OLAMUFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H23FN4O3
Molecular Weight	386.42
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(N2C[C@@H](N)C3(CC3)C2)C(F)=C(N)C4=C1N(C=C(C(O)=O)C4=O)C5CC5

InChI

InChIKey=LEILBPMISZFZQK-GFCCVEGCSA-N

InChI=1S/C20H23FN4O3/c1-9-16-13(18(26)11(19(27)28)6-25(16)10-2-3-10)15(23)14(21)17(9)24-7-12(22)20(8-24)4-5-20/h6,10,12H,2-5,7-8,22-23H2,1H3,(H,27,28)/t12-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14613952
Curator's Comment: description was created based on several sources, including http://adisinsight.springer.com/drugs/800006301 | http://www.ncbi.nlm.nih.gov/pubmed/12957636 | https://www.ncbi.nlm.nih.gov/pubmed/15608441

Olamufloxacin (HSR-903) is an oral fluoroquinolone antimicrobial agent which has been reported to have a potent activity against respiratory pathogens, such as Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Klebsiella pneumoniae, Staphylococcus aureus, Chlamydia spp. and Legionella spp., as well. Olamufloxacin inhibits DNA gyrase from the susceptible and resistant bacterial strains. It has been shown that olamufloxacin possesses a more potent antibacterial activity against potential respiratory pathogens compared with other quinolone derivatives. An oral formulation of olamufloxacin was undergoing phase III for Bacterial infections in Japan (Discontinued).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608441	Inhibitor 8297		20.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial infections 234 Sources: http://adisinsight.springer.com/drugs/800006301	Curative	Phase III 656	Unknown Approved Use Unknown
Pneumonia caused by S. pneumoniae 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9559783	Curative	Basic research	Unknown Approved Use Unknown
Chlamydial pneumonia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9087506	Curative	Basic research	Unknown Approved Use Unknown
Systemic infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11418525	Curative	Basic research	Unknown Approved Use Unknown
Urinary tract infections 205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11418525	Curative	Basic research	Unknown Approved Use Unknown
L. pneumophila pneumonia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14613952	Curative	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro and in vivo antichlamydial activities of HSR-903, a new fluoroquinolone antibiotic.	1997 Apr	9087506
In-vitro antimicrobial activity of HSR-903, a new fluoroquinolone, against clinical isolates of Klebsiella pneumoniae and Enterobacter cloacae with fluoroquinolone resistance-associated amino acid alterations in GyrA and ParC.	1997 Dec	9462448
In vitro activity of HSR-903, a new quinolone.	1997 Jun	9174193
In-vitro antimicrobial activity of HSR-903, a new fluoroquinolone, against clinical isolates of Neisseria gonorrhoeae with quinolone resistance-associated alterations in GyrA and ParC.	1997 Sep	9338500
In vivo activity of HSR-903, a new fluoroquinolone, against respiratory pathogens.	1998 Apr	9559783
Hepatobiliary transport kinetics of HSR-903, a new quinolone antibacterial agent.	1998 Nov	9806954
Carrier-mediated lung distribution of HSR-903, a new quinolone antibacterial agent.	1999 Apr	10086990
Comparative in vitro antimicrobial activities of the newly synthesized quinolone HSR-903, sitafloxacin (DU-6859a), gatifloxacin (AM-1155), and levofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.	1999 Dec	10582897
In vitro activity of HSR-903, a new oral quinolone, against bacteria causing respiratory infections.	1999 Jul	10390240
Efflux transport of a new quinolone antibacterial agent, HSR-903, across the blood-brain barrier.	1999 Jul	10381759
Effect of HSR-903, a new fluoroquinolone, on the concentration of theophylline in serum.	1999 Jun	10348779
The in vivo activity of olamufloxacin (HSR-903) in systemic and urinary tract infections in mice.	2001 Jul	11418525
Susceptibility of Yersinia pestis to novel and conventional antimicrobial agents.	2003 Aug	12865386
In vitro and in vivo activity of olamufloxacin (HSR-903) against Legionella spp.	2003 Dec	14613952

Patents

Sample Use Guides

In Vivo Use Guide

The tablet form of Olamufloxacin (HSR-903) containing 100 mg of active ingredient.

Route of Administration: Oral

In Vitro Use Guide

Olamufloxacin was tested against different strains of chlamydia. The MICs for standard strains were 0.016 to 0.063 mg/ml.

Name

Type

Language

OLAMUFLOXACIN

Official Name

English

(-)-5-AMINO-7-((S)-7-AMINO-5-AZASPIRO(2,4)HEPT-5-YL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHYL-4-OXO-3-QUINOLINECARBOXYLIC ACID

Systematic Name

English

Olamufloxacin [WHO-DD]

Common Name

English

olamufloxacin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795