SITAFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C19H18ClF2N3O3.3H2O
Molecular Weight	873.674
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O.N[C@@H]1CN(CC12CC2)C3=C(Cl)C4=C(C=C3F)C(=O)C(=CN4[C@@H]5C[C@@H]5F)C(O)=O.N[C@@H]6CN(CC67CC7)C8=C(Cl)C9=C(C=C8F)C(=O)C(=CN9[C@@H]%10C[C@@H]%10F)C(O)=O

InChI

InChIKey=MPORYQCGWFQFLA-ONPDANIMSA-N

InChI=1S/2C19H18ClF2N3O3.3H2O/c2*20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19;;;/h2*3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28);3*1H2/t2*10-,12+,13+;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H18ClF2N3O3
Molecular Weight	409.814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21504249
Curator's Comment: description was created based on several sources, including http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597 https://www.ncbi.nlm.nih.gov/pubmed/18806900 https://www.ncbi.nlm.nih.gov/pubmed/10588315

Sitafloxacin hydrate (DU-6859a, Gracevit), a new-generation, broad-spectrum oral fluoroquinolone that is very active against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, was recently approved in Japan for the treatment of respiratory and urinary tract infections. This is a new quinolone oral antibacterial to inhibit DNA replication of bacteria at the time of infection, and shows antibacterial action. Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci. Sitafloxacin has also demonstrated activity against clinical isolates of Klebsiella pneumoniae (including about 67% of strains producing extended-spectrum, beta-lactamases and resistant to ciprofloxacin), Enterobacter cloacae, Pseudomonas aeruginosa with some activity against quinolone-resistant strains and Acinetobacter baumannii. The in vitro activity against anaerobes is comparable to imipenem or metronidazole. Sitafloxacin showed dual inhibitory activity against both enzymes: Streptococcus pneumoniae DNA gyrase and topoisomerase IV.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Topoisomerase IV 62 Target ID: CHEMBL2363033 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10588315	Inhibitor 8504
DNA gyrase 26 Target ID: CHEMBL2311225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10588315	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Respiratory infections 12 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597	Curative	Approved 8583	Gracevit(R) Approved Use It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date 2008
Urologic infection 3 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597	Curative	Approved 8583	Gracevit(R) Approved Use It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date 2008
Gynecologic infections 19 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597	Curative	Approved 8583	Gracevit(R) Approved Use It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date 2008
Otorhinological infections 5 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597	Curative	Approved 8583	Gracevit(R) Approved Use It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date 2008
Dental infection 3 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597	Curative	Approved 8583	Gracevit(R) Approved Use It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date 2008

C_max

Value	Dose	Analyte	Population
0.29 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.51 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35 \| https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=6	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.86 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=36	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.88 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=4	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.38 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=1	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.5 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=1	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.84 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=3	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1.09 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=3	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.61 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.91 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.63 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.75 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.6 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.44 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	400 mg 2 times / day multiple, intravenous dose: 400 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.2 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.08 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	600 mg 2 times / day multiple, intravenous dose: 600 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.44 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	600 mg 2 times / day steady-state, intravenous dose: 600 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.18 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	800 mg 2 times / day multiple, intravenous dose: 800 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.07 μg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	800 mg 2 times / day steady-state, intravenous dose: 800 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1.52 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.62 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.55 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35 \| https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=6	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.04 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=36	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.81 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=4	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.2 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=1	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.71 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=1	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.34 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=3	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
5.9 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=3	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6.35 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.86 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.66 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.04 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.95 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
17.23 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	400 mg 2 times / day multiple, intravenous dose: 400 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
24.16 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
27.32 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	600 mg 2 times / day multiple, intravenous dose: 600 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
39.12 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	600 mg 2 times / day steady-state, intravenous dose: 600 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
38.09 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	800 mg 2 times / day multiple, intravenous dose: 800 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
56.36 μg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K128_2.pdf#page=10	800 mg 2 times / day steady-state, intravenous dose: 800 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	SITAFLOXACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
5.2 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.2 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.7 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35 \| https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=6	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=36	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.5 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=4	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
5.1 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=1	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.6 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=3	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#page=5	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.5 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.5 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K102_2.pdf#pag3=7	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SITAFLOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
45% OTHER GOV'T https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_A100_2.pdf#page=35 \| https://www.pmda.go.jp/drugs/2008/P200800006/430574000_22000AMX00015_K101_2.pdf#page=6	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		SITAFLOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	Other AEs: Diarrhea, Alanine aminotransferase increase... Other AEs: Diarrhea (3.3%) Alanine aminotransferase increase (7%) Fatigue (0.9%) Nausea (3.5%) Vomiting (0.9%) Dizziness (1.8%) Platelet count increased (0.9%) Aspartate aminotransferase increase (2.6%) Gamma-glutamyltransferase increased (2.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
400 mg 1 times / day multiple, intravenous Studied dose Dose: 400 mg, 1 times / day Route: intravenous Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	Other AEs: fever, Congestive cardiac failure... Other AEs: fever (6.33%) Congestive cardiac failure (7.39%) Diarrhea (9.5%) Skin rash (5.28%) Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/

