هتاسیلین

Also 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 Å²
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

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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)

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