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2D Structure
Also known as: 88-12-0, 1-vinylpyrrolidin-2-one, N-vinylpyrrolidone, 1-vinyl-2-pyrrolidone, N-vinyl-2-pyrrolidinone, Polyvinylpyrrolidone
Molecular Formula
C6H9NO
Molecular Weight
111.14  g/mol
InChI Key
WHNWPMSKXPGLAX-UHFFFAOYSA-N
FDA UNII
76H9G81541

A polyvinyl polymer of variable molecular weight; used as suspending and dispersing agent and vehicle for pharmaceuticals; also used as blood volume expander. See [povidone] for full details.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-ethenylpyrrolidin-2-one
2.1.2 InChI
InChI=1S/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2
2.1.3 InChI Key
WHNWPMSKXPGLAX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C=CN1CCCC1=O
2.2 Other Identifiers
2.2.1 UNII
76H9G81541
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-vinyl-2-pyrrolidone

2. N- Vinyl Pyrrolidone

3. N-vinyl-2-pyrrolidinone

4. N-vinylpyrrolidone

2.3.2 Depositor-Supplied Synonyms

1. 88-12-0

2. 1-vinylpyrrolidin-2-one

3. N-vinylpyrrolidone

4. 1-vinyl-2-pyrrolidone

5. N-vinyl-2-pyrrolidinone

6. Polyvinylpyrrolidone

7. Vinylpyrrolidone

8. 9003-39-8

9. 1-vinyl-2-pyrrolidinone

10. Povidone

11. 2-pyrrolidinone, 1-ethenyl-

12. 1-ethenylpyrrolidin-2-one

13. N-vinylpyrrolidinone

14. Polyvidone

15. 1-vinylpyrrolidone

16. Vinylbutyrolactam

17. Plasdone

18. Vinylpyrrolidinone

19. V-pyrol

20. Luviskol

21. 1-vinylpyrrolidinone

22. Vinyl-2-pyrrolidone

23. 25249-54-1

24. Polyclar At

25. N-vinyl Pyrrolidone

26. 1-ethenyl-2-pyrrolidinone

27. N-vinylpyrrolidone-2

28. 2-pyrrolidinone, 1-vinyl-

29. Poly(n-vinylpyrrolidone)

30. 1-vinyl-2-pyrrolidinone, Monomer

31. Poly(1-vinyl-2-pyrrolidone)

32. Pvp 40

33. Pvp

34. Nsc 10222

35. Mpk 90

36. 143 Rp

37. At 717

38. 1-vinyl-pyrrolidin-2-one

39. K 15

40. K 90

41. Pvp-40

42. Dtxsid2021440

43. Chebi:82551

44. Poly[1-(2-oxo-1-pyrrolidinyl)-1,2-ethanediyl]

45. Mfcd00003197

46. Nsc-10222

47. 2-pyrrolidinone, 1-ethenyl-, Trimer

48. 2-pyrrolidinone, Polymers

49. 76h9g81541

50. Dsstox_cid_1440

51. Dsstox_rid_76160

52. Dsstox_gsid_21440

53. Wln: /t5nvtj Ay*1*/

54. Mfcd01076626

55. Cas-88-12-0

56. Polyvinylpyrrolidine

57. 109412-11-5

58. K 25

59. K 115

60. Hsdb 7231

61. Einecs 201-800-4

62. Polyvinylpyrrolidone K 90

63. Polyvinylpyrrolidone K-30

64. 2-pyrrolidinone, Polymers, Compd. With Aluminum Acetate

65. Brn 0110513

66. Ccris 8581

67. Povidonepvp

68. Vinyl Pyrrolidone

69. Polyvinylpyrrolidon

70. Poly[1-(2-oxo-1-pyrrolidinyl)-1, .alpha.-hydro-.omega.-[[4-(iodo-131i)phenyl]methyl]-

71. Unii-76h9g81541

72. N-vinyl-pyrrolidone

73. N -vinylpyrrolidinone

74. 1-vinyl-2-pyrrolidon

75. Povidone Monomer

76. Vinylbutylolactam

77. N-vinylpyrrolidin-2-one

78. N-vinyl Pyrrolidin-2-one

79. N-vinyl-pyrrolidin-2-one

80. Pvp K3o

81. Crospovidone ~40,000

82. Ec 201-800-4

83. Poly (n-vinyl Pyrrolidone)

84. Schembl10869

85. Wln: T5nvtj A1u1

86. Pvp K15

