CA1322529C - Dosage form of fenofibrate - Google Patents

Dosage form of fenofibrate

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Publication number
CA1322529C
CA1322529C CA000589673A CA589673A CA1322529C CA 1322529 C CA1322529 C CA 1322529C CA 000589673 A CA000589673 A CA 000589673A CA 589673 A CA589673 A CA 589673A CA 1322529 C CA1322529 C CA 1322529C
Authority
CA
Canada
Prior art keywords
fenofibrate
therapeutic composition
composition according
sulfate
sodium lauryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA000589673A
Other languages
French (fr)
Inventor
Bernard Curtet
Eric Teillaud
Philippe Reginault
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fournier Industrie et Sante SAS
Original Assignee
Fournier Industrie et Sante SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Fournier Industrie et Sante SAS filed Critical Fournier Industrie et Sante SAS
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Classifications

    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61K9/145—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 organic 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics

Abstract

ABSTRACT OF THE DISCLOSURE
The present invention relates to a novel dosage form of fenofibrate containing fenofibrate and a solid surfactant which have been co-micronized.
It also relates to the method for the prepara-tion of this dosage form and its use for improving the bioavailability in vivo.

Description

22:~2~

NOVEL DOSAGE FORM OF FE~OFIBRATF
The present invention relates to a novel dosage form of fenofibrate. It relates more precisely to a therapeutic composition containing fenofibrate and ensuring an improved bioavailability, and to a method for the preparation of this composition.
Fenofibrate (international common name), which is recommended in the treatment of hyperlipidemia and hypercholesterolemia, corresponds to the nomenclature isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-propionate. The customary adult dosage is three gelatincapsules per day, each containing 100 mg of fenofibrate.
For the patient's comfort, it is advantageous to try and find a dosage form which has to be taken only once a day and whose physiological effect is lS identical to that obtained when multiple doses are taken. A gelatin capsule containing 300 mg of feno-fibrate has therefore been proposed, the dosage recommended in this case bein8 only one administration per day.
However, it is possible to try and improve the dosage form still further. It is known, in fact, that the bioavailability of fenofibrate is not equal to 100%. It is therefore desirable to develop a dosage form in which the bioavailability of the fenofibrate is improved and which can be administered only once a day.
It is known that the micronization of an active principle is capable of improving the dissolution of the said active principle in vivo, and hence its bio-availability. It is also known that the addition of a .~

.
., .

- 1~22~29 surfactant excipient to a formulation of an active principle is capable of improving the absorption and consequently the bioavailability of the said active principle.
It has now been discovered that the co-micro-nization of fenofibrate and a solid surfactant (i.e. the micronization of an intimate mixture of fenofibrate and a solid surfactant) makes it possible to improve the bioavailability of the fenofibrate to a significantly greater extent than that which would be achieved either by adding a surfactant, or by micronizing the fenofibrate on its own, or by intimately mixing the separately micronized fenofibrate and surfactant.
The present invention therefore proposes a novel therapeutic composition, which is useful especially in the oral treatment of hyperlipidemia and hypercholesterolemia, the said composition containing fenofibrate and a solid surfactant which have been co-micronized.
The recommended amount of fenofibrate is about 200 mg per therapeutic unit.
The surfactant will be selected from solid surfactants so that it can be co-micronized with the fenofibrate. An alkali metal sulfate of lauryl alcohol, for example sodium lauryl-sulfate (alternative name:
sodium dodecyl-sulfate), will be preferred. The recommended amount of sodium lauryl-sulfate will be between 0.5% and 7% by weight, relative to the total weight of the formulation. The weight ratio surfactant/
fenofibrate will advantageously be between about 0.75/
100 and 10.5tlO0.
The co-micronization of the fenofibrate and the solid surfactant will advantageously be carried out in an accelerated air-jet mill until the powder obtained is such that the mean particle size is less than 15 ~m, r ~ A
AJ

