Crystallization and transformation of acetaminophen trihydrate

Crystal Growth and Design

Volumn 3, Issue 5, 2003, Pages 761-765

  Peterson, Matthew L ^a   McIlroy, David ^b   Shaw, Paul ^a   Mustonen, J Peter ^a   Oliveira, Mark ^a   Almarsson, Örn ^a  

^a TransForm Pharmaceuticals Inc   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL; PARACETAMOL; PROPYLENE GLYCOL;

AQUEOUS SOLUTION; ARTICLE; CRYSTALLIZATION; PHYSICAL CHEMISTRY; SOLVATION; THERMODYNAMICS; THERMOSTABILITY;

EID: 0141627915     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0340603     Document Type: Article

References (13)

1. Nichols, G.; Frampton, C. S. J. Pharm. Sci. 1998, 87, 684-693.
2. Burger, A. Acta Pharm. Technol. 1982, 28, 1-20.
3. Beyer, T.; Day, G. M.; Price, S. L. J. Am. Chem. Soc. 2001, 123, 5086-5094.
4. Peterson, M. L.; Morissette, S. L.; McNulty, C.; Goldsweig, A.; Shaw, P. ; LeQuesne, M.; Monagle, J.; Encina, N.; Marchionna, J.; Johnson, A.; Gonzalez-Zugasti, J.; Lemmo, A. V.; Ellis, S. J.; Cima, M. J.; Almarsson, O. J. Am. Chem. Soc. 2002, 124, 10958-10959.
5. Di Martino, P.; Conflant, P.; Drache, M.; Huvenne, J.-P.; Guyot-Hermann, A.-M. J. Therm. Anal. 1997, 48, 447-458.
6. Oswald, I. D. H.; Allan, D. R.; McGregor, P. A.; Motherwell, W. D. S.; Parsons, S.; Pulham, C. R. Acta Crystallogr. 2002, B58, 1057-1066.
7. Fachaux, J.-M.; Guyot-Hermann, A.-M.; Guyot, J.-C.; Conflant, P.; Drache, M.; Veesler, S.; Boistelle, R. Powder Technol. 1995, 82, 123-128.
8. Room temperature aqueous solubility of form 1 acetaminophen was measured to be 13.8 mg/mL at 20°C. (b) Aqueous solubility was reported to be 12.8 mg/mL in Granberg, R. A.; Rasmuson, A. C. J. Chem. Eng. Data 1999, 44, 1391-1395.
9. Powder X-ray diffractograms of acetaminphen trihydrate were obtained from samples removed from the crystallization vials by pipeting directly into a glass X-ray capillary tube. The capillary was quickly mounted in the aluminum sample holder that had been cooled in liquid nitrogen. The sample holder was transferred to the diffractometer quickly and the pattern was recorded. It was important to keep the sample cold during the transfer, and to quickly obtain the powder pattern so as to avoid conversion into form 1.
10. The experimental powder patterns were compared with one calculated from the single-crystal structure using Materials Studio Version 2.1, 2001, Accelrys Inc.
11. Byrn, S.; Pfeiffer, R.; Ganey, M.; Hoiberg, C.; Poochikian, G. Pharm. Res. 1995, 12, 945-954.
12. Children's Tylenol Suspension Liquid (made by McNeil Consumer) contains the active ingredient acetaminophen (160 mg/mL) and the following inactive ingredients: butylparaben, cellulose, citric acid, corn syrup, flavors, glycerin, propylene glycol, purified water, sodium benzoate, sorbitol, xanthan gum. In addition to the above ingredients cherry-flavored suspension contains FD&C Red #40, bubble gumflavored suspension contains D&C Red #33 and FD&C Red #40, and grape-flavored suspension contains D&C Red #33 and FD&C Blue #1.
13. For a discussion of the effect of structurally related substances on the nucleation kinetics of acetaminophen see Hendriksen, B. A.; Grant, D. W. J. Cryst. Growth 1995, 156, 252-260.