EP1824474A1 - Anthelmintic composition - Google Patents

Anthelmintic composition

Info

Publication number
EP1824474A1
EP1824474A1 EP05823841A EP05823841A EP1824474A1 EP 1824474 A1 EP1824474 A1 EP 1824474A1 EP 05823841 A EP05823841 A EP 05823841A EP 05823841 A EP05823841 A EP 05823841A EP 1824474 A1 EP1824474 A1 EP 1824474A1
Authority
EP
European Patent Office
Prior art keywords
composition
anthelmintic
praziquantel
anthelmintic composition
oxyclosanide
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.)
Withdrawn
Application number
EP05823841A
Other languages
German (de)
French (fr)
Inventor
Ernest Schay
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.)
Elanco Animal Health GmbH
Original Assignee
Bayer Healthcare AG
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
Application filed by Bayer Healthcare AG filed Critical Bayer Healthcare AG
Publication of EP1824474A1 publication Critical patent/EP1824474A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides

Definitions

  • This invention relates to an anthelmintic composition.
  • Praziquantel and Oxyclosanide are known anthelmintics and, for this purpose, are generally available in suspensions. Although fairly effective, the suspensions do suffer the disadvantage that they are difficult to formulate and are relatively limited as to the amount of immediately bioavailable active compound that they contain.
  • an anthelmintic composition comprising an active ingredient selected from any one or more of Praziquantel, Closantel Sodium, Levimasole and Oxyclosanide dissolved in propylene glycol.
  • compositions to contain between 0.5 and 4%m/v Praziquantel, preferably 2.8%m/v Praziquantel; alternatively for the composition to contain between 1 and 5%m/v Levimasole, preferably 2.5 to 3.75%m/v Levimasole; further alternatively for the composition to contain between 1 and 5%m/v Oxyclosanide, preferably 2.55% Oxyclosanide; still further alternatively for the composition to contain between 1 and 4%m/v Closantel Sodium, preferably 2.5% Closantel Sodium.
  • compositions according to the present invention may contain Chlorbutanol and/or benzyl alcohol.
  • Preferred concentrations of Chlorbutanol are 2 to 5%m/v, in particular 3,3 to 4,l%m/v; preferred concentrations of benzyl alcohol are 1 to 4%m/v, in particular 2,3 to 2,8%m/v.
  • a suitable amount of an active ingredient selected from Praziquantel, Levimasole and Oxyclosanide was dissolved in propylene glycol to provide the solutions of varying concentration. These solutions were tested against suspensions that are available on the market to find concentrations in solution have the same efficacy as suspensions. The results are shown in table below.
  • Solution 2 uses has a higher concentration of Praziquantel than the Endotape Suspension. This concentration was selected simply to match that of Solution 1 but it has nonetheless been found that Solution 2 is effective against a much broader spectrum of tape worms than the Endotape Suspension.
  • Chlorbutanol and benzyl alcohol are defined as preservatives, in this formulation they function as free radical scavengers, possibly due to their OH groups. According to this theory, degradation releases free radicals, and these free radicals function as a catalyst for further degradation. Hence the preservatives, by functioning as free radical scavengers, retard the degradation process.
  • solutions of the invention are easy to formulate, contain less excipients and are more effective than prior art suspensions and highly effective. It will be appreciated, however, that many other embodiments of anthelmintic solutions exists which fall within the scope of the invention, particularly as regards the concentration of the active ingredient.

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (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)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

An anthelmintic composition is provided which includes an active ingredient selected from any one or more of Praziquantel, Closantel Sodium, Levimasole and Oxyclosanide dissolved in propylene glycol.

Description

ANTHELMINTIC COMPOSITION
FIELD OF THE INVENTION
This invention relates to an anthelmintic composition.
BACKGROUND TO THE INVENTION
Praziquantel and Oxyclosanide are known anthelmintics and, for this purpose, are generally available in suspensions. Although fairly effective, the suspensions do suffer the disadvantage that they are difficult to formulate and are relatively limited as to the amount of immediately bioavailable active compound that they contain.
OBJECT OF THE INVENTION
It is an object of this invention to provide an anthelmintic composition which at least partially alleviates the abovementioned problem.
SUMMARY OF THE INVENTION
In accordance with this invention there is provided an anthelmintic composition comprising an active ingredient selected from any one or more of Praziquantel, Closantel Sodium, Levimasole and Oxyclosanide dissolved in propylene glycol.
Further features of the invention provide for the composition to contain between 0.5 and 4%m/v Praziquantel, preferably 2.8%m/v Praziquantel; alternatively for the composition to contain between 1 and 5%m/v Levimasole, preferably 2.5 to 3.75%m/v Levimasole; further alternatively for the composition to contain between 1 and 5%m/v Oxyclosanide, preferably 2.55% Oxyclosanide; still further alternatively for the composition to contain between 1 and 4%m/v Closantel Sodium, preferably 2.5% Closantel Sodium.
Moreover, the compositions according to the present invention may contain Chlorbutanol and/or benzyl alcohol. Preferred concentrations of Chlorbutanol are 2 to 5%m/v, in particular 3,3 to 4,l%m/v; preferred concentrations of benzyl alcohol are 1 to 4%m/v, in particular 2,3 to 2,8%m/v.
Embodiments of the invention are described, by way of example only, in the following example. EXAMPLE 1
A suitable amount of an active ingredient selected from Praziquantel, Levimasole and Oxyclosanide was dissolved in propylene glycol to provide the solutions of varying concentration. These solutions were tested against suspensions that are available on the market to find concentrations in solution have the same efficacy as suspensions. The results are shown in table below.
From these results it will be noted that lower amounts of the active compounds can be used to achieve efficacies equal to those of the prior art suspensions. It must be noted that Solution 2 uses has a higher concentration of Praziquantel than the Endotape Suspension. This concentration was selected simply to match that of Solution 1 but it has nonetheless been found that Solution 2 is effective against a much broader spectrum of tape worms than the Endotape Suspension.
It is suspected that the better efficacy of the solutions according to the invention is as a result of better bioavailability than the suspensions.
In Solution 1, Praziquantel is dissolved in 100% undiluted propylene glycol together with 3,7 %m/v Chlorbutanol and 2,5%m/v benzyl alcohol. Normally concentrations of propylene glycol in excess of 70% are considered to be self preserving due to the osmotic effect created by the concentrate propylene glycol on micro organisms. Thus it appears counter-intuitive that, although 100% propylene glycol is used and the product should thus be self preserving, the preservatives Chlorbutanol and benzyl alcohol are also included. During development it was found that if these "preservatives" were not included the stability of the product was severely effected in that the shelf life was severely reduced. It is thus surmised that although Chlorbutanol and benzyl alcohol are defined as preservatives, in this formulation they function as free radical scavengers, possibly due to their OH groups. According to this theory, degradation releases free radicals, and these free radicals function as a catalyst for further degradation. Hence the preservatives, by functioning as free radical scavengers, retard the degradation process.
The solutions of the invention are easy to formulate, contain less excipients and are more effective than prior art suspensions and highly effective. It will be appreciated, however, that many other embodiments of anthelmintic solutions exists which fall within the scope of the invention, particularly as regards the concentration of the active ingredient.

