WO2004014339A1 - Injectable composition comprising ceftiofur sodium as an active ingredient - Google Patents
Injectable composition comprising ceftiofur sodium as an active ingredient Download PDFInfo
- Publication number
- WO2004014339A1 WO2004014339A1 PCT/KR2003/001264 KR0301264W WO2004014339A1 WO 2004014339 A1 WO2004014339 A1 WO 2004014339A1 KR 0301264 W KR0301264 W KR 0301264W WO 2004014339 A1 WO2004014339 A1 WO 2004014339A1
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- WIPO (PCT)
- Prior art keywords
- injectable suspension
- suspension composition
- ceftiofur
- fatty acid
- composition according
- Prior art date
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- Ceased
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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
- A61K9/0012—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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
-
- 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
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/26—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
Definitions
- the present invention relates to an injectable composition comprising ceftiofur sodium as an active ingredient and an excipient, and more particularly to an injectable suspension composition comprising ceftiofur sodium as an active ingredient which has a low viscosity and excellent redispersibility and bioavailability.
- Ceftiofur ([6R-[6 ⁇ , 7 ⁇ (Z)]]7-[[(2-amino-4- thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8- oxo-5-thia-l-azacyclo[4.2.0]oct -2-ene-2-carboxylic acid) is a third- generation cephalosporin-based antiobiotic, and exhibits an extended beta-lactamase resistance and a broad antibacterial activity against pathogenic bacterial strains including gram-positive and gram-negative bacteria. Ceftiofur is widely used for veterinary purposes (Brown, S.
- Korean Patent No. 96- 0008236 discloses an aqueous composition containing nicotine amide as a solution adjuvant for improving the stability of ceftiofur in water. Hovfeever, the aqueous composition still has a problem in terms of instable formulation.
- a technique for preparing a sustained-release composition in which active ingredients are dispersed in a vegetable oil as a non-aqueous injectable suspension is disclosed in PCT Publication WO 94/20505.
- PCT Publication WO 98/25621 discloses an oil suspension of ceftiofur hydrochloride salt with improved dispersibility. The oil suspension is prepared by adding water to a ceftiofur hydrochloride salt containing lecithin and a surfactant and having a particle size of lO ⁇ m or less.
- ceftiofur sodium formulations are those prepared by lyophilizing in a sterilized state for stabilizing active ingredients, followed by powdering. Thus, these formulations must be dissolved in water before use, and have a problem of complex preparation processes.
- the present inventor has conducted intensive research to solve the above- mentioned problems of prior arts. As a result, the present inventor has found that when a vegetable fatty acid ester is used as a dispersion medium of ceftiofur sodium, redispersibility and bioavailability of an active ingredient are improved, thus accomplishing the present invention.
- an object of the present invention to provide an injectable suspension composition with increased viscosity and excellent redispersibility and bioavailability, comprising ceftiofur sodium as an active ingredient.
- an injectable suspension composition comprising ceftiofur sodium as an active ingredient, an excipient, and a vegetable fatty acid ester as a dispersion medium.
- the term 'vegetable fatty acid ester' used herein refers to an esterified compound obtained through a condensation reaction between a known fatty acid present in a vegetable oil and a known primary, secondary or tertiary alcohol.
- the vegetable fatty acid ester may be a single component or a mixture of at least two components.
- fatty acid ester preferably include monoglyceride, diglyceride, triglyceride, benzyl alcohol, benzyl benzoate, ethyl oleate, ethyl linolate, isopropylpalmitate and isopropylmyristate.
- the content of the fatty acid ester in the injectable composition of the present invention varies according to the kind of the fatty acid ester used, but is not particularly limited.
- the weight ratio of the ceftiofur sodium to the fatty acid ester is preferably within the range of 1: 0.1-40, and more preferably 1: 0.5 ⁇ 3. When the ratio is less than 1: 0.1, the dispersibility of the active ingredient is poor. When the ratio exceeds 1: 10, there is a problem of inconvenient use due to too diluted concentration.
- this range is given only for the purpose of illustration, and is not to be construed as limiting the scope of the invention.
- the injectable suspension composition of the present invention may further comprise an appropriate amount of ethanol (or anhydrous ethanol), etc., as a viscosity enhancing agent for improving redispersibility and controlling viscosity of the composition.
