ALATROFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H25F3N6O5
Molecular Weight	558.5091
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CN(C[C@]1([H])[C@H]2NC(=O)[C@H](C)NC(=O)[C@H](C)N)C3=C(F)C=C4C(=O)C(=CN(C5=CC=C(F)C=C5F)C4=N3)C(O)=O

InChI

InChIKey=UUZPPAMZDFLUHD-VUJLHGSVSA-N

InChI=1S/C26H25F3N6O5/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/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H25F3N6O5
Molecular Weight	558.5091
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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is a fluoroquinolone antibiotic developed as a mesylate salt and was sold under brand name Trovan, but was withdrawn from the U.S. market in 2001.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	Inhibitor 8,297
Streptococcus pneumoniae 25	Inhibitor 8,297
Moraxella catarrhalis 10	Inhibitor 8,297
Staphylococcus aureus 67	Inhibitor 8,297
Escherichia coli 82	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Nosocomial pneumonia 10	Curative	Withdrawn	TROVAN PRESERVATIVE FREE
Pneumonia 90	Curative	Approved 8,429	TROVAN
Intra-abdominal infections 49	Curative	Approved 8,429	TROVAN
Complicated skin and skin structure infections 11	Curative	Approved 8,429	TROVAN
Pneumonia 90	Curative	Withdrawn	TROVAN PRESERVATIVE FREE
Complicated intra-abdominal infections 20	Curative	Withdrawn	TROVAN PRESERVATIVE FREE
Gynecologic infections 18	Curative	Withdrawn	TROVAN PRESERVATIVE FREE
Skin infections 59	Curative	Withdrawn	TROVAN PRESERVATIVE FREE

C_max

Value	Dose	Analyte	Population
1 mg/L	100 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
2.9 mg/L	300 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
1.1 mg/L	100 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
3.3 mg/L	300 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
2.9 μg/mL	200 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
2.7 μg/mL	200 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
3.1 μg/mL	200 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens
3.6 μg/mL	300 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
4.4 μg/mL	300 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
9.4 mg × h/L	100 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
26.2 mg × h/L	300 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
11.8 mg × h/L	100 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
34.6 mg × h/L	300 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
32.2 μg × h/mL	200 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
28.1 μg × h/mL	200 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
32.2 μg × h/mL	200 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens
46.1 μg × h/mL	300 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
46.3 μg × h/mL	300 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
9.2 h	100 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
10.5 h	300 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
10.5 h	100 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
12.2 h	300 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
13.6 h	200 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
9.4 h	200 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
11.7 h	200 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens
11.2 h	300 mg single, intravenous	TROVAFLOXACIN serum	Homo sapiens
12.7 h	300 mg 1 times / day multiple, intravenous	TROVAFLOXACIN serum	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
20.3%	100 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
25.6%	300 mg single, oral	TROVAFLOXACIN serum	Homo sapiens
22%	100 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens
28.3%	300 mg 1 times / day steady-state, oral	TROVAFLOXACIN serum	Homo sapiens

Doses

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Dose	Population	Adverse events
1000 mg single, oral Highest studied dose	healthy, 27 years	Other AEs: Nausea, Vomiting...
200 mg 1 times / day steady, oral Recommended	unhealthy, adult	Disc. AE: Gastrointestinal disorder NOS, CNS disorder (NOS)...

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AEs

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AE	Significance	Dose	Population
Vomiting	1 patient	1000 mg single, oral Highest studied dose	healthy, 27 years
Lightheadedness	4 patients	1000 mg single, oral Highest studied dose	healthy, 27 years
Nausea	4 patients	1000 mg single, oral Highest studied dose	healthy, 27 years
Gastrointestinal disorder NOS	11 patient Disc. AE	200 mg 1 times / day steady, oral Recommended	unhealthy, adult
Dermatitis	2 patients Disc. AE	200 mg 1 times / day steady, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461	UGT 192 sulfotransferases 38

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,650	inhibitor 3,277	yes

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
UGT 192	substrate 3,367	yes
sulfotransferases 38	substrate 3,367	yes

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Sourcing

Sourcing

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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
BioSynth	J-008289	https://www.biosynth.com/en/products/all-products/products/J-008289.html
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

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PubMed

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Title	Date	PubMed
Trovafloxacin-induced acute hepatitis.	2000 Feb	10671353
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
[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin].	2001 Dec	11856983
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].	2001 Dec	11856982
In vitro activity of new quinolones against Clostridium difficile.	2001 Feb	11157906

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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

Substance Class	Chemical
Record UNII	7QVV6I50DT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALATROFLOXACIN

Official Name

English

ALATROFLOXACIN [VANDF]

Common Name

English

Alatrofloxacin [WHO-DD]

Common Name

English

alatrofloxacin [INN]

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

Common Name

English

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Classification Tree

Code System

Code

Antibiotic

NCI_THESAURUS

C795

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Code System

Code

Type

Description

NCI_THESAURUS

C79898

PRIMARY

EVMPD

SUB05293MIG

PRIMARY

EPA CompTox

DTXSID4057893

PRIMARY

FDA UNII

7QVV6I50DT

PRIMARY

INN

7495

PRIMARY

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Related Record

Type

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					2IXX802851

ALATROFLOXACIN MESYLATE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

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TROVAFLOXACIN

METABOLITE ACTIVE -> PRODRUG

Amount:

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TROVAFLOXACIN

ACTIVE MOIETY

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator