Optochin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424978166

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=522-60-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4W030VS2OG

| PubChem=71542

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 534999

| MeSHName=Optochin

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 79283

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 86455

| SMILES = CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c3ccnc4c3cc(cc4)OCC)O

| InChI = 1/C21H28N2O2/c1-3-14-13-23-10-8-15(14)11-20(23)21(24)17-7-9-22-19-6-5-16(25-4-2)12-18(17)19/h5-7,9,12,14-15,20-21,24H,3-4,8,10-11,13H2,1-2H3/t14-,15-,20-,21+/m0/s1

| InChIKey = SUWZHLCNFQWNPE-LATRNWQMBV

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C21H28N2O2/c1-3-14-13-23-10-8-15(14)11-20(23)21(24)17-7-9-22-19-6-5-16(25-4-2)12-18(17)19/h5-7,9,12,14-15,20-21,24H,3-4,8,10-11,13H2,1-2H3/t14-,15-,20-,21+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = SUWZHLCNFQWNPE-LATRNWQMSA-N

| Formula=C₂₁H₂₈N₂O₂

| MolarMass=340.46 g/mol

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'''Optochin''' (or '''ethylhydrocupreine hydrochloride''') is a derivative of [[quinine]] introduced in 1911 by Morgenroth and Levy with the intention to treat pneumococci infection.<ref>{{cite journal | pmc = 2125335 | pmid=19867915 | volume=22 | year=1915 | journal=J. Exp. Med. | pages=269–85 | author=Moore HF | title=The Action of Ethylhydrocuprein (Optochin) on Type Strains of Pneumococci in Vitro and in Vivo, and on Some Other Microorganisms in Vitro | issue=3 | doi=10.1084/jem.22.3.269}}</ref> 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 [[Antibiotic sensitivity|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.<ref>{{cite web | url=http://chestofbooks.com/health/materia-medica-drugs/Pharmacology-Therapeutics-Prescription-Writing/Ethylhydrocupreine.html | title=Ethylhydrocupreine }}</ref>

For decades, ''Streptococcus pneumoniae'' has been considered susceptible to optochin; but some strains have been found to be resistant to optochin in laboratory testing. This is notable because the emergence of optochin-resistant strains would invalidate the distinguishing test described above.<ref>{{citation |title=Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications |journal=Journal of Infectious Diseases |volume=184 |issue=5 |pages=582–590 |vauthors=Pikis A, Campos JM, Rodriguez WJ, Keith JM |year=2001 |pmid=11474432 |doi=10.1086/322803 |jstor=30137322|doi-access=free }}</ref>

== See also ==

* [[Quinine]]

{{Clinical microbiology techniques}}

[[Category:Secondary alcohols]]

[[Category:Ethoxy compounds]]