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2D Structure
Also known as: Penicillin v potassium salt, 132-98-9, Penicillin vk, Antibiocin, Phenoxymethylpenicillin potassium, Beepen-vk
Molecular Formula
C16H17KN2O5S
Molecular Weight
388.5  g/mol
InChI Key
HCTVWSOKIJULET-LQDWTQKMSA-M
FDA UNII
146T0TU1JB

A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
potassium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
2.1.2 InChI
InChI=1S/C16H18N2O5S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
2.1.3 InChI Key
HCTVWSOKIJULET-LQDWTQKMSA-M
2.1.4 Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)COC3=CC=CC=C3)C(=O)[O-])C.[K+]
2.1.5 Isomeric SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)[O-])C.[K+]
2.2 Other Identifiers
2.2.1 UNII
146T0TU1JB
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apocillin

2. Beromycin

3. Beromycin, Penicillin

4. Berromycin, Penicillin

5. Betapen

6. Fenoxymethylpenicillin

7. Pen Vk

8. Penicillin Beromycin

9. Penicillin Berromycin

10. Penicillin V

11. Penicillin V Sodium

12. Penicillin Vk

13. Penicillin, Phenoxymethyl

14. Phenoxymethyl Penicillin

15. Phenoxymethylpenicillin

16. Potassium, Penicillin V

17. Sodium, Penicillin V

18. V Cillin K

19. V Sodium, Penicillin

20. V-cillin K

21. Vcillin K

22. Vegacillin

2.3.2 Depositor-Supplied Synonyms

1. Penicillin V Potassium Salt

2. 132-98-9

3. Penicillin Vk

4. Antibiocin

5. Phenoxymethylpenicillin Potassium

6. Beepen-vk

7. Potassium Penicillin V

8. Primcillin

9. Veetids

10. Ledercillin Vk

11. Pfizerpen Vk

12. Uticillin Vk

13. Betapen-vk

14. V-cillin K

15. Pen-vee K

16. Suspen

17. Penapar-vk

18. Penicillin-vk

19. Penicillin Potassium Phenoxymethyl

20. Beromycin

21. Vamosyn

22. Penicillin V (potassium)

23. 146t0tu1jb

24. Chebi:7967

25. Calciopen K

26. Phenoxymethylpenicillin Potassium Salt

27. Sk-penicillin Vk

28. Nsc-757258

29. Monopotassium (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

30. Phenoxymethylpenicillinic Acid Potassium

31. Arcacil

32. Cliacil

33. Isocillin

34. Ispenoral

35. Kavepenin

36. Ospeneff

37. Pedipen

38. Penagen

39. Pencompren

40. Penvikal

41. Roscopenin

42. Icipen

43. Orapen

44. Megacillin Oral

45. Vepen

46. Compocillin-vk

47. Robicillin Vk

48. Dsstox_cid_1102

49. Veetids '125'

50. Veetids '250'

51. Veetids '500'

52. Rocillin-vk

53. Distaquaine V-k

54. Penapar Vk

55. Sumapen Vk

56. Distakaps V-k

57. Oracil-vk

58. Qidpen Vk

59. Apsin Vk

60. Aspin Vk

61. Dov-k

62. Dsstox_rid_75941

63. Dsstox_gsid_21102

64. Pen-v-k Powder

65. Dowpen V-k

66. Pen-vee-k Powder

67. Dqv-k

68. Potassium Penicillin V Salt

69. Pen Vk

70. V-cil-k

71. Beromycin (penicillin)

72. Potassium Phenoxymethylpenicillin

73. Potassium Phenoxymethyl Penicillin

74. Stabillin Vk Syrup 125

75. Phenoxymethylpenicillin Potassium (jan)

76. Stabillin Vk Syrup 62.5

77. Cas-132-98-9

78. Potassium (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

79. Potassium (2s,5r,6r)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

80. Ccris 750

81. Penicillin V Potassium [usan]

82. Phenoxymethylpenicillin Potassium [jan]

83. Hsdb 6315

84. Einecs 205-086-5

85. Mfcd00051771

86. Unii-146t0tu1jb

87. D-alpha-phenoxymethylpenicillinate K Salt

88. Potassium;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

89. Penicillin V Potassium [usan:usp]

90. Veetids (tn)

91. Penicilline V Potassium

92. Schembl41271

93. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(( Phenoxyacetyl)amino)-, Monopotassium Salt, (2s-(2alpha,5alpha,6beta))-

94. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(2 -phenoxyacetamido)-, Monopotassium Salt

95. Penicillinvpotassiumsalt

96. Spectrum1500467

97. Penicillin V Potassium (usp)

98. Chembl1200852

99. Dtxsid7021102

100. Hms502g21

101. Hms1920f14

102. Hms2091n14

103. Hy-b0975

104. Tox21_202176

105. Tox21_302914

106. Ccg-39570

107. Penicillin V Potassium [hsdb]

108. Phenoxymethylpenicillin Potassium,(s)

109. Akos024418766

110. Penicillin V Potassium [vandf]

111. Cs-4465

112. Nsc 757258

113. Mehyl-7-azaindole-4-carboxylate

114. Penicillin V Potassium [usp-rs]

115. Ncgc00164005-01

116. Ncgc00256459-01

117. Ncgc00259725-01

118. Penicillin Phenoxymethyl Potassium

119. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, Monopotassium Salt, (2s,5r,6r)-

