CA2364027C - Iodine preparation composition - Google Patents
Iodine preparation composition Download PDFInfo
- Publication number
- CA2364027C CA2364027C CA2364027A CA2364027A CA2364027C CA 2364027 C CA2364027 C CA 2364027C CA 2364027 A CA2364027 A CA 2364027A CA 2364027 A CA2364027 A CA 2364027A CA 2364027 C CA2364027 C CA 2364027C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- iodine
- combination
- wounds
- iodide
- 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.)
- Expired - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/12—Iodine, e.g. iodophors; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/106—Halogens or compounds thereof, e.g. iodine, chlorite
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/13—Burn treatment
Abstract
An iodine preparation composition suitable for use on wounds comprising an iodide source, an oxidant and a buffer characterised in that the iodide is held separately from the oxidant until the point of use, and that the buffer is capable of maintaining the pH of the composition at between pH 4.5 and pH 6 so that iodine is generated at a physiologically acceptable dose rate.
Description
Iodine Preparation Composition This invention relates to an antimicrobial composition which can be applied to wounds, cuts, abrasions or burns for the prevention or treatment of infections.
More particularly the invention relates to a composition capable of providing effective antimicrobial activity while at the same time avoiding wound and skin irntation and retardation of wound healing.
Topical antimicrobial materials and preparations containing them have long been recognised as important parts of antisepsis of intact skin and wounds. Iodine has been recognized as an antimicrobial agent with effectiveness against a wide range of micro-organisms. There are however several barriers to making an effective antimicrobial composition for application to wounds based on iodine. One problem is that iodine tends to react with organic materials found in the wound other than the intended microbial targets. This means that to be effective, iodine needs to be included at high levels such as 0.9% by weight, as described in "Handbook of Wound Dressings" edited by Stephen Thomas, 1994 Journal of Wound Care. . At such levels and with continued use iodine may have undesirable local side effects such as cell toxicity, hypersensitivity reactions, skin staining, and unpleasant odour and systemic adverse effects such as metabolic acidosis and impairment of renal function. For this reason application of iodine is recommended at levels below 1.35g in one week.
More particularly the invention relates to a composition capable of providing effective antimicrobial activity while at the same time avoiding wound and skin irntation and retardation of wound healing.
Topical antimicrobial materials and preparations containing them have long been recognised as important parts of antisepsis of intact skin and wounds. Iodine has been recognized as an antimicrobial agent with effectiveness against a wide range of micro-organisms. There are however several barriers to making an effective antimicrobial composition for application to wounds based on iodine. One problem is that iodine tends to react with organic materials found in the wound other than the intended microbial targets. This means that to be effective, iodine needs to be included at high levels such as 0.9% by weight, as described in "Handbook of Wound Dressings" edited by Stephen Thomas, 1994 Journal of Wound Care. . At such levels and with continued use iodine may have undesirable local side effects such as cell toxicity, hypersensitivity reactions, skin staining, and unpleasant odour and systemic adverse effects such as metabolic acidosis and impairment of renal function. For this reason application of iodine is recommended at levels below 1.35g in one week.
A further problem is that iodine has a relatively short shelf life when in aqueous solution meaning either that compositions which include water need to be freshly prepared before each application or again that iodine is included at high levels.
These factors limit product form.
In the past these problems with iodine have sought to be addressed by the use of iodophors which act as a release mechanism for iodine. Iodophors are readily dissociable, loose complexes of iodine with polymers or surfactants. Iodophor compositions are not best suited to use on wounds because when applied to a wound, all iodine present in the composition is readily available for reaction and therefore the adverse reactions associated with high levels of iodine are not necessarily avoided.
There thus exists a need for a composition which delivers iodine to a wound at a rate which is high enough to provide effective antisepsis but which is low enough to avoid the problems of adverse reactions associated with high levels of iodine.
GB-B-2276546 to Diversey relates to improved iodophors which are prepared at the point of use. The composition comprises an iodide source, an oxidant and an acid source, the oxidant becoming active only when the composition is dissolved in an aqueous medium. The composition is said to overcome the stability problems associated with producing teat dip/spray iodine formulations for use in the control of bovine mastitis. The rate of generation of iodine needed for these topical formulations for use on intact skin far exceeds that tolerable to a wound.
