WO2014098623A1 - Formulation d'éprinomectine injectable et utilisation anthelmintique de celle-ci - Google Patents

Formulation d'éprinomectine injectable et utilisation anthelmintique de celle-ci Download PDF

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Publication number
WO2014098623A1
WO2014098623A1 PCT/NZ2013/000240 NZ2013000240W WO2014098623A1 WO 2014098623 A1 WO2014098623 A1 WO 2014098623A1 NZ 2013000240 W NZ2013000240 W NZ 2013000240W WO 2014098623 A1 WO2014098623 A1 WO 2014098623A1
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WO
WIPO (PCT)
Prior art keywords
formulation
eprinomectin
anthelmintic
injectable
animal
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Application number
PCT/NZ2013/000240
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English (en)
Inventor
Robert William Lachlan Holmes
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Alleva Animal Health Limited
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Publication of WO2014098623A1 publication Critical patent/WO2014098623A1/fr

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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7135—Compounds containing heavy metals
    • A61K31/714—Cobalamins, e.g. cyanocobalamin, i.e. vitamin B12
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • 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
    • 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
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • This invention relates to the treatment of cattle especially in large herds.
  • Treatment of cattle to prevent and control parasite infection is an important aspect of modern farming, especially the treatment of roundworm.
  • Typical roundworm parasite known to infect cattle include parasite belonging to the following genera: Haemonchus, Trichostrongylus, Ostertagia, Nemaodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Unicinaria, Toxascaris and Parascaris.
  • these parasites are controlled by specific chemical agents developed to meet certain criteria. These criteria include:
  • the first chemical class of modern anthelmintics developed was the benzimidazoles (BZD).
  • BZD benzimidazoles
  • thiabendazole (TBZ) was introduced in 1961.
  • Other members of the benzimidazole class includes fenbendazole, albendazole and oxfendazole.
  • Benzimidazole based anthelmintics interfere with the worm's energy metabolism on a cellular level.
  • the molecule binds to a specific building block called beta tubulin and prevents its incorporation into certain cellular structures called microtubules, which are essential for energy metabolism. Interfering with energy metabolism is a much more basic mode of activity than that which occurs with other classes of anthelmintics. For this reason, benzimidazoles are also able to kill worm eggs. Benzimidazoles have a wide margin of safety and broad spectrum activity.
  • Nicotinic agonists comprise the secod class of anthelmintics. They include imidazothiazoles and tetrahydropyrimidines .
  • the imidazothiazole group includes levamisole, while the tetrahydropyrimidine group includes pyrantel pamoate, pyrantel tartrate, and morantel tartrate.
  • Tetrahydropyrimidines mimic the activity of acetylcholine, a naturally occuring neurotransmitter that initiates muscular contraction. Upon exposure to the active ingredient, the worm is unable to feed and quickly starves. Tetrahydroyrimidines only affect adult populations of worms. They do not have activity against the larval stages and are ineffective against cestodes (tapeworms) and trematodes (liver flukes). Imidazothiaoles have a similar mode of action causing spastic paralysis of the worms. The group includes the drug levamisoie discovered in 1966.
  • levamisoie Compared to other anthelmintics, levamisoie has the narrowest margin of safety, though toxicity is usually the result of excess dosage. Levamisoie has a broad spectrum of activity and is effective against many larval stages of parasites; though not arrested larvae.
  • the next anthelmintic class to be developed was the macrocyclic lactones (MLs) developed from the Streptomyces genus of soil dwelling-organisms.
  • the first drug of the class, ivermectin was introduced in the early 1980s.
  • Macrocyclic lactones consist of two closely related chemical groups: avermectins and milbemycins.
  • the avermectins include abamectin, ivermectin doramectin and eprinomectin.
  • the milbemycin group is represented by milbemycin oxime and moxidectin, introduced in 1997.
  • Macrocyclic lactones are the most potent killer of worms and are more persistent in their effect. The duration of persistent activity varies according to the drug and formulation.
  • Macrocyclic lactones have the unique quality of also killing several types of external parasite such as lice, mites, and ticks. Because of this they are also known as "endectocides" (end- ecto-cides), meaning control of internal and external parasites. Generally, the macrocyclic lactones have a wide margin of safety in treated livestock and are effective against all stages of worms, including inactive forms. Amino-acetonitrile derivatives
  • anthelmintic types have been used to treat adult dairy cattle. Over the years, there have been anthelmintic formulations from at least the benzimidazole, nicotinic agonist and macrocyclic lactone classes that have been used to fulfil this requirement. Formulation types have included slow-release bolus formulations, oral drenches and in-feed materials and, more recently, topical or "pour-on" formulations of the macrocyclic lactone class of chemicals. It is this latter class that has now become the de-facto norm for treatment of lactating dairy cows.
  • Nail-milk” or zero-milk withholding period pour-on formulations have been developed with all of the commercially available macrocyclic lactone active ingredients including; abamectin, ivermectin, doramectin, eprinomectin and moxidectin.
