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124858-35-1

Basic Information
CAS No.: 124858-35-1
Name: Nadifloxacin
Article Data: 2
Molecular Structure:
Molecular Structure of 124858-35-1 (Nadifloxacin)
Formula: C19H21FN2O4
Molecular Weight: 360.385
Synonyms: 1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (±)-;Jinofloxacin;OPC 7251;
EINECS: 638-863-6
Density: 1.467 g/cm3
Melting Point: 245-247 °C
Boiling Point: 624.891 °C at 760 mmHg
Flash Point: 331.722 °C
Appearance: off-white crystalline solid
PSA: 82.77000
LogP: 2.37210
Synthetic route
5382-16-1

4-HYDROXYPIPERIDINE

77483-92-2

9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

124858-35-1

nadifloxacin

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 160℃; for 7h;25%
1128-61-6

6-fluoro-2-methyl-quinoline

124858-35-1

nadifloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 87 percent / Br2, Ag2SO4, cc H2SO4, / 1 h
2: 68 percent / H2, / PtO2, / acetic acid / Ambient temperature
3: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H2O, reflux, 2 h,
4: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C
View Scheme
80290-18-2

5-bromo-6-fluoro-2-methylquinoline

124858-35-1

nadifloxacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / H2, / PtO2, / acetic acid / Ambient temperature
2: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H2O, reflux, 2 h,
3: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C
View Scheme
79085-71-5

5-bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

124858-35-1

nadifloxacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H2O, reflux, 2 h,
2: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C
View Scheme
124858-35-1

nadifloxacin

74-88-4

methyl iodide

129672-74-8

methyl-9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H,5H-benzoquinolizine-2-carboxylate

Conditions
ConditionsYield
With potassium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol at 60℃; for 1.5h;91%
1201939-89-0

4-((6,7-dimethoxyquinazolin-4-yl)oxy)-3-fluoroaniline

124858-35-1

nadifloxacin

N-(4-((6,7-dimethoxyquinazolin-4-yl)oxy)-3-fluorophenyl)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1,5,6,7-tetrahydropyrido[3,2,1-ij]quinoline-2-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;70%
124858-35-1

nadifloxacin

64-19-7

acetic acid

81962-90-5

8-(4-acetoxy-1-piperidyl)-9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzoquinolizine-2-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 5h; Heating;57%
124858-35-1

nadifloxacin

80441-55-0

6-(S-tritylmercapto)hexanoic acid

1398623-75-0

C44H45FN2O5S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 22℃; for 13h; Inert atmosphere;24%
124858-35-1

nadifloxacin

130539-79-6

9-fluoro-6,7-dihydro-5-methyl-8-(4-sulfoxy-1-piperidyl)-1-oxo-1H,5H-benzoquinolizine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / 85percent potassium hydroxide / hexamethylphosphoric acid triamide; ethanol / 1.5 h / 60 °C
2: 1) chlorosulfonic acid / 1) 50-55 deg C, 30 min, 2a) 50-55 deg C, 6 h, 2b) r.t., overnight
3: 38 percent / 0.1N KOH / methanol
View Scheme
124858-35-1

nadifloxacin

130539-78-5

pyridinium 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidyl)-2-methoxycarbonyl-5-methyl-1-oxo-1H,5H-benzoquinolizine sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / 85percent potassium hydroxide / hexamethylphosphoric acid triamide; ethanol / 1.5 h / 60 °C
2: 1) chlorosulfonic acid / 1) 50-55 deg C, 30 min, 2a) 50-55 deg C, 6 h, 2b) r.t., overnight
View Scheme
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  • Nadifloxacin

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    Nadifloxacin

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    TIANFUCHEM--124858-35-1---Nadifloxacin

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    Nadifloxacin

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    TIANFUCHEM--124858-35-1---Nadifloxacin

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    Nadifloxacin

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  • TIANFUCHEM--124858-35-1---Nadifloxacin

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    124858-35-1

    TIANFUCHEM--124858-35-1---Nadifloxacin

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  • Nadifloxacin

  • Casno:

    124858-35-1

    Nadifloxacin

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Standards and Recommendations

Following a single topical application of 10gm nadifloxacin 1% cream to normal human back skin, the highest plasma concentration was determined to be 107ng./ml with an elimination half-life of 19.4 hours. Approximately 0.09% of the administered dose was excreted in the urine over 48 hours post- dosing. The plasma concentration reached a steady state on Day 5 of repeated administration study when nadifloxacin 1% cream was applied at 5 gm twice daily to normal healthy individuals for a period of 7 days. The plasma concentration reached a peak of 4.1 ng/ml at 8 hours post-final dosing with an elimination half-Life of 23.2 hours. The urinary excretion rate reached 0.16% on Day 7.

Specification

The Nadifloxacin, with the CAS registry number 124858-35-1, is also known as 1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (±)-. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C19H21FN2O4 and molecular weight is 360.38. What's more, its systematic name is 9-Fluoro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid. This chemical is a topical fluoroquinolone antibiotic for the treatment of acne vulgaris. It is also used to treat bacterial skin infections.

Physical properties of Nadifloxacin are: (1)ACD/LogP: 2.491; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.25; (4)ACD/LogD (pH 7.4): 0.71; (5)ACD/BCF (pH 5.5): 26.17; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 306.78; (8)ACD/KOC (pH 7.4): 8.90; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 81.08 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 91.62 cm3; (15)Molar Volume: 245.686 cm3; (16)Polarizability: 36.321×10-24cm3; (17)Surface Tension: 71.7 dyne/cm; (18)Density: 1.467 g/cm3; (19)Flash Point: 331.722 °C; (20)Enthalpy of Vaporization: 97.264 kJ/mol; (21)Boiling Point: 624.891 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C2=C\N4c1c(c(c(F)cc1C2=O)N3CCC(O)CC3)CCC4C
(2)Std. InChI: InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)
(3)Std. InChIKey: JYJTVFIEFKZWCJ-UHFFFAOYSA-N