In these compositions such high levels of iodine are generated that a hydrotrope must be included to prevent the iodine from crystallising. In addition, iodine has a complex chemistry in aqueous solutions and exists in a number of equilibria.
At high iodine concentrations in the presence of iodide there is a strong tendency for the tri-iodide ion to form. We believe that this ion has very little antimicrobial activity but can still be absorbed with the risk of systemic toxicity.
We have found that it is possible to prepare a composition which is capable of generating iodine at a rate and level that makes it suitable for use in wounds.
This is achieved by separating certain of the ingredients and controlling the kinetics of the generation of iodine through the manipulation of pH.
Accordingly the present invention provides an iodine preparation composition suitable for use on wounds comprising an iodide source, an oxidant and a buffer characterised in that the oxidant is held separately from the iodide until the point of use, and that the buffer is capable of maintaining the pH of the composition at between pH 4.5 and pH 6 so that iodine is generated at a physiologically acceptable and efficacious rate.
The invention allows the preparation of compositions generating a low but effective iodine level for example up to about 2000~g per g of composition per hour, preferably in the range of Spg per g of composition per hour to 1500pg per g of composition per hour, more preferably in the range SO~.g per g of composition per hour to 1000pg per g of composition per hour so that the amount of free iodine available for antisepsis at any time is at least 0.001 %.
The compositions of the invention are preferably formulated to generate the above levels of iodine over a period of about 3 days.
The pH of the composition of the invention is generally below 5.8. We have found that if the pH is greater than about 6, the rate of production of iodine by reaction of the oxidising agent with iodide ions is too low to balance any losses of iodine by reaction with the organic matter. We have found that it is generally desired that the pH of the compositions is not below about 4.5 as otherwise there is a danger that the rate of oxidation of the iodide ions will be too fast with the result that the composition could become toxic.
The desired pH of the compositions may be achieved by incorporating buffering agents therein. Examples of buffering agents which may be included are citric acid/disodium hydrogen phosphate, citric acid/sodium citrate, acetic acid/sodium acetate. The buffering agent may conveniently be present in an amount of about 2% to 10%, preferably about 4% to 6% by weight and particularly about 5% by weight so as to provide an isotonic composition.
These factors limit product form.
In the past these problems with iodine have sought to be addressed by the use of iodophors which act as a release mechanism for iodine. Iodophors are readily dissociable, loose complexes of iodine with polymers or surfactants. Iodophor compositions are not best suited to use on wounds because when applied to a wound, all iodine present in the composition is readily available for reaction and therefore the adverse reactions associated with high levels of iodine are not necessarily avoided.
There thus exists a need for a composition which delivers iodine to a wound at a rate which is high enough to provide effective antisepsis but which is low enough to avoid the problems of adverse reactions associated with high levels of iodine.
GB-B-2276546 to Diversey relates to improved iodophors which are prepared at the point of use. The composition comprises an iodide source, an oxidant and an acid source, the oxidant becoming active only when the composition is dissolved in an aqueous medium. The composition is said to overcome the stability problems associated with producing teat dip/spray iodine formulations for use in the control of bovine mastitis. The rate of generation of iodine needed for these topical formulations for use on intact skin far exceeds that tolerable to a wound.
In these compositions such high levels of iodine are generated that a hydrotrope must be included to prevent the iodine from crystallising. In addition, iodine has a complex chemistry in aqueous solutions and exists in a number of equilibria.
At high iodine concentrations in the presence of iodide there is a strong tendency for the tri-iodide ion to form. We believe that this ion has very little antimicrobial activity but can still be absorbed with the risk of systemic toxicity.
We have found that it is possible to prepare a composition which is capable of generating iodine at a rate and level that makes it suitable for use in wounds.
This is achieved by separating certain of the ingredients and controlling the kinetics of the generation of iodine through the manipulation of pH.
Accordingly the present invention provides an iodine preparation composition suitable for use on wounds comprising an iodide source, an oxidant and a buffer characterised in that the oxidant is held separately from the iodide until the point of use, and that the buffer is capable of maintaining the pH of the composition at between pH 4.5 and pH 6 so that iodine is generated at a physiologically acceptable and efficacious rate.
The invention allows the preparation of compositions generating a low but effective iodine level for example up to about 2000~g per g of composition per hour, preferably in the range of Spg per g of composition per hour to 1500pg per g of composition per hour, more preferably in the range SO~.g per g of composition per hour to 1000pg per g of composition per hour so that the amount of free iodine available for antisepsis at any time is at least 0.001 %.
