CAS 3413-58-9|Ethylhydrocupreine hydrochloride
| Common Name | Ethylhydrocupreine hydrochloride | ||
|---|---|---|---|
| CAS Number | 3413-58-9 | Molecular Weight | 376.92000 |
| Density | / | Boiling Point | 508.7ºC at 760 mmHg |
| Molecular Formula | C21H29ClN2O2 | Melting Point | 121-123ºC |
| MSDS | USA | Flash Point | 261.5ºC |
Names
| Name | ethylhydrocupreine hydrochloride |
|---|---|
| Synonym | More Synonyms |
Ethylhydrocupreine hydrochloride BiologicalActivity
| Description | Ethylhydrocupreine hydrochloride (Optochin hydrochloride) is a quinine derivate with antimicrobial activity against S. pneumoniae. Ethylhydrocupreine hydrochloride also possesses antimalarial activity against Plasmodium falciparum, with an IC50 of 25.75 nM. Ethylhydrocupreine hydrochloride is a Gallus gallus taste 2 receptors (ggTas2r1, ggTas2r2 and ggTas2r7) agonist[1][2][3][4]. |
|---|---|
| Related Catalog | Research Areas >>InfectionSignaling 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
| Boiling Point | 508.7ºC at 760 mmHg |
|---|---|
| Melting Point | 121-123ºC |
| Molecular Formula | C21H29ClN2O2 |
| Molecular Weight | 376.92000 |
| Flash Point | 261.5ºC |
| Exact Mass | 376.19200 |
| PSA | 45.59000 |
| LogP | 4.52720 |
| InChIKey | QNRATNLHPGXHMA-XZHTYLCXSA-N |
| SMILES | CCOc1ccc2nccc(C(O)C3CC4CCN3CC4CC)c2c1.Cl |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 31 mg/kg/3D
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - visual field changes Vascular - regional or general arteriolar constriction
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 500 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Amphibian - frog
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5575 No. of Facilities: 90 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 557 (estimated) No. of Female Employees: 502 (estimated)
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xi |
| Risk Phrases | 36/37/38 |
| Safety Phrases | S22;S24/25 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | MW6300000 |
| HS Code | 29392900 |
Articles25
More 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... |
Synonyms
| numoquinhydrochloride |
| OPTICHIN HYDROCHLORIDE |
| Aethyl-hydrocuprein-hydrochlorid |
| MFCD00135594 |
| EINECS 222-302-3 |
| neumolisina |
| o-ethyl-hydrocupreinhydrochloride |
| hydrocupreine,ethylester,hydrochloride |
| OptochineHCl |
| optoquinhydrochloride |
| optochinhydrochloride |
