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PHRM 100 – PDD > PDD 03: Pharmaceutical Solutions > Flashcards

PDD 03: Pharmaceutical Solutions Flashcards

1
Q

What are true solutions?

A

mixture of two or more components that form a homogeneous molecular dispersion

  • transparent but not necessarily colourless
  • one-phase
  • solute are < 1 nm in diameter and not large enough to scatter light
  • ie. sugar in water
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2
Q

What are colloidal dispersions?

A

dispersion containing particles between 1-500 nm in diameter

  • Tyndall effect
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3
Q

What is the Tyndall effect?

A

particles scatter light and may appear visibly turbid (depending on concentration of drug)

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4
Q

What are coarse dispersions?

A

dispersion containing particles > 500 nm in diameter

  • particles scatter light and appear visibly cloudy
  • solute can settle over time
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5
Q

What are the 2 types of coarse dispersions?

A
  • suspension
  • emulsion
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6
Q

What is a suspension?

A

solid in liquid coarse dispersion

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7
Q

What is an emulsion?

A

liquid in liquid coarse dispersion

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8
Q

What are the advantages of formulating a drug as a solution? (3)

A
  • more easily administered orally to individuals who have difficulty swallowing (ie. geriatrics, pediatrics) compared to tablets, capsules, etc.
  • drug is already dissolved in the formulation and is therefore immediately available for absorption – potentially enhanced bioavailability over oral solid dosage forms
  • taste-masking is achievable
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9
Q

What are the disadvantages of formulating a drug as a solution? (5)

A
  • unsuitable for therapeutic agents that are chemically unstable in the presence of water
  • poor solubility of some drugs can prohibit their formulation into pharmaceutical solutions (there are techniques to help improve solubility though)
  • preservative is usually required to avoid growth of microorganisms
  • expensive to ship and bulky
  • inconvenient for the patient to carry and use
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10
Q

What are the components of pharmaceutical solutions? (9)

A
  • active pharmaceutical ingredient (API)
  • solvent (or vehicle)
  • buffers
  • solubility enhancers (co-solvents, complexing agents, surfactants)
  • taste-masking agents (sweeteners, flavoring agents, etc.)
  • preservatives
  • rheology (viscosity) enhancers
  • antioxidants and chelators
  • colorants
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11
Q

Solvent/Vehicle

What are the 3 types?

A
  • water
  • aromatic water
  • non-aqeuous solutions
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12
Q

Solvent/Vehicle

What is the preferred and most commonly used vehicle in solutions for oral administration?

A

Purified Water USP (low cost, low toxicity)

  • prepared by distillation, ion exchange or reverse osmosis
  • solid residue is < 1 mg/100 mL
  • not to be confused with water for injections
  • should NEVER use tap/drinking water (ie. mineral/organic impurities, presence of particulates, etc.)
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13
Q

Solvent/Vehicle

What is aromatic water?

A

saturated aqueous solutions of volatile oils

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14
Q

Solvent/Vehicle

How is aromatic water prepared?

A
  • volatile oil is triturated with powdered talc or pulped filter paper in mortar
  • mixed with purified water 500x volume of oil
  • by absorbing the oil to the large surface area of the talc/paper, oil quickly dissolves in the water
  • solution is filtered to remove talc/paper (distributing agents)
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15
Q

Solvent/Vehicle

What is an example of aromatic water?

A

peppermint water

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16
Q

Solvent/Vehicle

Why might non-aqueous solutions be used?

A

sometimes it is not possible to ensure complete solution of the ingredients at all storage temperatures

  • drug might be unstable in aqueous system
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17
Q

Solvent/Vehicle

Name some alternative non-aqueous solvent systems. (3)

A
  • alcohols: ethanol, isopropyl alcohol, glycerol
  • non-volatile oils: peanut, corn, soybean, peppermint, etc. oil
  • ketones: acetone
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18
Q

Buffers

How does a buffer control the pH of a pharmaceutical solution? (2)

A
  • maintains the solubility of the therapeutic agent (which can be compromised by small changes in pH since it is pH-dependent)
  • increases the stability of the therapeutic agents as well as the other ingredients
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19
Q

Buffers

What is a formulation method to enhance/optimize the aqueous solubility of therapeutic agents?

A

optimization of pH

  • adjust and maintain pH with a buffer system so that API is in its more soluble ionized state
  • APIs with ionizable groups within pH 2-8 are good candidates for improving solubility with pH optimization
  • chosen pH does not conflict with other product requirements (stability of the drug or other ingredients – ie. colours, preservatives, flavours)
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20
Q

Buffers

What does the choice of suitable buffer depend on? (3)

A
  • pH
  • buffering capacity required
  • compatibility with the other excipients
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21
Q

Buffers

What are some common buffers used in pharmaceutical solutions? (3)

A
  • acetate (acetic acid + sodium acetate): pH 3.6 – 5.6
  • citrate (citric acid + sodium citrate): pH 3.0 – 6.2
  • phosphate (sodium phosphate + disodium phosphate): pH 5.8 – 8.0
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22
Q

Solubility Enhancers

What are the 3 types?

A
  • co-solvents
  • complexing agents
  • surfactants (surface-active agents)
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23
Q

Solubility Enhancers

What is a co-solvent?

A

addition of a water miscible organic solvent in which the compound is also soluble

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24
Q

Solubility Enhancers

What is the purpose of a co-solvent?

A

to alter (reduce) polarity of an aqueous system to help solubilize non-polar/non-ionized drugs and the un-ionized components of ionizable drug

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25
Q

Solubility Enhancers

What are some common co-solvents? (4)

A
  • ethanol
  • low molecular weight (200-400 g/mol) poly(ethylene) glycol (PEG) – also called poly(ethylene oxide) (PEO)
  • propylene glycol
  • glycerol
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26
Q

Solubility Enhancers

What are complexing agents?

A

complexation of a poorly soluble drug with a soluble material to form a soluble intermolecular complex

  • after administration the complex should dissociate
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27
Q

Solubility Enhancers – Complexing Agents

What are cyclodextrins (CDs)?

A

family of cyclic oligosaccharides derived from starch

  • form cup-like structure
  • exterior contains large number of hydroxyl groups and is highly water-soluble
  • interior is relatively non-polar and creates hydrophobic microenvironment
  • hydrophobic regions of APIs can form non-covalent complexes with CDs to improve aqueous solubility
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28
Q

Solubility Enhancers – Complexing Agents

What are the 3 general classes of cyclodextrins (CDs)?

A
  • αCD: 6 glucopyranoside units, 972 g/mol, 0.47-0.53 nm cavity
  • βCD: 7 glucopyranoside units, 1135 g/mol, 0.60-0.65 nm cavity
  • ƴCD: 8 glucopyranoside units, 1297 g/mol, 0.75-0.83 nm cavity

(thousands of different CD derivatives by attaching various –R- groups to α/β/ƴ backbone)

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29
Q

Solubility Enhancers – Complexing Agents

What do cyclodextrins (CDs) do in oral drug delivery?

A
  • enhanced solubility of drugs
  • enhanced bioavailability of drugs
  • enhanced stability of drugs
  • reduced gastric ulceration
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30
Q

Solubility Enhancers

What are surfactants (surface-active agents)?

A

possess both hydrophilic and hydrophobic regions (ie. amphiphilic molecules)

  • at dilute concentrations, surfactants orient at interface between the two phases (ie. water/oil, water/air)
  • above critical micelle concentration (CMC), surfactants form into colloidal structures called micelles
  • in aqueous systems, non-polar drugs can partition into these micelles and be solubilized
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31
Q

Solubility Enhancers

What are some examples of surfactants (surface-active agents)?