The compositions of the invention are preferably formulated to generate the above levels of iodine over a period of about 3 days.
The pH of the composition of the invention is generally below 5.8. We have found that if the pH is greater than about 6, the rate of production of iodine by reaction of the oxidising agent with iodide ions is too low to balance any losses of iodine by reaction with the organic matter. We have found that it is generally desired that the pH of the compositions is not below about 4.5 as otherwise there is a danger that the rate of oxidation of the iodide ions will be too fast with the result that the composition could become toxic.
The desired pH of the compositions may be achieved by incorporating buffering agents therein. Examples of buffering agents which may be included are citric acid/disodium hydrogen phosphate, citric acid/sodium citrate, acetic acid/sodium acetate. The buffering agent may conveniently be present in an amount of about 2% to 10%, preferably about 4% to 6% by weight and particularly about 5% by weight so as to provide an isotonic composition.
The amount of oxidant in the composition is tailored to provide a stoichiometric match with iodide. Preferably the oxidant is iodate and is provided in a molar ratio of 1:5 with iodide. In this way the iodide present in the composition fully reacts with all the oxidant. To provide the levels and rate of production of iodine in the range described above it is desirable to include up to 2% by weight of iodide, preferably, from 0.2 % to 2 % by weight of iodide. Iodide and iodate are preferably present as sodium salts although other usual counter ions may be used.
Convenient forms of administration of the composition include aqueous gels, films, creams, tablets and capsules.
The following examples are illustrative of the present invention.
Example 1.
Gel A Weight g Hydroxyethyl cellulose 30.00 Propylene Glycol 150.00 NaZHP04 3 S .61 Citric Acid 21.01 Potassium Iodate 1.124 Water 762.256 2~ Gel B Wei_h~ t in g _6_ Hydroxyethyl cellulose30.0 Propylene Glycol 150.0 Potassium Iodide 4.36 Water 815.64 Gel A was made by dissolving the buffer salt in a water/propylene glycol mix and then adding the iodate. When the solution is clear the hydroxyethyl cellulose is added and mixed until gelation is complete. Gel B was made by dissolving iodide in a water/propylene glycol mix. Hydroxyethyl cellulose was added to this mixture and mixed until gelation was complete.
The gels were packaged in separate syringes which were bound together with their nozzles fitted into a Y-shaped connecter. The contents were sterilised by autoclaving at 121 C for 15 minutes. Simultaneous depression of the plungers allows the gels to be co-extruded and allows the gels to react while being dispensed into a wound. The co-extrusion of the gels results in a product producing approximately 100~g per g of composition per hour at a pH of about 5.4. The composition generated a greater than 5 log kill of S. aureous (NCIMB
9518) which is regarded as being an acceptable level of antimicrobial activity.
Example 2 Film A g _7_ Hydroxypropylcellulose 16 Propylene Glycol 4 Potassium Iodate 0.1124 Sodium phosphate 1.7805 Citric acid 1.0505 Water 77.0566 Film B
Hydroxypropylcellulose 16 Propylene Glycol 4 Potassium Iodide 0.436 Water 79.564 The films are produced by knife over roller coating of aqueous solution onto an inert carrier followed by drying at a temperature not exceeding 100 C and sterilised by gamma irradiation.
The films may be cut into rectangles and added to a wound whereupon they dissolve in the wound fluid and reaction takes place.
Convenient forms of administration of the composition include aqueous gels, films, creams, tablets and capsules.
The following examples are illustrative of the present invention.
Example 1.
Gel A Weight g Hydroxyethyl cellulose 30.00 Propylene Glycol 150.00 NaZHP04 3 S .61 Citric Acid 21.01 Potassium Iodate 1.124 Water 762.256 2~ Gel B Wei_h~ t in g _6_ Hydroxyethyl cellulose30.0 Propylene Glycol 150.0 Potassium Iodide 4.36 Water 815.64 Gel A was made by dissolving the buffer salt in a water/propylene glycol mix and then adding the iodate. When the solution is clear the hydroxyethyl cellulose is added and mixed until gelation is complete. Gel B was made by dissolving iodide in a water/propylene glycol mix. Hydroxyethyl cellulose was added to this mixture and mixed until gelation was complete.