~22~29 preferably less than lO ~m and particularly preferably less than 5 ~m.
To obtain a powder which can be formulated into gelatin capsules, conventional filling, dispersing and flow-enhancing excipients, for example lactose, starch, polyvinylpyrrolidone and magnesium stearate, may be added to the co-micronizate of fenofibrate and solid surfactant.
According to the invention, a method for the preparation of a therapeutic composition containing fenofibrate and a solid surfactant is recommended which comprises:
(i) intimately mixing and then co-micronizing the fenofibrate and the solid surfactant, (ii) adding lactose and starch to the mixture obtained, (iii) converting the whole to granules in the presence of water, (iv) drying the granules until they contain no more than 1% of water, (v) grading the granules, (vi) adding polyvinylpyrrolidone and magnesium stearate to the graded granules, and (vii) filling gelatin capsules with the mixture obtained in stage (vi).
The invention will be understood more clearly from the description of the Preparative Examples which follow and from the description of the results obtained in comparative tests, which show that the invention is non-obvious.

PREPARATION I
For 100,000 gelatin capsules, each weighing 350 mg and containing 200 mg of fenofibrate, the amounts of products used are as follows:

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~ 3 ~ 2 91 fenofibrate : 20.0 kg sodium lauryl-sulfate : 0.7 kg ~-lactose monohydrate : lO.l kg pregelatinized starch : 3.0 kg crosslinked polyvinyl-pyrrolidone : 0.7 kg magnesium stearate : 0.5 kg The fenofibrate/sodium lauryl-sulfate mixture is co-micronized in an air-jet micronizer to give a powder with a median particle size of 3 ~m. The lactose and the starch are then added to this powder and the whole is converted to granules in the presence of 8.9%
of distilled water, relative to the total weight of the mixture. The granules obtained in this way are dried for one day at 50C and then graded so as to retain only the particles with sizes less than or equal to 1000 ~m. The polyvinylpyrrolidone and the magnesium stearate are then added and the whole is mixed until homogeneous. The powder obtained is used to fill size 1 gelatin capsules on an automatic machine with the compression set to a maximum of 150 N.

PREPARATION II
_ _ _ _ The procedure indicated in Preparation I is followed using a fenofibrate/sodium lauryl-sulfate mixture with a median particle size of 6-7 ~m.

PREPARATION III
_ _ For lOO,OOO size 1 gelatin capsules, each weighing 297 mg and containing 200 mg of active principle, the amounts of products used are as follows:

fenofibrate : 20.0 kg sodium lauryl-sulfate : 0.3 kg d-lactose monohydrate : 6.8 kg pregelatinized starch : 1.5 kg crosslinked polyvinyl-pyrrolidone : 0.6 kg magnesium stearate : 0.5 kg The procedure is analogous to that used for Preparation I, the co-micronization of the fenofibrate/
sodium lauryl-sulfate mixture being such that the median particle size is 6-7 ~m and the granulation being carried out in the presence of 10% of distilled water, relative to the weight of the fenofibrate/sodium lauryl-sulfate/lactose/starch mixture.

PREPARATION IV
... . _ Following a procedure analogous to that described in Preparation I, using a co-micronized mixture of fenofibrate and sodium lauryl-sulfate with a median particle size of 6-7 ~m, the formulations collated in Table I below were prepared:

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2 ~ .

