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Chemistry

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Also known as: 25655-41-8, Povidone-iodine, Betadine, Isodine, Pvp iodine, Pvp-iodine

Molecular Formula

C₆H₉I₂NO

Molecular Weight

364.95 g/mol

InChI Key

CPKVUHPKYQGHMW-UHFFFAOYSA-N

An iodinated polyvinyl polymer used as topical antiseptic in surgery and for skin and mucous membrane infections, also as aerosol. The iodine may be radiolabeled for research purposes.

1 2D Structure

Povidone-Iodine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-ethenylpyrrolidin-2-one;molecular iodine

2.1.2 InChI

InChI=1S/C6H9NO.I2/c1-2-7-5-3-4-6(7)8;1-2/h2H,1,3-5H2;

2.1.3 InChI Key

CPKVUHPKYQGHMW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C=CN1CCCC1=O.II

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Alphadine

2. Alphadines

3. Betadine

4. Betadines

5. Betaisodona

6. Disadine

7. Disadines

8. Isodine

9. Isodines

10. Pharmadine

11. Pharmadines

12. Polyvinylpyrrolidone Iodine

13. Polyvinylpyrrolidone Iodines

14. Povidone-iodine

15. Povidone-iodines

16. Providine

17. Providines

18. Pvp Iodine

19. Pvp-i

20. Pvp-iodine

21. Pvp-iodines

2.2.2 Depositor-Supplied Synonyms

1. 25655-41-8

2. Povidone-iodine

3. Betadine

4. Isodine

5. Pvp Iodine

6. Pvp-iodine

7. Pvp-i

8. Isobetadyne

9. Bridine

10. Disphex

11. Povadyne

12. Ultradine

13. Efo-dine

14. Iodopoly(vinyl Pyrrolidinone)

15. 1-ethenylpyrrolidin-2-one;molecular Iodine

16. Nsc26245

17. 2-pyrrolidinone, 1-ethenyl-, Homopolymer, Compd. With Iodineother Ca Index Names:iodine, Compd. With 1-ethenyl-2-pyrrolidinone Homopolymer

18. Iodine-poly(vinylpyrrolidinone)

19. Poly(vinylpyrrolidinone) Iodide

20. Iodinated Poly(vinylpyrrolidone)

21. Poly(vinylpyrrolidone)-iodine Adduct

22. Poly(vinylpyrrolidinone)-iodine Complex

23. Poly(vinylpyrrolidone) - Iodine Complex

24. Polyvinylpyrrolidone Compound With Iodine

25. Povidone.iodine

26. 1-ethenyl-2-pyrrolidinone Homopolymer Compound With Iodine

27. Molecular Iodine; 1-vinylpyrrolidin-2-one

28. 1-ethenylpyrrolidin-2-one; Molecular Iodine

29. Povidone Iodine-ip, 9-12%

30. Schembl1652685

31. Bcp28568

32. Nsc28655

33. Mfcd00084483

34. Nsc-26245

35. Nsc-28655

36. Akos015898248

37. Polyvinylpyrrolidone-iodinecomplex

38. 1-ethenyl-2-pyrrolidinone; Molecular Iodine

39. Ft-0655804

40. 2-pyrrolidinone, Polymers, Compd. With Iodine

41. A16118

42. 2-pyrrolidinone, Homopolymer, Compd. With Iodine

43. A817952

44. Q241516

45. 1-vinylpyrrolidin-2-one Compound With Diiodine (1:1)

46. Poly[1-(2-oxo-1-pyrrolidinyl)ethylene]iodine Complex

47. Povidone (iodinated), European Pharmacopoeia (ep) Reference Standard

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₆H₉I₂NO
Molecular Weight	364.95 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	364.87736 g/mol
Monoisotopic Mass	364.87736 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	120
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Betadine
PubMed Health	Povidone Iodine (Into the eye)
Drug Classes	Antiseptic
Drug Label	Povidone-Iodine is a broad-spectrum microbicide with the chemical formulas:2-pyrrolidinone, 1- ethenyl-, homopolymer, compound with iodine; 1-vinyl-2-pyrrolidinone polymer, compound with iodine. The structural formula is as follows:BETADINE 5% Ster...
Active Ingredient	Povidone-iodine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	5%
Market Status	Prescription
Company	Alcon Pharms