The gels were packaged in separate syringes which were bound together with their nozzles fitted into a Y-shaped connecter. The contents were sterilised by autoclaving at 121 C for 15 minutes. Simultaneous depression of the plungers allows the gels to be co-extruded and allows the gels to react while being dispensed into a wound. The co-extrusion of the gels results in a product producing approximately 100~g per g of composition per hour at a pH of about 5.4. The composition generated a greater than 5 log kill of S. aureous (NCIMB
9518) which is regarded as being an acceptable level of antimicrobial activity.
Example 2 Film A g _7_ Hydroxypropylcellulose 16 Propylene Glycol 4 Potassium Iodate 0.1124 Sodium phosphate 1.7805 Citric acid 1.0505 Water 77.0566 Film B
Hydroxypropylcellulose 16 Propylene Glycol 4 Potassium Iodide 0.436 Water 79.564 The films are produced by knife over roller coating of aqueous solution onto an inert carrier followed by drying at a temperature not exceeding 100 C and sterilised by gamma irradiation.
The films may be cut into rectangles and added to a wound whereupon they dissolve in the wound fluid and reaction takes place.
Claims (10)
1. An iodine preparation combination for use on wounds comprising a first composition and a second composition, wherein:
the first composition comprises an iodide source; and the second composition comprises an oxidant and a buffer;
wherein said first composition and said second composition are held separately until the point of use, and wherein the buffer maintains a pH of between pH 4.5 and pH 6 following mixture of the first composition with the second composition, so that iodine is generated at a physiologically acceptable dose and rate.
the first composition comprises an iodide source; and the second composition comprises an oxidant and a buffer;
wherein said first composition and said second composition are held separately until the point of use, and wherein the buffer maintains a pH of between pH 4.5 and pH 6 following mixture of the first composition with the second composition, so that iodine is generated at a physiologically acceptable dose and rate.
2. An iodine preparation combination as claimed in claim 1 characterised in that following mixture of the first composition with the second composition, the combination generates from 5 µg of iodine per g of combination per hour to 1500µg of iodine per g of combination per hour.
3. An iodine preparation combination as claimed in claim 1 characterised in that following mixture of the first composition with the second composition, the combination generates approximately 100µg of iodine per g of combination per hour.
4. An iodine preparation combination as claimed in claim 2 or claim 3 formulated to generate the said levels of iodine over a period of three days.
5. An iodine preparation combination according to any one of claims 1 - 4, wherein following mixture of the first composition with the second composition, the pH of the combination is maintained between 5.4 and 5.8.
6. An iodine preparation combination according to any one of claims 1 - 5, which includes from 0.2% to 2% by weight of iodide.
7. The use of an iodine preparation combination as defined in any one of claims 1 - 6 for the manufacture of a medicament for use on wounds.
8. Use of an iodine preparation combination as defined in any one of claims 1 - 6 for the treatment of wounds.
9. The use according to claim 7, wherein said medicament is for the treatment of sepsis in wounds.
10. The use according to claim 8 for the treatment of sepsis in wounds.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9905663.2A GB9905663D0 (en) | 1999-03-12 | 1999-03-12 | Iodine preparation composition |
| GB9905663.2 | 1999-03-12 | ||
| PCT/EP2000/002194 WO2000054593A1 (en) | 1999-03-12 | 2000-03-13 | Iodine preparation compositon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2364027A1 CA2364027A1 (en) | 2000-09-21 |
| CA2364027C true CA2364027C (en) | 2011-09-06 |
Family
ID=10849464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2364027A Expired - Lifetime CA2364027C (en) | 1999-03-12 | 2000-03-13 | Iodine preparation composition |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7014871B1 (en) |