TABLE I

COMPOSITION (in mg) PER GELATIN CAPSULE

FORMULATION
INGRE~IENT
. A B C D E F

Fenofibrate 200 200 200 200 200200 Na lauryl-sulfate0 3 7 12 17.526.5 Lactose 108 105 101 95 90.583.5 Starch 30 30 30 30 30 30 15 Polyvinylpyrrolidone7 7 7 7 7 7 Mg stearate 5 5 5 5 5 5 .
.. Percentage of Na lauryl-sulfate 00.86 2 3.4 57.53 Taking these formulations, the dissolution curve shown in Figure 1 was plotted, the percentage of dissolved fenofibrate (Y) being given as a function of the percentage of sodium lauryl-sulfate contained in the formulation (X). The dissolution kinetics are determined, as specified in the European Pharmacopoeia, using a rotating-vane apparatus, the eluent consisting of water and 0.1 M sodium lauryl-sulfate. The feno-fibrate is determined by UV spectrophotometry at 282 nm. The curve in Figure 1 is given by the values obtained after 20 minutes.
These results show that 82% of fenofibrate is : dissolved at a sodium lauryl-sulfate concentration of 0%, 87% of fenofibrate is dissolved at a concentration ~ .
,:

of 0.5%, 92% of fenofibrate is dissolved at a con-centration of 1% and a maximum dissolution of 95 to 96% of fenofibrate is obtained as from a sodium lauryl-sulfate concentration of 4%.
The dissolution curves were also plotted, in a continuous-flow cell with a flow rate of 20 ml/min of 0.1 M sodium lauryl-sulfate, for formulations containing co-micronized fenofibrate and sodium lauryl-sulfate (NaLS), by comparison with micronized feno-fibrate and with formulations obtained by intimately mixing separately micronized fenofibrate and lauryl-sulfate. The comparison is made by means of T 50%, i.e. the time required for 50% of the fenofibrate to dissolve. The results obtained are collated in Table II
below:

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. - : . . :~, ,, :

- 8 - ~ ~22~

TABLE II

VALUE OF THE T 50% TIMES (in minutes) _ .
INGREDIENTS C
Micronized pure fenofibrate 37.165 37.165 O

Fenofibrate + 1%
of NaLS 18.018.62 -52.14 Fenofibrate + 3%
15 of NaLS 23.75 12.68 -46.61 Fenofibrate + 5%
of NaLS 20.35 ll.425 -43.86 Fenofibrate + 7%
20 of NaLS 14.5 10.76 -25.79 Notes A: mixture of micronizates B: co-micronization of the mixture of ingredients C: variation B - A x 100 (in %) A
.. .. i These results show that the T 50% of the feno-fibrate is very significantly reduced (hence the dis-solution rate of the fenofibrate is very significantly increased) when the fenofibrate and the sodium lauryl-sulfate are co-micronized, compared with the mixture of . separately micronized fenofibrate and sodium laury~-sulfate and compared with fenofibrate alone.

.~ .

~ 3 ~ 9 _ 9 The dissolution rate of fenofibrate is correlated with the bioavailability of fenofibrate, which increases with the dissolution rate. The above results show that it was not within the understanding of those skilled in the art to prepare a therapeutic composition characterized by the co-micronization of fenofibrate and a solid surfactant.
These results have been confirmed in clinical trials. Fenofibrate was administered to groups of healthy subjects, (a) in the form of a single adminis-tration (1 gelatin capsule) of 300 mg of non-micronized fenofibrate (marketed under the tradename "LIPANTHYL
300") and (b) in the form of a single administration of 200 mg of co-micronized fenofibrate obtained according to Preparation III described above. Blood samples are taken from the subjects at regular intervals and one of the active metabolites - 2-[4-(4-chloro-benzoyl)phenoxy]-2-methylpropionic acid - is determined.
The curve showing the concentration of this metabolite as a function of time is plotted and the area under the curve [AUC(O- ~)], expressed in mg/l.h, is calculated.
The results obtained are shown in Table III
below:

TABLE III

BIOAVAILABILITY FENOFIBRATE FENOFIBRATE
PARAMETER200 mg 3o(o2)mg AUC(O- ~)(mg/l.h) 174.15 i 48.67 168.85 ~ 57.6 C msx (mg/l)10.86 ~ 2.13 10.39 i 2.89 t max (h) 5.97 + 2.50 5.52 1 1.70 t 1/2 (h) 15.13 i 4.27 -17.79 + 8.77 , Notes (1) co-micronized fenofibrate (200 mg) (2) non-micronized fenofibrate (300 mg) ~ ~ r~