A
  • sodium dodecyl sulfate (anionic)
  • trialkylammonium (cationic)
  • glycine (zwitterionic)
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32
Q

Taste Masking Agents

What are some taste masking approaches? (5)

A
  • numbing taste buds (taste blockade) – research
  • obscuration of taste – viscosity, sweeteners/flavouring agents
  • modification of API – solubility (salt, pH), prodrug
  • create a molecular ‘barrier’ around API by complexation – cyclodextrins
  • apply a physical ‘barrier’ on API or dosage form – polymeric and lipidic coatings
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33
Q

Taste Masking Agents

What are the 5 types?

A
  • mixing with food/dilution
  • sweeteners
  • flavouring agents
  • taste receptor blockers
  • complexation
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34
Q

Taste Masking Agents

Why is mixing/diluting the API with food not ideal? (3)

A
  • requires compatibility testing for each food/beverage
  • entire dose may not be consumed if quantity/volume of food/beverage is too large or taste is not appropriately masked
  • child may be put off by the food source – issue with breastfeeding infants
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35
Q

Taste Masking Agents

What are the 2 types of sweeteners?

A
  • bulk sweeteners
  • intense sweeteners
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36
Q

Taste Masking Agents

What are bulk sweeteners?

A

provides body and texture to the solution (ie. high viscosity sucrose syrup)

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37
Q

Taste Masking Agents

What are intense sweeteners?

A

provides sweet taste at very low concentration (ie. aspartame)

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38
Q

Taste Masking Agents

How are sweeteners chosen?

A

based on its processability (temperature/pH stability) and sensory qualities (texture, sweetness intensity over time, etc.)

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39
Q

Taste Masking Agents

What safety issues must be considered with sweeteners? (3)

A
  • carcinogenicity
  • effect on blood glucose
  • caloric content
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40
Q

Taste Masking Agents

What are flavouring agents?

A

used to complement the taste profile of the API

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41
Q

Taste Masking Agents

What are the 2 types of flavouring agents?

A
  • natural
  • artificial
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42
Q

Taste Masking Agents

What are natural flavouring agents?

A
  • complex mixtures – exact composition is often not known
  • available as concentrated extracts, alcoholic or aqueous solutions, syrups or spirits
  • fruit juices, aromatic oils (ie. peppermint and lemon), herbs, spices
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43
Q

Taste Masking Agents

What are artificial flavouring agents?

A
  • less batch to batch variability in chemical composition
  • greater chemical stability
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44
Q

Taste Masking Agents

What type of receptors are bitter taste receptors?

A

G-protein coupled

45
Q

Taste Masking Agents – Taste Receptor Blockers

2 Steps

A
  • bitter receptor antagonists (Step 1 in slides) (R&D stage)
  • taste transduction cascade blockers (Steps 2-6 in slides) (R&D stage)
46
Q

Taste Masking Agents – Taste Receptor Blockers

What are bitter receptor antagonists

A
  • tasteless or sweet compounds derived from known bitter compounds
  • competitively block binding site of one or more bitter receptors – block release of receptor-associated G-protein (Gustductin)
  • ie. adenosine 5’monophosphate (AMP), neohesperidine dihydrochalacone (E959), caffeic acid, etc
47
Q

Taste Masking Agents – Taste Receptor Blockers

What are taste transduction cascade blockers?

A
  • block signal transduction from taste receptor
  • potential for broader blockade of bitter taste receptors compared to receptor antagonists
  • ie. TRPM5 ion channel blockers turn bitter tastes into a sweet/umami taste
48
Q

Taste Masking Agents

What is complexation?

A

cyclodextrins complex with the API, impeding its interaction with the taste receptors

  • ie. bitter taste of cetirizine dihydrochloride improved with ƴCD, ditto for oseltamivir phosphate with βCD
49
Q

Colourants/Dyes

Is addition of a colourant required?

A

no – but often added for pharmaceutical elegance

50
Q

Viscosity Enhancing Agents

Why must the viscosity of a formulation be controlled?

