Polyvinylpyrrolidone

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Polyvinylpyrrolidone
Polyvinylpyrrolidon.svg
Sample of polyvinyl pyrrolidone.jpg
Names
IUPAC name
1-Ethenylpyrrolidin-2-one
Other names
PVP, Povidone

PVPP, Crospovidone, Polyvidone
PNVP
Poly[1-(2-oxo-1-pyrrolidinyl)ethylen]
1-Ethenyl-2-pyrrolidon homopolymer
1-Vinyl-2-pyrrolidinon-Polymere,

Kollidon

Contents


Poly-N-vinylpyrrolidine
Identifiers
3D model (JSmol)
AbbreviationsPVP, PVPP, NVP, PNVP
ChEMBL
ChemSpider
  • none
ECHA InfoCard 100.111.937 OOjs UI icon edit-ltr-progressive.svg
E number E1201 (additional chemicals)
UNII
  • N1(C(CCC1)=O)[C@@H](C*)*
Properties
(C6H9NO)n
Molar mass 2,500 – 2,500,000 g·mol−1
Appearancewhite to light yellow, hygroscopic, amorphous powder
Density 1.2 g/cm3
Melting point 150 to 180 °C (302 to 356 °F; 423 to 453 K) (glass temperature)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Polyvinylpyrrolidone (PVP), also commonly called polyvidone or povidone, is a water-soluble polymer compound made from the monomer N-vinylpyrrolidone. [1] PVP is available in a range of molecular weights and related viscosities, and can be selected according to the desired application properties. [2]

Uses

Medical

Structure of povidone-iodine complex, a common antiseptic Povidone-iodine.svg
Structure of povidone-iodine complex, a common antiseptic

There are high-purity injectable grades of PVP available on the market, for specific use in intravenous, intramuscular, and subcutaneous applications. [4]

It is used as a binder in many pharmaceutical tablets; [5] it simply passes through the body when taken orally.

PVP added to iodine forms a complex called povidone-iodine that possesses disinfectant properties. [6] This complex is used in various products such as solutions, ointment, pessaries, liquid soaps, and surgical scrubs. It is sold under the trade names Pyodine and Betadine, among others.

It is used in pleurodesis (fusion of the pleura because of incessant pleural effusions). For this purpose, povidone-iodine is as effective and safe as talc, and may be preferred because of its easy availability and low cost. [7]

PVP is used in some contact lenses and their packaging solutions. It reduces friction, thus acting as a lubricant, or wetting agent, built into the lens. Examples of this use include Bausch & Lomb's Ultra contact lenses with MoistureSeal Technology [8] and Air Optix contact lens packaging solution (as an ingredient called "copolymer 845"). [9]

PVP is used as a lubricant in some eye drops, e.g. Bausch & Lomb's Soothe. [10]

PVP was used as a plasma volume expander for trauma victims after the 1950s. It is not preferred as a volume expander due to its ability to provoke histamine release and also interfere with blood grouping.

Autopsies have found that crospovidone (PVPP) contributes to pulmonary vascular injury in substance abusers who have injected pharmaceutical tablets intended for oral consumption. [11] The long-term effects of crospovidone or povidone within the lung are unknown.

Technical

PVP is also used in many technical applications:

Other uses

PVP binds to polar molecules exceptionally well, owing to its polarity. This has led to its application in coatings for photo-quality ink-jet papers and transparencies, as well as in inks for inkjet printers.

PVP is also used in personal care products, such as shampoos and toothpastes, in paints, and adhesives that must be moistened, such as old-style postage stamps and envelopes. It has also been used in contact lens solutions and in steel-quenching solutions. [18] [19] PVP is the basis of the early formulas for hair sprays and hair gels, and still continues to be a component of some.

As a food additive, PVP is a stabilizer and has E number E1201. PVPP (crospovidone) is E1202. It is also used in the wine industry as a fining agent for white wine and some beers.

In in-vitro fertilisation laboratories, polyvinylpyrrolidone is used to slow down spermatozoa in order to capture them for e.g. ICSI.

In molecular biology, PVP can be used as a blocking agent during Southern blot analysis as a component of Denhardt's buffer. It is also exceptionally good at absorbing polyphenols during DNA purification. Polyphenols are common in many plant tissues and can deactivate proteins if not removed and therefore inhibit many downstream reactions like PCR.

