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Phenethicillin Potassium

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Also known as: Pheneticillin potassium, Maxipen, Astracillin, Oralopen, Potassium phenethicillin, 132-93-4

Molecular Formula

C₁₇H₁₉KN₂O₅S

Molecular Weight

402.5 g/mol

InChI Key

ORMNNUPLFAPCFD-DVLYDCSHSA-M

FDA UNII

70978WUK7C

Phenethicillin Potassium is the potassium salt form of phenethicillin, a narrow-spectrum, beta-lactamase-sensitive penicillin with antibacterial activity. Phenethicillin binds to and inactivates the penicillin binding proteins (PBPs) located inside the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.

1 2D Structure

Phenethicillin Potassium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

potassium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxypropanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C17H20N2O5S.K/c1-9(24-10-7-5-4-6-8-10)13(20)18-11-14(21)19-12(16(22)23)17(2,3)25-15(11)19;/h4-9,11-12,15H,1-3H3,(H,18,20)(H,22,23);/q;+1/p-1/t9?,11-,12+,15-;/m1./s1

2.1.3 InChI Key

ORMNNUPLFAPCFD-DVLYDCSHSA-M

2.1.4 Canonical SMILES

CC(C(=O)NC1C2N(C1=O)C(C(S2)(C)C)C(=O)[O-])OC3=CC=CC=C3.[K+]

2.1.5 Isomeric SMILES

CC(C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-])OC3=CC=CC=C3.[K+]

2.2 Other Identifiers

2.2.1 UNII

70978WUK7C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3,3-dimethyl-7-oxo-6-(2-phenoxypropionamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

2. Broxil

3. Chemipen

4. Maxipen

5. Optipen

6. Penicillin, Phenoxyethyl

7. Pensig

8. Phenethicillin

9. Phenethicillin, (2s-(2alpha,5alpha,6beta(r*)))-isomer

10. Phenethicillin, (2s-(2alpha,5alpha,6beta))-isomer

11. Phenethicillin, (2s-(2alpha,5alpha,6beta,(s*)))-isomer

12. Phenethicillin, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(r*)))-isomer

13. Phenethicillin, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(s*)))-isomer

14. Phenethicillin, Monosodium Salt, (2s-(2alpha,5alpha,6beta))-isomer

15. Potassium Phenethicillin

16. Syncillin

2.3.2 Depositor-Supplied Synonyms

1. Pheneticillin Potassium

2. Maxipen

3. Astracillin

4. Oralopen

5. Potassium Phenethicillin

6. 132-93-4

7. Phenethicillin Potassium Salt

8. Dramcillin S

9. Penicillin-152 Potassium

10. Phenethicillin K Salt

11. A-phenoxyethylpenicillinic Acid Potassium Salt

12. Chebi:31987

13. 70978wuk7c

14. 6-(a-phenoxypropionamido)penicillanic Acid Potassium Salt

15. Chemipen

16. Optipen

17. Syncillin

18. Broxil

19. Penova

20. Pensig

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

22. Alfacillin

23. Feneticilline

24. Synerpenin

25. Synthecillin

26. Synthecilline

27. Alticina

28. Bendralan

29. Brocsil

30. Penemve

31. Peniplus

32. Priospen

33. Semopen

34. Synapen

35. Triospen

36. Darcil

37. Alpha-oracillin

38. Penicillin Mv

39. Synthepen Tabl

40. Dramcillin-s

41. K Phenethicillin

42. Chemipen-c

43. Ro-cillin

44. Pheno-m-penicillin

45. Penicillin-152

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

47. Pen 200

48. Phenoxyaethylpenicillin K-salz

49. Unii-70978wuk7c

50. Phenethicillin Potassium [jan]

51. Hsdb 3167

52. Brl 152

53. Syncillin (tn)

54. Synthepen (tn)

55. Ncgc00017019-01

56. 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-4-thia-1-azabicyclo(3.2.0)-heptane-2-carboxylic Acid Potassium Salt

57. Cas-132-93-4

58. Prestwick_142

59. Einecs 205-084-4

60. Phenethicillin Potassium [usp:jan]

61. Potassium (1-phenoxyethyl)penicillin

62. Phenethicillin-kalium

63. Potassium Methylphenoxymethylpenicillin

64. Phenoxyaethylpenicillin K-salz [german]

65. Potassium (alpha-phenoxyethyl)penicillin

66. Alpha-phenoxyethylpenicillin Potassium Salt

67. Dsstox_cid_25546

68. Dsstox_rid_80947

69. Dsstox_gsid_45546

70. Schembl34264

71. Spectrum1500643

72. Potassium 6-(alpha-phenoxypropionamido)penicillanate

73. Chembl2364720

74. Dtxsid5045546

75. Hms500l16

76. Phenethicillin Potassium (jp17)

77. Hms1570a08

78. Hms2092e16

79. Hms2097a08

80. Hms3714a08

81. Tox21_110739

82. Ccg-39275

83. Phenethicillin Potassium [mi]

84. Phenethicillin Potassium [hsdb]

85. Pheneticillin Potassium [mart.]

86. Pheneticillin Potassium [who-dd]

87. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-, Monopotassium Salt, (2s-(2alpha,5alpha,6beta))-

88. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(2-phenoxypropionamido)-, Monopotassium Salt

89. D01178

90. Q27114742

91. Potassium 6beta-(2-phenoxypropanamido)-2,2-dimethylpenam-3alpha-carboxylate

92. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-, (2s-(2alpha,5alpha,6beta))-, Monopotassium Salt

93. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-, 92s-(2.alpha.,5.alpha.,6.beta.))-, Monopotassium Salt

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₉KN₂O₅S
Molecular Weight	402.5 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	402.06517437 g/mol
Monoisotopic Mass	402.06517437 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	582
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

THIS CONGENER OF PENICILLIN IS PHENOXYETHYL ANALOG OF PENICILLIN G. ... STABILITY IN ACIDIC MEDIA & BETTER ABSORPTION FROM GI TRACT...IS ITS SOLE ADVANTAGE IN COMPARISON TO PENICILLIN G. IT IS AVAIL ONLY FOR ORAL USE & HENCE IS NOT SUBSTITUTE FOR PARENTERAL PENICILLIN, WHEN SUCH THERAPY IS INDICATED. /PHENETHICILLIN/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1142

GINGIVOSTOMATITIS, PULMONARY INFECTIONS, & GENITAL DISEASE PRODUCED BY SYNERGISTIC ACTION OF FUSOBACTERIUM NUCLEATUM (FUSIFORM) & SPIROCHETES PRESENT IN RESPIRATORY TRACT ARE READILY TREATABLE WITH PENICILLIN. /PENICILLIN/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1156

PENICILLIN PROPHYLAXIS OF PROVEN VALUE. STREPTOCOCCAL INFECTIONS...RHEUMATIC FEVER RECURRENCES...GONORRHEA...SYPHILIS...SURGICAL PROCEDURES IN PATIENTS WITH VALVULAR HEART DISEASE. /PENICILLIN/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1157

4.2 Drug Warning

...PENICILLIN CAN MARKEDLY ALTER NORMAL BACTERIAL FLORA OF MAN. ... SUPERIMPOSED INFECTION BY PENICILLIN-RESISTANT MICROORGANISM MAY DEVELOP... VERY HIGH CONCN OF PENICILLIN ARE NEUROTOXIC... /PENICILLIN/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1126

MECHANISM MOST COMMONLY INVOLVED IN PATHOGENESIS OF UNTOWARD EFFECTS FROM ANY TYPE OF PENICILLIN IS HYPERSENSITIZATION. ALLERGIC REACTIONS TO PENICILLINS VARY FROM 0.7 TO 10%... /PENICILLINS/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1082

IN SOME PERSONS...SUPRAINFECTION RESULTS FROM CHANGES IN FLORA. DERMATITIS INVOLVING PRIMARILY SCROTAL & INGUINAL SKIN...HAS BEEN OBSERVED... DRAMATIC EFFECT THAT MAY FOLLOW USE OF PENICILLIN IN SYPHILIS IS JARISCH-HERXHEIMER REACTION... /PENICILLINS/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1085

HIGH INCIDENCE OF CONTACT ALLERGIC REACTIONS WAS RECOGNIZED EARLY & TOPICAL APPLICATION OF PENICILLIN TO EYE HAS BEEN ESSENTIALLY ABANDONED CLINICALLY. /PENICILLIN/

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 793

For more Drug Warnings (Complete) data for PHENETHICILLIN POTASSIUM (7 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 Absorption, Distribution and Excretion

FOOD RETARDS ABSORPTION & THEREBY PROLONGS DURATION OF ACTION OF CMPD. PEAK PLASMA CONCN OCCUR ABOUT 1 HR AFTER ORAL ADMIN OF DRUG.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1142

GIVEN ORALLY, DRUG IS WELL ABSORBED & ESCAPES DESTRUCTION IN ACIDIC GASTRIC CONTENTS; DESPITE THIS FACT, INTESTINAL ABSORPTION IS INCOMPLETE. IN EQUAL ORAL DOSES, IT PRODUCES HIGHER PLASMA CONCN THAN DOES PENICILLIN G OR PENICILLIN V.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1142

PENICILLIN T/2 IN HUMAN SERUM INCR FROM ABOUT 25 MIN IN YOUNG ADULTS TO 2 HR IN ELDERLY SUBJECTS & IS ALSO MARKEDLY INCR BY DRUGS WHICH ARE ACTIVELY SECRETED BY KIDNEY TUBULES. SERUM PENICILLIN LEVELS IN NEW-BORN INFANTS ARE HIGHER & MORE PROLONGED THAN IN CHILDREN & ADULTS AFTER EQUIV DOSES. /PENICILLIN/

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 167

...RAPIDLY ELIMINATED FROM BODY, MAINLY BY KIDNEY BUT IN SMALL PART IN BILE & BY OTHER CHANNELS. ... CLEARANCE VALUES ARE CONSIDERABLY LOWER IN NEONATES & INFANTS, BECAUSE OF INCOMPLETE DEVELOPMENT OF RENAL FUNCTION... /PENICILLIN G/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1071

SIGNIFICANT AMT APPEAR IN LIVER, BILE, KIDNEY, SEMEN, LYMPH, & INTESTINE. ... PENICILLIN DOES NOT READILY ENTER CSF WHEN MENINGES ARE NORMAL. /PENICILLIN G/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1070

5.3 Biological Half-Life

PENICILLIN T/2 IN HUMAN SERUM INCR FROM ABOUT 25 MIN IN YOUNG ADULTS TO 2 HR IN ELDERLY SUBJECTS. /PENICILLIN/

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 167

5.4 Mechanism of Action

...ACT TO INHIBIT SYNTH OF COMPONENTS OF BACTERIAL CELL WALL... /PENICILLIN/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1135

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

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