AEs

AE	Significance	Dose	Population
Fatigue	0.9%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Platelet count increased	0.9%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Vomiting	0.9%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Dizziness	1.8%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Aspartate aminotransferase increase	2.6%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Gamma-glutamyltransferase increased	2.6%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Diarrhea	3.3%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Nausea	3.5%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Alanine aminotransferase increase	7%	100 mg 2 times / day multiple, oral Studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33534617/
Skin rash	5.28%	400 mg 1 times / day multiple, intravenous Studied dose Dose: 400 mg, 1 times / day Route: intravenous Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/
fever	6.33%	400 mg 1 times / day multiple, intravenous Studied dose Dose: 400 mg, 1 times / day Route: intravenous Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/
Congestive cardiac failure	7.39%	400 mg 1 times / day multiple, intravenous Studied dose Dose: 400 mg, 1 times / day Route: intravenous Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/
Diarrhea	9.5%	400 mg 1 times / day multiple, intravenous Studied dose Dose: 400 mg, 1 times / day Route: intravenous Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11020265/

PubMed

Title	Date	PubMed
In vitro and in vivo antimycobacterial activities of a new quinolone, DU-6859a.	1994 Dec	7695276
Pharmacokinetics and tolerance of DU-6859a, a new fluoroquinolone, after single and multiple oral doses in healthy volunteers.	1995 Jan	7695301
In vitro and in vivo antifungal activities of DU-6859a, a fluoroquinolone, in combination with amphotericin B and fluconazole against pathogenic fungi.	1995 Jul	7492096
[In vitro anti-MAC activities of new quinolones in focus (2)].	1996 Sep	8999137
In vitro antibacterial activity and pharmacodynamics of new quinolones.	2003 Apr	12687416
Comparative antimicrobial activities of gatifloxacin, sitafloxacin and levofloxacin against Mycobacterium tuberculosis replicating within Mono Mac 6 human macrophage and A-549 type II alveolar cell lines.	2003 Aug	12865388
Factors influencing fluoroquinolone resistance.	2003 Dec	14725310
A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity.	2003 Dec	14674902
Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.	2003 Feb	12696183
Adverse drug reactions: implications for the development of fluoroquinolones.	2003 May	12702700
A topological-substructural molecular design (TOPS-MODE) approach to determining pharmacokinetics and pharmacological properties of 6-fluoroquinolone derivatives.	2003 Sep	12957633
In vivo experimental approach for the risk assessment of fluoroquinolone antibacterial agents-induced long QT syndrome.	2004 Feb 20	14975708
Investigational new drugs for the treatment of resistant pneumococcal infections.	2005 Aug	16050791
Reproducibility of gemifloxacin and comparison fluoroquinolone MIC results using Sensititre commercial dry-form panels.	2005 Mar	15766610
Characterization of fluoroquinolone and carbapenem susceptibilities in clinical isolates of levofloxacin-resistant Pseudomonas aeruginosa.	2005 May	15870499
Fluoroquinolones: an important class of antibiotics against tuberculosis.	2006	16475933
[In-vitro susceptibilites to levofloxacin and various antibacterial agents of 18,639 clinical isolates obtained from 77 centers in 2004].	2006 Dec	17334061
In vitro activity of sitafloxacin against clinical strains of Streptococcus pneumoniae with defined amino acid substitutions in QRDRs of gyrase A and topoisomerase IV.	2006 Dec	17056610
New trends in development of antimycobacterial compounds.	2006 Jun	16789877
[Separation of sitafloxacin epimers by capillary electrophoresis].	2006 Sep	17165551
The potent antibacterial activity of Sitafloxacin against fluoroquinolone-resistant clinical isolates of Vibrio cholerae O1.	2007	17446687
History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents.	2007 Dec	18516271
Susceptibilities of healthcare- and community-associated methicillin-resistant staphylococci to the novel des-F(6)-quinolone DX-619.	2007 Dec	17890283
Skin and skin structure infections: treatment with newer generation fluoroquinolones.	2007 Jun	18360639
Pseudomonas aeruginosa: resistance and therapeutic options at the turn of the new millennium.	2007 Jun	17266725
Successful treatment of Mycobacterium ulcerans osteomyelitis with minor surgical debridement and prolonged rifampicin and ciprofloxacin therapy: a case report.	2008 Apr 27	18439310
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
Sitafloxacin hydrate for bacterial infections.	2008 Jul	18806900
Dual-targeting properties of the 3-aminopyrrolidyl quinolones, DC-159a and sitafloxacin, against DNA gyrase and topoisomerase IV: contribution to reducing in vitro emergence of quinolone-resistant Streptococcus pneumoniae.	2008 Jul	18390884
Quinolones: action and resistance updated.	2009	19747119
Quinolones with enhanced bactericidal activity induce autolysis in Streptococcus pneumoniae.	2009	19468224
[In vitro susceptibilities to levofloxacin and various antibacterial agents of 12,919 clinical isolates obtained from 72 centers in 2007].	2009 Aug	19860322
Convulsant activity of sitafloxacin and its interactions with anti-inflammatory drugs in mice.	2009 Aug	19688249
[Present status and future prospect of 3rd rescue regimen for H. pylori infection].	2009 Dec	19999116
A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy.	2009 Dec 1	19935799
[Pharmacological profile and clinical efficacy of sitafloxacin, a novel quinolone antibacterial agent].	2009 Jan	19145050
[Clinical position of sitafloxacin in outpatient chemotherapy. (discussion)].	2009 Jun	19882979
Quinolone-Based Third-Line Therapy for Helicobacter pylori Eradication.	2009 Mar	19308265
Comparative mutant prevention concentration and mutant selection window of sitafloxacin versus other quinolones using strains of Haemophilus influenzae with decreasing susceptibility to levofloxacin.	2009 May	19150226
Susceptibility and bactericidal activity of 8 oral quinolones against conventional-fluoroquinolone-resistant Streptococcus pneumoniae clinical isolates.	2009 Sep	19679241
In vivo efficacy of sitafloxacin in a new murine model of non-typeable Haemophilus influenzae pneumonia by sterile intratracheal tube.	2009 Sep	19394203
Imipenem resistance of Pseudomonas in pneumonia: a systematic literature review.	2010 Aug 26	20796312
[In vitro activity of sitafloxacin against clinical isolates in 2009].	2010 Dec	21425595
Studies on mechanism of thermal crystal transformation of sitafloxacin hydrates through melting and recrystallization, yielding different anhydrates depending on initial crystalline forms.	2010 Dec 15	20933072
Characterization of the quinolone resistant determining regions in clinical isolates of pneumococci collected in Canada.	2010 Jan 18	20082699
Changes in 12-Year First-Line Eradication Rate of Helicobacter pylori Based on Triple Therapy with Proton Pump Inhibitor, Amoxicillin and Clarithromycin.	2010 Jul	20664731
In vitro susceptibility to antimicrobial agents and ultrastructural characteristics related to swimming motility and drug action in Campylobacter jejuni and C. coli.	2010 Jun	20225076
[Update on antimicrobial chemotherapy].	2010 Mar	19959306
[Susceptibility test of the Mycobacterium avium complex to sixteen anti-infective agents].	2010 May	20646615
Comparative in vitro and in vivo antimicrobial activities of sitafloxacin, gatifloxacin and moxifloxacin against Mycobacterium avium.	2011 Apr	21353489