- ethanol or anhydrous ethanol
- the amount of ethanol added can be appropriately varied by those skilled in the art according to a desired viscosity and dispersibility, but is not particularly limited.
- the injectable suspension composition of the present invention may further comprise medically acceptable additives.
- these additives include surfactants (sorbitan monooleate, polyoxyethylene 20 oleate, polyoxy 20 cetyl ether, etc), antioxidants (butylparahydroxy benzoic acid, butylhydroquinone, tocopherol, etc.), viscosity enhancing agents (sodium alginate, carboxymethylcellulose, methylcellulose, tragacanth, agar, polyvinylpyrrolidone, etc.) and the like.
- the injectable suspension composition of the present invention comprising ceftiofur sodium as an active ingredient can be intramuscularly injected at different doses in accordance with needs of animals to be treated.
- ceftiofur sodium is dissolved in 20ml of an injectable solution containing the dispersion medium.
- the solution is intramuscularly injected in the volume of l ⁇ 2ml/50kg of body weight once daily (the solution can be injected for three consecutive days, and in the case of no improvements for five consecutive days).
- the solution is intramuscularly injected in the volume of 0.6 ⁇ lml/10kg of body weight once daily (the solution can be injected for three consecutive days).
- Fig. 1 is a graph showing the concentration of an active ingredient in blood, measured at predetermined time intervals after an injectable suspension of the present invention (Example 1) and a commercially available preparation (Excenel) as a control group are intramuscularly injected to male rats.
- the concentrations of ceftiofur in the blood samples are shown in Fig. 1.
- the bioavailability of ceftiofur in the experimental animal groups was identified to be excellent.
- the injectable suspension composition according to the present invention comprising ceftiofur sodium as an active ingredient, shows improved viscosity and excellent redispersibility and bioavailability.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosed herein is an injectable suspension composition comprising ceftiofur sodium as an active ingredient, an excipient, and a vegetable fatty acid ester as a dispersion medium. The injectable suspension composition comprising ceftiofur sodium as an active ingredient exhibits improved viscosity and excellent redispersibility and bioavailability.
Description
INJECTABLE COMPOSITION COMPRISING CEFTIOFUR SODIUM AS AN ACTIVE INGREDIENT
Technical Field
The present invention relates to an injectable composition comprising ceftiofur sodium as an active ingredient and an excipient, and more particularly to an injectable suspension composition comprising ceftiofur sodium as an active ingredient which has a low viscosity and excellent redispersibility and bioavailability.
Background Art
Ceftiofur ([6R-[6α, 7β (Z)]]7-[[(2-amino-4- thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8- oxo-5-thia-l-azacyclo[4.2.0]oct -2-ene-2-carboxylic acid) is a third- generation cephalosporin-based antiobiotic, and exhibits an extended beta-lactamase resistance and a broad antibacterial activity against pathogenic bacterial strains including gram-positive and gram-negative bacteria. Ceftiofur is widely used for veterinary purposes (Brown, S. A., Comparison of plasma pharmacokinetics and bioavailability of ceftiofur sodium and ceftiofur hydrochloride in pigs after a single intramuscular injection. J. Vet. Pharmacol. Therap. 22, 35-40, 1999; R. J. Yancey et al., In vivo and in vitro antibacterial activity and β-lactamase stability: Am. J. Vet. Res. 48, 1050). Ceftiofur is very poorly soluble in water and typically formulated in the form of hydrochloride salt or sodium salt. However, ceftiofur is limited in its development into an injectable suspension due to its instability in water.
As a prior art relating to an injectable suspension, Korean Patent No. 96- 0008236 discloses an aqueous composition containing nicotine amide as a solution adjuvant for improving the stability of ceftiofur in water. Hovfeever, the aqueous composition still has a problem in terms of instable formulation. To overcome this problem, a technique for preparing a sustained-release composition in which active ingredients are dispersed in a vegetable oil as a non-aqueous injectable suspension is disclosed in PCT Publication WO 94/20505. In addition, PCT Publication WO 98/25621 discloses an oil suspension of ceftiofur hydrochloride salt with improved dispersibility. The oil suspension is prepared by adding water to a ceftiofur hydrochloride salt containing lecithin and a
surfactant and having a particle size of lOμm or less.
