WO2001095723A1 - Composition parasiticide - Google Patents

Composition parasiticide Download PDF

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Publication number
WO2001095723A1
WO2001095723A1 PCT/GB2001/002610 GB0102610W WO0195723A1 WO 2001095723 A1 WO2001095723 A1 WO 2001095723A1 GB 0102610 W GB0102610 W GB 0102610W WO 0195723 A1 WO0195723 A1 WO 0195723A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
composition
imidazole
triazole
alcohol
Prior art date
Application number
PCT/GB2001/002610
Other languages
English (en)
Inventor
Ian Whelan
Original Assignee
Ssl International Plc
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
Priority claimed from GB0014667A external-priority patent/GB0014667D0/en
Priority claimed from GB0019255A external-priority patent/GB0019255D0/en
Priority claimed from GB0027435A external-priority patent/GB0027435D0/en
Application filed by Ssl International Plc filed Critical Ssl International Plc
Priority to AU2001264110A priority Critical patent/AU2001264110A1/en
Publication of WO2001095723A1 publication Critical patent/WO2001095723A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the invention relates to a parasiticidal composition and in particular to a composition for controlling headlice infestation in humans.
  • Lice infestation in man is generally caused by insects from the families Pediculidae and Pthiridae, in particular Pedicuhis humanus species and Pthirus pubis.
  • the azole antifungal agents have five-membered organic rings that contain either two or three nitrogen molecules (the imidazoles and the triazoles respectively). Two types of antifungal affect the cell membrane-polyenes and imidazoles.
  • the clinically useful imidazoles are clotrimazole, miconazole, and ketoconazole, two important triazoles are itraconazole and fluconazole.
  • the azole antifungal agents are thought to inhibit cytochrome P 50 - dependent enzymes involved in the biosynthesis of cell membranes
  • kitoconazole was the original model for the orally administered antifungal azoles. It can be administered both orally and topically and has a range of activity including infections. It is also active against mucosal candidiasis and a variety of cutaneous mycoses, including dermatophyte infections, pityriasis versicolor, and cutaneous candidiasis.
  • the triazoles (fluconazole, itraconazole) have become the standard for the azoles, and have replaced amphotericin B for managing certain forms of the systemic mycoses.
  • the compounds work by binding to sterols in the cell membrane.
  • the principal sterol in fungal cell membranes is ergosterol, while the principal sterol in mammalian cell membranes is cholesterol.
  • Polyenes have a stronger affinity for ergosterol than cholesterol, so they show greater activity against fungal cells than mammalian cells.
  • the binding forms channels of about 0.8nm in diameter, which in turn allows leakage of up to 90% of cellular potassium ions (K+). This is followed by a loss of magnesium ions (Mg++). The loss of K+ ions inhibits a variety of metabolic processes, including glycolysis and respiration.
  • Imidazoles bind to the fungal cytochrome P- 45 o. This inhibits production of ergosterol synthesis or its incorporation into the cell membrane. This interferes with the membrane function and permeability. This means many components, including K+, leak out of the cell. Examples include ketoconazole, miconazole, econazole, fluconazole, clotrimazole, and intraconazole. According to the present invention there is provided a parasiticidal composition comprising an imidazole and/or a triazole and a physiologically acceptable carrier.
  • the imidazole is selected from one or more of the group consisting of clotrimazole, ketoconazole, and miconazole and that the triazole is selected from fluconazole and itraconazole.
  • composition is adapted for topical application to a subject. It is particularly preferred that the composition is adapted for application as a lotion or mousse for the hair.
  • composition may further comprise alcohol, such as isopropanol and/or ethanol, and the physiologically acceptable carrier may comprise the alcohol.
  • alcohol such as isopropanol and/or ethanol
  • physiologically acceptable carrier may comprise the alcohol.
  • composition may comprise at least about 0.2% v/v imidazole and/or triazole.
  • the composition may further comprise a constituent having ovicidal activity.
  • the ovicidal agent may comprise a terpene, preferably one or both of d- limonene and geranyl acetate.
  • composition is for use in the treatment and/or prevention of human infestation by parasites from the families Pediculidae and Pthiridae.
  • a process for preparing a parasiticidal composition which comprises bringing an imidazole and/or a triazole into association with at least one carrier therefor.
  • a process for preparing a parasiticidal composition which comprises bringing an imidazole and/or a triazole into association with at least one carrier therefor.
  • an imidazole and/or a triazole in the manufacture of a composition for use in controlling parasite infestations in humans, in particular infestation by parasites from the families Pediculidae and Pthiridae.
