CA2467611A1 - Azithromycin dosage forms with reduced side effects - Google Patents

Azithromycin dosage forms with reduced side effects Download PDF

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Publication number
CA2467611A1
CA2467611A1 CA002467611A CA2467611A CA2467611A1 CA 2467611 A1 CA2467611 A1 CA 2467611A1 CA 002467611 A CA002467611 A CA 002467611A CA 2467611 A CA2467611 A CA 2467611A CA 2467611 A1 CA2467611 A1 CA 2467611A1
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Canada
Prior art keywords
azithromycin
dosage form
oral dosage
glyceryl
multiparticulates
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Granted
Application number
CA002467611A
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French (fr)
Other versions
CA2467611C (en
Inventor
Timothy Arthur Hagen
Scott Max Herbig
Julian Belknap Lo
Avinash Govind Thombre
Leah Elizabeth Appel
Marshall David Crew
Dwayne Thomas Friesen
David Keith Lyon
Scott Baldwin Mccray
James Blair West
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Pfizer Products Inc
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Pfizer Products Inc
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Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc
Publication of CA2467611A1 publication Critical patent/CA2467611A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1611—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Abstract

An oral dosage form comprising azithromycin and an effective amount of an alkalizing agent. Preferably, said oral dosage form comprises an effective amount of an alkalizing agent and an azithromycin multiparticulate wherein said multiparticulate comprises azithromycin, a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and a poloxamer. Typically, the oral dosage form includes any suitable oral dosing means such as a powder for oral suspension, a unit dose packet or sachet, a tablet or a capsule. Additionally disclosed is an oral suspension comprising azithromycin, an effective amount of an alkalizing agent and a vehicle. Preferably, the azithromycin is in multiparticulate form wherein said multiparticulate comprises azithromycin, a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and a poloxamer. Also disclosed is a method for reducing gastrointestinal side effects, associated with administering azithromycin to a mammal, comprising contiguously administering azithromycin and an effective amount of alkalizing agent to said mammal wherein the frequency of gastrointestinal side effects is lower than that experienced by administering an equal dose of azithromycin without said alkalizing agent. Further disclosed is a method of treating a bacterial or protozoal infection in a mammal in need thereof comprising contiguously administering to said mammal a single dose of an oral dosage form wherein said oral dosage form comprises azithromycin and an effective amount of an alkalizing agent. Additionally disclosed are azithromycin multiparticulates comprising azithromycin, a surfactant; and a pharmaceutically acceptable carrier.

Claims (40)

