Hetacillin

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Hetacillin
Hetacillin structure.svg
Clinical data
Trade names Hetacin, Versapen
AHFS/Drugs.com Veterinary Use
Routes of
administration
Intramammary injection
ATC code
Legal status
Legal status
Identifiers
  • (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.466 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H23N3O4S
Molar mass 389.47 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)c4ccccc4)C(=O)O)C
  • InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1 X mark.svgN
  • Key:DXVUYOAEDJXBPY-NFFDBFGFSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and has no antibacterial activity itself, [1] but quickly splits off acetone in the human body to form ampicillin, [2] which is active against a variety of bacteria.

Contents

Administration

Hetacillin can be administered orally. The potassium salt, hetacillin potassium, is administered by injection, either intravenously [3] or intramuscularly. [4] It is sold under the trade name Hetacin for intramammary injection in veterinary use. [5]

Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin. [6]

Chemistry

Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at 37 °C (99 °F) and pH 7, quickly releasing acetone again. [7]

As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro .[ citation needed ]

Related Research Articles

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<span class="mw-page-title-main">Aztreonam</span>

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The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

References

  1. "Hetacillin". Drugbank.
  2. Sutherland R, Robinson OP (June 1967). "Laboratory and pharmacological studies in man with hetacillin and ampicillin". British Medical Journal. 2 (5555): 804–8. doi:10.1136/bmj.2.5555.804. PMC   1843140 . PMID   5182358.
  3. Tsuji Y, Tomita M (August 1970). "[Clinical effect of intravenous injection of potassium hetacillin (Versapen 'Bristol') on pre- and post-operative infections] (in Japanese)". The Japanese Journal of Antibiotics. 23 (4): 400–2. PMID   5312791.
  4. Hara M, Takemoto S, Kawazu T (December 1970). "[Therapeutic experience with intramuscular injection of hetacillin (Versapen 'Bristol') in infection in children] (in Japanese)". The Japanese Journal of Antibiotics. 23 (5): 482–6. PMID   5314634.
  5. Hetacin-K Intramammary Infusion for Veterinary Use
  6. Smith JT, Hamilton-Miller J (1970). "Hetacillin: A Chemical and Biological Comparison with Ampicillin". Chemotherapy. 15 (6): 366–78. doi:10.1159/000220703. PMID   5514976.
  7. Faine S, Harper M (January 1973). "Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods". Antimicrobial Agents and Chemotherapy. 3 (1): 15–8. doi:10.1128/aac.3.1.15. PMC   444353 . PMID   4597707.