A

to ensure accurate measurement of dispensed volume/ease of handling

51
Q

Viscosity Enhancing Agents

What are higher viscosity solutions better for?

A

taste-masking bitter APIs

52
Q

Viscosity Enhancing Agents

How is viscosity increased?

A

by addition of non-ionic and ionic hydrophilic polymers:

  • non-ionic polymers: polyvinylpyrrolidone, methylcellulose
  • ionic polymers: sodium alginate (anionic), sodium carboxymethylcellulose (anionic)
53
Q

Preservatives

What are preservatives used for?

A

to prevent or control microbial growth in the formulation

54
Q

Preservatives

What are the properties of an ideal preservative? (4)

A
  • broad spectrum antimicrobial activity against Gram-positive and negative bacteria as well as fungi
  • adequate aqueous solubility and partitioning
  • chemical and physical stability over the shelf-life of the product
  • low toxicity to patients
55
Q

Acidic Preservatives

What are the 2 common types of acidic preservatives?

A
  • benzoic acid (pKa 4.2) and its salts (0.1-0.3% w/v)
  • sorbic acid (pKa 4.8) and its salts (0.05-0.2% w/v)
56
Q

Acidic Preservatives

What is the mechanism of action (MOA)?

A
  1. unionized acidic preservatives partition across the membrane of a microorganism
  2. within cytoplasm of microorganism where pH is ~neutral, acidic preservatives ionize
  3. this leads to acidification of cytoplasm, denaturation of proteins, and inhibition of growth
57
Q

Acidic Preservatives

Which form has preservative capability?

A

only the unionized form

  • concentration of unionized preservative must be > minimum inhibitory concentration (MIC) of the preservative
  • ionized form cannot penetrate into the microorganisms
58
Q

Acidic Preservatives

What are the factors affecting preservative efficacy in oral solutions? (3)

A
  • pH of formulation
  • presence of micelles
  • presence of hydrophilic polymers (ie. methycellulose and polyvinylpurrolidone)
59
Q

Acidic Preservatives

What is the optimal pH of a formulation?

A

pH < 4.5

60
Q

Acidic Preservatives

How does the presence of micelles affect preservative efficacy?

A

preservatives can partition and become sequestered in the lipophilic interior of micelles – reduced [preservative] that can partition into microbe

61
Q

Acidic Preservatives

How does the presence of hydrophilic polymers affect preservative efficacy?

A

preservative can interact chemically or electrostatically with the dissolved polymer – reduces [preservative] that can partition into microbe

62
Q

Preservatives

What are some other preservatives? (4)

A
  • parabens
  • quaternary ammonium compounds
  • mercurials
  • alcohols
63
Q

Preservatives

Parabens

  • MOA
  • optimal pH
  • example
A
  • MOA: denatures proteins
  • optimal pH: 4-8
  • ie. alkyl esters of parahydroxybenzoic acid)
64
Q

Preservatives

Quaternary Ammonium Compounds

  • MOA
  • optimal pH
  • example
A
  • MOA: lysis of cell membrane
  • optimal pH: 4-10
  • ie. benzalkonium chloride
65
Q

Preservatives

Mercurials

  • MOA
  • optimal pH
  • example
A
  • MOA: disrupts function of enzymes by reacting with thiol groups
  • optimal pH: <7
  • ie. thiomersal
66
Q

Preservatives

Alcohols

  • MOA
  • optimal pH
  • example
A
  • MOA: lysis of cell membrane and denatures protein
  • ie. > 12% v/v EtOH
67
Q

Antioxidants

What are antioxidants?

A

molecules that have a higher oxidative potential than the API or compounds that inhibit free radical-induced drug decomposition

68
Q

Antioxidants

What do antioxidants do?

A

enhance stability of API (and excipients) that are prone to chemical degradation by oxidation

69
Q

Antioxidants

What are the two types of antioxidants?