1. An oral dosage form of azithromycin, comprising:
a) azithromycin; and b) an effective amount of an alkalizing agent.
2. An oral dosage form of Claim 1 wherein the alkalizing agent further comprises an aluminum salt, a magnesium salt, a calcium salt, a bicarbonate, a phosphate, a metal hydroxide, a metal oxide, N-methyl glucamine, arginine, an arginine salt, an amine, or a combination thereof.
3. An oral dosage form of Claims 1-2 wherein said azithromycin comprises an immediate release form of azithromycin.
4. An oral dosage form of Claims 1-2 wherein said azithromycin comprises a sustained release form of azithromycin.
5. An oral dosage form of Claims 1-2 wherein said azithromycin comprises azithromycin multiparticulates wherein said azithromycin multiparticulates further comprise:
(a) azithromycin; and (b) a pharmaceutically acceptable carrier.
6. An oral dosage form of Claim 5 wherein said carrier is a wax, a glyceride or a mixture thereof.
7. An oral dosage form of Claim 6 wherein said glyceride comprises a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate.
8. An oral dosage form of Claim 6 further comprising a dissolution enhancer.
9. An oral dosage form of Claim 8 wherein said dissolution enhancer comprises a surfactant selected from the group consisting of poloxamers, docusate salts, polyoxyethylene alkyl ethers, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters, sorbitan esters, alkyl sulfates, polysorbates and polyoxyethylene alkyl esters.
10. An oral dosage form comprising:
(a) an effective amount of an alkalizing agent; and (b) multiparticulates wherein said multiparticulates comprise (i) azithromycin, (ii) a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and (iii) a poloxamer.
11. An oral dosage form of Claim 10 wherein the poloxamer comprises poloxamer 407.
12. An oral dosage form of Claim 11 wherein the alkalizing agent comprises tribasic sodium phosphate.
13. An oral dosage form of Claim 12 wherein the alkalizing agent further comprises magnesium hydroxide.
14. An oral dosage form of Claims 1, 2, 10-13 further comprising about 250 mgA to about 7 gA of azithromycin.
15. An oral dosage form of Claim 14 further comprising 1.8 to 2.2 gA of azithromycin.
16. An azithromycin oral dosage form, comprising:
(a) at least about 200 mg of tribasic sodium phosphate;
(b) At least about 100 mg of magnesium hydroxide, and (c) multiparticulates, wherein said multiparticulates comprise (i) azithromycin, (ii) a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and (iii) poloxamer 407, and wherein said dosage form contains about 1.5 gA to about 4 gA of azithromycin.
17. An oral dosage form of Claim 16, further comprising:
(a) 300 mg to 400 mg of tribasic sodium phosphate; and (b) 200 mg to 300 mg of magnesium hydroxide.
18. An oral dosage form of Claim 17 further comprising 1.8 to 2.2 gA of azithromycin.
19. An oral dosage form of Claims 1-2, 10-13, and 16-8 wherein said azithromycin is azithromycin dihydrate.
20. An oral dosage form of Claims 1, 2, 10-13 and 16-18 wherein said azithromycin is at least 70 wt% crystalline.
21. A method for reducing the frequency of gastrointestinal side effects, associated with administering azithromycin to a human, comprising contiguously administering azithromycin and an effective amount of alkalizing agent to said human wherein the frequency of gastrointestinal side effects is reduced as compared to the frequency experienced when administering an equal dose of azithromycin without said alkalizing agent.
22. A method of treating a bacterial or protozoal infection in a human in need thereof comprising contiguously administering to said human azithromycin and an effective amount of an alkalizing agent.
23. A method of Claims 21-22 further comprising administering between about 250 mgA and about 7 gA of azithromycin to said human.
24. A method of Claim 23 wherein the azithromycin is administered in a single dose.
25. A method of Claim 24 further comprising administering between about 1.5 and about 4 gA of azithromycin.
26. A method of Claim 24 further comprising administering between 1.8 and 2.2 gA of azithromycin to said human in a single dose.
27. A method of Claims 21-22 further comprising administering between 30 mgA/kg and 90 mgA /kg of azithromycin to a human, wherein said human is a child weighing 30 kg or less.
28. A method of Claim 27 wherein the azithromycin is administered in a single dose.
29. A method of Claim 28 further comprising administering between 45 mgA/kg and 75 mgA /kg of azithromycin to a child weighing 30 kg or less.
30. A method of Claims 21-22 wherein said azithromycin comprises azithromycin multiparticulates wherein said azithromycin multiparticulates further comprise:
(a) azithromycin; and (b) a pharmaceutically acceptable carrier.
31. A method of Claim 30 wherein said carrier comprises a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate.
32. A method of Claim 30 wherein said azithromycin multiparticulates further comprise a dissolution enhancer.
33. A method of Claim 32 wherein said dissolution enhancer comprises a surfactant selected from the group consisting of poloxamers, docusate salts, polyoxyethylene alkyl ethers, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters, sorbitan esters, alkyl sulfates, polysorbates and polyoxyethylene alkyl esters.
34. A method of Claim 33 wherein the alkalizing agent comprises tribasic sodium phosphate.
35. A method of Claim 34 wherein the alkalizing agent further comprises magnesium hydroxide.
36. A method of Claims 25 and 29 wherein (a) the alkalizing agent comprises at least about 200 mg of tribasic sodium phosphate and at least about 100 mg of magnesium hydroxide; and (b) the azithromycin comprises azithromycin multiparticulates, wherein said multiparticulates comprise (i) azithromycin, (ii) a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and (iii) poloxamer 407.
37. A method of Claim 36 comprising contiguously administering to said human a single dose of an oral dosage form wherein said oral dosage form comprises:
(a) 300 mg to 400 mg of tribasic sodium phosphate;
(b) 200 mg to 300 mg of magnesium hydroxide; and (c) multiparticulates, wherein said multiparticulates comprise (i) azithromycin, (ii) a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate, and (iii) poloxamer 407, and wherein said dosage form contains 1.5 gA to 4 gA of azithromycin.
38. A method of Claim 37 wherein the azithromycin comprises azithromycin dihydrate.
39. Azithromycin multiparticulates comprising:
(a) azithromycin;
(b) a surfactant; and (b) a pharmaceutically acceptable carrier, wherein at least 70% of the azithromycin is crystalline.
40. A multiparticulate of Claim 39 wherein said surfactant comprises a poloxamer and said carrier comprises a mixture of glyceryl monobehenate, glyceryl dibehenate and glyceryl tribehenate.
CA2467611A 2003-12-04 2004-05-18 Azithromycin dosage forms with reduced side effects Active CA2467611C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US52708403P 2003-12-04 2003-12-04
US60/527,084 2003-12-04
US10/763,340 2004-01-23
US10/763,340 US6984403B2 (en) 2003-12-04 2004-01-23 Azithromycin dosage forms with reduced side effects

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CA2467611A1 true CA2467611A1 (en) 2005-06-04
CA2467611C CA2467611C (en) 2010-03-30

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US (4) US6984403B2 (en)
EP (1) EP1537859B1 (en)
JP (2) JP4602711B2 (en)
KR (1) KR100906290B1 (en)
AR (1) AR045630A1 (en)
AT (1) ATE407663T1 (en)
BR (1) BRPI0403935B8 (en)
CA (1) CA2467611C (en)
CL (1) CL2004001501A1 (en)
CR (1) CR7500A (en)
CY (1) CY1108486T1 (en)
DE (1) DE602004016444D1 (en)
DK (1) DK1537859T3 (en)
DO (1) DOP2004000994A (en)
EA (1) EA010110B1 (en)
ES (1) ES2312929T3 (en)
GE (1) GEP20074056B (en)
HK (1) HK1080367B (en)
HR (1) HRP20040865A2 (en)
IL (1) IL164165A (en)
IS (1) IS2672B (en)
MA (1) MA27848A1 (en)
MX (1) MXPA04009424A (en)
NL (1) NL1026315C2 (en)
NO (1) NO20043903L (en)
NZ (1) NZ535464A (en)
OA (1) OA12858A (en)
PA (1) PA8611501A1 (en)
PE (1) PE20050573A1 (en)
PL (2) PL1537859T3 (en)
PT (1) PT1537859E (en)
RS (1) RS84704A (en)
SI (1) SI1537859T1 (en)
TW (1) TWI351969B (en)
UY (1) UY28509A1 (en)
WO (1) WO2005053650A1 (en)

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