Claims

- A -CLAIMS
1. An anthelmintic composition comprising an active ingredient selected from any one or more of Praziquantel, Closantel Sodium, Levimasole and Oxyclosanide dissolved in propylene glycol.
2. An anthelmintic composition as claimed in claim 1 wherein the composition contains between 0.5 and 4%m/v Praziquantel.
3. An anthelmintic composition as claimed in claim 2 wherein the composition contains 2.8%m/v Praziquantel.
4. An anthelmintic composition as claimed in any one of the preceding claims wherein the composition contains between 1 and 5%m/v Levimasole.
5. An anthelmintic composition as claimed in claim 4 wherein the composition contains between 2.5 to 3.75%m/v Levimasole.
6. An anthelmintic composition as claimed any one of the preceding claims wherein the composition contains between 1 and 5%m/v Oxyclosanide.
7. An anthelmintic composition as claimed in claim 6 wherein the composition contains 2.55% Oxyclosanide.
8. An anthelmintic composition as claimed in any one of the preceding claims wherein the composition contains between 1 and 4%m/v Closantel Sodium.
9. An anthelmintic composition as claimed in claim 8 wherein the composition contains 2.5% Closantel Sodium.
10. An anthelmintic composition substantially as herein described and as illustrated with reference to Solutions 1 to 4 in Example 1.
EP05823841A 2004-12-10 2005-12-08 Anthelmintic composition Withdrawn EP1824474A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ZA200410001 2004-12-10
PCT/EP2005/013139 WO2006061214A1 (en) 2004-12-10 2005-12-08 Anthelmintic composition

Publications (1)

Publication Number Publication Date
EP1824474A1 true EP1824474A1 (en) 2007-08-29

Family

ID=36267185

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05823841A Withdrawn EP1824474A1 (en) 2004-12-10 2005-12-08 Anthelmintic composition

Country Status (3)

Country Link
EP (1) EP1824474A1 (en)
WO (1) WO2006061214A1 (en)
ZA (1) ZA200704633B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI1009199A2 (en) 2009-03-17 2016-03-08 Concert Pharmaceuticals Inc pyrazinoisoquinoline compounds

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ247278A (en) * 1991-02-12 1995-03-28 Ancare Distributors Veterinary anthelmintic drench comprising a suspension of praziquantel in a liquid carrier
NZ248486A (en) * 1993-08-24 1996-07-26 Ashmont Holdings Limited Subst Stable anthelmintic formulation containing closantel and one or more avermectins or milbemycins in a glycol based solvent
AU711820B3 (en) * 1996-07-30 1999-10-21 Ashmont Holdings Limited Anthelmintic formulations
US6429211B1 (en) * 2000-05-23 2002-08-06 Bayer Corporation Praziquantel compounds for treating diseases due to Sarcocystis Neospora Toxoplasma and Isospora
AUPR510001A0 (en) * 2001-05-18 2001-06-14 Jupitar Pty Ltd Formulation and method
GB2386066A (en) * 2002-02-28 2003-09-10 Norbrook Lab Ltd Long-acting parasiticidal composition with improved bioavailability comprising a salicylanilide, a further anti-parasitic compound & a polymeric species
AU2002952597A0 (en) * 2002-11-11 2002-11-28 Schering-Plough Pty. Limited Topical parasiticide formulations and methods of treatment
BRPI0409185B1 (en) * 2003-04-04 2018-05-15 Merial, Inc TOPICAL ANTI-HELMINTIC VETERINARY FORMULATIONS
US7666444B2 (en) * 2004-02-02 2010-02-23 Wyeth Antiparasitic composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006061214A1 *

Also Published As

Publication number Publication date
WO2006061214A1 (en) 2006-06-15
ZA200704633B (en) 2008-09-25

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