Ethylhydrocupreine

Names

[ CAS No. ]:
522-60-1

[ Name ]:
Ethylhydrocupreine

[Synonym ]:
Optochine
hydrocupreineethylether
ETHYLHYDROCUPREINE
Hydrocupureine ethyl ether
Numoquine
Ethylhydrocuprein
numoquin
optoquine

Biological Activity

[Description]:

Ethylhydrocupreine (Optochin) is a quinine derivate with antimicrobial activity against S. pneumoniae. Ethylhydrocupreine also possesses antimalarial activity against Plasmodium falciparum, with an IC50 of 25.75 nM. Ethylhydrocupreine is a Gallus gallus taste 2 receptors (ggTas2r1, ggTas2r2 and ggTas2r7) agonist[1][2][3][4].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

S. pneumoniae[1] IC50: 25.75 nM (Plasmodium falciparum)[3] ggTas2r1, ggTas2r2 and ggTas2r7[4]

[In Vitro]

The mutation rate to Ethylhydrocupreine (Optochin) resistance is estimated using fluctuation analysis in three capsulated S. pneumoniae strains (S. pneumoniae D39 NCTC 7466, S. pneumoniae R6 ATCC BAA-255 and S. pneumoniae ATCC 49619). The exposure to subinhibitory concentrations of penicillin increased the mutation rate (expressed as mutation per cell division) to Ethylhydrocupreine (Optochin) resistance between 2.1- and 3.1-fold for all three strains studied[2].

[In Vivo]

The injection of 1 cc. of a 24 hour dextrose blood broth culture of virulent Type I pneumococci into the right pleural cavity of guinea pigs produces acute suppurative pleuritis on both sides associated with suppurative pericarditis. The injection of 1 cc. of 1:500 solutions of Ethylhydrocupreine hydrochloride into each pleural cavity of guinea pigs at varying intervals up to 24 hours after pleural infection has usually shown a marked curative influence. Similar results are observed with dogs[1].

[References]

[1]. J A Kolmer, et al. CHEMOTHERAPEUTIC STUDIES WITH ETHYLHYDROCUPREINE HYDROCHLORIDE IN EXPERIMENTAL PNEUMOCOCCUS PLEURITIS. J Exp Med. 1921 May 31;33(6):693-711.

[2]. Paulo R Cortes, et al. Subinhibitory Concentrations of Penicillin Increase the Mutation Rate to Optochin Resistance in Streptococcus Pneumoniae. J Antimicrob Chemother. 2008 Nov;62(5):973-7.

[3]. Nassira Mahmoudi, et al. Identification of New Antimalarial Drugs by Linear Discriminant Analysis and Topological Virtual Screening. J Antimicrob Chemother. 2006 Mar;57(3):489-97.

[4]. Antonella Di Pizio, et al. Molecular Features Underlying Selectivity in Chicken Bitter Taste Receptors. Front Mol Biosci. 2018 Jan 31;5:6.

Chemical & Physical Properties

[ Density]:
1.18g/cm3

[ Boiling Point ]:
508.7ºC at 760mmHg

[ Melting Point ]:
123-128° when solvent-free

[ Molecular Formula ]:
C₂₁H₂₈N₂O₂

[ Molecular Weight ]:
340.45900

[ Flash Point ]:
261.5ºC

[ Exact Mass ]:
340.21500

[ PSA ]:
45.59000

[ LogP ]:
3.72520

[ Index of Refraction ]:
1.618

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MW5950000

CHEMICAL NAME :: Hydrocupreine, O(sup 6')-ethyl-

CAS REGISTRY NUMBER :: 522-60-1

BEILSTEIN REFERENCE NO. :: 0092227

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H28-N2-O2

MOLECULAR WEIGHT :: 340.51

WISWESSER LINE NOTATION :: T66 BNJ HO2 EYQ- DT66 A B CNTJ G2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: OPHTAD Ophtalmologica. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.96- 1978- Volume(issue)/page/year: 143,154,1962 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
MW5950000

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Identifying mutator phenotypes among fluoroquinolone-resistant strains of Streptococcus pneumoniae using fluctuation analysis.

Antimicrob. Agents Chemother. 51 , 3225-9, (2007)

The occurrence of mutator phenotypes among laboratory-generated and clinical levofloxacin-resistant strains of Streptococcus pneumoniae was determined using fluctuation analysis. The in vitro selectio...

Genotypic identification of presumptive Streptococcus pneumoniae by PCR using four genes highly specific for S. pneumoniae.

J. Med. Microbiol. 55(Pt 6) , 709-14, (2006)

It was previously reported that two oligonucleotide primer sets (spn9802 and spn9828) for discriminating Streptococcus pneumoniae from pneumococcus-like oral streptococcal isolates using PCR had been ...

Possible overestimation of penicillin resistant Streptococcus pneumoniae colonization rates due to misidentification of oropharyngeal streptococci.

Diagn. Microbiol. Infect. Dis. 42(4) , 263-8, (2002)

Standard identification of Streptococcus pneumoniae by optochin and bile solubility testing can lead to ambiguous results for certain isolates. Newer bacteriologic identification techniques (e.g., DNA...

Related Compounds

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