87. Pvp K30

88. Pvp-k30

89. Polyvinylpyrrolidone Pvp K30

90. Povidone Monomer [mi]

91. Vinyl Pyrrolidone (vp)

92. Poly(1-vinylpyrrolidin-2-one)

93. Chembl1878943

94. Pvp - K-30 (pharm Grade)

95. Polyvinylpyrrolidone, Cross Linked

96. N-vinyl Pyrrolidone [inci]

97. 1-vinyl-2-pyrrolidone(stabilized With 200ppm Ammonium Hydroxide)

98. Nsc10222

99. Zinc3590964

100. Polyvinylpyrrolidone, M.w. 8,000

101. Tox21_202462

102. Tox21_300073

103. Nsc114022

104. Nsc142693

105. Nsc683040

106. N-vinyl-2-pyrrolidone, Optical Grade

107. Polyvinylpyrrolidone (mw ~40,000)

108. Polyvinylpyrrolidone, M.w. 10.000

109. Polyvinylpyrrolidone, M.w. 40.000

110. Polyvinylpyrrolidone, M.w. 58,000

111. Akos000119985

112. N-vinyl-2-pyrrolidone [iarc]

113. At18510

114. Cs-w020981

115. Fg-0420

116. Nsc-114022

117. Nsc-142693

118. Nsc-683040

119. Polyvinylpyrrolidone, M.w. 360.000

120. Ncgc00166252-01

121. Ncgc00166252-02

122. Ncgc00166252-03

123. Ncgc00254200-01

124. Ncgc00260011-01

125. Polyvinylpyrrolidone, M.w. 1,300,000

126. 2-pyrrolidinone, 1-ethenyl-[hsdb]

127. Ft-0608329

128. Ft-0645144

129. Ft-0655284

130. V0026

131. C19548

132. A817742

133. A843417

134. Poly(n-vinyl-2-pyrrolidone) (low M.wt.)

135. Q420628

136. Sr-01000944531

137. J-015891

138. Sr-01000944531-1

139. W-100417

140. 1-vinyl-2-pyrrolidinone, Saj First Grade, >=99.0%

141. F8881-5579

142. 3-chloro-5,6-difluoro-1-benzothiophene-2-carbonylchloride

143. 1-vinyl-2-pyrrolidinone, Contains Sodium Hydroxide As Inhibitor, >=99%

144. 1-vinyl-2-pyrrolidinone, Pharmaceutical Secondary Standard; Certified Reference Material

145. 1-vinyl-2-pyrrolidone (stabilized With N,n'-di-sec-butyl-p-phenylenediamine)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 111.14 g/mol
Molecular Formula C6H9NO
XLogP30.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass111.068413911 g/mol
Monoisotopic Mass111.068413911 g/mol
Topological Polar Surface Area20.3 Ų
Heavy Atom Count8
Formal Charge0
Complexity120
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Pharmaceutic Aids; Plasma Substitutes

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


CLINICAL INDICATIONS: ...FOR ALL PATHOLOGICAL CONDITIONS WHERE THERE IS DECR IN MASS OF LIQ BLOOD: SHOCK STATE... HEMORRHAGE...SERIOUS BURNS. ANTHREPSIA & NEURO-TOXICOSES OF INFANTS.

Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 292


...HAS BEEN USED IN A...SERIES OF PATIENTS TO REPLACE THE AQ HUMOR AFTER EXTRACTION OF CATARACTS, CORNEAL TRANSPLANTS, & ANTIGLAUCOMA OPERATIONS.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 758


4.2 Minimum/Potential Fatal Human Dose

1. 1= PRACTICALLY NONTOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) ABOVE 15 G/KG, MORE THAN 1 QUART (2.2 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-245


4.3 Drug Indication

When in complex with iodine, indicated for inducing antisepsis for prevention of infection in minor cuts, scrapes, and burns.


