WO2003009854A1 - Lipid lowering composition comprising carnitine and phytosterol - Google Patents

Lipid lowering composition comprising carnitine and phytosterol Download PDF

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Publication number
WO2003009854A1
WO2003009854A1 PCT/EP2002/004663 EP0204663W WO03009854A1 WO 2003009854 A1 WO2003009854 A1 WO 2003009854A1 EP 0204663 W EP0204663 W EP 0204663W WO 03009854 A1 WO03009854 A1 WO 03009854A1
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Prior art keywords
carnitine
phytosterol
composition
present
phytostanol
Prior art date
Application number
PCT/EP2002/004663
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French (fr)
Inventor
Gilles Reiss
Original Assignee
Lonza Ag
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Publication date
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Publication of WO2003009854A1 publication Critical patent/WO2003009854A1/en

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    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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

Definitions

  • the present invention relates to field of nutritional suppelements for human consumption and in particular to compositions comprising L-carnitine and at least one phytosterol or phystostanol.
  • Elevated blood serum levels of triglycerides and cholesterol are a major cause of arteriosclerotic disease.
  • the object of the present invention is to avoid the disadvantages of prior art and to devise a composition that can be used as a lipid-lowering, in particular cholesterol lowering, agent.
  • composition comprising L-carnitine and a phytosterol or derivative thereof.
  • a composition according to the present invention comprises carnitine or Acyl-carnitine or a salt thereof and at least one phytosterol or phytostanol or a derivative thereof.
  • Carnitine is racemic (DL)-Carnitine or, preferably, essentially pure L-Carnitine.
  • Such Carnitine may as well be an Acyl-Carnitine (3-Acyloxy-(N- trimethyl-)-4-amino-butyric acid), in particular 3-Acetyl- or 3-Propionyl-Caraitine.
  • the Carnitine may be employed either as an inner salt or as a simple or complex salt together with other ionic substances such as, but not limited to, chloride, fumarate, tartrate, citrate, isocitrate, (-)-hydroxycitrate, magnesium, calcium, cholin, either alone or in suitable combinations, particularly as non-hygroscopic complex salts, e.g. L-Carnitine-magnesium-citrate, L-
  • Carnitine-magnesium-(-)hydroxycitrate or L-Carnitine-cholin-tartrate is either L-Carnitine-tartrate, L- Carnitine-magnesium-citrate or L-Carnitine-magnesium-(-)-hydroxycitrate.
  • Carnitine is, in its L-form, a naturally occurring compound involved in energy metabolism in mitochondria that has been used as a nutritional supplement for decades now and without adverse effects having been reported.
  • Carnitine has proven to have lipid lowering effects, in particular carnitine administration has been shown to lower serum cholesterol levels (Cacciatore, L. et al., 1991, Drugs Exp. Clin. Res.
  • the carnitine according to the present invention is L-carnitine or a salt thereof.
  • the carnitine according to the present invention is Acetyl-L-carnitine or Propionyl-L-carnitine or salts thereof.
  • lipid-lowering effect of carnitine or acyl- carnitine is enhanced if administered together with a phytosterol or phytostanol.
  • Phytosterols according to the present invention are plant sterols found, for example, in small amounts in vegetable oils such as corn, bean or other plant oils, where they occur as the free sterols, fatty acid esters and glycosides, the latter two being examples of suitable derivatives according to the present invention. It is also possible e.g. to employ non-natural esters such as esters with ascorbic acid as described in WOOl/00653.
  • esters Prefered derivatives are esters, more preferably C18-C26 fatty acid esters, most preferably the esters of omega-3 polyunsaturated fatty acids such as dodecosahexanoic acid (DHA) or Eicospentanoic acid (EPA).
  • DHA dodecosahexanoic acid
  • EPA Eicospentanoic acid
  • Omega-3 PUFAs are known for cardioprotective and lipid- lowering effects both if applied as free acid or as a synthetic ester.
  • L-carnitinoyl- or Acyl-L- carnitinoyl-esters of phytosterols or phytostanols are also possible to employ, in a further preferred embodiment, L-carnitinoyl- or Acyl-L- carnitinoyl-esters of phytosterols or phytostanols. Said esters are cleaved in vivo in order to produce the combination medicine of the the present invention.
  • Stanol- or sterol-esters according to the present invention preferably have a Gardner color value of less than 5, more preferably less than about 4 and most preferably less than about 3 on the Gardner color scale.
