Skip to main content
SpringerLink
Log in

The Semi-synthetic Penicillins

  • Chapter
Antibacterial Drugs Today

  • 233 Accesses

Abstract

The separation of 6-APA from its side chain by amidase (fig. 1) has allowed a very wide variety of new side chains to be attached to the nucleus semi-synthetically giving rise to different therapeutic properties, including acid resistance as with the Phenoxymethylpenicillins, penicillinase resistance as with methicillin and the isoxazolyl penicillins, and a wider antibacterial spectrum as with ampicillin, amoxycillin, epicillin, hetacillin and carbenicillin (fig. 2).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Baldwin, D.S.; Levine, B.B.; McCluskey, R.T. and Gallo, G.R.: Renal failure and interstitial nephritis due to penicillin and methicillin. New England Journal of Medicine 279: 1245–1252 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Bear, D.M.; Turck, M. and Petersdorf, R.G.: Ampicillin. Medical Clinics of North America 54: 1145–1159(1970).

    PubMed  CAS  Google Scholar 

  • Bond, J.M.; Lightbrown, J.W.; Barber, M. and Waterworth, P.M.: Four phenoxypenicillins. British Medical Journal 2: 956–961 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Brauninger, G.E. and Remington, J.S.: Neuropathy associated with methicillin therapy. Journal of the American Medical Association 203: 103–105 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Brogden, R.N. and Avery, G.S.: New Antibiotics: Epicillin, minocycline and spectinomycin. A summary of their antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 3: 314–330(1972).

    Article  PubMed  CAS  Google Scholar 

  • Brogden, R.N.; Speight, T.M. and Avery, G.S.: Amoxycillin: A review of its antibacterial and pharmacokinetic properties and therapeutic use. Drugs 9: 88–140 (1975).

    Article  CAS  Google Scholar 

  • Cameron, S.J. and Richmond, J.-. Ampicillin hypersensitivity in lymphatic leukaemia. Scottish Medical Journal 16: 425–427 (1971).

    PubMed  CAS  Google Scholar 

  • Clayton, J.P.; Cole, M.; Elson, S.W. and Ferres, H.: BRL 8988 (talampicillin), a well-absorbed oral form of ampicillin. Antimicrobial Agents and Chemotherapy 5: 670–671 (1974).

    PubMed  CAS  Google Scholar 

  • Clymo, A.B. and Harper, I.A.: Ampicillin-resistant Haemophilus influenzae meningitis. Lancet 1: 453–454(1974).

    Google Scholar 

  • Collaborative Study Group: Prospective study of ampicillin rash. British Medical Journal 1: 7–9 (1973).

    Article  Google Scholar 

  • Daehne, W.V.; Godtfredsen, W.O.; Roholt, K. and Tybring, L.: Pivampicillin, a new orally active ampicillin ester. Antimicrobial Agents and Chemotherapy 1970, p.431 (1971).

    Google Scholar 

  • Dahnsjo, H.; Andersson, H.; Hallander, H.O. and Rudberg, R.D.: Tone audiometry control of children treated for meningitis with large intravenous doses of ampicillin. Acta Paediatrica Scandinavica 65: 733–737(1976).

    Article  PubMed  CAS  Google Scholar 

  • Garrod, L.P.; Lambert, H.P. and O’Grady, F.: in Antibiotic and Chemotherapy, 4th ed, p.72 and 76 (Churchill Livingstone, Edinburgh and London 1973).

    Google Scholar 

  • Gilbert, D.N. and Sanford, J.P.: Methicillin. Critical appraisal after a decade of experience. Medical Clinics of North America 54: 1113–1125 (1970).

    PubMed  CAS  Google Scholar 

  • Hambleton, G. and Davies, Pamela A.: Diagnosis and management of bacterial meningitis. Drugs 8: 15–53(1974).

    Article  PubMed  CAS  Google Scholar 

  • Heineman, H.S. and Israel, W.: Carbenicillin in the first nine months of unrestricted use. A chapter in the natural history of an antibiotic. Journal of Clinical Pharmacology 12: 241–248 (1972).

    CAS  Google Scholar 

  • Hewitt, W.L. and Winters, R.E.: The current status of parenteral carbenicillin. Journal of Infectious Diseases 127: 120–129(1973).

    Article  PubMed  Google Scholar 

  • Kjellander, J.O. and Finland, M.: Studies of the penicillinase of Staphylococcus albus. Proceedings of the Society for Experimental Biology (N.Y.) 113: 1031–1037 (1963).

