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Chemistry

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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

Penicillin V Potassium

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 Formula	C₁₆H₁₇KN₂O₅S
Molecular Weight	388.5 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	388.04952431 g/mol
Monoisotopic Mass	388.04952431 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	553
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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 2
Drug Name	Penicillin v potassium
Drug Label	Penicillin 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 Ingredient	Penicillin v potassium
Dosage Form	Tablet; For solution
Route	Oral
Strength	eq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market Status	Prescription
Company	Aurobindo Pharma; Sandoz; Hikma Pharms; Dava Pharms

2 of 2
Drug Name	Penicillin v potassium
Drug Label	Penicillin 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 Ingredient	Penicillin v potassium
Dosage Form	Tablet; For solution
Route	Oral
Strength	eq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market Status	Prescription
Company	Aurobindo 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

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API Reference Price

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D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"UNITED STATES PHARMACOPEIAL ","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0002","unit":"KGS","unitRateFc":"1415000","totalValueFC":"306.1","currency":"USD","unitRateINR":"128603300","date":"30-Oct-2024","totalValueINR":"25720.66","totalValueInUsd":"306.1","indian_port":"Hyderabad Air","hs_no":"29411090","bill_no":"6428123","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK, MD, US 21704 SDNF United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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ACTIVE PHARMA INGREDIENTS

15 API Suppliers

12 USDMF

3 CEP/COS

2 NDC API

3 Listed Suppliers

$ API Reference Price

FINISHED DOSAGE FORMULATIONS

78 FDF Dossiers

74 FDA Orange Book

1 Europe

1 Canada

2 South Africa

RELATED EXCIPIENT COMPANIES

2 Rochem International Inc

1 SPI Pharma

2 Seqens

4 DKSH

3 Faran Shimi Pharmaceutical

6 Boai NKY Pharmaceuticals Ltd

7 Gangwal Healthcare

1 Nanjing Well Pharmaceutical

1 Pfanstiehl

1 ACG Worldwide

5 Actylis

1 Aeon Procare

4 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

22 BASF

1 Clariant

10 Corel Pharma Chem

2 DFE Pharma

1 Finar

8 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

16 Kerry

3 Kima Chemical

6 Lonza Capsugel

9 Microlex e.U

2 Nomisma Healthcare

2 Novo Excipients

2 Pharmatrans-Sanaq

3 Pluviaendo

2 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

10 Roquette

6 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shanghai Welltone Material Technology Co., Ltd

9 Sigachi Industries

2 The Dow Chemical Company

2 Ulanqab Kema New Material

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EXCIPIENTS BY APPLICATIONS

48 Coating Systems & Additives

38 Fillers, Diluents & Binders

29 Controlled & Modified Release

22 Thickeners and Stabilizers

20 Direct Compression

16 Lubricants & Glidants

16 Granulation

14 Co-Processed Excipients

12 Solubilizers

10 Film Formers & Plasticizers

10 Taste Masking

9 Topical

7 Disintegrants & Superdisintegrants

6 Parenteral

5 Empty Capsules

5 API Stability Enhancers

4 Emulsifying Agents

4 Chewable & Orodispersible Aids

4 Vegetarian Capsules

4 Coloring Agents

3 Rheology Modifiers