  • the Gardner color scale is known to those in the art.
  • the solid ester product is formed into a block and the color block is compared to samples of a predetermined color.
  • Phytosterols are structurally similiar to cholesterol, the main differences occuring in carbon skeleton of their side chains. Phytosterols are capable of lowering serum cholesterol (Kuccodkar et al., 1976, Effects of plant sterols on cholesterol metabolism, Artheriosclerosis, 23:239 and US 5770749). A number of different phytosterol structures are found in nature. The most common ones are campesterol, beta-sitosterol and stigmasterol. Reduction of phytosterols yields saturated phytosterols, called phytostanols, such as campestantol or sitostanol, which also occur naturally in small amounts. A normal human diet typically leads to ingestion of less than one half gram a day of such substances in various forms.
  • the composition according to the present invention comprises a mixture of several phytosterols which has been found to be highly effective in lowering serum cholesterol as disclosed in US 5770 749.
  • Prefered derivatives as defined above also apply to such embodiment.
  • Such mixture comprises no more than 70% by weight of beta-sitosterol, at least 10% by weight campersterol and stigmasterol (beta-sitostanol).
  • the phytosterol/phytostanol is beta-sitosterol or stigmasterol and campesterol, or beta-sitostanol and campestanol or mixtures therof. Most preferred are beta-sitosterol, beta-sitostanol or mixtures therof.
  • composition according to the present invention may not only be ingested, i.e. taken orally, but may be applied in any way, e.g. parenterally by means of injection or infusion.
  • a suitable pharmaceutical or nutritional composition according to the present invention incorporates a pharmaceutically acceptable carrier.
  • the pharmaceutically acceptable carrier is a tablet, capsule, microbead, emulsion, powder, granule, suspension, syrup, an effervescent preparation or elixir.
  • Such compositions may comprise carnitine and phytosterol in admixture with one or more of the following agents: sweeteners, flavoring agents, coloring agents, pharmaceutical excepients and preservatives.
  • “Pharmaceutically acceptable” means that the agent should be acceptable in the sense of being compatible with the other ingredients of the formulation (as well as non-injurious to the individual).
  • excipients include inert diluents such as calcium carbonate, sodium carbonate, lactose, calcium phosphate or sodium phosphate; granulating and disintegrating agents, such as corn starch and alginic acid; binding agents such as starch, gelatin or acacia; and lubricating agents such as magnesium stearate, stearic acid or talc. Tablets or capsules may be uncoated or may be coated with known techniques to delay disintegration and absorption in the gastrointestinal tract and thereby provide a sustained action over a longer period of time.
  • a time delay material such as glyceryl monostearate or glyceryl stearate alone or with a wax may be employed.
  • a pharmaceutical dosage form as described above comprising the composition of the present invention is a further object of the present invention.
  • composition according to the present invention may as well be administered as an ingredient of a nutrional supplement such as a beverage, a cookie, an energy/cereals bar and the like.
  • a nutrional supplement such as a beverage, a cookie, an energy/cereals bar and the like.
  • the amount of carnitine to be administered to a human per day or dosage is 0.05 g to 8 g, more preferably 0.2 to 4 g of carnitine, most preferably 0.5 to 2 g according to the present invention.
  • the mixing ratio with the phytosterol/phytostanol or a derivative thereof according to the present invention can be in the range from 1 :100 to 100:1, more preferably in the range of 1:10 to 10:1.
  • the amount of phytosterol/phytostanol to be administered to a human per day or dosage is 0.05 g to 0.8 g, more preferably in the range of 0.2 to 4 g, most preferably in the range of 0.5 to 2 g.
  • a hard gelatine capsule is filled with a powder mixture.
  • the particle size is ⁇ 0.8 ⁇ m.
  • the powder has been mixed by addition of the fine-milled, solid compounds in a conventional knedding machine.
  • the composition of the powder mixture is given below:
  • VitosterolTM (Forbes Medi-Tech Inc.) lg
  • Polyvinylpolypyrrolidon 10 mg Two such capsules may be ingested per day, for instance.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A lipid lowering composition comprising carnitine and at least one phytosterole or phytostanol is described.