  • Human lice pediculus humanus, were obtained from the culture colony maintained by the Medical Entomology Centre. Adult female and male lice, in approximately equal numbers, were used for each test. The lice were fed on the morning of the test and allowed a minimum of 4 hours to recover, during which time they were able to excrete excess water imbibed with their blood meal. Lice were counted into batches that were provided with squares of an open meshed nylon gauze (tulle), as a substrate upon which to stand, and each batch allocated to a marked 30 millimetre plastic Petri dish.
  • tulle open meshed nylon gauze
  • the gauze bearing lice was immersed in the fluid for 10 seconds, during which time the gauze was turned at least twice to ensure removal of air bubbles. After removal from the fluid the gauze and insects were lightly blotted to remove excess fluid and returned to their marked Petri dish. The same procedure was repeated for the other replicate gauze squares in that batch.
  • Gauze squares bearing lice were incubated under normal maintenance conditions (30° ⁇ 2° Celsius and 50% ⁇ 15% relative humidity) for the remainder of the test period.
  • the insects and gauze were washed using a bland toiletry shampoo (Boots frequent wash shampoo) diluted one part shampoo with fourteen parts water (FWS 1:15) after which they were rinsed three times using 250 millilitres of warm (34° Celsius) tap water poured through and over the gauze squares. They were then blotted dry using medical wipe tissue and incubated under normal maintenance conditions in clean plastic Petri dishes of the appropriate size until the results were recorded.
  • Mortality percentages were corrected by Abbott's formula. The percent of mortality in a control was subtracted from the percent mortality in the test and then divided by the percent mortality in the test.
  • An insect's exoskeleton serves not only as a protective covering over the body, but also as a surface for muscle attachment, a water-tight barrier against desiccation, and a sensory interface with the environment.
  • the typical insect exoskeleton is a multi-layered structure with four functional regions, epicuticle, procuticle, epidermis, and basement membrane.
  • the epidermis is a single layer of epithelial cells. It is responsible for producing at least part of the basement membrane as well as all of the overlying layers of cuticle.
  • the procuticle lies immediately above the epidermis. It contains microfibers of chitin surrounded by a matrix of protein that varies in composition from insect to insect and even from place to place within the body of a single insect.
  • procuticle stratifies into a hard, outer exocuticle and a soft, inner endocuticle.
  • exocuticle Differentiation of exocuticle involves a chemical process (called sclerotization) that occurs shortly after each molt.
  • sclerotization individual protein molecules are linked together by quinone compounds. These reactions "solidify” the protein matrix, creating rigid "plates” of exoskeleton known as sclerites.
  • Quinone cross-linkages do not form in parts of the exoskeleton where resilin (an elastic protein) is present in high concentrations. These areas are membranes and they remain soft and flexible because they never develop a well-differentiated exocuticle.
  • the epicuticle is the outermost part of the cuticle. Its function is to reduce water loss and block the invasion of foreign matter.
  • the innermost layer of epicuticle is often called the cuticulin layer, a stratum composed of lipoproteins and chains of fatty acids.
  • a layer of wax molecules lies just above the cuticulin layer, it serves as a barrier to movement of water into or out of the insect's body. In many insects a cement layer covers the wax and protects it from abrasion.
  • imidazoles act as either sclerotisizers or they simply cause a diffusion gradient across the louse resulting in death.
  • the results tend to indicate also that this effect may be enhanced by the use of an alcoholic vehicle.
  • formulations having parasiticidal activity were prepared as follows:
  • formulations which can be prepared in accordance with this invention include lotions and mousses as well as, potentially, other hair treatments.
  • additional constituents which are required will vary according to the desired properties of the final product.
  • the skilled worker will be familiar with such constituents and their usage, which can include, for example, surfactants, silicone compounds, suspending agents colourings and perfumes.
  • compositions according to the invention To enhance the activity of the compositions according to the invention it has been found that further constituents having ovicidal activity can be added without adversely affecting their efficacy.
  • further constituents are terpenes and in particular, the te ⁇ enes d-limonene and geranyl acetate can be used, each at a concentration of from 0.2% v/v to 1.0% v/v.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un imidazole sélectionné dans un ou plusieurs groupes comprenant clotrimazole, kétoconazole et miconazole, le triazole étant sélectionné parmi fluconazole et itraconazole.
PCT/GB2001/002610 2000-06-15 2001-06-15 Composition parasiticide WO2001095723A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001264110A AU2001264110A1 (en) 2000-06-15 2001-06-15 Parasiticidal composition

