Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H18F3N3O3.ClH |
Molecular Weight | 453.842 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1CN(CCN1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4=C(F)C=C(F)C=C4)C(O)=O
InChI
InChIKey=DDVJEYDLTXRYAJ-UHFFFAOYSA-N
InChI=1S/C21H18F3N3O3.ClH/c1-11-9-26(5-4-25-11)19-8-18-13(7-16(19)24)20(28)14(21(29)30)10-27(18)17-3-2-12(22)6-15(17)23;/h2-3,6-8,10-11,25H,4-5,9H2,1H3,(H,29,30);1H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/1662889Curator's Comment: description was created based on several sources, including:
https://www.wikigenes.org/e/chem/e/60021.html
http://www.wikidoc.org/index.php/Temafloxacin
https://www.ncbi.nlm.nih.gov/pubmed/8086558
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1662889
Curator's Comment: description was created based on several sources, including:
https://www.wikigenes.org/e/chem/e/60021.html
http://www.wikidoc.org/index.php/Temafloxacin
https://www.ncbi.nlm.nih.gov/pubmed/8086558
Temafloxacin (marketed by Abbott Laboratories as Omniflox) is almost completely absorbed from the gastrointestinal tract, with an absolute bioavailability of approximately 93% and is not greatly affected by food. The time to reach peak concentrations ranges between 2 and 3 hours. In addition to the broad spectrum of activity all fluoroquinolones have against gram-negative pathogens, temafloxacin has improved antimicrobial activity against gram-positive aerobic cocci, intracellular microorganisms, and anaerobes. The bactericidal action of temafloxacin results from interference with the activity of the bacterial enzymes DNA gyrase. Omniflox was approved to treat lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections in the U.S. by the Food and Drug Administration in January 1992. Severe adverse reactions, including allergic reactions and hemolytic anemia, developed in about fifty patients during the first four months of its use, leading to three patient deaths. Abbott withdrew the drug from sale in June 1992.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311224 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Omniflox Approved UseOmniflox has been approved for the treatment of lower respiratory tract infections (pneumonia and bronchitis), genitourinary infections (prostatitis and urinary tract infections) and skin infections. Launch Date1992 |
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Curative | Omniflox Approved UseOmniflox has been approved for the treatment of lower respiratory tract infections (pneumonia and bronchitis), genitourinary infections (prostatitis and urinary tract infections) and skin infections. Launch Date1992 |
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Curative | Omniflox Approved UseOmniflox has been approved for the treatment of lower respiratory tract infections (pneumonia and bronchitis), genitourinary infections (prostatitis and urinary tract infections) and skin infections. Launch Date1992 |
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Curative | Omniflox Approved UseOmniflox has been approved for the treatment of lower respiratory tract infections (pneumonia and bronchitis), genitourinary infections (prostatitis and urinary tract infections) and skin infections. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.33 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.7 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.61 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.43 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.87 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
92.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15.02 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
29.69 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
49.54 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
11.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2039194 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1319868 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TEMAFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: |
unhealthy, 18-91 years n = 49 Health Status: unhealthy Condition: bacterial pneumonia Age Group: 18-91 years Sex: M Population Size: 49 Sources: |
|
800 mg 2 times / day steady, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: steady Dose: 800 mg, 2 times / day Sources: |
healthy, 19 - 28 years n = 6 Health Status: healthy Age Group: 19 - 28 years Sex: M Population Size: 6 Sources: |
|
400 mg single, oral Overdose |
unhealthy, 4 years n = 1 Health Status: unhealthy Condition: urinary tract infaction Age Group: 4 years Sex: F Population Size: 1 Sources: |
Disc. AE: Psychomotor hyperactivity... AEs leading to discontinuation/dose reduction: Psychomotor hyperactivity (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Psychomotor hyperactivity | 1 patient Disc. AE |
400 mg single, oral Overdose |
unhealthy, 4 years n = 1 Health Status: unhealthy Condition: urinary tract infaction Age Group: 4 years Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
In vitro and in vivo activities of clarithromycin against Mycobacterium avium. | 1989 Sep |
|
In-vitro evaluation of clarithromycin, temafloxacin, and ethambutol in combination against Mycobacterium avium complex. | 1993 May |
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History of quinolones and their side effects. | 2001 |
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Antimicrobial safety and tolerability: differences and dilemmas. | 2001 Mar 15 |
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Oral contraceptive efficacy and antibiotic interaction: a myth debunked. | 2002 Jun |
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Levofloxacin-induced autoimmune hemolytic anemia. | 2003 Jul-Aug |
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Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
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Quinolone safety and efficacy more important than potency. | 2004 Jan |
|
An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in? | 2008 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8086558
400 or 600 mg twice daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1881670
Temafloxacin was highly active against Haemophilus mode MIC: less than or equal to 0.008), Gonococci (mode MIC: 0.008-0.032), Meningococci (mode MIC: 0.08) and B. catarrhalis (mode MIC: 0.016).
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NCI_THESAURUS |
C795
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Z-28
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DTXSID70909733
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295217
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C72858
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DBSALT000794
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CHEMBL277100
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OC5IGJ7J6I
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C054745
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100000084772
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SUB04715MIG
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m10544
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60020
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105784-61-0
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ACTIVE MOIETY
SUBSTANCE RECORD