120. As-83778

121. Penicillin V Potassium [green Book]

122. Penicillin V Potassium [orange Book]

123. Penicillin V Potassium [usp Impurity]

124. Penicillin V Potassium [usp Monograph]

125. C72320

126. D00497

127. Phenoxymethylpenicillin Potassium [mart.]

128. Penicilline V Potassium 100 Microg/ml In Methanol

129. Phenoxymethylpenicillin Potassium [who-dd]

130. Phenoxymethylpenicillin Potassium [who-ip]

131. W-109072

132. Q27107637

133. Phenoxymethylpenicillin Potassium [ep Monograph]

134. Phenoxymethylpenicillinum Kalicum [who-ip Latin]

135. Penicillin V Potassium Salt, Vetranal(tm), Analytical Standard

136. Penicillin V Potassium Salt, Powder, Bioreagent, Suitable For Cell Culture

137. Penicillin V Potassium, United States Pharmacopeia (usp) Reference Standard

138. Phenoxymethylpenicillin Potassium, Antibiotic For Culture Media Use Only

139. Phenoxymethylpenicillinic Acid Potassium Salt, Potency: >=1460 Units Per Mg

140. Potassium 2,2-dimethyl-6beta-(phenoxyacetamido)penam-3alpha-carboxylate

141. Phenoxymethylpenicillin Potassium, British Pharmacopoeia (bp) Reference Standard

142. Phenoxymethylpenicillin Potassium, European Pharmacopoeia (ep) Reference Standard

143. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((2-phenoxyacetyl)amino)-, Potassium Salt (1:1), (2s,5r,6r)-

144. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, Monopotassium Salt, (2s-(2.alpha.,5.alpha.,6.beta.))-

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 388.5 g/mol
Molecular Formula C16H17KN2O5S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass388.04952431 g/mol
Monoisotopic Mass388.04952431 g/mol
Topological Polar Surface Area124 Ų
Heavy Atom Count25
Formal Charge0
Complexity553
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NamePenicillin v potassium
Drug LabelPenicillin V is the phenoxymethyl analog of penicillin G. Penicillin V potassium is the potassium salt of penicillin V. Penicillin V Potassium is designated chemically as 4-Thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo- 6-[(...
Active IngredientPenicillin v potassium
Dosage FormTablet; For solution
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market StatusPrescription
CompanyAurobindo Pharma; Sandoz; Hikma Pharms; Dava Pharms

2 of 2  
Drug NamePenicillin v potassium
Drug LabelPenicillin V is the phenoxymethyl analog of penicillin G. Penicillin V potassium is the potassium salt of penicillin V. Penicillin V Potassium is designated chemically as 4-Thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo- 6-[(...
Active IngredientPenicillin v potassium
Dosage FormTablet; For solution
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market StatusPrescription
CompanyAurobindo Pharma; Sandoz; Hikma Pharms; Dava Pharms

4.2 Therapeutic Uses

Penicillins

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


Penicillin V /is/ indicated in the treatment of acute otitis media caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2149


Penicillin V /is/ indicated in the treatment of bacterial pharyngitis cuased by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2149


Penicillin V /is/ indicated in the treatment of sinusitis caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2150


For more Therapeutic Uses (Complete) data for PENICILLIN VK (18 total), please visit the HSDB record page.


4.3 Drug Warning

Penicillins are distributed into breast milk, some in low concentrations. Although significant problems in humans have not been documented, the use of penicillins by nursing mothers may lead to sensitization, diarrhea, candidiasis, and skin rash in the infant. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2151


Many penicillins have been used in pediatric patients and no pediatrics-specific problems have been documented to date. However, the incompletely developed renal function of neonates and young infants may delay the excretion of renally eliminated penicillins. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2151


Penicillins have been used in geriatric patients and no geriatrics-specific problems have been documented to date. However, elderly patients are more likely to have age-related renal function impairment, which may require an adjustment in dosage in patients receiving penicillins. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2151


Prolonged use of penicillins may lead to the development of oral candidiasis. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2151


For more Drug Warnings (Complete) data for PENICILLIN VK (9 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]
5.3 Absorption, Distribution and Excretion

A dose of 1,000,000 units of the acid gives peak plasma levels of about 2 to 3 ug/ml, but the potassium salt will provide levels of 4.5 to 9 ug/ml.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1142


Penicillin VK provides faster and higher blood levels of antibiotic than Penicillin V.

Osol A, Hoover JE et al (eds); Remington's Pharmaceutical Sciences. 14th ed. Easton, PA: Mack Publishing Co., p. 1230 (1975)


5.4 Biological Half-Life

The half-life is 0.5 to 0.6 hr.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1142


5.5 Mechanism of Action

The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 953


Bactericidal; inhibit bacterial cell wall synthesis. Action is dependent on the ability of penicillins to reach and bind penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Penicillin-binding proteins (which include transpeptidases, carboxypeptidases, and endopeptidases) are enzymes that are involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Penicillins bind to, and inactivate, penicillin-binding proteins, resulting in the weakening of the bacterial cell wall and lysis. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2150