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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 of OLAMUFLOXACIN

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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:14:33 UTC 2023
Edited
by admin
on Sat Dec 16 16:14:33 UTC 2023
Record UNII
LJG8KL1435
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLAMUFLOXACIN
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
Code System Code Type Description
PUBCHEM
477670
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
FDA UNII
LJG8KL1435
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
EVMPD
SUB03495MIG
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
NCI_THESAURUS
C84030
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
MESH
C106426
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
SMS_ID
100000085936
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
INN
7740
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
CAS
167887-97-0
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL2078925
Created by admin on Sat Dec 16 16:14:34 UTC 2023 , Edited by admin on Sat Dec 16 16:14:34 UTC 2023
PRIMARY
Related Record Type Details
STREPTOCOCCUS PNEUMONIAE
TARGET ORGANISM->INHIBITOR
BACTERIAL DNA GYRASE
TARGET -> INHIBITOR
ESCHERICHIA COLI
TARGET ORGANISM->INHIBITOR
HAEMOPHILUS INFLUENZAE
TARGET ORGANISM->INHIBITOR
Structure of OLAMUFLOXACIN MESILATE
SALT/SOLVATE -> PARENT
KLEBSIELLA PNEUMONIAE
TARGET ORGANISM->INHIBITOR
STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
MORAXELLA CATARRHALIS
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of OLAMUFLOXACIN
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