The }esults in Table III show that there is not a statistically significant difference between the in vivo bioavailability of 200 mg of co-micronized fenofibrate according to the invention and 300 mg of non-micronized fenofibrate (which is currently the preferred dosage form for a single daily administration).
In other words, co-micronized fenofibrate at a 200 mg dose is bioequivalent to non-micronized fenofibrate at a 300 mg dose.
According to another aspect of the invention, a method for improving the bioavailability of feno-fibrate in vivo is recommended, the said method comprising co-micronization of the fenofibrate and a solid sur-factant, the said co-micronization being carried out by micronization of a fenofibrate/solid surfactant mixture until the particle size of the powder obtained is less than 15 ~m and preferably less than or equal to 5 /um.

: ` :

Claims (11)

1. A therapeutic composition which is useful especially in the oral treatment of hyperlipidemia and hypercholesterolemia, said composition containing fenofibrate and a solid surfactant which have been co-micronized.
2. The therapeutic composition according to claim 1, wherein the weight ratio surfactant/fenofibrate is between about 0.75/100 and 10.5/100.
3. The therapeutic composition according to claim 1, wherein the amount of fenofibrate is equal to 200 mg per therapeutic unit.
4. The therapeutic composition according to claim 1, wherein the solid surfactant is sodium lauryl-sulfate.
5. The therapeutic composition according to claim 4, wherein the amount of sodium lauryl-sulfate is between 0.5 and 7% by weight, relative to the total weight of the formulation.
6. The therapeutic composition according to claim 1, wherein the mean particle size of the co-micronized fenofibrate and sodium lauryl-sulfate is less than 15 µm, preferably less than or equal to 10 µm and particularly preferably less than or equal to 5 µm.
7. The therapeutic composition according to claims 1, 2, 3, 4, 5 or 6, which also contains excipients such as dispersants, fillers and flow enhancers.
8. A method for the manufacture of a therapeutic composition according to claim 1, which comprises:

(i) intimately mixing and then co-micronizing the fenofibrate and a solid surfactant, (ii) adding lactose and starch to the mixture obtained, (iii) converting the whole to granules in the presence of water, (iv) drying the granules until they contain no more than 1% of water, (v) grading the granules, (vi) adding polyvinylpyrrolidone and magnesium stearate, and (vii) filling gelatin capsules.
9. The method according to claim 8, wherein the mean particle size of the co-micronized fenofibrate and sodium lauryl-sulfate is less than 15 µm.
10. A method for improving the bioavailability of fenofibrate in vivo, which comprises co-micronization of the fenofibrate and a solid surfactant, said co-micronization being carried out by micronization of a fenofibrate/solid surfactant mixture until the particle size of the powder obtained is less than 15 µm and preferably less than or equal to 5 µm.
11. A therapeutic composition according to claim 1, which is presented in the form of gelatin capsules.
CA000589673A 1988-02-26 1989-01-31 Dosage form of fenofibrate Expired - Lifetime CA1322529C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8802359A FR2627696B1 (en) 1988-02-26 1988-02-26 NEW GALENIC FORM OF FENOFIBRATE
FR8802359 1988-02-26

Publications (1)

Publication Number Publication Date
CA1322529C true CA1322529C (en) 1993-09-28

Family

ID=9363657

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000589673A Expired - Lifetime CA1322529C (en) 1988-02-26 1989-01-31 Dosage form of fenofibrate

Country Status (11)

Country Link
US (1) US4895726A (en)
EP (1) EP0330532B1 (en)
JP (1) JPH0714876B2 (en)
AT (1) ATE83374T1 (en)
AU (1) AU614577B2 (en)
CA (1) CA1322529C (en)
DE (1) DE68903846T2 (en)
ES (1) ES2054040T3 (en)
FR (1) FR2627696B1 (en)
GR (1) GR3006798T3 (en)
NZ (1) NZ228130A (en)

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