2 of 4
Drug Name	Povidone iodine
PubMed Health	Povidone Iodine (Into the eye)
Drug Classes	Antiseptic
Drug Label	Other InformationStore below 98F/37C avoid direct heat and sunlight...
Active Ingredient	Povidone-iodine
Dosage Form	Solution
Route	Topical
Strength	1%
Market Status	Over the Counter
Company	Allegiance Hlthcare

3 of 4
Drug Name	Betadine
PubMed Health	Povidone Iodine (Into the eye)
Drug Classes	Antiseptic
Drug Label	Povidone-Iodine is a broad-spectrum microbicide with the chemical formulas:2-pyrrolidinone, 1- ethenyl-, homopolymer, compound with iodine; 1-vinyl-2-pyrrolidinone polymer, compound with iodine. The structural formula is as follows:BETADINE 5% Ster...
Active Ingredient	Povidone-iodine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	5%
Market Status	Prescription
Company	Alcon Pharms

4 of 4
Drug Name	Povidone iodine
PubMed Health	Povidone Iodine (Into the eye)
Drug Classes	Antiseptic
Drug Label	Other InformationStore below 98F/37C avoid direct heat and sunlight...
Active Ingredient	Povidone-iodine
Dosage Form	Solution
Route	Topical
Strength	1%
Market Status	Over the Counter
Company	Allegiance Hlthcare

4.2 Therapeutic Uses

Anti-Infective Agents, Local

National Library of Medicine's Medical Subject Headings online file (MeSH, 2014)

Povidone-iodine is an iodophore that is used as a disinfectant and antiseptic mainly for the treatment of contaminated wounds and pre-operative preparation of the skin and mucous membranes as well as for disinfection of equipment.

SWEETMAN, S.C. (ed.) Martindale-The Complete Drug Reference. 36th ed. London: The Pharmaceutical Press, 2009., p. 1659

BETADINE 5% Sterile Ophthalmic Prep Solution for the eye is indicated for prepping of the periocular region (lids, brow, and cheek) and irrigation of the ocular surface (cornea, conjunctiva, and palpebral fornices).

NIH; DailyMed. Current Medication Information for BETADINE- povidone-iodine solution (Revised: July 2011). Available from, as of October 14, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b026de1b-9949-4557-ac49-c7b0038c24cd

4.3 Drug Warning

No studies are available in patients with thyroid disorders; therefore, caution is advised in using BETADINE 5% Sterile Ophthalmic Prep Solution in these patients due to the possibility of iodine absorption.

Because of the potential for serious adverse reactions in nursing infants from BETADINE 5% Sterile Ophthalmic Prep Solution, a decision should be made to discontinue nursing or discontinue the drug, taking into account the importance of the drug to the mother.

FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

For external use only. Not for intraocular injection or irrigation.

For more Drug Warnings (Complete) data for Povidone-iodine (9 total), please visit the HSDB record page.

4.4 Drug Indication

For topical application in the treatment and prevention of infection in wounds.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Povidone iodine is a kind of iodine disinfectant which directly cause in vivo protein denaturation, precipitation of bacteria, and further resulting in the death of pathogenic microorganisms. Therefore, it is effective in disinfection and sterilization. It can kill viruses, bacteria, spores, fungi, and protozoa with low toxicity to human. Povidone-iodine aqueous solution has strong pharmacological activity against Staphylococcus aureus, Neisseria gonorrhoeae, Pseudomonas aeruginosa, syphilis, hepatitis B virus, HIV, and Trichomonas vaginalis. Povidone iodine gel is a gynecological topical semi-mobile colloidal agent made by povidone iodine and hydrophilic matrix. It is a system for maintaining its sustained release. Owing to the continuous release of free iodine, it can enable the skin and mucous membranes to maintain a certain effective concentration of iodine for killing bacteria. It is mainly used for gynecological vaginal infection. It exerted its effect through being miscible with vaginal secretions and further killing the inside pathogenic microorganisms, and thus blocking the spread of sexually transmitted diseases and invasion, as well as treating other infected vaginal diseases caused by other kinds of bacteria. Published reports on the in vitro antimicrobial efficacy of iodophors demonstrate that iodophors are bactericidal, mycobactericidal, and virucidal but can require prolonged contact times to kill certain fungi and bacterial spores. Three brands of povidone-iodine solution have demonstrated more rapid kill (seconds to minutes) of S. aureus and M. chelonae at a 1:100 dilution than did the stock solution. The virucidal activity of 75150 ppm available iodine was demonstrated against seven viruses. Other investigators have questioned the efficacy of iodophors against poliovirus in the presence of organic matter and rotavirus in distilled or tapwater. Manufacturers' data demonstrate that commercial iodophors are not sporicidal, but they are tuberculocidal, fungicidal, virucidal, and bactericidal at their recommended use-dilution.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