However, these prior arts have drawbacks that main ingredients are precipitated during a prolonged storage to form aggregates, making redispersibility of the main ingredients difficult. Further, the high density of cottonseed oil used as a dispersion medium causes its use to be inconvenient. Commercially available ceftiofur sodium formulations are those prepared by lyophilizing in a sterilized state for stabilizing active ingredients, followed by powdering. Thus, these formulations must be dissolved in water before use, and have a problem of complex preparation processes.
Disclosure of the Invention
The present inventor has conducted intensive research to solve the above- mentioned problems of prior arts. As a result, the present inventor has found that when a vegetable fatty acid ester is used as a dispersion medium of ceftiofur sodium, redispersibility and bioavailability of an active ingredient are improved, thus accomplishing the present invention.
Therefore, it is an object of the present invention to provide an injectable suspension composition with increased viscosity and excellent redispersibility and bioavailability, comprising ceftiofur sodium as an active ingredient.
In order to accomplish the above object of the present invention, there is provided an injectable suspension composition comprising ceftiofur sodium as an active ingredient, an excipient, and a vegetable fatty acid ester as a dispersion medium. The term 'vegetable fatty acid ester' used herein refers to an esterified compound obtained through a condensation reaction between a known fatty acid present in a vegetable oil and a known primary, secondary or tertiary alcohol. The vegetable fatty acid ester may be a single component or a mixture of at least two components. Examples of the fatty acid ester preferably include monoglyceride, diglyceride, triglyceride, benzyl alcohol, benzyl benzoate, ethyl oleate, ethyl linolate, isopropylpalmitate and isopropylmyristate.
The content of the fatty acid ester in the injectable composition of the present invention varies according to the kind of the fatty acid ester used, but is not particularly limited. The weight ratio of the ceftiofur sodium to the fatty acid ester is preferably within the range of 1: 0.1-40, and more preferably 1: 0.5~3.
When the ratio is less than 1: 0.1, the dispersibility of the active ingredient is poor. When the ratio exceeds 1: 10, there is a problem of inconvenient use due to too diluted concentration. However, although the ceftiofur sodium and the fatty acid ester are out of this range, it will be appreciated that the present invention can be sufficiently realized. Accordingly, this range is given only for the purpose of illustration, and is not to be construed as limiting the scope of the invention.
The injectable suspension composition of the present invention may further comprise an appropriate amount of ethanol (or anhydrous ethanol), etc., as a viscosity enhancing agent for improving redispersibility and controlling viscosity of the composition. The amount of ethanol added can be appropriately varied by those skilled in the art according to a desired viscosity and dispersibility, but is not particularly limited.
If necessary, the injectable suspension composition of the present invention may further comprise medically acceptable additives. Examples of these additives include surfactants (sorbitan monooleate, polyoxyethylene 20 oleate, polyoxy 20 cetyl ether, etc), antioxidants (butylparahydroxy benzoic acid, butylhydroquinone, tocopherol, etc.), viscosity enhancing agents (sodium alginate, carboxymethylcellulose, methylcellulose, tragacanth, agar, polyvinylpyrrolidone, etc.) and the like. The injectable suspension composition of the present invention comprising ceftiofur sodium as an active ingredient can be intramuscularly injected at different doses in accordance with needs of animals to be treated. First, lg of ceftiofur sodium is dissolved in 20ml of an injectable solution containing the dispersion medium. For cattle, the solution is intramuscularly injected in the volume of l~2ml/50kg of body weight once daily (the solution can be injected for three consecutive days, and in the case of no improvements for five consecutive days). For pig, the solution is intramuscularly injected in the volume of 0.6~lml/10kg of body weight once daily (the solution can be injected for three consecutive days).
BRIEF DESCRIPTION OF THE DRAWINGS
The above and other objects, features and other advantages of the present invention will be more clearly understood from the following detailed description taken in conjunction with the accompanying drawing, in which: Fig. 1 is a graph showing the concentration of an active ingredient in blood, measured at predetermined time intervals after an injectable suspension of the
present invention (Example 1) and a commercially available preparation (Excenel) as a control group are intramuscularly injected to male rats.
Best Mode for Carrying Out the Invention
Hereinafter, the present invention will be described in more detail with reference to the following Examples. However, these Examples are given for the purpose of illustration and are not to be construed as limiting the scope of the invention.
<Examples 1~8> Preparation of injectable suspension Injectable preparations comprising ceftiofur sodium were prepared so as to have the compositions shown in Table 1 below.
<Table 1> Compositions of injectable preparations
All the injectable preparations thus prepared showed improved redispersibility and a low viscosity.
<Test Example> Measurement of pharmacological effects
The injectable preparations prepared in Example 1 (ceftiofur 45mg/kg) and a commercially available preparation, Excenel (Pharmacia & Upjohn
Company), as a control group were intramuscularly injected for an adsorption experiment. As experimental animals, Sprague-Dawley rats (male, body weight
300±20g) were used. The three rats were divided into one group, respectively, and starved before the experiment. Relative bioavailability was measured on the experimental animal groups. Blank blood samples were obtained prior to the administration. Blood samples (0.2ml) were obtained from the jugular veins at predetermined time intervals after administration for analysis of ceftiofur in blood. High performance liquid chromatography (HPLC) was used to analyze the concentrations of ceftiofur in the blood samples.
The concentrations of ceftiofur in the blood samples are shown in Fig. 1. The bioavailability of ceftiofur in the experimental animal groups was identified to be excellent.
Industrial Applicability
As apparent from the above description, the injectable suspension composition according to the present invention comprising ceftiofur sodium as an active ingredient, shows improved viscosity and excellent redispersibility and bioavailability.
Although the preferred embodiments of the present invention have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.
Claims
1. An injectable suspension composition comprising ceftiofur sodium as an active ingredient, an excipient, and a vegetable fatty acid ester as a dispersion medium.
2. The injectable suspension composition according to claim 1, further comprising ethanol.
3. The injectable suspension composition according to claim 2, wherein the ethanol is anhydrous ethanol.
4. The injectable suspension composition according to claim 1, wherein the fatty acid ester is at least one compound selected from the group consisting of monoglyceride, diglyceride, triglyceride, benzyl alcohol, benzyl benzoate, ethyl oleate, ethyl linolate, isopropylpalmitate and isopropylmyristate.
5. The injectable suspension composition according to claim 1, wherein the weight ratio of the ceftiofur sodium to the fatty acid ester is within the range of 1: 0.1-10.
6. The injectable suspension composition according to claim 1, wherein the weight ratio of the ceftiofur sodium to the fatty acid ester is within the range of 1: 0.5-3.
7. The injectable suspension composition according to claim 1, wherein the excipient is at least one compound selected from the group consisting of sorbitan monooleate, polyoxyethylene 20 oleate, polyoxy 20 cetyl ether, butylparahydroxy benzoic acid, butylhydroquinone, tocopherol, sodium alginate, carboxymethylcellulose, methylcellulose, tragacanth, agar and polyvinylpyrrolidone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003244255A AU2003244255A1 (en) | 2002-08-13 | 2003-06-27 | Injectable composition comprising ceftiofur sodium as an active ingredient |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0047908 | 2002-08-13 | ||
| KR1020020047908A KR20040015622A (en) | 2002-08-13 | 2002-08-13 | Injectable Composition Comprising Ceftiofur Sodium as Active Ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2004014339A1 true WO2004014339A1 (en) | 2004-02-19 |
Family
ID=31713126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2003/001264 Ceased WO2004014339A1 (en) | 2002-08-13 | 2003-06-27 | Injectable composition comprising ceftiofur sodium as an active ingredient |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20040015622A (en) |
