ALATROFLOXACIN MESYLATE

US Previously Marketed

First approved in 1997

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H25F3N6O5.CH4O3S
Molecular Weight	654.615
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.[H][C@@]12CN(C[C@]1([H])[C@H]2NC(=O)[C@H](C)NC(=O)[C@H](C)N)C3=NC4=C(C=C3F)C(=O)C(=CN4C5=CC=C(F)C=C5F)C(O)=O

InChI

InChIKey=CYETUYYEVKNSHZ-LGOOQLFJSA-N

InChI=1S/C26H25F3N6O5.CH4O3S/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28;1-5(2,3)4/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40);1H3,(H,2,3,4)/t10-,11-,14-,15+,20+;/m0./s1

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00685https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=da9b26bb-d2d7-4113-a0f9-c6c2280f4875#Clinical_Pharmacology
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/dosage/trovan.html

Alatrofloxacin is a fluoroquinolone antibiotic developed as a mesylate salt and was sold under brand name Trovan, but was withdrawn from the U.S. market in 2001. Trovan was indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. After intravenous administration, alatrofloxacin is rapidly converted to trovafloxacin, which is responsible for therapeutic effect. Plasma concentrations of alatrofloxacin are below quantifiable levels within 5 to 10 minutes of completion of a 1 hour infusion.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Plasmodium falciparum 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12878530	Inhibitor 8297
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11892894	Inhibitor 8297
Moraxella catarrhalis 10 Target ID: CHEMBL614429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11892894	Inhibitor 8297
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20407243	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11418510	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Nosocomial pneumonia 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a.pdf	Curative	Withdrawn	TROVAN PRESERVATIVE FREE Approved Use Trovan is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. NOTE: Trovan has not been studied in the treatment of osteomyelitis. Launch Date 1997
Pneumonia 90 Sources: https://www.drugs.com/pro/trovan.html	Curative	Approved 8429	TROVAN Approved Use Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. Launch Date 1997
Intra-abdominal infections 49 Sources: https://www.drugs.com/dosage/trovan.html	Curative	Approved 8429	TROVAN Approved Use Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. Launch Date 1997
Complicated skin and skin structure infections 11 Sources: https://www.drugs.com/dosage/trovan.html	Curative	Approved 8429	TROVAN Approved Use Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. Launch Date 1997
Pneumonia 90 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a.pdf	Curative	Withdrawn	TROVAN PRESERVATIVE FREE Approved Use Trovan is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. NOTE: Trovan has not been studied in the treatment of osteomyelitis. Launch Date 1997
Complicated intra-abdominal infections 20 Sources: https://www.drugs.com/pro/trovan.html#Indications_And_Usage	Curative	Withdrawn	TROVAN PRESERVATIVE FREE Approved Use Trovan is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. NOTE: Trovan has not been studied in the treatment of osteomyelitis. Launch Date 1997
Gynecologic infections 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a.pdf	Curative	Withdrawn	TROVAN PRESERVATIVE FREE Approved Use Trovan is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. NOTE: Trovan has not been studied in the treatment of osteomyelitis. Launch Date 1997
Skin infections 59 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a.pdf	Curative	Withdrawn	TROVAN PRESERVATIVE FREE Approved Use Trovan is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below. Nosocomial pneumonia caused by Escherichia coli, Pseudomonas aeruginosa, Haemophilus influenzae, or Staphylococcus aureus. As with other antimicrobials, where Pseudomonas aeruginosa is a documented or presumptive pathogen, combination therapy with either an aminoglycoside or aztreonam may be clinically indicated. Community acquired pneumonia caused by Streptococcus pneumoniae, Haemophilus influenzae, Klebsiella pneumoniae, Staphylococcus aureus, Mycoplasma pneumoniae, Moraxella catarrhalis, Legionella pneumophila, or Chlamydia pneumoniae. Complicated intra-abdominal infections, including post-surgical infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Peptostreptococcus species, or Prevotella species. Gynecologic and pelvic infections including endomyometritis, parametritis, septic abortion and post-partum infections caused by Escherichia coli, Bacteroides fragilis, viridans group streptococci, Enterococcus faecalis, Streptococcus agalactiae, Peptostreptococcus species, Prevotella species, or Gardnerella vaginalis. Complicated skin and skin structure infections, including diabetic foot infections, caused by Staphylococcus aureus, Streptococcus agalactiae, Pseudomonas aeruginosa, Enterococcus faecalis, Escherichia coli, or Proteus mirabilis. NOTE: Trovan has not been studied in the treatment of osteomyelitis. Launch Date 1997

