Structure via PubChem · Public domain (PubChem)
Optochin
Sign in to saveOptochin (or ethylhydrocupreine hydrochloride) is a derivative of quinine introduced in 1911 by Morgenroth and Levy with the intention to treat pneumococci infection. In very high dilutions, it inhibits the growth of representatives of all four groups of pneumococci in vitro. That is the main reason it is now used in bacteriology for the differentiation of Streptococcus pneumoniae, which is optochin-sensitive, from the other, resistant alpha-hemolytic streptococci, sometimes called the viridans streptococci because of the green colouration on blood agar around colonies.
Chemical data
- Formula
- C21H28N2O2
- Molecular weight
- 340.5 g/mol
- IUPAC name
- (R)-(6-ethoxyquinolin-4-yl)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol
- SMILES
- CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OCC)O
- InChIKey
- SUWZHLCNFQWNPE-LATRNWQMSA-N
- XLogP
- 3.5
- Polar surface area
- 45.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 340.21507813599993
Show 3 more facts
- chemical formula
- C₂₁H₂₈N₂O₂
- canonical SMILES
- CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OCC)O
- isomeric SMILES
- CCOc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)c2c1
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Resistance
- See also
- References
Optochin (or ethylhydrocupreine hydrochloride) is a derivative of quinine introduced in 1911 by Morgenroth and Levy with the intention to treat pneumococci infection. In very high dilutions, it inhibits the growth of representatives of all four groups of pneumococci in vitro. That is the main reason it is now used in bacteriology for the differentiation of Streptococcus pneumoniae, which is optochin-sensitive, from the other, resistant alpha-hemolytic streptococci, sometimes called the viridans streptococci because of the green colouration on blood agar around colonies.
The growth of bacteria that are optochin-sensitive will show a zone of inhibition around an optochin disc, while the growth of bacteria that are resistant to optochin will not be affected. In vitro, a minimum inhibitory concentration (MIC) of 1:10,000,000 will inhibit the growth of pneumococci, and 1:500,000 is bactericidal.
Excerpted from Wikipedia’s “Optochin” article, available under the CC BY-SA 4.0 licence.