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Mohammed A. Al-Omar
Department of Pharmaceutical Chemistry
College of Pharmacy, King Saud University
P.O. Box 2457, Riyadh-11451
Kingdom of Saudi Arabia
CONTENTS
1. GENERAL INFORMATION
1.1 Nomenclature
1.1.1 Systematic chemical names [1, 2]
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-
quinolinecarboxylic acid.
CIPROFLOXACIN: PHYSICAL PROFILE 165
1.2 Formulae
1.2.1 Empirical formula, molecular weight, CAS number [3, 4]
C17H18FN3O3 331.35 [0085721-33-1].
HN
N N
F COOH
2. PHYSICAL CHARACTERISTICS
2.1 Solution pH
A 2.5% solution in water has a pH of 3.0–4.5 [3].
166 M.A. AL-OMAR
10 15 20 25 30 35 40 45 50 55
Scattering Angle
(degrees 2-θ)
Figure 1. X-ray powder diffraction pattern of ciprofloxacin.
Table 1
167
(continued)
168
Table 1 (continued)
M.A. AL-OMAR
24.783 3.5895 11.12 25.094 3.5458 8.16
169
170 M.A. AL-OMAR
2.6 Spectroscopy
2.6.1 Ultraviolet spectroscopy
The UV spectrum of ciprofloxacin dissolved in methanol was recorded
using a Shimadzu ultraviolet–visible Spectrophotometer 1601 PC, and is
Wavelength (nm)
Figure 3. The ultraviolet absorption spectrum of ciprofloxacin in methanol.
880 960 1040 1120 1200 1280 1360 1440 1520 1600 1680 1760 1840 1920 2000 2080 2160 2240
Table 2
10 9 8 7 6
Chemical Shift (ppm)
1
Figure 5. The H-NMR spectrum of ciprofloxacin in D2O.
174 M.A. AL-OMAR
Table 3
3'
HN 4' 2' 1c
5' 1'
6' N 8a N
8 1
7 2
6 3
5 4 3a
4a
F COOH
H-2 8.63 s 1
H-5 7.46 d 1
H-8 7.52 d 1
H-1a 1.22 s 1
H-1b, 1c 1.47 d 2
13
Assignments for the Observed Resonance Bands in the C-NMR Spectrum of
Ciprofloxacin
3'
HN 4' 2' 1c
5' 1'
6' N 8a N
8 1
7 2
6 3
5 4 3a
4a
F COOH
175
(continued)
176
Table 4 (continued)
M.A. AL-OMAR
C-3a 169.31 1 C-30 , C-50 47.05 2
Table 5
314 55 M–H2O
4. REFERENCES
1. Remington’s: Pharmaceutical Sciences, 20th edn., A.R. Gennaro,
ed., Mack Publishing Co., Pennsylvania, p. 1539 (2000).
2. The Merck Index, 12th edn., S. Budavari, ed., Merck and Co., NJ,
p. 2374 (1996).
3. Martindale, The Complete Drug Reference, 33rd edn., S.C.
Sweetman, ed., The Pharmaceutical Press, Chicago, p. 182
(2002).
4. Index Nominum 2000: International Drug Directory, 17th edn.,
Swiss Pharmaceutical Society, Medpharm Scientific Publishers,
Ontario, p. 239 (2000).
5. Drug Information, 95 edn., G.K. McEvoy, ed., American Society
of Health-System Pharmacists, p. 493 (1995).
6. S. Tammilehto, H. Salomies, and K. Torniainen, J. Planar.
Chromatogr. Mod. TLC, 7, 368 (1994).