Sitafloxacin Hydrate

Sitafloxacin hydrate was approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on January 25, 2008. It was developed and marketed as Gracevit® by Daiichi Sankyo in JP.

Sitafloxacin hydrate is a fluoroquinolone antibiotic. It is indicated for the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Gracevit® is available as tablet or fine granules for oral use, containing 50 mg of free Sitafloxacin for tablet or 10% of free Sitafloxacin for fine granules. The recommended dose is 50 mg of Sitafloxacin twice daily, or 100 mg of Sitafloxacin once daily.

Index：

General Information

Update Date：2016-03-24

Drug Name：
Sitafloxacin Hydrate
Research Code：
DU-6859a
Trade Name：
Gracevit®
MOA：
Quinolone antibiotic
Indication：
Otorhinolaryngological Infection; Gynecologic Infection; Urinary tract infections; Respiratory tract infection; Dental Infection
Status：
Approved
Company：
Daiichi Sankyo (Originator) , Daiichi Sankyo
Sales：
ATC Code：
J01MA21
Approved Countries or Area

Update Date：2015-07-29

Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
2008-01-25 Marketing approval Gracevit Respiratory tract infection,Urinary tract infections,Gynecologic Infection,Otorhinolaryngological Infection,Dental Infection Granule 10% Daiichi Sankyo
2008-01-25 Marketing approval Gracevit Respiratory tract infection,Urinary tract infections,Gynecologic Infection,Otorhinolaryngological Infection,Dental Infection Tablet Eq. 50 mg Sitafloxacin Daiichi Sankyo
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Chemical Structure

Update Date：2015-08-27

Molecular Weight 436.84
Formula C19H18ClF2N3O3 • 1.5H2O
CAS No. 127254-12-0 (Sitafloxacin);
163253-35-8 (Sitafloxacin Sesquihydrate);
Chemical Name (-)-7-[(7S)-7-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid sesquihydrate
Sitafloxacin （Free Acid/Base）Parameters：
MW HD HA FRB* PSA* cLogP*
409.81 3 6 4 86.9 2.624±0.920
*：Calculated by ACD/Labs software V11.02.
Related Patents

Update Date：2015-08-31

No. Major Technical Classification Publication No. Patent No. Legal Status Filling Date Estimated Expiry Date
1 Preparation CN1037507A CN1033751C Granted/expired 1989/4/27 2009/4/27
2 Preparation CN1062906A CN1038509C Granted/expired 1991/10/18 2011/10/18
3 Preparation CN1106006A CN1057297C Granted/abandoned 1994/9/10 2013/9/10
4 Formulation CN1438888A CN1326524C Granted 2001/4/23 2021/4/23
5 Formulation CN1444480A CN1214792C Granted 2001/8/7 2021/8/7
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Synthesis & Impurities

Update Date：2015-10-16


1. J. Med. Chem. 1994, 37, 3344-3352.

2. US5767127A.

3. CN103360310A.


1. Tetrahedron Lett. 1992, 33, 3487-3490.


1. Tetrahedron Lett. 1992, 33, 3483-3486.


1. Chem. Pharma. Bull. 1998, 46, 587-590.

1
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity A C19H18ClF2N3O3 409.81 127254-10-8 
2
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity B C19H18ClF2N3O3 409.81 127254-11-9
3
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity C C19H18ClF2N3O3 409.81 127199-06-8
4
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity D C16H16FN3O3 317.31 148693-51-0
5
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity E C19H20ClF2N3O3 411.83
6
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity F C19H18ClF2N3O3 409.81
7
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity G C19H18ClF2N3O3 409.81
8
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity H C19H18ClF2N3O3 409.81
9
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Sitafloxacin Hydrate Impurity I C19H18ClF2N3O3 409.81