C_max

Value	Dose	Analyte	Population
1.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.3 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9935250	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
11.8 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
26.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
34.6 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.4 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
32.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9935250	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
12.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9935250	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Analyte	Population
22% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
25.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
28.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8737145	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TROVAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/	healthy, 27 years n = 4 Health Status: healthy Age Group: 27 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (4 patients) Vomiting (1 patient) Lightheadedness (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	unhealthy, adult n = 881 Health Status: unhealthy Condition: chronic bronchitis or pneumonia Age Group: adult Sex: M+F Population Size: 881 Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	Disc. AE: Gastrointestinal disorder NOS, CNS disorder (NOS)... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder NOS (11 patient) CNS disorder (NOS) (4 patients) Dizziness (2 patients) Dermatitis (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/

AEs

AE	Significance	Dose	Population
Vomiting	1 patient	1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/	healthy, 27 years n = 4 Health Status: healthy Age Group: 27 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/
Lightheadedness	4 patients	1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/	healthy, 27 years n = 4 Health Status: healthy Age Group: 27 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/
Nausea	4 patients	1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/	healthy, 27 years n = 4 Health Status: healthy Age Group: 27 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/8522468/
Gastrointestinal disorder NOS	11 patient Disc. AE	200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	unhealthy, adult n = 881 Health Status: unhealthy Condition: chronic bronchitis or pneumonia Age Group: adult Sex: M+F Population Size: 881 Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/
Dermatitis	2 patients Disc. AE	200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	unhealthy, adult n = 881 Health Status: unhealthy Condition: chronic bronchitis or pneumonia Age Group: adult Sex: M+F Population Size: 881 Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/
Dizziness	2 patients Disc. AE	200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	unhealthy, adult n = 881 Health Status: unhealthy Condition: chronic bronchitis or pneumonia Age Group: adult Sex: M+F Population Size: 881 Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/
CNS disorder (NOS)	4 patients Disc. AE	200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/	unhealthy, adult n = 881 Health Status: unhealthy Condition: chronic bronchitis or pneumonia Age Group: adult Sex: M+F Population Size: 881 Sources: https://pubmed.ncbi.nlm.nih.gov/9758292/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461	UGT 192 sulfotransferases 38

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23401306/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a_clinpharmr.pdf#page=4 Page: 4.0	yes
sulfotransferases 38	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a_clinpharmr.pdf#page=4 Page: 4.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MB-18104	http://www.ahhchemical.com/product/MB-18104.html
AK Scientific, Inc. (AKSCI)	X2115	http://www.aksci.com/item_detail.php?cat=X2115
Alfa Chemistry	146961-76-4	https://www.alfa-chemistry.com/alatrofloxacin-cas-146961-76-4-item-290329.htm
BOC Sciences	146961-76-4	https://www.bocsci.com/l-alaninamide-l-alanyl-n-1a-5a-6a-3-6-carboxy-8-2-4-difluorophenyl-3-fluoro-5-8-dihydro-5-oxo-1-8-naphthyridin-2-yl-3-azabicyclo-3-1-0-hex-6-yl-cas-146961-76-4-item-166826.html
BioSynth	J-008289	https://www.biosynth.com/en/products/all-products/products/J-008289.html
ChEBI	CHEBI:9763	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9763
ChemMol	99045884	http://www.chemmol.com/chemmol/99045884.html
Lab Network	LN01284338	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01284338
MolPort	MolPort-018-615-902	https://www.molport.com/shop/molecule-link/MolPort-018-615-902
MuseChem	M093915	https://www.musechem.com/product/M093915.html
Smolecule	S517830	http://www.smolecule.com/products/s517830
THE BioTek	bt-259048	https://www.thebiotek.com/product/inhibitors/bt-259048
ZINC	ZINC000100030989	http://zinc15.docking.org/substances/ZINC000100030989
eNovation Chemicals	D674817	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674817