  • the pour-on formulation consists of a quantity of the macrocydic lactone active dissolved in one or more organic solvents. This is then applied topically to the back of the animal from where it is absorbed through the skin.
  • the dose rate typically applied is 500mcg/kg at a dose volume of around lmL/lOkg or lmL/20kg.
  • such formulations have been the only nil-milk treatments available for at least the past 20 years. This has been due to their supposed convenience and the absence of alternative treatment forms and methods of treatment. In large dairy herds, it can be difficult to treat cows with an anthelmintic due to the design of modern dairy sheds and the lack of effective formulations designed for use in such situations.
  • Injectable formulations are capable of delivering much higher blood levels of the drug.
  • Injectable anthelmintic formulations (designed for injection to the anterior neck portion of a cow) containing a macrocyclic lactone anthelmintic are usually formulated to deliver 200mcg/kg of the drug. Typically, this is administered from a 1% formulation via a lmL/50kg dose rate. This size of injectable anthelmintic dose is very impractical for such large animals. If a typical injectable were administered a 500kg cow would generally be given a dose of around lOmls. This would mean a standard 500mL pack would only be capable of treating 50 cows.
  • a rotary platform holds 70-80 cows.
  • lOmL is a relatively large dose that would take a reasonable period of time to inject.
  • doses of this size to leak from the injection site, particularly when the injection is administered subcutaneously.
  • the design of the rotary platform makes it difficult for the farmer to access the anterior portion of the neck where such treatments are typically administered. Attempting to reach between or across cows to reach the anterior neck portion could also be highly dangerous and subject the farmer to possible injury. The time taken to do this would also make it impracticable.
  • the rotary cow shed has become the most popular form of milking parlour. This is due to the high speed at which large groups of cows can be milked. Unlike older walk through and herringbone designs, the flow of cows through a rotary cow shed is continuous. As shown in figure 1, the un-milked cows walk into stalls on to a large platform, which moves in a gradual circular movement around a central point. It is important to note that the cows are facing toward the centre with their posterior end toward the outside of the platform. Such a positioning means that it is easy for the milker standing at position X to place the milking machine "cups" on the teats of the cow.
  • the cow As the platform gradually rotates, the cow is milked. At the end of the rotation the cups are removed either automatically, or by a second milker standing at position Y. After cup removal the cow then backs off the platform.
  • the farmer may alternatively treat the cows while they are moving down a race or while they are stationery within the race. Even in such situations the large numbers of animals means that is desirable that the time taken to treat each animal is relatively fast.
  • pour-on type formulations have become the preferred form of anthelmintic delivery as they:
  • each cow should be able to be treated in a similar period of time to what it would take the farmer to put the milking machine cups on the teats of the cow. If treatment were to take longer than this time the farmer would not keep up with the speed at which the platform is moving.
  • the invention provides a method of treating cattle by injecting an animal at an injection site at or near the rear of the animal with an anthelmintic injectable formulation comprising eprinomectin in a suitable liquid carrier.
  • the invention provides a method of treating cattle by injecting an animal at an injection site at or near the rear of the animal with a nil milk withholding time approved anthelmintic injectable formulation comprising eprinomectin in a suitable liquid carrier, wherein the concentration of eprinomectin is greater than 1% w/v.
  • the injection site is chosen from the group comprising: the base of the tail, the tail fold, and the depressions on either side of the tail head of the cow.
  • the liquid carrier is an organic solvent and anthelmintic injectable formulation comprises eprinomectin dissolved in the organic solvent.
  • each animal is provided with an injection delivering at least 200mcg/kg of eprinomectin: per kg of body weight of the animal.
  • each animal is injected whilst being held head first in bail of a milking installation such as a rotary milking shed, or a herringbone-milking shed.
  • a milking installation such as a rotary milking shed, or a herringbone-milking shed.
  • anthelmintic injectable formulation is a nil milk withholding injection containing both eprinomectin and vitamin E.
  • the invention can be said to be the use of an anthelmintic injectable formulation containing eprinomectin as an injection applied at an injection site at or near the rear of the animal.
  • the invention involves the use of eprinomectin in the manufacture of an anthelmintic injectable formulation to be applied at an injection site at or near the rear of the animal.
  • the invention provides an injectable anthelmintic formulation suitable for treatment of cattle, the formulation comprising:
  • sorbitan monooleate a Vegetable oil or derivative
  • the formulation contains at least 1.5% eprinomectin w/v.
  • co-solvent(s) is selected from glycerol formal, dimethyl acetamide and dimethyl isosorbide.
  • the formulation further includes Vitamin E acetate.
  • the formulation further includes water and a water-soluble vitamin such as Vitamin B12.
  • the invention provides a method of treating a herd of cattle with an anthelmintic injectable formulation containing eprinomectin dissolved in an organic solvent and in which the dosage recommendations provide for a dose rate of no less than 200mcg/kg and the injection site to be at or near the rear of each animal.