Patents

Sample Use Guides

In Vivo Use Guide

for adults: 1 tablet (50 mg of sitafloxacin) at a time, twice daily, or 2 tablets (100 mg) at a time, once daily. If the effect is insufficient, the dosage may be increased to 2 tablets (100 mg) at a time, twice daily.

Route of Administration: Oral

In Vitro Use Guide

The minimum inhibitory concentration of sitafloxacin (STFX) at which 90% of isolates (MIC90) was 0.5 microg/mL for methicillin-susceptible Staphylococcus aureus. STFX inhibited the growth of all the isolates of Streptococcus pneumoniae at 0.06 microg/mL or less. The MIC90 of STFX was 0.03 microg/mL. Against Streptococcus pyogenes, the MIC90 of STFX was 0.06 microg/mL. The MIC90 of STFX was 2 microg/mL for Enterococcus faecalis. The MIC90 of STFX for Escherichia coli was 2 microg/mL. The MIC90 of STFX for Pseudomonas aeruginosa isolates recovered from urinary infections was 4 microg/mL. The MIC90 of STFX for P. aeruginosa isolates recovered from respiratory infections was 4 microg/mL. STFX inhibited the growth of all the isolates of Haemophilus influenzae at 0.004 microg/mL or less. The MIC90 of STFX was 0.015 microg/mL for Moraxella catarrhalis. The MIC90(s) of STFX ranged from 0.03 to 0.25 microg/mL for all the species of anaerobic bacteria and were the lowest values of all the antimicrobial agents tested

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:42 GMT 2025`
Record UNII	9TD681796G
Record Status	`Validated (UNII)`
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Related Record	Type

Name

Type

Language

SITAFLOXACIN HYDRATE

Preferred Name

English

SITAFLOXACIN

Official Name

English

3-QUINOLINECARBOXYLIC ACID, 7-(7-AMINO-5-AZASPIRO(2.4)HEPT-5-YL)-8-CHLORO-6-FLUORO-1-(2-FLUOROCYCLOPROPYL)-1,4-DIHYDRO-4-OXO-, HYDRATE (2:3), (1R-(1.ALPHA.(S*), 2.ALPHA.))-

Common Name

English

DU-6859A

Code

English

SITAFLOXACIN [USAN]

Common Name

English

SITAFLOXACIN HYDRATE [JAN]

Common Name

English

(-)-7-((7S)-7-AMINO-5-AZASPIRO(2.4)HEPT-5-YL)-8-CHLORO-6-FLUORO-1-((1R,2S)-2-FLUOROCYCLOPROPYL)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID, SESQUIHYDRATE

Common Name

English

SITAFLOXACIN SESQUIHYDRATE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA21