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

Molecular Formula	C20H23FN4O3
Molecular Weight	386.42
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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 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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:14:33 GMT 2023` Edited by `admin` on `Sat Dec 16 16:14:33 GMT 2023`
Record UNII	LJG8KL1435
Record Status	`Validated (UNII)`
Record Version

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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