  • the injection site is at the base of the tail, the tail fold or the depression on either side of the tail head of the cow.
  • the formulation contains greater than 1.5% w/v eprinomectin.
  • the method involves treating cattle with a nil milk withholding injection containing both eprinomectin and vitamin E.
  • the invention provides an injectable anthelmintic formulation suitable for treatment of cattle containing:
  • the co-solvent is selected from glycerol formal, dimethyl acetamide and dimethyl isosorbide.
  • the injectable anthelmintic formulation also contains a water-soluble vitamin such as Vitamin B12 as well as water and other optional elements, including surfactants, water, antioxidants, buffers and preservatives.
  • a water-soluble vitamin such as Vitamin B12
  • water and other optional elements including surfactants, water, antioxidants, buffers and preservatives.
  • the method of treatment subject to this invention is such that it enables the farmer to treat animals by injection in a period of time substantially similar to that needed to administer pour-on treatments.
  • Figure 1 is a schematic drawing of a conventional rotary cowshed.
  • Figure 2 is a graph showing the mean concentration of Eprinomectin (over time) in bovine plasma after treatment with Eprinomectin injection or Pour-on.
  • Figure 3 is a front on view of the posterior end of a cow showing the preferred application site.
  • Figure 4 is a top view of a conventional herringbone milking shed.
  • Figure 5 is a further schematic drawing of a conventional rotary cowshed. DETAILED DESCRIPTION OF THE INVENTION
  • FIG 3 shows the preferred injection site (20) on the cattle.
  • This site has the advantage of being easily accessiable, contains sufficiently "loose" skin to enable the area to be 'tented' to permit subcutaneous administration.
  • cattle enter (32) the shed from the yard (36), wherein the milker/farmer (30) is located in a central race located below the level of the cattle, which is accessed by the steps (31).
  • the milker/farmers eye level is in line with the prosterior end of the cattle.
  • the suction cups are then placed on the cattle by the farmer in preparation for for milking. Once milking is completed, the suction cups are removed and the the exit gate (33) is opened allowing the cattle to exit out to pasture (34).
  • cows are presented in an inline position on either side of a central race.
  • a farmer/milker (30) to access the back of the cow to permit treatment with a topical/pour-on formulation.
  • the inventive formulation permits treatment at a larger number of admnistration points (marked with an X).
  • X admnistration point
  • the only practical position in which the cow can be treated is at the entry (42)or exit (45) points.
  • the inventive formulation permits treatment at a larger number of admnistration points (such as those marked with an X) even while the platform is turning.
  • Table 1 Geometric mean AUC and Cmax values for animals treated with an Eprinomectin injection or an Eprinomectin pour-on
  • FIG. 1 is a graph that shows the mean concentration of Eprinomectin in bovine plasma after treatment with Eprinomectin injection or Pour-on.
  • Injection efficiency is a function of the following factors:
  • a second aspect to treatment of large animals by injection is that the practice can be inherently dangerous as the cow may react violently to attempts to move its head or to lift its neck into a position where the injection can be given. There are also practical difficulties involved with "tenting" the skin so that the injection can be given subcutaneously.
  • the time taken to inject the anthelmintic solution also means that the head/neck must be held relatively stationery for a period of time.
  • Treatment of a cow by injection at other sites at or near the rear of the animal is preferred.
  • sites on the body of the animal which allow for easy access, easy "tenting" of the skin and are not likely to cause tissue damage/residue concerns at the injection site if the cow is slaughtered.
  • the base of the tail, the tail fold, or the depression on either side of the tail head would offer the best combination of these factors.
  • the administration of an anthelmintic in the desired timeframe would become easy to accomplish.
  • the inventive concept of a high concentration eprinomectin-based injection combined with a low administration dose, convenient injection site and nil milk-withholding periods offers an effective and desirable alternative to pour-on formulations in all of these situations.
  • the method ensures that the milker was not unnecessarily inconvenienced by the need to administer the treatment.
  • the method of treatment also ensures greater safety to the farmer and less stress to the animal.
  • This product is to be given by subcutaneous injection only.
  • the recommended dose is ImL per 100kg bodyweight (200mcg eprinomectin per kg). Inject under loose skin in one of the two sites indicated in the illustration: A. Anterior portion of the neck
  • injectable formulations Treatment with an injectable formulation is better than a topical delivery (pour on) as injectable formulations are capable of delivering much higher blood levels of drug.
  • the method allows rapid treatment by injection the preferred formulation at an injection site on the rear of the animal typically while it is trapped in the bail of a (rotary) milking shed.
  • the injectable formulation provides a nil-milk withholding injectable anthelmintic formulation. This means that it is possible to treat cows with this injectable formation all the year round whether they are lactating or not.
  • the method provides a specific method of injectable anthelmintic treatment suitable for large herds and particularly lactating dairy cows, which can be administered in a dairy shed situation.
  • the preferred formulation also provides for the supplemental delivery of other trace elements important to the health of cattle, in particular Vitamin E and/or Vitamin B12

