Hetacillin: Difference between revisions

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{{SI}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461767356
| IUPAC_name = (2''S'',5''R'',6''R'')-6-[(4''R'')-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


<!--Clinical data-->
| tradename = Hetacin
| Drugs.com = {{Drugs.com|vet|hetacin-k-intramammary-infusion}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = Rx-only
| legal_status =
| routes_of_administration = [[Mammary gland|Intramammary]] injection


[[Image:hetacillin.png|thumb|left|Hetacillin ]]
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 


'''Hetacillin''' is a [[beta-lactam antibiotic|beta-lactam]]. Hetacillin is a [[prodrug]] and it has no intrinsic antibacterial activity, but is converted by the body to [[ampicillin]], which is active against a variety of organisms.
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3511-16-8
| ATC_prefix = J01
| ATC_suffix = CA18
| PubChem = 193260
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00739
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 167708
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TN4JSC48CV
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01074
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201116
 
<!--Chemical data-->
| chemical_formula = 
| C=19 | H=23 | N=3 | O=4 | S=1
| molecular_weight = 389.469 g/mol
| smiles = O=C(O)[C@@H]3N4C(=O)[C@@H](N2C(=O)C(c1ccccc1)NC2(C)C)[C@H]4SC3(C)C
| InChI = 1/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
| InChIKey = DXVUYOAEDJXBPY-XQERAMJGBD
| StdInChI_Ref = {{stdinchicite|correct|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|correct|chemspider}}
| StdInChIKey = DXVUYOAEDJXBPY-XQERAMJGSA-N
}}
'''Hetacillin''' is a [[beta-lactam antibiotic]] that is part of the [[aminopenicillin]] family. It is a [[prodrug]] and it has no antibacterial activity itself,<ref name="DrugBank">Drugbank: [http://www.drugbank.ca/drugs/DB00739 Hetacillin]</ref> but quickly splits of [[acetone]] in the human body to form [[ampicillin]],<ref name="Sutherland">{{cite pmid|5182358}}</ref> which is active against a variety of bacteria.


==Administration==
==Administration==
Hetacillin is administered orally. The potassium salt, hetacillin potassium, is administered by [[Injection (medicine)|injection]], either intravenously or intramuscularly.
Hetacillin can be administered orally.<ref name="Sutherland" /> The [[potassium]] salt, hetacillin potassium, is administered by [[Injection (medicine)|injection]], either intravenously or intramuscularly.{{fact|date=February 2014}} It is sold under the trade name '''Hetacin''' for [[Mammary gland|intramammary]] injection in veterinary use.<ref>Hetacin-K Intramammary Infusion for {{Drugs.com|vet|hetacin-k-intramammary-infusion}}</ref>
 
Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the gastrointestinal tract to formaldehyde and had no advantages over ampicillin.{{fact|date=February 2014}}
 
==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&nbsp;7, quickly releasing acetone again.<ref name="DrugBank" /><ref name="Faine">{{cite pmid|4597707}}</ref>
 
As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme [[beta-lactamase]], at least ''[[in vitro]]''.<ref name="Faine" />


Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the GI tract to formaldehyde and had no benefit to non-ester derivatives (i.e. Ampicillin).
==References==
{{reflist}}


{{Cell wall disruptive antibiotics}}


[[Category:Beta-lactam antibiotics]]
[[Category:Beta-lactam antibiotics]]
[[Category:Prodrugs]]
[[Category:Prodrugs]]
[[Category:Withdrawn drugs]]
[[Category:Withdrawn drugs]]
[[Category:Imidazolidinones]]




[[th:ฮีตาซิลลิน]]
{{Antibiotic-stub}}
{{WH}}
{{WikiDoc Sources}}

Revision as of 14:52, 8 April 2015

Hetacillin
File:Hetacillin structure.svg
Clinical data
Trade namesHetacin
AHFS/Drugs.comVeterinary Use
Routes of
administration		Intramammary injection
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H23N3O4S
Molar mass389.469 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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

Administration

Hetacillin can be administered orally.[2] The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly.[citation needed] It is sold under the trade name Hetacin for intramammary injection in veterinary use.[3]

Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the gastrointestinal tract to formaldehyde and had no advantages over ampicillin.[citation needed]

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 (98.6 °F) and pH 7, quickly releasing acetone again.[1][4]

As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.[4]

References

  1. ↑ 1.0 1.1 Drugbank: Hetacillin
  2. ↑ 2.0 2.1 PMID 5182358 (PMID 5182358)
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  3. ↑ Hetacin-K Intramammary Infusion for Veterinary Use
  4. ↑ 4.0 4.1 PMID 4597707 (PMID 4597707)
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