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Hetacillin

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Chemical compound

Pharmaceutical compound
Hetacillin
Clinical data
Trade namesHetacin, Versapen
AHFS/Drugs.comVeterinary Use
Routes of
administration		Intramammary injection
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • (2S,5R,6R)-6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.466 Edit this at Wikidata
Chemical and physical data
FormulaC19H23N3O4S
Molar mass389.47 g·mol
3D model (JSmol)
SMILES
  • CC1((N2(S1)(C2=O)N3C(=O)(NC3(C)C)c4ccccc4)C(=O)O)C
InChI
  • 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
  • Key:DXVUYOAEDJXBPY-NFFDBFGFSA-N
  (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, but quickly splits off acetone in the human body to form ampicillin, which is active against a variety of bacteria.

Administration

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

Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin.

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.

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). " (in Japanese)". The Japanese Journal of Antibiotics. 23 (4): 400–2. PMID 5312791.
  4. Hara M, Takemoto S, Kawazu T (December 1970). " (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.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
Xenobiotic-sensing receptor modulators
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
See also
Receptor/signaling modulators
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