PubMed

Title	Date	PubMed
Latest industry information on the safety profile of levofloxacin in Japan.	2001	11549788
Comparison of side effects of levofloxacin versus other fluoroquinolones.	2001	11549784
History of quinolones and their side effects.	2001	11549783
Telithromycin.	2001	11398913
In vitro activity of fluoroquinolones (gatifloxacin, levofloxacin and trovafloxacin) and seven other antibiotics against Streptococcus pneumoniae.	2001 Apr	11493408
Trovafloxacin hepatotoxicity.	2001 Apr	11330435
Trovofloxacin for the treatment of chronic granuloma inguinale.	2001 Apr	11287695
Comparative anti-staphylococcal effects of gemifloxacin and trovafloxacin in an in vitro dynamic model in terms of AUC/MIC and dose relationships.	2001 Aug	11576789
Determining the frequency of resistance of Streptococcus pneumoniae to ciprofloxacin, levofloxacin, trovafloxacin, grepafloxacin, and gemifloxacin.	2001 Dec	11837640
pH-metric solubility. 3. Dissolution titration template method for solubility determination.	2001 Dec	11684402
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001 Dec 26	11754677
Lack of interaction between levofloxacin and oxycodone: pharmacokinetics and drug disposition.	2001 Feb	11210403
Susceptibility of the Bacteroides fragilis group to newer quinolones and other standard anti-anaerobic agents.	2001 Jul	11418523
Antimicrobial susceptibility patterns of enterococci in intensive care units in Sweden evaluated by different MIC breakpoint systems.	2001 Jul	11418512
Activity of non-fluorinated quinolones (NFQs) against quinolone-resistant Escherichia coli and Streptococcus pneumoniae.	2001 Jul	11418510
Use of broad spectrum antibiotics in six non-university Swiss hospitals.	2001 Jul 28	11582634
[Are the antimicrobials used in community-acquired respiratory infection useful for preventing transmission of meningococcal disease? In vitro study].	2001 Jun	11704772
Efficacy of gemifloxacin in acute exacerbations of chronic bronchitis: a randomised, double-blind comparison with trovafloxacin.	2001 Jun	11450888
Determination of trovafloxacin in human serum by time resolved terbium-sensitised luminescence.	2001 Jun	11384852
Effects of fluoroquinolones on the locomotor activity in rats.	2001 Mar	11357519
Comparative in-vitro activity of trovafloxacin and other related drugs against isolates of streptococcus oralis.	2001 Mar	11307110
Antimicrobial safety and tolerability: differences and dilemmas.	2001 Mar 15	11249832
Penicillin-resistant Streptococcus pneumoniae endocarditis: a case report and review.	2001 Mar 15	11247720
Comparative in vitro activity of the new quinolone gemifloxacin (SB-265805) with other fluoroquinolones against respiratory tract pathogens.	2001 May	11328784
Comparative study of treatment with penicillin, ceftriaxone, trovafloxacin, quinupristin-dalfopristin and vancomycin in experimental endocarditis due to penicillin- and ceftriaxone-resistant Streptococcus pneumoniae.	2001 May	11328774
Emerging importance of multidrug-resistant Acinetobacter species and Stenotrophomonas maltophilia as pathogens in seriously ill patients: geographic patterns, epidemiological features, and trends in the SENTRY Antimicrobial Surveillance Program (1997-1999).	2001 May 15	11320451
Activity of BMS284756 (T-3811) tested against anaerobic bacteria, Campylobacter jejuni, Helicobacter pylori and Legionella spp.	2001 May-Jun	11448563
In vitro activity of ABT-773 versus macrolides and quinolones against resistant respiratory tract pathogens.	2001 May-Jun	11448561
Efficacy and safety of gemifloxacin in the treatment of community-acquired pneumonia: a randomized, double-blind comparison with trovafloxacin.	2001 Nov	11679567
Comparison of antimicrobial in vitro activities against Streptococcus pneumoniae independent of MIC susceptibility breakpoints using MIC frequency distribution curves, scattergrams and linear regression analyses.	2001 Nov	11679549
Multicentre study of the in vitro evaluation of moxifloxacin and other quinolones against community acquired respiratory pathogens.	2001 Oct	11691572
Seizures associated with fluoroquinolones.	2001 Oct	11675843
High rates of multiple antibiotic resistance in Streptococcus pneumoniae from healthy children living in isolated rural communities: association with cephalosporin use and intrafamilial transmission.	2001 Oct	11581436
Fluoroquinolone susceptibilities of efflux-mediated multidrug-resistant Pseudomonas aeruginosa, Stenotrophomonas maltophilia and Burkholderia cepacia.	2001 Oct	11581236
Frequency of selection of fluoroquinolone-resistant mutants of Neisseria gonorrhoeae exposed to gemifloxacin and four other quinolones.	2001 Oct	11581235
Influence of diminished susceptibility of Streptococcus pneumoniae to ciprofloxacin on the serum bactericidal activity of gemifloxacin and trovafloxacin after a single dose in healthy volunteers.	2001 Sep	11673035
Is more than one quinolone needed in clinical practice?	2001 Sep	11573860
Future of the quinolones.	2001 Sep	11562902
Single- and multi-step resistance selection study of gemifloxacin compared with trovafloxacin, ciprofloxacin, gatifloxacin and moxifloxacin in Streptococcus pneumoniae.	2001 Sep	11533001
Fluoroquinolone-resistant Streptococcus pneumoniae associated with levofloxacin therapy.	2001 Sep 15	11517444
Human research. Nigerian families sue Pfizer, testing the reach of U.S. law.	2001 Sep 7	11546842
Drug company sued over research trial in Nigeria.	2001 Sep 8	11564494
In vitro susceptibility of Stenotrophomonas maltophilia to various antimicrobial combinations.	2001 Sep-Oct	11687317
In vitro activity of novel fluoroquinolones against Streptococcus pneumoniae isolated from children with acute otitis media.	2001 Sep-Oct	11561138
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center.	2001 Spring	11310803
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.	2002 Feb	11858908
Antimicrobial resistance trends in community-acquired respiratory tract pathogens in the Western Pacific Region and South Africa: report from the SENTRY antimicrobial surveillance program, (1998-1999) including an in vitro evaluation of BMS284756.	2002 Feb	11850165
In vitro assessment of urinary isolates of ampicillin-resistant enterococci.	2002 Feb	11847942
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
Susceptibility of human isolates of Salmonella typhimurium DT 104 to antimicrobial agents used in human and veterinary medicine.	2002 Jan	11821166