In microscopy, PVP is useful for making an aqueous mounting medium. [20]

PVP can be used to screen for phenolic properties, as referenced in a 2000 study on the effect of plant extracts on insulin production. [21]


Safety

The U.S. Food and Drug Administration (FDA) has approved this chemical for many uses, [22] and it is generally recognized as safe (GRAS). PVP is included in the Inactive Ingredient Database for use in oral, topical, and injectable formulations.

However, there have been documented cases of allergic reactions to PVP/povidone, particularly regarding subcutaneous (applied under the skin) use and situations where the PVP has come in contact with autologous serum (internal blood fluids) and mucous membranes.

Examples of documented allergic reactions:

Additionally, Povidone is commonly used in conjunction with other chemicals. Some of these, such as iodine, are blamed for allergic responses. Yet subsequent testing results in some patients show no signs of allergy to the suspect chemical. Allergies attributed to these other chemicals may possibly be caused by the PVP instead. [26] [27]


Properties

PVP is soluble in water and other polar solvents. For example, it is soluble in various alcohols, such as methanol and ethanol, [28] as well as in more exotic solvents like the deep eutectic solvent formed by choline chloride and urea (Relin). [29] When dry it is a light flaky hygroscopic powder, readily absorbing up to 40% of its weight in atmospheric water. In solution, it has excellent wetting properties and readily forms films. This makes it good as a coating or an additive to coatings.

A 2014 study found fluorescent properties of PVP and its oxidized hydrolyzate. [30]

History

PVP was first synthesized by BASF chemist Walter Reppe, and a patent was filed in 1939 for one of the derivatives of acetylene chemistry. PVP was initially used as a blood plasma substitute and later in a wide variety of applications in medicine, pharmacy, cosmetics and industrial production. [31] [32] BASF continues to make PVP, including a pharmaceutical portfolio under the brand name of Kollidon. [33]

Cross-linked derivatives

See also

Related Research Articles

<span class="mw-page-title-main">Iodine</span> Chemical element, symbol I and atomic number 53

Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at 114 °C (237 °F), and boils to a violet gas at 184 °C (363 °F). The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης 'violet-coloured'.

<span class="mw-page-title-main">Conjunctivitis</span> Inflammation of the eye

Conjunctivitis, also known as pink eye, is inflammation of the outermost layer of the white part of the eye and the inner surface of the eyelid. It makes the eye appear pink or reddish. Pain, burning, scratchiness, or itchiness may occur. The affected eye may have increased tears or be "stuck shut" in the morning. Swelling of the white part of the eye may also occur. Itching is more common in cases due to allergies. Conjunctivitis can affect one or both eyes.

<span class="mw-page-title-main">Polyethylene glycol</span> Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

<span class="mw-page-title-main">Tincture of iodine</span> Antiseptic solution rubbed on skin before surgical operations

Tincture of iodine, iodine tincture, or weak iodine solution is an antiseptic. It is usually 2 to 3% elemental iodine, along with potassium iodide or sodium iodide, dissolved in a mixture of ethanol and water. Tincture solutions are characterized by the presence of alcohol. It was used from 1908 in pre-operative skin preparation by Italian surgeon Antonio Grossich.

<span class="mw-page-title-main">Topical medication</span> Medication applied to body surfaces

A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes including creams, foams, gels, lotions, and ointments. Many topical medications are epicutaneous, meaning that they are applied directly to the skin. Topical medications may also be inhalational, such as asthma medications, or applied to the surface of tissues other than the skin, such as eye drops applied to the conjunctiva, or ear drops placed in the ear, or medications applied to the surface of a tooth. The word topical derives from Greek τοπικόςtopikos, "of a place".

An excipient is a substance formulated alongside the active ingredient of a medication. Excipients serve various purposes, including long-term stabilization, bulking up solid formulations containing potent active ingredients in small amounts, or enhancing the therapeutic properties of the active ingredient in the final dosage form. They can facilitate drug absorption, reduce viscosity, or enhance solubility. Excipients can also aid in the manufacturing process by improving the handling of active substances, facilitating powder flowability, or preventing denaturation and aggregation during the expected shelf life. The selection of excipients depends on factors such as the route of administration, dosage form, and active ingredient.

<span class="mw-page-title-main">Iodinated contrast</span> Substance to enhance X-ray imaging

Iodinated contrast is a form of water-soluble, intravenous radiocontrast agent containing iodine, which enhances the visibility of vascular structures and organs during radiographic procedures. Some pathologies, such as cancer, have particularly improved visibility with iodinated contrast.