5.3 ATC Code

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AG - Iodine products

D08AG02 - Povidone-iodine

D - Dermatologicals

D09 - Medicated dressings

D09A - Medicated dressings

D09AA - Medicated dressings with antiinfectives

D09AA09 - Povidone-iodine

D - Dermatologicals

D11 - Other dermatological preparations

D11A - Other dermatological preparations

D11AC - Medicated shampoos

D11AC06 - Povidone-iodine

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AX - Other antiinfectives and antiseptics

G01AX11 - Povidone-iodine

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA15 - Povidone-iodine

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AX - Other antiinfectives

S01AX18 - Povidone-iodine

5.4 Absorption, Distribution and Excretion

Absorption

Povidone-Iodine is intended for topical application and is not absorbed.

Route of Elimination

Povidone-Iodine is intended for topical application and is not eliminated.

Volume of Distribution

Povidone-Iodine is intended for topical application and has no volume of distribution.

Clearance

Povidone-Iodine is intended for topical application and is not eliminated.

Topical application of povidone iodine on the umbilical cord and normal intact skin of newborn infants resulted in significantly elevated plasma iodine levels. High iodine levels were also found in two neonates who had povidone iodine applied to denuded skin. No significant alteration in thyroid function was seen. The possible toxic manifestations of high plasma iodine levels are discussed.

PMID:909027 Pyati SP et al; J Pediatr. 91 (5): 825-8 (1977)

In 12 nonpregnant women, total iodine, protein-bound iodine, inorganic iodine, and thyroxine values were measured in serum before and 15, 30, 45 or 60 minutes after a two-minute vaginal disinfection with povidone-iodine (Betadine). Only 15 minutes after application, serum iodine levels were raised and remained significantly elevated 30, 45 and 60 minutes after disinfection. Serum concentrations of total iodine and inorganic iodine were increased up to fivefold to 15-fold, respectively; during the relative short period of observation, thyroxine levels were not altered.

PMID:7431610 Vorherr H et al; JAMA. 244 (23): 2628-9 (1980)

5.5 Metabolism/Metabolites

Povidone-Iodine is not absorbed or metabolized.

5.6 Biological Half-Life

Povidone-Iodine is intended for topical application and is not eliminated.

5.7 Mechanism of Action

Povidone-iodine is called iodophore which means povidone acts as a carrier of iodine. Iodine is considered as the active moiety that mediates microbicidal actions. When released from the complex, free iodine (I2) penetrates the cell wall of microorganisms quickly, and the lethal effects are believed to result from disruption of protein and nucleic acid structure and synthesis. While the full mechanism of action is not fully elucidated, iodine is thought to inhibit vital bacterial cellular mechanisms and structures, and oxidizes nucleotides fatty or amino acids in bacterial cell membranes. Additionally, free iodine disrupts the function of the cytosolic enzymes involved in the respiratory chain, causing them to become denatured and deactivated. _In vitro_ evidence suggests that iodine also counteracts inflammation elicited by both pathogens and the host response via multifactorial effects. In hosts, povidone-iodine was demonstrated to modulate the redox potential, inhibit the release of inflammatory mediators such as TNF- and -galactosidase, inhibit metalloproteinase production, and potentiate the healing signals from pro-inflammatory cytokines by activation of monocytes, T-lymphocytes, and macrophages, _in vitro_.

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