When in complex with iodine, indicated for inducing antisepsis for prevention of infection in minor cuts, scrapes, and burns.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Povidone itself has no microbicidal activity. [DB06812] exhibits rapid, potent, broad-spectrum antimicrobial properties. The clinical effectiveness of povidon-iodine on wound healing remains somewhat controversial; in few clinical studies investigating the effects of povidone-iodine on wound healing, topical administration of the complex was associated with no significant infections, but slower healing and mild to moderate discomfort on application.


Povidone itself has no microbicidal activity. [Povidone-iodine] exhibits rapid, potent, broad-spectrum antimicrobial properties. The clinical effectiveness of povidon-iodine on wound healing remains somewhat controversial; in few clinical studies investigating the effects of povidone-iodine on wound healing, topical administration of the complex was associated with no significant infections, but slower healing and mild to moderate discomfort on application.


5.2 MeSH Pharmacological Classification

Biocompatible Materials

Synthetic or natural materials, other than DRUGS, that are used to replace or repair any body TISSUES or bodily function. (See all compounds classified as Biocompatible Materials.)


5.3 Absorption, Distribution and Excretion

Absorption

This pharmacokinetic data does not apply to povidone.


Route of Elimination

This pharmacokinetic data does not apply to povidone.


Volume of Distribution

This pharmacokinetic data does not apply to povidone.


Clearance

This pharmacokinetic data does not apply to povidone.


Absorption

This pharmacokinetic data does not apply to povidone.


Route of Elimination

This pharmacokinetic data does not apply to povidone.


Volume of Distribution

This pharmacokinetic data does not apply to povidone.


Clearance

This pharmacokinetic data does not apply to povidone.


WHEN GIVEN PARENTERALLY, UNEXCRETED PARTICLES ARE PHAGOCYTIZED BY CELLS OF RETICULOENDOTHELIAL SYSTEM & DEPOSITED IN STORAGE SITES IN LIVER, SPLEEN, LUNG, BONE MARROW...

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-245


...30-40% OF SUBTOSAN PASSES INTO THE URINE IN THE FIRST 24 HR & ABOUT 50% IN THE FIRST 2 DAYS. ...SMALLEST MOLECULES ARE...FIRST & MOST RAPIDLY EXCRETED. IT TAKES 10 DAYS AFTER PERFUSION FOR 80% OF AMT INJECTED TO BE ELIMINATED.

Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 292


INTERMEDIATE MOLECULR WT PARTICLES MAY BE SLOWLY EXCRETED OVER SEVERAL MONTHS TO A YR.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-245


IN GROUPS OF RATS FED DIETS CONTAINING 1 & 10% PVP (MOLECULAR WEIGHT 38,000) FOR 2 YEARS...THERE WAS NO EVIDENCE THAT PVP WAS ABSORBED FROM THE INTESTINAL TRACT.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V19 471


For more Absorption, Distribution and Excretion (Complete) data for POLYVINYLPYRROLIDONE (6 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

This pharmacokinetic data does not apply to povidone.


This pharmacokinetic data does not apply to povidone.


PVP LABELLED WITH (14)C OR (131)I WAS NOT METABOLIZED TO ANY SIGNIFICANT DEGREE BY RATS, RABBITS OR DOGS FOLLOWING ITS IV INJECTION.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V19 472


5.5 Biological Half-Life

This pharmacokinetic data does not apply to povidone.


This pharmacokinetic data does not apply to povidone.


5.6 Mechanism of Action

Povidone-iodine is a water-soluble complex that mediates a bactericidal or virucidal action following the gradual liberation of free iodine from the complex at the application site to react with the pathogen. Please refer to the drug entry for [DB06812] for the full mechanism of action of the complex.


Povidone-iodine is a water-soluble complex that mediates a bactericidal or virucidal action following the gradual liberation of free iodine from the complex at the application site to react with the pathogen. Please refer to the drug entry for [Povidone-iodine] for the full mechanism of action of the complex.


ONE OF MAJOR PROPERTIES OF PVP IS ITS PHYSIO-CHEMICAL BEHAVIOR, WHICH IS... COMPARABLE TO THAT OF SERUM ALBUMEN... THUS IT FIXES & TRANSPORTS WATER AS WELL AS THE PRODUCTS FIXED BY SERUM ALBUMEN... IT CAN ALSO CARRY SUCH SUBSTANCES AS UREA, CREATININE, LACTOFLAVIN, COLORING MATTERS, HORMONES, & GLUCOSE.

Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 290