hetacillin

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461767356

| IUPAC_name = (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

| image = Hetacillin structure.svg

| tradename = Hetacin, Versapen

| Drugs.com = {{Drugs.com|vet|hetacin-k-intramammary-infusion}}

| pregnancy_AU =

| pregnancy_category =

| routes_of_administration = Intramammary injection

| ATC_prefix = J01

| ATC_suffix = CA18

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Rx-only

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

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| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 3511-16-8

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00739

| PubChem = 443387

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 391616

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TN4JSC48CV

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D01074

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201116

| chemical_formula =

| C=19 | H=23 | N=3 | O=4 | S=1

| smiles = CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)c4ccccc4)C(=O)O)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DXVUYOAEDJXBPY-NFFDBFGFSA-N

}}

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and has no antibacterial activity itself,{{cite web | work = Drugbank | url = http://www.drugbank.ca/drugs/DB00739 | title = Hetacillin }} but quickly splits off acetone in the human body to form ampicillin,{{cite journal | vauthors = Sutherland R, Robinson OP | title = Laboratory and pharmacological studies in man with hetacillin and ampicillin | journal = British Medical Journal | volume = 2 | issue = 5555 | pages = 804–8 | date = June 1967 | pmid = 5182358 | pmc = 1843140 | doi = 10.1136/bmj.2.5555.804 }} which is active against a variety of bacteria.

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Administration

Hetacillin can be administered orally. The potassium salt, hetacillin potassium, is administered by injection, either intravenously{{cite journal | vauthors = Tsuji Y, Tomita M | title = [Clinical effect of intravenous injection of potassium hetacillin (Versapen 'Bristol') on pre- and post-operative infections] (in Japanese) | journal = The Japanese Journal of Antibiotics | volume = 23 | issue = 4 | pages = 400–2 | date = August 1970 | pmid = 5312791 }} or intramuscularly.{{cite journal | vauthors = Hara M, Takemoto S, Kawazu T | title = [Therapeutic experience with intramuscular injection of hetacillin (Versapen 'Bristol') in infection in children] (in Japanese) | journal = The Japanese Journal of Antibiotics | volume = 23 | issue = 5 | pages = 482–6 | date = December 1970 | pmid = 5314634 }} It is sold under the trade name Hetacin for intramammary injection in veterinary use.Hetacin-K Intramammary Infusion for {{Drugs.com|vet|hetacin-k-intramammary-infusion}}

Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin.{{cite journal | vauthors = Smith JT, Hamilton-Miller J | title = Hetacillin: A Chemical and Biological Comparison with Ampicillin | journal = Chemotherapy | volume = 15 | issue = 6 | pages = 366–78 | year = 1970 | pmid = 5514976 | doi = 10.1159/000220703 }}

Chemistry

Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at {{convert|37|°C|°F}} and pH 7, quickly releasing acetone again.{{cite journal | vauthors = Faine S, Harper M | title = Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods | journal = Antimicrobial Agents and Chemotherapy | volume = 3 | issue = 1 | pages = 15–8 | date = January 1973 | pmid = 4597707 | pmc = 444353 | doi = 10.1128/aac.3.1.15 }}

References

Category:Penicillins

Category:Prodrugs

Category:Withdrawn drugs

Category:Imidazolidinones