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé de traitement d'un troupeau de bovins dans une salle de traite par injection, à un animal à un site d'injection au niveau ou près de l'arrière de l'animal, d'une formulation anthelminthique pouvant être injectée, comprenant de l'éprinomectine dissoute dans un solvant organique. Les injections peuvent être appliquées à des positions X d'une salle de traite rotative tandis que les vaches sont dans leurs enclos sur la plateforme rotative. Des positions d'injection pour une salle de traite en épi sont également décrites et illustrées. La formulation pouvant être injectée a une période de retrait de lait nulle de telle sorte qu'elle peut être utilisée sur des vaches en lactation.
PCT/NZ2013/000240 2012-12-20 2013-12-19 Formulation d'éprinomectine injectable et utilisation anthelmintique de celle-ci WO2014098623A1 (fr)

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NZ604990 2012-12-20
NZ60499012 2012-12-20

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114642632A (zh) * 2022-02-25 2022-06-21 河北科技大学 一种莫西克汀注射液及其制备方法

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US4389397A (en) * 1980-08-04 1983-06-21 Merck & Co., Inc. Solubilization of ivermectin in water
WO2010116267A1 (fr) * 2009-02-16 2010-10-14 Pfizer Inc. Formulation de doramectine à dosage élevé
US20100266628A1 (en) * 2009-04-14 2010-10-21 Majid Razzak Macrocyclic lactone combination compositions, vaccines and methods for producing same
BRPI1001224A2 (pt) * 2010-04-07 2011-03-15 Clarion Biociencias Ltda processo de fabricação de formulação injetável a base de fluazuron associado a avermectinas para o controle e prevenção de endo e ectoparasitas em animais domésticos
WO2011143479A1 (fr) * 2010-05-12 2011-11-17 Merial Limited Formulations parasiticides injectables de lévamisole et de lactones macrocycliques
BRPI1001593A2 (pt) * 2010-05-12 2012-01-03 Clarion Biociencias Ltda processo de fabricaÇço de formulaÇço injetÁvel a base de eprinomectina para controle e prevenÇço de endo e ectoparasitas em animais
WO2012001083A2 (fr) * 2010-06-29 2012-01-05 Ceva Sante Animale Sa Nouvelles compositions injectables d'éprinomectine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4389397A (en) * 1980-08-04 1983-06-21 Merck & Co., Inc. Solubilization of ivermectin in water
WO2010116267A1 (fr) * 2009-02-16 2010-10-14 Pfizer Inc. Formulation de doramectine à dosage élevé
US20100266628A1 (en) * 2009-04-14 2010-10-21 Majid Razzak Macrocyclic lactone combination compositions, vaccines and methods for producing same
BRPI1001224A2 (pt) * 2010-04-07 2011-03-15 Clarion Biociencias Ltda processo de fabricação de formulação injetável a base de fluazuron associado a avermectinas para o controle e prevenção de endo e ectoparasitas em animais domésticos
WO2011143479A1 (fr) * 2010-05-12 2011-11-17 Merial Limited Formulations parasiticides injectables de lévamisole et de lactones macrocycliques
BRPI1001593A2 (pt) * 2010-05-12 2012-01-03 Clarion Biociencias Ltda processo de fabricaÇço de formulaÇço injetÁvel a base de eprinomectina para controle e prevenÇço de endo e ectoparasitas em animais
WO2012001083A2 (fr) * 2010-06-29 2012-01-05 Ceva Sante Animale Sa Nouvelles compositions injectables d'éprinomectine

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BAOLIANG, P. ET AL.: "Pharmacokinetics of Eprinomectin in Plasma and Milk following Subcutaneous Administration to Lactating Dairy Cattle", VETERINARY RESEARCH COMMUNICATIONS, vol. 30, 2006, pages 263 - 270 *
JIANG, H. ET AL.: "Residue depletion of eprinomectin in bovine tissues after subcutaneous administration", J. AGRIC. FOOD CHEM., vol. 53, 2005, pages 9288 - 9292 *
ROEBER ET AL.: "Frequencies of injection-site lesions in muscles from rounds of dairy and beef cow carcasses", J. DAIRY SCI., vol. 85, 2002, pages 532 - 536 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114642632A (zh) * 2022-02-25 2022-06-21 河北科技大学 一种莫西克汀注射液及其制备方法

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