Ciprofloxacin → Ciprofloxacin Hydrochloride Anhydrous

HRID 256790

Reaction equation

HRID 256790 reaction equation
[Na+].[Cl-:2].[CH:3]1[C:4]2[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]([CH:24]3[CH2:26][CH2:25]3)[C:5]=2[CH:6]=[C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[C:8]=1[F:9]>O>[CH:3]1[C:4]2[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]([CH:24]3[CH2:25][CH2:26]3)[C:5]=2[CH:6]=[C:7]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[C:8]=1[F:9].[ClH:2]

Participants

4

Reactant 2

HCID 2764Ciprofloxacin3×HCID 5234Sodium Chloride

Product 1

HCID 62999Ciprofloxacin Hydrochloride Anhydrous

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The bandage was placed in a capped vial containing 1 ml of 0.9% NaCl in distilled water at 25° C. After 1 hr of gentle stirring, the aqueous phase was collected and the bandage was placed in a fresh 1 ml portion of 0.9% NaCl. This process was repeated for a total of 24 one hour periods. The following procedure for HPLC analysis of ciprofloxacin was essentially that of Darouiche, R. et al, [J. Inf Dis 162, 1124-1125 (1990)]. The conditions were a Whatman Partisil 50D5-3 (C8) column with a mobile phase of 25 ml 0.5M Bu4NHPO4 made up to 2.5 L with distilled water, pH adjusted to 2.34 with 85% H3PO4, which was added to 278 ml HPLC grade acetonitrile, filtered through a 0.2μ membrane and degassed. The flow rate was 1.5 ml/min at 25° C. with a 500 μl injection loop with detection at 280 nm. Under these conditions ciprofloxacin eluted as a single peak at 9 min. HPLC analysis of the 24 aqueous fractions gave the elution profile shown in Table 2. The data in Table 2 showed that 74% of the initial charge of ciprofloxacin was released in the first 4 hrs and the release of ciprofloxacin in the subsequent 5 to 24 hrs was remarkably constant. This was thought to be due to the gradual release of ciprofloxacin trapped in the cryogel matrix.

Workup

  1. customthe aqueous phase was collected
  2. customwas repeated for a total of 24 one hour periods
  3. additionwas added to 278 ml HPLC grade acetonitrile
  4. filtrationfiltered through a 0.2μ membrane
  5. customdegassed
  6. customat 25° C.
  7. washUnder these conditions ciprofloxacin eluted as a single peak at 9 min
  8. customHPLC analysis of the 24 aqueous fractions gave the elution profile
  9. customwas released in the first 4 hrs
  10. customin the subsequent 5 to 24 hrs

Sources & evidence

ORD record
ord-322ac87ede3c483cad472422e267659f
Source dataset
uspto-grants-1993_11
Patent number
US05260066

Linked notes

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