A
  • water-soluble antioxidants: sodium sulphite, sodium metabisulphite, sodium formaldehyde sulphoxylate, ascorbic acid
  • water-insoluble antioxidants: butylated hydroxytoluene (BHT), propyl gallate
70
Q

Antioxidants

How do chelators act as antioxidants?

A
  • heavy metals (like Pd) contribute to oxidative degradation of APIs – can catalyze degradation
  • chelators form complexes (ie. coordinate) with heavy-metal to slow this form of oxidative degradation
  • ie. ethylenediamine tetraacetic acid (EDTA), citric acid
71
Q

What are the 3 methods to prepare pharmaceutical solutions?

A
  • simple solutions
  • solution by chemical reaction
  • solution by extraction
72
Q

What are simple solutions?

A

dissolve solute in suitable solvent

73
Q

What are solutions by chemical reaction?

A

react two or more substances together in appropriate solvent to increase solubility

  • esterification
  • formation of aluminum subacetate solution USP
74
Q

What are solutions by extraction?

A

used to isolate pharmaceutical products from vegetable or animal origin

75
Q

What are the common solutions administered to the GI tract?

A
  • syrups
  • elixirs
  • tinctures
  • aromatic waters and spirits
  • gargles and mouthwashes
  • colonic lavages
  • enemas
76
Q

What are syrups?

A

concentrated aqueous preparations of a sugar/sugar substitute with or without flavouring agents and APIs

77
Q

What are non-medicated syrups?

A

syrups containing flavouring agents but no API

  • used for extemporaneous compounding of solutions, suspensions, and other DDSs
  • ie. ora-sweet, SF alka
78
Q

Why are syrups common with pediatric formulations? (2)

A
  • excellent at masking disagreeable-tasting APIs
  • contains little or no alcohol (< 10% v/v EtOH)
79
Q

What sugar is the most frequently used in syrups?

A

sucrose

80
Q

What is a commonly used alternative to sucrose in syrups?

A

sorbitol (64% w/v)

  • high [sugar] (up to 85%) acts as a natural preservative since they are able to resist bacterial growth by osmotic effect – but many commercial preparations contain a preservative as a precaution
  • inherent sweetness and high viscosity taste-mask APIs
81
Q

What do sugar-free syrups contain?

A

contain an intense sweetener (aspartame or saccharin sodium), non-glycogenic viscosity modifier (ie. methylcellulose) and require a preservative (ie. paraben)

82
Q

What are elixirs?

A

sweetened hydroalcoholic solution

  • better able than aqueous syrups to maintain water-soluble or alcohol-soluble APIs in solution
  • level of EtOH co-solvent depends on the API – generally, [EtOH] >10% v/v
  • polyol co-solvents (i.e., propylene glycol, PEG) are often used to improve API/ excipient solubility or decrease the [EtOH] required
  • natural or artificial sweetener
83
Q

Compare elixirs to syrups.

A

elixirs are usually less sweet, less viscous, and less effective in masking unpleasant API taste

84
Q

Are preservatives required in elixirs?

A

not required in elixirs that contain >12% v/v EtOH due to inherent anti-microbial properties of the co-solvent

85
Q

How should elixirs be packaged/stored?

A

due to volatile nature of EtOH, elixirs should be packaged in air-tight containers and not stored at high temperatures

86
Q

Is viscosity enhancement required for elixirs?

A

often required to optimize rheological properties of the formulation

87
Q

What are tinctures?

A

hydroalcoholic solutions prepared via extraction from vegetable/animal materials or minerals

  • contain ~15-90% alcohol
  • do not require preservatives
  • must be tightly stoppered and protected from high temperature
  • ie. opium tincture USP
88
Q

Are tinctures common?

A

no – more pleasant tasting elixirs or syrups with lower [EtOH] preferred

89
Q

What are aromatic waters?

A

aqueous solution of volatile materials

  • needs preservatives (ie. sodium methyl, ethyl and propyl hydroxybenzoates)
  • ie. concentrated peppermint water BP (has anti-flatulent properties)
90
Q

What are spirits?

A

alcoholic or hydroalcoholic solutions of volatile compounds

  • [EtOH] usually > 60%
  • do not require preservatives
  • must be tightly stoppered and protected from high temperature
  • because of the greater solubility of aromatic/volatile compounds in EtOH, spirits can contain a greater concentration of these materials than the corresponding aromatic waters
  • can be used as flavouring agents and medicinally for the therapeutic value of the aromatic/volatile solute
91
Q

What are gargles?

A

aqueous solutions designed for prevention/treatment of infection and inflammation of nasopharynx region (gargles)

92
Q

What are mouthwashes?

A

aqueous solutions designed for prevention/treatment of infection and inflammation of oral cavity (mouthwash)

93
Q

What are gargles and mouthwashes often formulated with?

A

these aqueous solutions are often formulated with ethanol as a co-solvent

  • improve API solubility
  • enhance antimicrobial properties of gargle/mouthwash

often formulated with colorants, flavouring agents, and non-cariogenic sweeteners

94
Q

What are colonic lavages?

A

solution is iso-osmotic with a balanced electrolyte concentration – allows large amount of solution to be administered without significant change in water/electrolyte balance

  • used to prepare the lower GI tract for procedures (ie. colonoscopy)
95
Q

What is the formula for colonic lavages?

A
  • 240.00 g PEG-3350
  • 22.72 g sodium sulfate
  • 6.72 g sodium bicarbonate
  • 5.84 g sodium chloride
  • 2.98 g potassium chloride
  • qs to 4 L with Purified Water USP
96
Q

What is colonic lavages used to replace?

A

replaces other strategies (ie. 24-48 h liquid diet + stimulating laxatives + evacuant enema) that suffer from compliance and malnutrition safety issues

97
Q

What are enemas?

A

aqueous or oil-based solutions available for the rectal administration of medicaments for cleansing, diagnostic, or therapeutic reasons

98
Q

What agents are often added to enemas?

A

viscosity enhancing agents are often added to aid retention of the solution within the rectum

99
Q

What are the 2 types of enemas?

A
  • retention enemas
  • evacuation enemas
100
Q

What are retention enemas?

A

medicated solution administered rectally for local effects or for systemic absorption

  • ie. hydrocortisone for ulcerative colitis – local effects
  • ie. aminophylline for asthma in pediatric patients) – systemic absorption
101
Q

What are evacuation enemas?

A

solutions adminstered rectally to aid clearancew of the bowel by:

  • softening and lubricating fecal matter (ie. mineral oil)
  • promoting intestinal motility (ie. peanut oil)
  • increase osmolality within rectum to increase water content of fecal matter (ie. glycerol, salts, PEG, etc.)
102
Q

Syrups

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water + sugar

preservation:

  • sorbitol 64%
  • sucrose 65-85%

examples:

  • tylenol syrup
103
Q

Aromatic Waters

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water + etheric oils

preservation:

  • needed (ie. benzoates)

examples:

  • concentrated peppermint water
104
Q

Colonic Lavages and Enemas

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water

preservation:

  • N/A (freshly made)

examples:

  • PEG3350 lavage
105
Q

Gargles and Mouthwashes

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water + (maybe) alcohol

preservation:

  • not needed if > 12% ethanol

examples:

  • chlorhexidine antiseptic mouthwash
106
Q

Elixirs

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water + alcohol

preservation:

  • not needed if > 12% ethanol

examples:

  • theophyllin elixir
107
Q

Tinctures

  • main solvent
  • preservation
  • examples
A

main solvent:

  • water + 15-90% alcohol

preservation:

  • N/A

examples:

  • opium tincture
  • iodine tincture
108
Q

Spirits

  • main solvent
  • preservation
  • examples
A

main solvent:

  • > 60% alcohol + water

preservation:

  • N/A

examples:

  • Klosterfrau Melissengeist

PHRM 100 – PDD (14 decks)

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