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB0014667.0 2000-06-15
GB0014667A GB0014667D0 (en) 2000-06-15 2000-06-15 Parasiticidal composition
GB0019255A GB0019255D0 (en) 2000-08-04 2000-08-04 Parasiticidal composition
GB0019255.9 2000-08-04
GB0027435.7 2000-11-09
GB0027435A GB0027435D0 (en) 2000-11-09 2000-11-09 Parasiticidal composition

Publications (1)

Publication Number Publication Date
WO2001095723A1 true WO2001095723A1 (fr) 2001-12-20

Family

ID=27255766

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2001/002610 WO2001095723A1 (fr) 2000-06-15 2001-06-15 Composition parasiticide

Country Status (2)

Country Link
AU (1) AU2001264110A1 (fr)
WO (1) WO2001095723A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005070421A1 (fr) * 2004-01-22 2005-08-04 Alparis S.A. De C.V. Association de fluconazole-tinidazole pour le traitement d'infections vaginales, sa composition, son procede de preparation et son utilisation

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3565992A (en) * 1968-03-08 1971-02-23 Dow Chemical Co Halogenated imidazole and imidazole salts used for controlling insect and helminth parasites
GB2092582A (en) * 1981-02-09 1982-08-18 Ciba Geigy Ag Substituted 2-(anilinomethyl)- 2-imidazoline derivatives and pesticidal compositions containing them
EP0113945A1 (fr) * 1983-01-19 1984-07-25 Eli Lilly And Company Sels d'amines
EP0496316A1 (fr) * 1991-01-19 1992-07-29 Hoechst Aktiengesellschaft Formulation de pour-on pour application d'agents anthelmintiques
US5174475A (en) * 1991-03-26 1992-12-29 Glaxo Inc. Sequential dosing of antifungal and antiinflammatory compositions
WO1993018010A1 (fr) * 1992-03-12 1993-09-16 Pfizer Limited Agents anthelminthiques a base de benzimidazole
EP0712847A1 (fr) * 1993-08-11 1996-05-22 Nippon Soda Co., Ltd. Derive d'imidazole et son procede de production, et substance anti-nuisibles
WO1997036486A1 (fr) * 1996-03-29 1997-10-09 Merial Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins
EP0957094A1 (fr) * 1998-05-14 1999-11-17 Pfizer Inc. 1-(2-Halogénaryl)azoles comme agents antiparasitaires

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3565992A (en) * 1968-03-08 1971-02-23 Dow Chemical Co Halogenated imidazole and imidazole salts used for controlling insect and helminth parasites
GB2092582A (en) * 1981-02-09 1982-08-18 Ciba Geigy Ag Substituted 2-(anilinomethyl)- 2-imidazoline derivatives and pesticidal compositions containing them
EP0113945A1 (fr) * 1983-01-19 1984-07-25 Eli Lilly And Company Sels d'amines
EP0496316A1 (fr) * 1991-01-19 1992-07-29 Hoechst Aktiengesellschaft Formulation de pour-on pour application d'agents anthelmintiques
US5174475A (en) * 1991-03-26 1992-12-29 Glaxo Inc. Sequential dosing of antifungal and antiinflammatory compositions
WO1993018010A1 (fr) * 1992-03-12 1993-09-16 Pfizer Limited Agents anthelminthiques a base de benzimidazole
EP0712847A1 (fr) * 1993-08-11 1996-05-22 Nippon Soda Co., Ltd. Derive d'imidazole et son procede de production, et substance anti-nuisibles
WO1997036486A1 (fr) * 1996-03-29 1997-10-09 Merial Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins
EP0957094A1 (fr) * 1998-05-14 1999-11-17 Pfizer Inc. 1-(2-Halogénaryl)azoles comme agents antiparasitaires

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005070421A1 (fr) * 2004-01-22 2005-08-04 Alparis S.A. De C.V. Association de fluconazole-tinidazole pour le traitement d'infections vaginales, sa composition, son procede de preparation et son utilisation

Also Published As

Publication number Publication date
AU2001264110A1 (en) 2001-12-24

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