Synonym
Phenethicillin potassium; Phenethicillin-potassium; Phenethicillinpotassium; ALPHA-PHENOXYETHYLPENICILLINIC ACID POTASSIUM SALT; PHENETHICILLIN POTASSIUM; PHENETHICILLIN POTASSIUM SALT;
IUPAC/Chemical Name
3,3-Dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-4-thia-1-azabicyclo(3.2.0)-heptane-2-carboxylic acid potassium salt
InChi Key
ORMNNUPLFAPCFD-UHFFFAOYSA-M
InChi Code
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
SMILES Code
O=C(C(C(C)(C)SC1C2NC(C(OC3=CC=CC=C3)C)=O)N1C2=O)[O-].[K+]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
402.51
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: MARTIN WJ, NICHOLS DR. Penicillin V and phenethicillin potassium in serum: comparison of concentrations and of antibacterial effects. Proc Staff Meet Mayo Clin. 1960 Sep 28;35:577-84. PubMed PMID: 13767422.
2: CAMPEAU L, LEFEBVRE M. Treatment of bacterial endocarditis by oral phenethicillin potassium (Syncillin). Can Med Assoc J. 1961 Mar 11;84:535-9. PubMed PMID: 13690283; PubMed Central PMCID: PMC1939332.
3: SABATINE JW, KARP A, FREEMAN SL. Phenethicillin vs. potassium penicillin G for ear, nose, and throat infections. Eye Ear Nose Throat Mon. 1963 May;42:53-4. PubMed PMID: 13975864.
4: Khan KA, Musikabhumma P. Effect of slugging pressure on the properties of granules and tablets prepared from potassium phenethicillin. J Pharm Pharmacol. 1981 Oct;33(10):627-31. PubMed PMID: 6117614.
5: Stenlake JB, Wood GC, Mital HC, Stewart S. The assay of potassium 6-(L-(+)- -phenoxypropionamido)penicillanate and 6-(D-(+)- -phenoxypropionamido)penicillanate in phenethicillin potassium by circular dichroism spectrometry. Analyst. 1972 Aug;97(157):639-43. PubMed PMID: 4341370.
6: GALIMI R. Bacterial infections of the ear, nose and throat treated with oral penicillin (potassium phenethicillin). Eye Ear Nose Throat Mon. 1961 Jul;40:475-6. PubMed PMID: 13703075.
7: Alpar HO, Walters V. The prolongation of the in vitro dissolution of a soluble drug (phenethicillin potassium) by microencapsulation with ethyl cellulose. J Pharm Pharmacol. 1981 Jul;33(7):419-22. PubMed PMID: 6115027.
8: Alpar OH. Sustained-release characteristics of tablets of ethylcellulose microcapsules containing potassium phenethicillin. Farmaco Prat. 1981 Aug;36(8):366-73. PubMed PMID: 6791959.
9: SCHWARTZ MA, GRANATEK AP, BUCKWALTER FH. Stability of potassium phenethicillin. I. Kinetics of degradation in aqueous solution. J Pharm Sci. 1962 Jun;51:523-6. PubMed PMID: 13909711.
10: CAMPEAU L, LEFEBVRE M. [Oral treatment of malignant streptococcal endocarditis by potassium phenethicillin: 10 cases]. Union Med Can. 1963 Aug;92:873-80. French. PubMed PMID: 14018160.
11: Marty JJ, Hersey JA. Absorption of phenethicillin from oral paediatric formulations. Med J Aust. 1975 Mar 22;1(12):382-4. PubMed PMID: 806767.
12: Wilson WL, Avdovich HW, Hughes DW, Buchanan GW. Application of proton and 13C-NMR spectroscopy to estimation of diastereoisomer ratio in phenethicillin. J Pharm Sci. 1977 Aug;66(8):1079-83. PubMed PMID: 408475.
13: PERRON YG, CRAST LB, GOTTSTEIN WJ, MINOR WF, CHENEY LC. Synthesis of potassium penicillin-152 [potassium (alpha-phenoxyethyl)-penicillin] and both diastereoisomers. Antibiot Annu. 1959-1960;7:107-10. PubMed PMID: 13854294.
14: Musikabhumma P, Khan KA. Effect of slugging pressure on the properties of granules and tablets prepared from potassium phenethicillin [proceedings]. J Pharm Pharmacol. 1979 Dec;31 Suppl:75P. PubMed PMID: 42753.
15: BREESE BB, DISNEY FA, TALPEY WB. BETA-HEMOLYTIC STREPTOCOCCAL INFECTIONS IN CHILDREN. COMPARISON OF THE THERAPEUTIC EFFECTIVENESS OF POTASSIUM PENICILLIN G, TETRACYCLINE PHOSPHATE COMPLEX, AND DEMETHYLCHLORTETRACYCLINE. Am J Dis Child. 1964 Mar;107:232-9. PubMed PMID: 14095108.
16: PINDELL MH, TISCH DE, HOEKSTRA JB, REIFFENSTEIN JC. Pharmacological studies on potassium penicillin-152 [potassium (alpha-phenoxyethyl)-penicillin]. Antibiot Annu. 1959-1960;7:119-26. PubMed PMID: 13854362.
17: GOUREVITCH A, HUNT GA, LEIN J. Microbiological studies on potassium penicillin-152 [potassium (alpha-phenoxyethyl)-penicillin]. Antibiot Annu. 1959-1960;7:111-8. PubMed PMID: 13851448.
18: CRONK GA, NAUMANN DE, ALBRIGHT H, WHEATLEY WB. Laboratory and clinical studies with potassium penicillin-152 [potassium (alpha-phenoxyethyl)-penicillin]. Antibiot Annu. 1959-1960;7:133-45. PubMed PMID: 13849468.
19: CRONK GA, WHEATLEY WB, FELLERS GF, ALBRIGHT H. The relationship of food intake to the absorption of potassium alpha-phenoxyethyl penicillin and potassium phenoxymethyl penicillin from the gastrointestinal tract. Am J Med Sci. 1960 Aug;240:219-25. PubMed PMID: 13812969.
20: Overbosch D, Mattie H, van Furth R. Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin. Br J Clin Pharmacol. 1985 May;19(5):657-68. PubMed PMID: 3924086; PubMed Central PMCID: PMC1463849.