Description

I PID LOWERING COMPOSITION COMPRISING CARNITINE AND PHYTOSTEROL
The present invention relates to field of nutritional suppelements for human consumption and in particular to compositions comprising L-carnitine and at least one phytosterol or phystostanol.
Elevated blood serum levels of triglycerides and cholesterol are a major cause of arteriosclerotic disease.
The object of the present invention is to avoid the disadvantages of prior art and to devise a composition that can be used as a lipid-lowering, in particular cholesterol lowering, agent.
This object is achieved by a composition comprising L-carnitine and a phytosterol or derivative thereof.
A composition according to the present invention comprises carnitine or Acyl-carnitine or a salt thereof and at least one phytosterol or phytostanol or a derivative thereof.
Carnitine according to the present invention is racemic (DL)-Carnitine or, preferably, essentially pure L-Carnitine. Such Carnitine may as well be an Acyl-Carnitine (3-Acyloxy-(N- trimethyl-)-4-amino-butyric acid), in particular 3-Acetyl- or 3-Propionyl-Caraitine. The Carnitine may be employed either as an inner salt or as a simple or complex salt together with other ionic substances such as, but not limited to, chloride, fumarate, tartrate, citrate, isocitrate, (-)-hydroxycitrate, magnesium, calcium, cholin, either alone or in suitable combinations, particularly as non-hygroscopic complex salts, e.g. L-Carnitine-magnesium-citrate, L-
Carnitine-magnesium-(-)hydroxycitrate or L-Carnitine-cholin-tartrate. In even more preferred embodiments, Carnitine according to the present invention is either L-Carnitine-tartrate, L- Carnitine-magnesium-citrate or L-Carnitine-magnesium-(-)-hydroxycitrate. Carnitine is, in its L-form, a naturally occurring compound involved in energy metabolism in mitochondria that has been used as a nutritional supplement for decades now and without adverse effects having been reported. Carnitine has proven to have lipid lowering effects, in particular carnitine administration has been shown to lower serum cholesterol levels (Cacciatore, L. et al., 1991, Drugs Exp. Clin. Res. 17:225) and serum triglyceride levels (Maebashi, M. et al., 1978, Lipid- lowering effect of carnitine in patients with type-IV hyperlipoproteinmia, Lancet 2:805; Spagnoli, L. et al., 1995, Propionyl-L-carnitine prevents the progression of atherosclerotic lesions in aged hyperlipemic rabits, Artheriosclerosis 114:29).
Preferably, the carnitine according to the present invention is L-carnitine or a salt thereof.
Further prefered, the carnitine according to the present invention is Acetyl-L-carnitine or Propionyl-L-carnitine or salts thereof.
Surprisingly, according to the present invention, the lipid-lowering effect of carnitine or acyl- carnitine is enhanced if administered together with a phytosterol or phytostanol. Phytosterols according to the present invention are plant sterols found, for example, in small amounts in vegetable oils such as corn, bean or other plant oils, where they occur as the free sterols, fatty acid esters and glycosides, the latter two being examples of suitable derivatives according to the present invention. It is also possible e.g. to employ non-natural esters such as esters with ascorbic acid as described in WOOl/00653. Prefered derivatives are esters, more preferably C18-C26 fatty acid esters, most preferably the esters of omega-3 polyunsaturated fatty acids such as dodecosahexanoic acid (DHA) or Eicospentanoic acid (EPA). The preparation of such esters is described in EP 1004 594. Omega-3 PUFAs are known for cardioprotective and lipid- lowering effects both if applied as free acid or as a synthetic ester.
It is also possible to employ, in a further preferred embodiment, L-carnitinoyl- or Acyl-L- carnitinoyl-esters of phytosterols or phytostanols. Said esters are cleaved in vivo in order to produce the combination medicine of the the present invention.
Stanol- or sterol-esters according to the present invention preferably have a Gardner color value of less than 5, more preferably less than about 4 and most preferably less than about 3 on the Gardner color scale. The Gardner color scale is known to those in the art. The solid ester product is formed into a block and the color block is compared to samples of a predetermined color.
