TEMAFLOXACIN

First approved in 1992

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

Structure Search

SMILES

CC1CN(CCN1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4=CC=C(F)C=C4F)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)

HIDE SMILES / InChI

Molecular Formula	C21H18F3N3O3
Molecular Weight	417.3811
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://adisinsight.springer.com/drugs/800000542 \| https://www.ncbi.nlm.nih.gov/pubmed/1662892	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 52 Sources: http://edudrugs.com/O/Omniflox/more.html	Curative	Withdrawn	Omniflox Approved Use Omniflox 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 Date 1992
Bacterial prostatitis 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8023771 http://edudrugs.com/O/Omniflox/more.html	Curative	Withdrawn	Omniflox Approved Use Omniflox 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 Date 1992
Urinary tract infections 207 Sources: http://edudrugs.com/O/Omniflox/more.html https://www.ncbi.nlm.nih.gov/pubmed/1310715	Curative	Withdrawn	Omniflox Approved Use Omniflox 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 Date 1992
Skin infections 59 Sources: http://edudrugs.com/O/Omniflox/more.html https://www.ncbi.nlm.nih.gov/pubmed/1662880	Curative	Withdrawn	Omniflox Approved Use Omniflox 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 Date 1992

C_max

Value	Dose	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	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

T_1/2

Value	Dose	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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/1664833/	unhealthy, 18-91 years Health Status: unhealthy Age Group: 18-91 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1664833/	Sources: https://pubmed.ncbi.nlm.nih.gov/1664833/
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: https://pubmed.ncbi.nlm.nih.gov/1318680/	healthy, 19 - 28 years Health Status: healthy Age Group: 19 - 28 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1318680/	Sources: https://pubmed.ncbi.nlm.nih.gov/1318680/
400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8806150/	unhealthy, 4 years Health Status: unhealthy Age Group: 4 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8806150/	Disc. AE: Psychomotor hyperactivity... AEs leading to discontinuation/dose reduction: Psychomotor hyperactivity (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8806150/

AEs

AE	Significance	Dose	Population
Psychomotor hyperactivity	1 patient Disc. AE	400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8806150/	unhealthy, 4 years Health Status: unhealthy Age Group: 4 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8806150/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/1510417/	minor [Inhibition 500 uM]

Sourcing

Vendor/Aggregator	ID	URL
Aaron Chemicals	AR0095TI	http://www.aaronchem.com/105784-61-0
abcr GmbH	AB436597	http://www.abcr.de/shop/en/AB436597
Achemtek	0101-001917	http://www.achemtek.com/105784-61-0
AEchem Scientific Corp., USA	AE1-014048	http://www.aechemsc.com/info_products/AE1-014048.php
Ambeed	A257138	https://www.ambeed.com/products/105784-61-0.html
Ambinter	Amb22269237	http://www.ambinter.com/reference/22269237
Ark Pharm	AK144522	http://www.arkpharminc.com/products/105784-61-0.html
Ark Pharma Scientific Limited	H-009255	http://www.arkpharmtech.com/product/14310.html
Aurora Fine Chemicals LLC	A24.102.845	http://online.aurorafinechemicals.com/info?ID=A24.102.845
BioChemPartner	BCP26073	http://www.biochempartner.com/105784-61-0-BCP26073
BioSynth	J-001480	https://www.biosynth.com/en/products/all-products/products/J-001480.html
BLD Pharm	BD152542	http://www.bldpharm.com/products/105784-61-0.html
BOC Sciences	105784-61-0	https://www.bocsci.com/temafloxacin-hydrochloride-cas-105784-61-0-item-53737.html
Chemspace	CSSB00016991847	https://chem-space.com/CSSB00016991847
Combi-Blocks	QP-6145	http://www.combi-blocks.com/cgi-bin/find.cgi?QP-6145
Debye Scientific	DA-15901	http://www.debyesci.com/cas_105784-61-0.html
eNovation Chemicals	D550134	https://www.enovationchem.com/ProductDetails.asp?ProductID=D550134
eNovation Chemicals	Y0985196	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0985196
Finetech	FT-0760604	http://www.finetechnology-ind.com/prod/detail/pub/105784-61-0.html
Glentham Life Sciences	GA3765	http://www.glentham.com/products/product/GA3765/
Lab Network	LN00361417	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00361417
Molcore	MC504559	https://www.molcore.com/product/105784-61-0
MolPort	MolPort-028-962-342	https://www.molport.com/shop/molecule-link/MolPort-028-962-342
MuseChem	R027004	https://www.musechem.com/product/R027004.html
Smolecule	S575379	https://www.smolecule.com/products/s575379

PubMed

Title	Date	PubMed
Ciprofloxacin induced nightmares in an adult patient.	2008-10	19823620
An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in?	2008	18495060
Evaluation of high-dose daptomycin for therapy of experimental Staphylococcus aureus foreign body infection.	2006-04-11	16608512
Antimicrobial safety: focus on fluoroquinolones.	2005-07-15	15942881
Method for inducing experimental pneumococcal meningitis in outbred mice.	2004-09-22	15385055
Effects of fluoroquinolones on insulin secretion and beta-cell ATP-sensitive K+ channels.	2004-08-16	15321742
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004-04	15047530
Quinolone safety and efficacy more important than potency.	2004-01	15112647
Levofloxacin-induced autoimmune hemolytic anemia.	2003-07-05	12841809
Adverse drug reactions: implications for the development of fluoroquinolones.	2003-05	12702700
Safety and tolerability of fluoroquinolones.	2003	14992418
[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].	2002-06	12199111
Oral contraceptive efficacy and antibiotic interaction: a myth debunked.	2002-06	12063491
Ultrastructural characterization of murine limb buds after in vitro exposure to grepafloxacin and other fluoroquinolones.	2002-01	11876506
Antimicrobial safety and tolerability: differences and dilemmas.	2001-03-15	11249832
History of quinolones and their side effects.	2001	11549783
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000-10	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000-10	10991858
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.	1998-06	10500768
Trovafloxacin is active against Toxoplasma gondii.	1996-08	8843293
Structure-activity relationships of the quinolone antibacterials against mycobacteria: effect of structural changes at N-1 and C-7.	1996-02-02	8576916
In-vitro activity of quinolones and macrolides against mycobacteria.	1994-09	7829409
In-vitro evaluation of clarithromycin, temafloxacin, and ethambutol in combination against Mycobacterium avium complex.	1993-05	8392998
Activity of clarithromycin against Mycobacterium avium complex infection in beige mice.	1992-11	1336945
Use of fluoroquinolones for prophylaxis of murine Pneumocystis carinii pneumonia.	1992-02	1605613
Activities of sparfloxacin, azithromycin, temafloxacin, and rifapentine compared with that of clarithromycin against multiplication of Mycobacterium avium complex within human macrophages.	1991-07	1656860
[Activity of antibiotics against pigmented and unpigmented variants of Mycobacterium avium-intracellulare].	1991-05	1652731
Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp.	1990-09	2228828
Oral temafloxacin versus vancomycin for therapy of experimental endocarditis caused by methicillin-resistant Staphylococcus aureus.	1990-06	2393273
In vitro and in vivo activities of clarithromycin against Mycobacterium avium.	1989-09	2530933
Comparative antimycobacterial activities of difloxacin, temafloxacin, enoxacin, pefloxacin, reference fluoroquinolones, and a new macrolide, clarithromycin.	1989-04	2524998

Patents

Sample Use Guides

In Vivo Use Guide

400 or 600 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:36 GMT 2025`
Record UNII	1WZ12GTT67
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMAFLOXACIN

Official Name

English

3-QUINOLINECARBOXYLIC ACID, 1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-7-(3-METHYL-1-PIPERAZINYL)-4-OXO-(±)-

Preferred Name

English

Temafloxacin [WHO-DD]

Common Name

English

TEMAFLOXACIN [MART.]

Common Name

English

TEMAFLOXACIN [MI]

Common Name

English

TEMAFLOXACIN [VANDF]

Common Name

English

temafloxacin [INN]

Common Name

English

(±)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-7-(3-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795