Structure via PubChem · Public domain (PubChem)
hetacillin
Sign in to saveAlso known as Natacillin, Versapen, Hetacin, BRL-804, BL-P-804, Phenazacillin, (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, 6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid
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. __TOC__
Chemical data
- Formula
- C19H23N3O4S
- Molecular weight
- 389.5 g/mol
- 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
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)O)C
- InChIKey
- DXVUYOAEDJXBPY-NFFDBFGFSA-N
- XLogP
- -0.6
- Polar surface area
- 115 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- oral
- Indications
- bacterial disease
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 389.140927
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₉H₂₃N₃O₄S
- canonical SMILES
- CC1(C(N2C(S1)C(C2=O)N3C(=O)C(NC3(C)C)C4=CC=CC=C4)C(=O)O)C
- isomeric SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)O)C
- World Health Organisation international non-proprietary name
- hetacillin
- defined daily dose
- 2.0
- subject has role
- bactericide
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Administration
- Chemistry
- References
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. __TOC__
==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.
Excerpted from Wikipedia’s “hetacillin” article, available under the CC BY-SA 4.0 licence.
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