Patents

Sample Use Guides

In Vivo Use Guide

Nosocomial Pneumonia - 300 mg I.V. followed by 200 mg oral, 10–14 days Community Acquired Pneumonia - 200 mg oral or 200 mg I.V. followed by 200 mg oral, 7–14 days Gynecologic and Pelvic Infections - 300 mg I.V. followed by 200 mg oral, 7–14 days

Route of Administration: Other

In Vitro Use Guide

Trovafloxacin inhibited Escherichia coli growth with MIC50 = 0.125mg/L

Name

Type

Language

ALATROFLOXACIN MESYLATE

Official Name

English

CP-116,517-27

Code

English

ALATROFLOXACIN MESYLATE [VANDF]

Common Name

English

ALATROFLOXACIN MESILATE [MART.]

Common Name

English

7-[(1R,5S,6S)-6-[(S)-2-[(S)-2-Aminopropionamido]propionamido]-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, monomethanesulfonate

Systematic Name

English

ALATROFLOXACIN MESYLATE [USAN]

Common Name

English

7-((1R,5S,6S)-6-((S)-2-((S)-2-AMINOPROPIONAMIDO)PROPIONAMIDO)-3-AZABICYCLO(3.1.0)HEX-3-YL)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, MONOMETHANESULPHONATE

Systematic Name

English

ALATROFLOXACIN MESYLATE [EMA EPAR]

Common Name

English

517-27

Code

English

L-ALANINAMIDE, L-ALANYL-N-(3-(6-CARBOXY-8-(2,4-DIFLUOROPHENYL)-3-FLUORO-5,8-DIHYDRO-5-OXO-1,8-NAPHTHYRIDIN-2-YL)-3-AZABICYCLO(3.1.0)HEX-6-YL)-, MONOMETHANESULFONATE, (1.ALPHA.,5.ALPHA.,6.ALPHA.)

Systematic Name

English

L-ALANINAMIDE, L-ALANYL-N-((1.ALPHA.,5.ALPHA.,6.ALPHA.)-3-(6-CARBOXY-8-(2,4-DIFLUOROPHENYL)-3-FLUORO-5,8-DIHYDRO-5-OXO-1,8-NAPHTHYRIDIN-2-YL)-3-AZABICYCLO(3.1.0)HEX-6-YL)-, METHANESULFONATE (1:1)

Systematic Name

English

Alatrofloxacin mesilate [WHO-DD]

Common Name

English

ALATROFLOXACIN MESYLATE [ORANGE BOOK]

Common Name

English

CP-116

Code

English

ALATROFLOXACIN MESILATE

Common Name

English

L-ALANINAMIDE, L-ALANYL-N-(3-(6-CARBOXY-8-(2,4-DIFLUOROPHENYL)-3-FLUORO-5,8-DIHYDRO-5-OXO-1,8-NAPHTHYRIDIN-2-YL)-3-AZABICYCLO(3.1.0)HEX-6-YL)-, MONOMETHANESULPHONATE, (1.ALPHA.,5.ALPHA.,6.ALPHA.)

Systematic Name

English

CP-11651727

Code

English

CP-116517-27

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C795