
* sources for radiotherapy
* Co-60
* Cs-137
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How do you dispose of Intermediate-level waste?
* long term storage in shielding containers or concrete chambers, then buried underground
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In green chemistry, what are the preferred solvents in synthesizing drugs?
* water
* methanol
* ethanol
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In green chemistry, what are the undesired solvents in synthesizing drugs?
* pentane
* dichloromethane
* dichloroethane
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True or False? Many undesirable solvents are VOC(volatile organic compounds)
True
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Why are VOCs used as solvents?
They have high volatility
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Chlorinated vs non-chlorinated solvent types
Chlorinated:

* ozone-depleting
* accumulates in ground water
* forms toxins if burned
* toxic, irritant, and forms greenhouse gases

Non-chlorinated:

* flammable
* toxic, irritant, and forms greenhouse gases
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What are some of the Green Chemistry principles?
* prevent waste
* design less hazardous chemical synthesis
* design safer chemicals and products
* use safer solvents
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How are some bacteria inactivating penicillin?
They produce penicillinase/enzyme that deactivates penicillin
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How has the structure of penicillin been modified to overcome this resistance?
the side chain has been changed to preserve the beta-lactam ring
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How do antacids neutralize stomach acid
weak base + stomach acid(HCl) →XCl + water

* CaCO3 + 2HCl →CaCl2 + H2O + CO2
* MgO + 2HCl → MgCl2 + H2O
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What are the advantages of taking ranitidine instead of antacid?
* ranitidine can treat stomach ulcers
* ranitidine prevents long term damage
* ranitidine lasts longer
* ranitidine doesn’t cause bloating