CA2484375C

CA2484375C - Oral dosage forms comprising fenofibrate

Oral dosage forms comprising fenofibrate Download PDF

Info

Publication number: CA2484375C
Authority: CA; Canada
Prior art keywords: dosage form; fenofibrate; amount; phospholipid; present
Prior art date: 2002-05-03
Legal status : Expired - Fee Related

Application number

CA2484375A

Other languages

English (en)

French (fr)

Other versions

CA2484375A1 (en

Inventor

Michael Vachon

Mishra K. Awadesh

Robert A. Snow

Pol-Henri Guivarc'h

Current Assignee

Jagotec AG

Original Assignee

Jagotec AG

Priority date

2002-05-03

Filing date

2003-05-02

Publication date

2012-04-10

2003-05-02 Application filed by Jagotec AG filed Critical Jagotec AG

2003-11-13 Publication of CA2484375A1 publication Critical patent/CA2484375A1/en

2012-04-10 Application granted granted Critical

2012-04-10 Publication of CA2484375C publication Critical patent/CA2484375C/en

2023-05-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 title claims abstract description 499
229960002297 fenofibrate Drugs 0.000 title claims abstract description 483
239000006186 oral dosage form Substances 0.000 title claims abstract description 24
150000003904 phospholipids Chemical class 0.000 claims abstract description 250
239000011859 microparticle Substances 0.000 claims abstract description 146
239000004067 bulking agent Substances 0.000 claims abstract description 103
239000013078 crystal Substances 0.000 claims abstract description 47
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 46
239000000463 material Substances 0.000 claims abstract description 46
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 46
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 32
229930195725 Mannitol Natural products 0.000 claims abstract description 32
235000010355 mannitol Nutrition 0.000 claims abstract description 32
239000000594 mannitol Substances 0.000 claims abstract description 32
239000011159 matrix material Substances 0.000 claims abstract description 29
239000011324 bead Substances 0.000 claims abstract description 26
239000000654 additive Substances 0.000 claims abstract description 24
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 23
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 23
230000000996 additive effect Effects 0.000 claims abstract description 22
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 22
239000005913 Maltodextrin Substances 0.000 claims abstract description 21
229920002774 Maltodextrin Polymers 0.000 claims abstract description 21
229940035034 maltodextrin Drugs 0.000 claims abstract description 21
235000019333 sodium laurylsulphate Nutrition 0.000 claims abstract description 21
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims abstract description 19
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims abstract description 19
239000000337 buffer salt Substances 0.000 claims abstract description 19
239000000377 silicon dioxide Substances 0.000 claims abstract description 16
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 15
229920002785 Croscarmellose sodium Polymers 0.000 claims abstract description 13
229960000913 crospovidone Drugs 0.000 claims abstract description 13
229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims abstract description 13
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims abstract description 13
235000012239 silicon dioxide Nutrition 0.000 claims abstract description 13
229960001681 croscarmellose sodium Drugs 0.000 claims abstract description 12
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims abstract description 12
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract 5
239000002552 dosage form Substances 0.000 claims description 225
239000007787 solid Substances 0.000 claims description 76
239000002775 capsule Substances 0.000 claims description 63
238000002156 mixing Methods 0.000 claims description 49
239000008280 blood Substances 0.000 claims description 46
210000004369 blood Anatomy 0.000 claims description 46
238000011282 treatment Methods 0.000 claims description 39
239000000843 powder Substances 0.000 claims description 36
241000124008 Mammalia Species 0.000 claims description 34
238000001035 drying Methods 0.000 claims description 33
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 28
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 21
239000008101 lactose Substances 0.000 claims description 21
239000001768 carboxy methyl cellulose Substances 0.000 claims description 16
238000003801 milling Methods 0.000 claims description 16
235000019359 magnesium stearate Nutrition 0.000 claims description 14
229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 10
239000007900 aqueous suspension Substances 0.000 claims description 10
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 10
239000008112 carboxymethyl-cellulose Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000000872 buffer Substances 0.000 claims description 8
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 7
229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 7
239000008119 colloidal silica Substances 0.000 claims description 5
229940075614 colloidal silicon dioxide Drugs 0.000 claims description 5
239000001488 sodium phosphate Substances 0.000 claims description 5
229910000162 sodium phosphate Inorganic materials 0.000 claims description 5
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 5
239000008344 egg yolk phospholipid Substances 0.000 claims description 4
239000011253 protective coating Substances 0.000 claims description 4
239000002245 particle Substances 0.000 description 332
239000003814 drug Substances 0.000 description 292
229940079593 drug Drugs 0.000 description 288
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239000003826 tablet Substances 0.000 description 140
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
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238000009472 formulation Methods 0.000 description 93
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238000000265 homogenisation Methods 0.000 description 86
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238000002844 melting Methods 0.000 description 79
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238000001816 cooling Methods 0.000 description 56
238000000576 coating method Methods 0.000 description 46
239000011248 coating agent Substances 0.000 description 42
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 36
229930006000 Sucrose Natural products 0.000 description 36
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 36
239000005720 sucrose Substances 0.000 description 36
239000012530 fluid Substances 0.000 description 34
-1 magnesium stearate Chemical class 0.000 description 33
150000002632 lipids Chemical class 0.000 description 31
239000003925 fat Substances 0.000 description 30
235000019197 fats Nutrition 0.000 description 30
238000003756 stirring Methods 0.000 description 30
229920000642 polymer Polymers 0.000 description 29
MQOBSOSZFYZQOK-UHFFFAOYSA-N fenofibric acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 MQOBSOSZFYZQOK-UHFFFAOYSA-N 0.000 description 28
229960000701 fenofibric acid Drugs 0.000 description 28
235000012054 meals Nutrition 0.000 description 28
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 27
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 27
235000013305 food Nutrition 0.000 description 27
239000000600 sorbitol Substances 0.000 description 27
239000008187 granular material Substances 0.000 description 26
239000000049 pigment Substances 0.000 description 26
239000003795 chemical substances by application Substances 0.000 description 25
239000008363 phosphate buffer Substances 0.000 description 25
230000000087 stabilizing effect Effects 0.000 description 25
238000004108 freeze drying Methods 0.000 description 24
238000002360 preparation method Methods 0.000 description 24
239000000243 solution Substances 0.000 description 24
239000007788 liquid Substances 0.000 description 23
235000000346 sugar Nutrition 0.000 description 22
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 21
239000003381 stabilizer Substances 0.000 description 21
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 20
239000013543 active substance Substances 0.000 description 20
230000009246 food effect Effects 0.000 description 20
239000008194 pharmaceutical composition Substances 0.000 description 20
235000021471 food effect Nutrition 0.000 description 19
239000007921 spray Substances 0.000 description 19
235000013601 eggs Nutrition 0.000 description 18
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 16
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 16
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238000007792 addition Methods 0.000 description 15
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 15
150000001720 carbohydrates Chemical class 0.000 description 15
235000014633 carbohydrates Nutrition 0.000 description 15
239000000306 component Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
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235000019441 ethanol Nutrition 0.000 description 11
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235000002639 sodium chloride Nutrition 0.000 description 11
LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 10
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GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
108010007622 LDL Lipoproteins Proteins 0.000 description 8
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UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 8
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WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 6
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
239000008121 dextrose Substances 0.000 description 5
BPHQZTVXXXJVHI-UHFFFAOYSA-N dimyristoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-UHFFFAOYSA-N 0.000 description 5
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