Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H18F3N3O3 |
Molecular Weight | 417.3811 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1CN(CCN1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4=C(F)C=C(F)C=C4)C(O)=O
InChI
InChIKey=QKDHBVNJCZBTMR-UHFFFAOYSA-N
InChI=1S/C21H18F3N3O3/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)
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 |
---|---|---|---|
Target ID: CHEMBL2311224 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 Date6.9664322E11 |
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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 Date6.9664322E11 |
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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 Date6.9664322E11 |
|||
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 Date6.9664322E11 |
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 |
---|---|---|
Comparative antimycobacterial activities of difloxacin, temafloxacin, enoxacin, pefloxacin, reference fluoroquinolones, and a new macrolide, clarithromycin. | 1989 Apr |
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Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp. | 1990 Sep |
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[Activity of antibiotics against pigmented and unpigmented variants of Mycobacterium avium-intracellulare]. | 1991 May |
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Use of fluoroquinolones for prophylaxis of murine Pneumocystis carinii pneumonia. | 1992 Feb |
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In-vitro evaluation of clarithromycin, temafloxacin, and ethambutol in combination against Mycobacterium avium complex. | 1993 May |
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In-vitro activity of quinolones and macrolides against mycobacteria. | 1994 Sep |
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Trovafloxacin is active against Toxoplasma gondii. | 1996 Aug |
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Structure-activity relationships of the quinolone antibacterials against mycobacteria: effect of structural changes at N-1 and C-7. | 1996 Feb 2 |
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A simple, inexpensive apparatus for performance of preparative scale solution phase multiple parallel synthesis of drug analogs. II. Biological evaluation of a retrospective library of quinolone antiinfective agents. | 1998 Jun |
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Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques. | 2000 Oct |
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Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening. | 2000 Oct |
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Antimicrobial safety and tolerability: differences and dilemmas. | 2001 Mar 15 |
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Ultrastructural characterization of murine limb buds after in vitro exposure to grepafloxacin and other fluoroquinolones. | 2002 Jan |
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[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration]. | 2002 Jun |
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Safety and tolerability of fluoroquinolones. | 2003 |
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Levofloxacin-induced autoimmune hemolytic anemia. | 2003 Jul-Aug |
|
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
|
Method for inducing experimental pneumococcal meningitis in outbred mice. | 2004 Sep 22 |
|
Antimicrobial safety: focus on fluoroquinolones. | 2005 Jul 15 |
|
Ciprofloxacin induced nightmares in an adult patient. | 2008 Oct |
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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C795
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LIVERTOX |
NBK547840
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WHO-ATC |
J01MA05
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WHO-VATC |
QJ01MA05
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DB01405
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77788
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1WZ12GTT67
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37771
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108319-06-8
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6224
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C054745
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SUB10877MIG
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DTXSID7044132
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CHEMBL277100
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2584
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100000082444
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TEMAFLOXACIN
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60021
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C87391
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m10544
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)