Phytosterols are structurally similiar to cholesterol, the main differences occuring in carbon skeleton of their side chains. Phytosterols are capable of lowering serum cholesterol (Kuccodkar et al., 1976, Effects of plant sterols on cholesterol metabolism, Artheriosclerosis, 23:239 and US 5770749). A number of different phytosterol structures are found in nature. The most common ones are campesterol, beta-sitosterol and stigmasterol. Reduction of phytosterols yields saturated phytosterols, called phytostanols, such as campestantol or sitostanol, which also occur naturally in small amounts. A normal human diet typically leads to ingestion of less than one half gram a day of such substances in various forms.
Preferably, the composition according to the present invention comprises a mixture of several phytosterols which has been found to be highly effective in lowering serum cholesterol as disclosed in US 5770 749. Prefered derivatives as defined above also apply to such embodiment. Such mixture comprises no more than 70% by weight of beta-sitosterol, at least 10% by weight campersterol and stigmasterol (beta-sitostanol).
In a further prefeπed embodiment, the phytosterol/phytostanol is beta-sitosterol or stigmasterol and campesterol, or beta-sitostanol and campestanol or mixtures therof. Most preferred are beta-sitosterol, beta-sitostanol or mixtures therof.
The composition according to the present invention may not only be ingested, i.e. taken orally, but may be applied in any way, e.g. parenterally by means of injection or infusion. Preferably, a suitable pharmaceutical or nutritional composition according to the present invention incorporates a pharmaceutically acceptable carrier. In a preferred embodiment, the pharmaceutically acceptable carrier is a tablet, capsule, microbead, emulsion, powder, granule, suspension, syrup, an effervescent preparation or elixir. Such compositions may comprise carnitine and phytosterol in admixture with one or more of the following agents: sweeteners, flavoring agents, coloring agents, pharmaceutical excepients and preservatives. "Pharmaceutically acceptable" means that the agent should be acceptable in the sense of being compatible with the other ingredients of the formulation (as well as non-injurious to the individual). Such excipients include inert diluents such as calcium carbonate, sodium carbonate, lactose, calcium phosphate or sodium phosphate; granulating and disintegrating agents, such as corn starch and alginic acid; binding agents such as starch, gelatin or acacia; and lubricating agents such as magnesium stearate, stearic acid or talc. Tablets or capsules may be uncoated or may be coated with known techniques to delay disintegration and absorption in the gastrointestinal tract and thereby provide a sustained action over a longer period of time. For example, a time delay material such as glyceryl monostearate or glyceryl stearate alone or with a wax may be employed. A pharmaceutical dosage form as described above comprising the composition of the present invention is a further object of the present invention.
The composition according to the present invention may as well be administered as an ingredient of a nutrional supplement such as a beverage, a cookie, an energy/cereals bar and the like.
Preferably, the amount of carnitine to be administered to a human per day or dosage is 0.05 g to 8 g, more preferably 0.2 to 4 g of carnitine, most preferably 0.5 to 2 g according to the present invention. The mixing ratio with the phytosterol/phytostanol or a derivative thereof according to the present invention can be in the range from 1 :100 to 100:1, more preferably in the range of 1:10 to 10:1. Preferably, the amount of phytosterol/phytostanol to be administered to a human per day or dosage is 0.05 g to 0.8 g, more preferably in the range of 0.2 to 4 g, most preferably in the range of 0.5 to 2 g.
Examples
Example 1
Pharmaceutical dosage form
A hard gelatine capsule is filled with a powder mixture. The particle size is <0.8 μm. The powder has been mixed by addition of the fine-milled, solid compounds in a conventional knedding machine. The composition of the powder mixture is given below:
L-Carnitine (Carnitine-tartrate) 1 g
Vitosterol™ (Forbes Medi-Tech Inc.) lg
Sodium-stearate 1.5 mg microcrystalline cellulose 40 mg
Vitamine E 2 mg Lactose 37 mg
Talcum 5 mg
Sodium-carboxymethyl-starch 10 mg
Polyvinylpolypyrrolidon 10 mg Two such capsules may be ingested per day, for instance.

