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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23FN4O3.CH4O3S
Molecular Weight 482.526
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLAMUFLOXACIN MESILATE

SMILES

CS(O)(=O)=O.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=QCRMQMNCFYYEFX-UTONKHPSSA-N
InChI=1S/C20H23FN4O3.CH4O3S/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;1-5(2,3)4/h6,10,12H,2-5,7-8,22-23H2,1H3,(H,27,28);1H3,(H,2,3,4)/t12-;/m1./s1

HIDE SMILES / InChI

Description
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

CNS Penetrant
2554
Curator's Comment: Known to be CNS penetrant in rats. Human data is not available. Tissue-to-plasma concentration ratio (Kp) in brain is extremely low, 0.11, demonstrating very poor distribution to the brain compared with other tissues. The blood-brain barrier permeability coefficient of [14C]Olamufloxacin ([14C]HSR-903) at a very low concentration (5 μm) was 10.5 μl/min/g. When the concentration of HSR-903 was increased to 20 or 50 mM, the permeability coefficient was increased 3- to 4-fold.

Originator

Hokuriku Seiyaku
2
Curator's Comment: As of 2002, Hokuriku Seiyaku Co., Ltd. (Japan) was acquired by Abbott Laboratories.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 20.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase III
656
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
In vitro activity of HSR-903, a new quinolone.
1997 Jun
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
In vivo activity of HSR-903, a new fluoroquinolone, against respiratory pathogens.
1998 Apr
Carrier-mediated lung distribution of HSR-903, a new quinolone antibacterial agent.
1999 Apr
In vitro activity of HSR-903, a new oral quinolone, against bacteria causing respiratory infections.
1999 Jul
Efflux transport of a new quinolone antibacterial agent, HSR-903, across the blood-brain barrier.
1999 Jul
The in vivo activity of olamufloxacin (HSR-903) in systemic and urinary tract infections in mice.
2001 Jul
Susceptibility of Yersinia pestis to novel and conventional antimicrobial agents.
2003 Aug
In vitro and in vivo activity of olamufloxacin (HSR-903) against Legionella spp.
2003 Dec
Patents

Patents

05547962
2
06825353
2
20030045544
5

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 MESILATE
JAN  
Common Name English
HSR-903
Code English
OLAMUFLOXACIN MESYLATE
Common Name English
3-QUINOLINECARBOXYLIC ACID, 5-AMINO-7-(7-AMINO-5-AZASPIRO(2.4)HEPT-5-YL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHYL-4-OXO-, (S)-, MONOMETHANESULFONATE
Common Name English
OLAMUFLOXACIN MESILATE [JAN]
Common Name English
(-)-OLAMUFLOXACIN MESILATE
Common Name English
3-QUINOLINECARBOXYLIC ACID, 5-AMINO-7-((7S)-7-AMINO-5-AZASPIRO(2.4)HEPT-5-YL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHYL-4-OXO-, METHANESULFONATE (1:1)
Common Name English
3-QUINOLINECARBOXYLIC ACID, 5-AMINO-7-((7S)-7-AMINO-5-AZASPIRO(2.4)HEPT-5-YL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHYL-4-OXO-, MONOMETHANESULFONATE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID20168419
Created by admin on Sat Dec 16 05:14:40 GMT 2023 , Edited by admin on Sat Dec 16 05:14:40 GMT 2023
PRIMARY
PUBCHEM
9826542
Created by admin on Sat Dec 16 05:14:40 GMT 2023 , Edited by admin on Sat Dec 16 05:14:40 GMT 2023
PRIMARY
FDA UNII
5Z27G7LBZV
Created by admin on Sat Dec 16 05:14:40 GMT 2023 , Edited by admin on Sat Dec 16 05:14:40 GMT 2023
PRIMARY
CAS
167888-07-5
Created by admin on Sat Dec 16 05:14:40 GMT 2023 , Edited by admin on Sat Dec 16 05:14:40 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of OLAMUFLOXACIN
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