Propicillin
Basic information
- CAS
551-27-9- Standard SMILES
CCC(Oc1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O- InChIKey
HOCWPKXKMNXINF-XQERAMJGSA-N- Molecular formula
- C18H22N2O5S
- Average molar mass
- 378.4 g/mol
- Monoisotopic mass
- 378.12494298
Overview
Propicillin is a penicillin. It is a conjugate acid of a propicillin(1-).
Names & identifiers
- Preferred name
- Propicillin
- IUPAC
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxybutanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- PROPICILLIN
- Molecular formula
- C18H22N2O5S
- Molecular weight
- 378.44
Names & synonyms
Propicillinpropicilline551-27-9PropicilinaPropicillinum(1-Phenoxypropyl)penicillinDTXSID3046291phenoxypropylpenicillinCHEBI:524298X1R260V33DTXCID10262916beta-(2-phenoxybutanamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Show more names
PROPICILLIN USP/EP/BPα-phenoxypropylpenicillin3,3-dimethyl-7-oxo-6-[2-(phenoxy)butanoylamino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid7-keto-3,3-dimethyl-6-[2-(phenoxy)butanoylamino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(2S,5β)-3,3-Dimethyl-7-oxo-6α-[(1-oxo-2-phenoxybutyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(1-oxo-2-phenoxybutyl)amino]-, (2S,5R,6R)-
PropibayRefChem:176404ALPHA-PHENOXYPROPYLPENICILLIN208-995-5(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxybutanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.alpha.-phenoxypropylpenicillin(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxybutanamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxybutanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 590
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Human DrugsPharmaceuticals
Physicochemical properties
- pka
- 2.72 · pKa 2.72±0.04(H2O t=25 c=0.01) (Uncertain)
- FDA UNII
- 8 X1R260V33 · 8X1R260V33
- ATC code
- 1 CE03 · J01CE03
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationPharmaceuticals
Applications
DescriptionPropicillin was synthesized by a collaboration of Beecham Research Laboratories with Bristol-Myers Laboratories in 1961 starting with 6-aminopenicillanic acid. It is stable against gastric acid and shows three- to fourfold higher serum concentrations than phenoxymethyl-penicillin when administered orally. Its antibacterial spectrum and activity are almost the same as those of phenoxymethylpenicillin. Propicillin has been used for therapy of infections caused by Streptococcus, Staphylococcus, and Neisseria.
UsesPropicillin, is a derivative of penicillin. Properties are similar to benzylpenicillin particularly used in streptococcal infections, not resistant to penicillinase.
Additional notes
DefinitionChEBI: Propicillin is a penicillin. It is a conjugate acid of a propicillin(1-).
Related reactions
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Compound notes
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