| AU (1) | AU2003244255A1 (en) |
| WO (1) | WO2004014339A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341125A (en) * | 2008-11-19 | 2012-02-01 | 梅里亚有限公司 | Formulations comprising ceftiofur and ketoprofen or ceftiofur and benzyl alcohol |
| CN104080456A (en) * | 2011-12-23 | 2014-10-01 | 拜耳新西兰有限公司 | Antibiotic formulations |
| CN105232458A (en) * | 2015-10-23 | 2016-01-13 | 四川恒通动物制药有限公司 | Ceftiofur crystal suspension injection and preparation method thereof |
| EP2874624B1 (en) | 2012-07-17 | 2019-08-21 | Bayer New Zealand Limited | Injectable antibiotic formulations and their methods of use |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113209015A (en) * | 2020-01-21 | 2021-08-06 | 江西邦诚动物药业有限公司 | Long-acting ceftiofur hydrochloride suspension injection and preparation process thereof |
| CN112645965B (en) * | 2020-12-22 | 2022-03-25 | 浙江华尔成生物药业股份有限公司 | Preparation process of ceftiofur sodium for vacuum freeze-drying injection |
| CN112870159A (en) * | 2021-02-03 | 2021-06-01 | 西安乐道生物科技有限公司 | Veterinary ceftiofur hydrochloride injection for clearing heat, detoxifying and reducing fever and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998025621A1 (en) * | 1996-12-09 | 1998-06-18 | Pharmacia & Upjohn Company | Improved pharmaceutical compositions |
| WO2000027369A1 (en) * | 1998-11-10 | 2000-05-18 | Idexx Laboratories, Inc. | Phospholipid-coated microcrystals for the sustained release of pharmacologically active compounds and methods of their manufacture and use |
| WO2002022107A2 (en) * | 2000-09-12 | 2002-03-21 | Pharmacia & Upjohn Company | Pharmaceutical composition having modified carrier |
| WO2002066006A1 (en) * | 2001-02-19 | 2002-08-29 | Lg Life Sciences Ltd. | Sustained-release suspension of ceftiofur hydrochloride |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0128242B1 (en) * | 1987-11-10 | 1998-04-02 | 로버트 에이. 아미테이지 | Cephalosporin antibiotics |
| DK0690864T3 (en) * | 1993-03-12 | 2001-09-17 | Upjohn Co | Crystalline ceftiofur in free acid form |
-
2002
- 2002-08-13 KR KR1020020047908A patent/KR20040015622A/en not_active Abandoned
-
2003
- 2003-06-27 AU AU2003244255A patent/AU2003244255A1/en not_active Abandoned
- 2003-06-27 WO PCT/KR2003/001264 patent/WO2004014339A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998025621A1 (en) * | 1996-12-09 | 1998-06-18 | Pharmacia & Upjohn Company | Improved pharmaceutical compositions |
| WO2000027369A1 (en) * | 1998-11-10 | 2000-05-18 | Idexx Laboratories, Inc. | Phospholipid-coated microcrystals for the sustained release of pharmacologically active compounds and methods of their manufacture and use |
| WO2002022107A2 (en) * | 2000-09-12 | 2002-03-21 | Pharmacia & Upjohn Company | Pharmaceutical composition having modified carrier |
| WO2002066006A1 (en) * | 2001-02-19 | 2002-08-29 | Lg Life Sciences Ltd. | Sustained-release suspension of ceftiofur hydrochloride |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341125A (en) * | 2008-11-19 | 2012-02-01 | 梅里亚有限公司 | Formulations comprising ceftiofur and ketoprofen or ceftiofur and benzyl alcohol |
| KR101748890B1 (en) | 2008-11-19 | 2017-06-19 | 메리얼 인코포레이티드 | Formulations comprising ceftiofur and ketoprofen or ceftiofur and benzyl alcohol |
| EP2367572B1 (en) * | 2008-11-19 | 2018-08-29 | Merial, Inc. | Formulations comprising ceftiofur and benzyl alcohol |
| CN104080456A (en) * | 2011-12-23 | 2014-10-01 | 拜耳新西兰有限公司 | Antibiotic formulations |
| EP2874624B1 (en) | 2012-07-17 | 2019-08-21 | Bayer New Zealand Limited | Injectable antibiotic formulations and their methods of use |
| CN105232458A (en) * | 2015-10-23 | 2016-01-13 | 四川恒通动物制药有限公司 | Ceftiofur crystal suspension injection and preparation method thereof |
| CN105232458B (en) * | 2015-10-23 | 2018-05-22 | 四川恒通动物制药有限公司 | A kind of ceftiofur crystalline suspension injection and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003244255A1 (en) | 2004-02-25 |
| KR20040015622A (en) | 2004-02-19 |
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