    CAS  Google Scholar 

  • Knudsen, E.T. and Harding, J.W.: A multicentre comparative trial of talampicillin and ampicillin in general practice. British Journal of Clinical Practice 29: 255–266 (1975).

    PubMed  CAS  Google Scholar 

  • Lacey, R.: A new type of penicillin resistance of Staphylococcus aureus? Journal of Antimicrobial Chemotherapy 3: 380–381 (1977).

    Article  PubMed  CAS  Google Scholar 

  • Leading Article: An oral carbenicillin. British Medical Journal 3: 555–556 (1973).

    Google Scholar 

  • Leading Article: Haemophilus influenzae. Lancet 2: 116–111 (1976).

    Google Scholar 

  • Levitt, B.H.; Gottlieb, A.J.; Rosenberg, I.R. and Klein, J.J.: Bone marrow depression due to methicillin, a semisynthetic penicillin. Clinical Pharmacology and Therapeutics 5: 301–306 (1964).

    PubMed  CAS  Google Scholar 

  • Marcy, S.M. and Klein, J.O.: The Isoxazolyl Penicillins: Oxacillin, Cloxacillin and Dicloxacillin. Medical Clinics of North America 54: 1127–1143 (1970).

    PubMed  CAS  Google Scholar 

  • May, J.R. and Ingold, A.: Amoxicillin in the treatment of infections of the lower respiratory tract. Journal of Infectious Diseases 129 (Suppl. June): 189–193 (1974).

    Article  Google Scholar 

  • Neu, H.C.: Antimicrobial activity and human pharmacology of amoxycillin. Journal of Infectious Diseases 129 (Suppl): 123–131 (1974).

    Article  Google Scholar 

  • Parker, M.T. and Hewitt, J.H.: Methicillin resistance in Staphylococcus aureus. Lancet 1: 800–804 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Pullen, H.; Wright, N. and Murdoch, J. McC.: Hypersensitivity reactions to antibacterial drugs in infectious mononucleosis. Lancet 2: 1176–1178 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Rolinson, G.N.; Stevens, S.; Batchelor, F.R.; Wood, J.C. and Chain, E.B.: Bacteriological studies on a new penicillin BRL 1241. Lancet 2: 564–567 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Schiffer, M.S.; MacLowry, J.; Schneerson, R.; Robbins, J.B.; McReynolds, J.W.; Thomas, W.J.; Bailey, D.W.; Clarke, E.J.; Mueller, E.J. and Escamilla, J.: Clinical, bacteriological and immunological characterisation of ampicillin-resistant Haemophilus influenzae type B. Lancet 2: 257–259 (1974).

    Article  PubMed  CAS  Google Scholar 

  • Sutherland, R. and Rolinson, G.N.: Characteristics of methicillin-resistant staphylococci. Journal of Bacteriology 87: 887–899(1964).

    PubMed  CAS  Google Scholar 

  • Sutherland, R.; Croydon, E.A.P. and Rolinson, G.N.: Amoxycillin: a new semi-synthetic penicillin. British Medical Journal 3: 13–16 (1972).

    Article  PubMed  CAS  Google Scholar 

  • Swarz, H. and Storari, F.E.: Indanyl carbenicillin. Excerpta Medica (1974).

    Google Scholar 

  • The Medical Letter on Drugs and Therapeutics: Hetacillin 13: 49–50 (Issue 324) (1971).

    Google Scholar 

  • Turk, D.C.: Ampicillin-resistant Haemophilus influenzae meningitis. Lancet 1: 453 (1974).

    Article  Google Scholar 

  • Wilcox, J.B.; Brogden, R.N. and Avery, G.S.: Pivampicillin: A preliminary report of its pharmacokinetic properties and therapeutic efficacy. Drugs 6: 94–103 (1973).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Medicine (Sub-department of Communicable and Tropical Diseases), The University of Birmingham, England

    A. P. Ball

  2. Infectious Diseases Unit, City Hospital, Greenbank Drive, Edinburgh, EH10 5SB, Scotland

    J. A. Gray & J. McM. Murdoch

Authors
  1. A. P. Ball
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. A. Gray
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. McM. Murdoch
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1978 ADIS Press

About this chapter

Cite this chapter

Ball, A.P., Gray, J.A., Murdoch, J.M. (1978). The Semi-synthetic Penicillins. In: Antibacterial Drugs Today. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-8004-7_4

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-8004-7_4

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-85200-505-7

  • Online ISBN: 978-94-011-8004-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation