Biowaiver monographs for immediate-release solid oral dosage forms: Codeine phosphate

Journal of Pharmaceutical Sciences

Volumn 103, Issue 6, 2014, Pages 1592-1600

  Dahan, Arik ^a   Wolk, Omri ^a   Zur, Moran ^a   Amidon, Gordon L ^b   Abrahamsson, Bertil ^c   Cristofoletti, Rodrigo ^d   Groot, D W ^e   Kopp, Sabine ^f   Langguth, Peter ^g   Polli, James E ^h   Shah, Vinod P ⁱ   Dressman, Jennifer B ^j  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b UNIVERSITY OF MICHIGAN   (United States)

^c ASTRAZENECA R AND D   (Sweden)

^d Agencia Nacional de Vigilancia Sanitaria Brazil   (Brazil)

^e NATIONAL INSTITUTE FOR PUBLIC HEALTH AND THE ENVIRONMENT   (Netherlands)

^f WORLD HEALTH ORGANIZATION   (Switzerland)

^g JOHANNES GUTENBERG UNIVERSITY   (Germany)

^h UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

ⁱ International Pharmaceutical Federation FIP   (Netherlands)

^j GOETHE UNIVERSITY   (Germany)

more..

Author keywords

absorption; bioavailability; bioequivalence; biopharmaceutics classification system (BCS); codeine phosphate; dissolution; permeability; solubility

Indexed keywords

CODEINE PHOSPHATE; CYTOCHROME P450 2D6; CODEINE; DRUG DOSAGE FORM; EXCIPIENT;

BIOEQUIVALENCE; CACO 2 CELL LINE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG DOSAGE FORM; DRUG ELIMINATION; DRUG METABOLISM; DRUG PENETRATION; DRUG RELEASE; DRUG SOLUBILITY; GENETIC POLYMORPHISM; HUMAN; INTESTINE ABSORPTION; INTESTINE PERFUSION; NONHUMAN; PHYSICAL CHEMISTRY; REVIEW; RISK BENEFIT ANALYSIS; SOLID; URINARY EXCRETION; SOLUBILITY;

CODEINE; DOSAGE FORMS; EXCIPIENTS; HUMANS; SOLUBILITY;

EID: 84901198556     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23977     Document Type: Article

References (54)

1. Goodman L, Gilman A,. 2006. The pharmacological basis of therapeutics. 11th ed. New York: The Macmillian Company.
2. Aylward M, Maddock J, Davies DE, Protheroe DA, Leideman T,. 1984. Dextromethorphan and codeine: Comparison of plasma kinetics and antitussive effects. Eur J Respir Dis 65 (4): 283-291.
3. Freestone C, Eccles R,. 1997. Assessment of the antitussive efficacy of codeine in cough associated with common cold. J Pharm Pharmacol 49 (10): 1045-1049.
4. Hutchings HA, Eccles R,. 1994. The opioid agonist codeine and antagonist naltrexone do not affect voluntary suppression of capsaicin induced cough in healthy subjects. Eur Respir J 7 (4): 715-719.
5. Bolser DC,. 2006. Cough suppressant and pharmacologic protussive therapy: ACCP evidence-based clinical practice guidelines. Chest 129 (1 Suppl): 238S-249S.
6. Mignat C, Wille U, Ziegler A,. 1995. Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci 56 (10): 793-799.
7. Volpe DA, McMahon Tobin GA, Mellon RD, Katki AG, Parker RJ, Colatsky T, Kropp TJ, Verbois SL,. 2011. Uniform assessment and ranking of opioid mu receptor binding constants for selected opioid drugs. Regul Toxicol Pharmacol 59 (3): 385-390.
8. Chau TT, Harris LS,. 1980. Comparative studies of the pharmacological effects of the d- and l-isomers of codeine. J Pharmacol Exp Ther 215 (3): 668-672.
9. Kahan M, Mailis-Gagnon A, Wilson L, Srivastava A,. 2011. Canadian guideline for safe and effective use of opioids for chronic noncancer pain: Clinical summary for family physicians. Part 1: General population. Can Fam Physician 57 (11): 1257-1266, e407-e418.
10. Gasche Y, Daali Y, Fathi M, Chiappe A, Cottini S, Dayer P, Desmeules J,. 2004. Codeine intoxication associated with ultrarapid CYP2D6 metabolism. N Engl J Med 351 (27): 2827-2831.
11. Crews KR, Gaedigk A, Dunnenberger HM, Klein TE, Shen DD, Callaghan JT, Kharasch ED, Skaar TC,. 2012. Clinical Pharmacogenetics Implementation Consortium (CPIC) guidelines for codeine therapy in the context of cytochrome P450 2D6 (CYP2D6) genotype. Clin Pharmacol Ther 91 (2): 321-326.
12. Kelly LE, Madadi P,. 2012. Is there a role for therapeutic drug monitoring with codeine ? Ther Drug Monit 34 (3): 249-256.
13. Leppert W,. 2011. CYP2D6 in the metabolism of opioids for mild to moderate pain. Pharmacology 87 (5-6): 274-285.
14. Kelly LE, Rieder M, van den Anker J, Malkin B, Ross C, Neely MN, Carleton B, Hayden MR, Madadi P, Koren G,. 2012. More codeine fatalities after tonsillectomy in North American children. Pediatrics 129 (5): e1343-e1347.
15. Ciszkowski C, Madadi P, Phillips MS, Lauwers AE, Koren G,. 2009. Codeine, ultrarapid-metabolism genotype, and postoperative death. N Engl J Med 361 (8): 827-828.
16. Brousseau DC, McCarver DG, Drendel AL, Divakaran K, Panepinto JA,. 2007. The effect of CYP2D6 polymorphisms on the response to pain treatment for pediatric sickle cell pain crisis. J Pediatr 150 (6): 623-626.
17. Zur M, Hanson AS, Dahan A,. 2014. The complexity of intestinal permeability: Assigning the correct BCS classification through careful data interpretation. Eur J Pharm Sci. [Epub ahead of print]
18. Dahan A, Amidon GL,. 2009. Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol 297 (2): G371-G377.
19. Dahan A, Amidon GL,. 2009. Grapefruit juice and its constituents augment colchicine intestinal absorption: Potential hazardous interaction and the role of p-glycoprotein. Pharm Res 26 (4): 883-892.
20. Dahan A, Amidon GL,. 2009. Segmental dependent transport of low permeability compounds along the small intestine due to P-glycoprotein: The role of efflux transport in the oral absorption of BCS class III drugs. Mol Pharm 6 (1): 19-28.
21. Dahan A, Lennernäs H, Amidon GL,. 2012. The fraction dose absorbed, in humans, and high jejunal human permeability relationship. Mol Pharm 9 (6): 1847-1851.
22. Dahan A, Miller JM, Hilfinger JM, Yamashita S, Yu LX, Lennernäs H, Amidon GL,. 2010. High-permeability criterion for BCS classification: Segmental/pH dependent permeability considerations. Mol Pharm 7 (5): 1827-1834.
23. Fairstein M, Swissa R, Dahan A,. 2013. Regional-dependent intestinal permeability and BCS classification: Elucidation of pH-related complexity in rats using pseudoephedrine. AAPS J 15 (2): 589-597.
24. Zur M, Gasparini M, Wolk O, Amidon GL, Dahan A,. 2014. The low/high BCS permeability class boundary: Physicochemical comparison of metoprolol and labetalol. Mol Pharmaceutics. [Epub ahead of print]
25. Beig A, Miller JM, Dahan A., 2012. Accounting for the solubility-permeability interplay in oral formulation development for poor water solubility drugs: the effect of PEG-400 on carbamazepine absorption. European Journal of Pharmaceutics and Biopharmaceutics 81 (2) 386-91.
26. Dahan A, Amidon GL., 2010. MRP2 mediated drug-drug interaction: indomethacin increases sulfasalazine absorption in the small intestine, potentially decreasing its colonic targeting. International Journal of Pharmaceutics 386 (1-2) 216-20.
27. Beig A, Agbaria R, Dahan A,. 2013. Oral delivery of lipophilic drugs: The tradeoff between solubility increase and permeability decrease when using cyclodextrin-based formulations. PLoS ONE 8 (7): e68237.
