Hetacillin

Hetacillin

Clinical data
Trade names	Hetacin
AHFS/Drugs.com	Veterinary Use
Routes of administration	Intramammary injection
ATC code	J01CA18 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
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
CAS Number	3511-16-8 Y
PubChem CID	193260
DrugBank	DB00739 Y
ChemSpider	167708 Y
UNII	TN4JSC48CV
KEGG	D01074 N
ChEMBL	ChEMBL1201116 N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H23N3O4S
Molar mass	389.469 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](N2C(=O)C(c1ccccc1)NC2(C)C)[C@H]4SC3(C)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 Y Key:DXVUYOAEDJXBPY-XQERAMJGSA-N Y
NY (what is this?)  (verify)

WikiDoc Resources for Hetacillin
Articles
Most recent articles on Hetacillin Most cited articles on Hetacillin Review articles on Hetacillin Articles on Hetacillin in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Hetacillin Images of Hetacillin Photos of Hetacillin Podcasts & MP3s on Hetacillin Videos on Hetacillin
Evidence Based Medicine
Cochrane Collaboration on Hetacillin Bandolier on Hetacillin TRIP on Hetacillin
Clinical Trials
Ongoing Trials on Hetacillin at Clinical Trials.gov Trial results on Hetacillin Clinical Trials on Hetacillin at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Hetacillin NICE Guidance on Hetacillin NHS PRODIGY Guidance FDA on Hetacillin CDC on Hetacillin
Books
Books on Hetacillin
News
Hetacillin in the news Be alerted to news on Hetacillin News trends on Hetacillin
Commentary
Blogs on Hetacillin
Definitions
Definitions of Hetacillin
Patient Resources / Community
Patient resources on Hetacillin Discussion groups on Hetacillin Patient Handouts on Hetacillin Directions to Hospitals Treating Hetacillin Risk calculators and risk factors for Hetacillin
Healthcare Provider Resources
Symptoms of Hetacillin Causes & Risk Factors for Hetacillin Diagnostic studies for Hetacillin Treatment of Hetacillin
Continuing Medical Education (CME)
CME Programs on Hetacillin
International
Hetacillin en Espanol Hetacillin en Francais
Business
Hetacillin in the Marketplace Patents on Hetacillin
Experimental / Informatics
List of terms related to Hetacillin

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself, but quickly splits of 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 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.

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.

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