<span class="mw-page-title-main">Povidone-iodine</span> Antiseptic solution

Povidone-iodine (PVP-I), also known as iodopovidone, is an antiseptic used for skin disinfection before and after surgery. It may be used both to disinfect the hands of healthcare providers and the skin of the person they are caring for. It may also be used for minor wounds. It may be applied to the skin as a liquid or a powder.

<span class="mw-page-title-main">Iodophor</span> Soluble complex that can release iodine

An iodophor is a preparation containing iodine complexed with a solubilizing agent, such as a surfactant or water-soluble polymers, for example, povidone. The result is a water-soluble material that releases free iodine when in solution. Iodophors are prepared by mixing iodine with the solubilizing agent; heat can be used to speed up the reaction.

<span class="mw-page-title-main">Liquid–liquid extraction</span> Method to separate compounds or metal complexes

Liquid–liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of chemical components that make up the solutes and the solvents are in a more stable configuration. The solvent that is enriched in solute(s) is called extract. The feed solution that is depleted in solute(s) is called the raffinate. Liquid-liquid extraction is a basic technique in chemical laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of the work-up, often including an acidic work-up.

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine. CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products and animal husbandry. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

<span class="mw-page-title-main">Triethanolamine</span> Chemical compound

Triethanolamine, or TEOA, is an organic compound with the chemical formula N(CH2CH2OH)3. It is a colourless, viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples may appear yellow because of impurities.

Poloxamer 407 is a hydrophilic non-ionic surfactant of the more general class of copolymers known as poloxamers. Poloxamer 407 is a triblock copolymer consisting of a central hydrophobic block of polypropylene glycol flanked by two hydrophilic blocks of polyethylene glycol (PEG). The approximate lengths of the two PEG blocks is 101 repeat units, while the approximate length of the propylene glycol block is 56 repeat units. This particular compound is also known by the BASF trade name Pluronic F-127 or by the Croda trade name Synperonic PE/F 127. BASF also offers a pharmaceutical grade, under trade name Kolliphor P 407.

2-Pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is an organic compound consisting of a 5-membered lactam, making it the simplest γ-lactam. It is a colorless liquid that is miscible with water and most common organic solvents.

Poloxamers are nonionic triblock copolymers composed of a central hydrophobic chain of polyoxypropylene flanked by two hydrophilic chains of polyoxyethylene. The word poloxamer was coined by BASF inventor, Irving Schmolka, who received the patent for these materials in 1973. Poloxamers are also known by the trade names Pluronic, Kolliphor, and Synperonic.

<span class="mw-page-title-main">Polyaminopropyl biguanide</span> Chemical compound

Polyaminopropyl biguanide (PAPB) is a disinfectant and a preservative used for disinfection on skin and in cleaning solutions for contact lenses. It is also an ingredient in many deodorant bodysprays. It is a polymer or oligomer where biguanide functional groups are connected by propyl hydrocarbon chains. PAPB is specifically bactericidal at very low concentrations (10 mg/L) and is also fungicidal.

<span class="mw-page-title-main">Iobitridol</span> Pharmaceutical drug

Iobitridol is a pharmaceutical drug used as an iodine-based radiocontrast agent in X-ray imaging. It is injected into blood vessels, joints, or body cavities such as the uterus, and filtered out by the kidneys. Its most common adverse effect is nausea. Severe allergic reactions are rare.

<span class="mw-page-title-main">Granulation</span> Forming grains or granules from a powdery or solid substance

Granulation is the process of forming grains or granules from a powdery or solid substance, producing a granular material. It is applied in several technological processes in the chemical and pharmaceutical industries. Typically, granulation involves agglomeration of fine particles into larger granules, typically of size range between 0.2 and 4.0 mm depending on their subsequent use. Less commonly, it involves shredding or grinding solid material into finer granules or pellets.

<span class="mw-page-title-main">Cosolvent</span>

In chemistry, cosolvents are substances added to a primary solvent in small amounts to increase the solubility of a poorly-soluble compound. Their use is most prevalent in chemical and biological research relating to pharmaceuticals and food science, where alcohols are frequently used as cosolvents in water to dissolve hydrophobic molecules during extraction, screening, and formulation. Cosolvents find applications also in environmental chemistry and are known as effective countermeasures against pollutant non-aqueous phase liquids, as well as in the production of functional energy materials and synthesis of biodiesel.

Topical gels are a topical drug delivery dosage form commonly used in cosmetics and treatments for skin diseases because of their advantages over cream and ointment. They are formed from a mixture of gelator, solvent, active drug, and other excipients, and can be classified into organogels and hydrogels. Drug formulation and preparation methods depend on the properties of the gelators, solvents, drug and excipients used.

References

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