Claims

Claims
1. A composition comprising carnitine or Acyl-carnitine or a salt thereof and at least one phytosterol or phytostanol or a derivative thereof.
2. Composition according to claim 1, characterized in that the phytostanol or phytosterol is an ester derivative that is esterified with an omega-3 polyunsaturated fatty acid, preferably is esterified with DHA or EPA.
3. Pharmaceutical dosage form comprising the composition as defined in claim 1 and a pharmaceutically acceptable excipient.
4. Dosage form of claim 2, characterized in that the dosage form is a tablet or capsule.
5. Composition of claim 1 for use as a medicine for treatment of hyperlipidemia.
6. Composition of claim 1 for use as a medicine for reduction of serum cholesterol.
7. Composition of claim 1 for use as a medicine for reduction of serum triglycerides.
PCT/EP2002/004663 2001-07-20 2002-04-26 Lipid lowering composition comprising carnitine and phytosterol WO2003009854A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP01117587.4 2001-07-20
EP01117587 2001-07-20
US35880802P 2002-02-25 2002-02-25
US60/358,808 2002-02-25

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1632137A1 (en) * 2004-08-10 2006-03-08 Kraft Foods Holdings, Inc. Compositions and processes for water-dispersible phytosterols and phytostanols
WO2007003425A2 (en) * 2005-07-05 2007-01-11 Lonza Ag Spray-drying process for producing a dry carnitine powder or granulate
WO2007135083A1 (en) 2006-05-22 2007-11-29 Beiersdorf Preparations for sebum reduction with a content of hydroxycitrate as active principle
WO2016127034A2 (en) 2015-02-06 2016-08-11 Lonza Inc. System and method for treating atheroma formation

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4526793A (en) * 1982-04-16 1985-07-02 Nestec, S.A. Lipid composition for oral, enteral or parenteral nutrition
EP0780124A1 (en) * 1995-12-21 1997-06-25 Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. Pharmaceutical composition comprising L-carnitine or an alkanoyl L-carnitine in combination with a polyunsaturated fatty acid of the omega-3 series for the prevention and the treatment of lipid metabolism disorders
US5770749A (en) * 1994-09-29 1998-06-23 The University Of British Columbia - University Maison Office (Industrial) Process of isolating a phytosterol composition from pulping soap
US5827853A (en) * 1996-10-23 1998-10-27 Sanofi Cosmetic composition containing a neuropeptide Y receptor antagonist
EP1004594A1 (en) * 1998-11-26 2000-05-31 F. Hoffmann-La Roche Ag Phytosterol and/or phytostanol derivatives
WO2001000653A1 (en) * 1999-06-23 2001-01-04 Forbes Medi-Tech Inc. Conjugates of phytosterol or phytostanol with ascorbic acid and use thereof in treating or preventing cardiovascular disease

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4526793A (en) * 1982-04-16 1985-07-02 Nestec, S.A. Lipid composition for oral, enteral or parenteral nutrition
US5770749A (en) * 1994-09-29 1998-06-23 The University Of British Columbia - University Maison Office (Industrial) Process of isolating a phytosterol composition from pulping soap
EP0780124A1 (en) * 1995-12-21 1997-06-25 Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. Pharmaceutical composition comprising L-carnitine or an alkanoyl L-carnitine in combination with a polyunsaturated fatty acid of the omega-3 series for the prevention and the treatment of lipid metabolism disorders
US5827853A (en) * 1996-10-23 1998-10-27 Sanofi Cosmetic composition containing a neuropeptide Y receptor antagonist
EP1004594A1 (en) * 1998-11-26 2000-05-31 F. Hoffmann-La Roche Ag Phytosterol and/or phytostanol derivatives
WO2001000653A1 (en) * 1999-06-23 2001-01-04 Forbes Medi-Tech Inc. Conjugates of phytosterol or phytostanol with ascorbic acid and use thereof in treating or preventing cardiovascular disease

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1632137A1 (en) * 2004-08-10 2006-03-08 Kraft Foods Holdings, Inc. Compositions and processes for water-dispersible phytosterols and phytostanols
WO2007003425A2 (en) * 2005-07-05 2007-01-11 Lonza Ag Spray-drying process for producing a dry carnitine powder or granulate
WO2007003425A3 (en) * 2005-07-05 2007-03-08 Lonza Ag Spray-drying process for producing a dry carnitine powder or granulate
US9084431B2 (en) 2005-07-05 2015-07-21 Lonza Ltd. Spray-Drying process for producing a dry caritine powder or granulate
WO2007135083A1 (en) 2006-05-22 2007-11-29 Beiersdorf Preparations for sebum reduction with a content of hydroxycitrate as active principle
WO2016127034A2 (en) 2015-02-06 2016-08-11 Lonza Inc. System and method for treating atheroma formation

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