28. Dahan A, Beig A, Ioffe-Dahan V, Agbaria R, Miller J,. 2013. The twofold advantage of the amorphous form as an oral drug delivery practice for lipophilic compounds: Increased apparent solubility and drug flux through the intestinal membrane. AAPS J 15 (2): 347-353.
29. Miller JM, Beig A, Carr RA, Webster GK, Dahan A,. 2012. The solubility-permeability interplay when using cosolvents for solubilization: Revising the way we use solubility-enabling formulations. Mol Pharm 9 (3): 581-590.
30. CDER/FDA. 2000. Guidance for industry: Waiver of in vivo bioavailability and bioequivalence studies for immediate-release solid oral dosage forms based on a biopharmaceutics classification system.
31. Meylan WM, Howard PH,. 1995. Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 84 (1): 83-92.
32. Fuguet E, Reta M, Gibert C, Roses M, Bosch E, Rafols C,. 2008. Critical evaluation of buffering solutions for pKa determination by capillary electrophoresis. Electrophoresis 29 (13): 2841-2851.
33. Bodd E, Beylich KM, Christophersen AS, Morland J,. 1987. Oral administration of codeine in the presence of ethanol: A pharmacokinetic study in man. Pharmacol Toxicol 61 (5): 297-300.
34. Vree TB, Verwey-van Wissen CP,. 1992. Pharmacokinetics and metabolism of codeine in humans. Biopharm Drug Dispos 13 (6): 445-460.
35. Skolnik S, Lin X, Wang J, Chen XH, He T, Zhang B,. 2010. Towards prediction of in vivo intestinal absorption using a 96-well Caco-2 assay. J Pharm Sci 99 (7): 3246-3265.
36. Yalkowsky SH, Johnson JL, Sanghvi T, Machatha SG,. 2006. A 'rule of unity' for human intestinal absorption. Pharm Res 23 (10): 2475-2481.
37. Dahan A, Sabit H, Amidon GL,. 2009. Multiple efflux pumps are involved in the transepithelial transport of colchicine: Combined effect of P-gp and MRP2 leads to decreased intestinal absorption throughout the entire small intestine. Drug Metab Dispos 37 (10): 2028-2036.
38. Hubatsch I, Ragnarsson EGE, Artursson P,. 2007. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat Protoc 2 (9): 2111-2119.
39. Moolenaar F, Grasmeijer G, Visser J, Meijer DK,. 1983. Rectal versus oral absorption of codeine phosphate in man. Biopharm Drug Dispos 4 (2): 195-199.
40. Cao X, Gibbs S, Fang L, Miller H, Landowski C, Shin H-C, Lennernas H, Zhong Y, Amidon G, Yu L, Sun D,. 2006. Why is it challenging to predict intestinal drug absorption and oral bioavailability in human using rat model. Pharm Res 23 (8): 1675-1686.
41. Quiding H, Anderson P, Bondesson U, Boréus LO, Hynning PÅ,. 1986. Plasma concentrations of codeine and its metabolite, morphine, after single and repeated oral administration. Eur J Clin Pharm 30 (6): 673-677.
42. Yue QY, Hasselstrom J, Svensson JO, Sawe J,. 1991. Pharmacokinetics of codeine and its metabolites in Caucasian healthy volunteers: Comparisons between extensive and poor hydroxylators of debrisoquine. Br J Clin Pharmacol 31 (6): 635-642.
43. Somogyi AA, Barratt DT, Coller JK,. 2007. Pharmacogenetics of opioids. Clin Pharmacol Ther 81 (3): 429-444.
44. Ammon S, Marx C, Behrens C, Hofmann U, Murdter T, Griese E-U, Mikus G,. 2002. Diclofenac does not interact with codeine metabolism in vivo: A study in healthy volunteers. BMC Clin Pharmacol 2 (1): 2.
45. Caraco Y, Sheller J, Wood AJJ,. 1999. Impact of ethnic origin and quinidine coadministration on codeine's disposition and pharmacodynamic effects. J Pharmacol Exp Ther 290 (1): 413-422.
46. Gil, Berglund E, Johannsson G, Beck O, Bengtsson BÅ, Rane A,. 2002. Growth hormone replacement therapy induces codeine clearance. Eur J Clin Invest 32 (7): 507-512.
47. Mohammed SS, Ayass M, Mehta P, Kedar A, Gross S, Derendorf H,. 1993. Codeine disposition in sickle cell patients compared with healthy volunteers. J Clin Pharmacol 33 (9): 811-815.
48. Rogers JF, Findlay JWA, Hull JH, Butz RF, Jones EC, Bustrack JA, Welch RM,. 1982. Codeine disposition in smokers and nonsmokers. Clin Pharm Ther 32 (2): 218-227.
49. Dahan A, Wolk O, Kim YH, Ramachandran C, Crippen GM, Takagi T, Bermejo M, Amidon GL,. 2013. Purely in silico BCS classification: Science based quality standards for the world's drugs. Mol Pharm 10 (11): 4378-4390.
50. Pham-The H, Garrigues T, Bermejo M, González-Álvarez I, Monteagudo MC, Cabrera-Pérez MÁ,. 2013. Provisional classification and in silico study of biopharmaceutical system based on Caco-2 cell permeability and dose number. Mol Pharm 10 (6): 2445-2461.
51. Zhao YH, Le J, Abraham MH, Hersey A, Eddershaw PJ, Luscombe CN, Boutina D, Beck G, Sherborne B, Cooper I, Platts JA,. 2001. Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors. J Pharm Sci 90 (6): 749-784.
52. Kasim NA, Whitehouse M, Ramachandran C, Bermejo M, Lennernas H, Hussain AS, Junginger HE, Stavchansky SA, Midha KK, Shah VP, Amidon GL,. 2004. Molecular properties of WHO essential drugs and provisional biopharmaceutical classification. Mol Pharm 1 (1): 85-96.
53. Takagi T, Ramachandran C, Bermejo M, Yamashita S, Yu LX, Amidon GL,. 2006. A provisional biopharmaceutical classification of the top 200 oral drug products in the United States, Great Britain, Spain, and Japan. Mol Pharm 3 (6): 631-643.
54. Benet LZ, Broccatelli F, Oprea TI,. 2011. BDDCS applied to over 900 drugs. AAPS J 13 (4): 519-547.