| EP (1) | EP1158859B1 (en) |
| JP (1) | JP2002539140A (en) |
| AT (1) | ATE254851T1 (en) |
| AU (1) | AU766031B2 (en) |
| BR (1) | BR0008952A (en) |
| CA (1) | CA2364027C (en) |
| DE (1) | DE60006788T2 (en) |
| ES (1) | ES2209862T3 (en) |
| GB (1) | GB9905663D0 (en) |
| NZ (1) | NZ513991A (en) |
| WO (1) | WO2000054593A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6838050B1 (en) | 1999-06-04 | 2005-01-04 | Oxibio, Inc. | Methods and devices for providing anti-infective activity to a medical device |
| US6592890B1 (en) | 1999-10-20 | 2003-07-15 | Oxibio, Inc. | Conveyance of anti-infective activity to wound dressings |
| WO2003045366A1 (en) * | 2001-11-29 | 2003-06-05 | Greystone Medical Group, Inc. | Treatment of wounds and compositions employed |
| GB0525504D0 (en) * | 2005-12-14 | 2006-01-25 | Bristol Myers Squibb Co | Antimicrobial composition |
| US8303994B2 (en) * | 2006-06-22 | 2012-11-06 | Jack Howard Kessler | Method for the eradication of pathogens including S. aureus and antibiotic resistant microbes from the upper respiratory tract of mammals and for inhibiting the activation of immune cells |
| GB201020236D0 (en) | 2010-11-30 | 2011-01-12 | Convatec Technologies Inc | A composition for detecting biofilms on viable tissues |
| CZ303548B6 (en) | 2011-01-05 | 2012-11-28 | Contipro Pharma A.S. | Iodine-forming health formulation, process of its preparation and bandage containing thereof |
| CN105008611A (en) | 2012-12-20 | 2015-10-28 | 康沃特克科技公司 | Processing of chemically modified cellulosic fibres |
| WO2016021215A1 (en) * | 2014-08-08 | 2016-02-11 | 日医工株式会社 | Jelly-like medicinal composition of potassium iodide |
| EP3936163B1 (en) | 2015-05-07 | 2024-04-03 | Solventum Intellectual Properties Company | A controlled release iodine structure for use with wound care |
| CA2990627A1 (en) | 2015-06-22 | 2016-12-29 | Infection Containment Company, LLC | Topical antiseptic system |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4271149A (en) * | 1979-09-21 | 1981-06-02 | West Agro-Chemical, Inc. | Germicidal iodine compositions with enhanced iodine stability |
| JPH02276549A (en) | 1989-04-17 | 1990-11-13 | Takahashi Shoten:Kk | Device for cutting and carrying tofu |
| US5128136A (en) * | 1990-07-16 | 1992-07-07 | The Oregon Health Sciences University | Wound healing kit comprised of gelable collagen |
| US5081106A (en) * | 1990-07-16 | 1992-01-14 | The Oregon Health Sciences University | Wound dressing protocol utilizing collagen gelatin formed with iodine |
| GB9306296D0 (en) * | 1993-03-26 | 1993-05-19 | Diversey Corp | Improved iodophors,production and use thereof |
| GB9322555D0 (en) * | 1993-11-02 | 1993-12-22 | Duncan Group Plc | Sterilant system |
| CA2335055A1 (en) | 1998-06-19 | 1999-12-23 | Jack Fellman | Medical device having anti-infective and contraceptive properties |
-
1999
- 1999-03-12 GB GBGB9905663.2A patent/GB9905663D0/en not_active Ceased
-
2000
- 2000-03-13 EP EP00920494A patent/EP1158859B1/en not_active Expired - Lifetime
- 2000-03-13 WO PCT/EP2000/002194 patent/WO2000054593A1/en active IP Right Grant
- 2000-03-13 DE DE60006788T patent/DE60006788T2/en not_active Expired - Lifetime
- 2000-03-13 US US09/936,421 patent/US7014871B1/en not_active Expired - Lifetime
- 2000-03-13 ES ES00920494T patent/ES2209862T3/en not_active Expired - Lifetime
- 2000-03-13 AU AU41049/00A patent/AU766031B2/en not_active Expired
- 2000-03-13 BR BR0008952-4A patent/BR0008952A/en not_active Application Discontinuation
- 2000-03-13 AT AT00920494T patent/ATE254851T1/en not_active IP Right Cessation
- 2000-03-13 JP JP2000604687A patent/JP2002539140A/en active Pending
- 2000-03-13 CA CA2364027A patent/CA2364027C/en not_active Expired - Lifetime
- 2000-03-13 NZ NZ513991A patent/NZ513991A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB9905663D0 (en) | 1999-05-05 |
| BR0008952A (en) | 2002-04-09 |
| DE60006788D1 (en) | 2004-01-08 |
| EP1158859A1 (en) | 2001-12-05 |
| DE60006788T2 (en) | 2004-07-29 |
| AU4104900A (en) | 2000-10-04 |
| ATE254851T1 (en) | 2003-12-15 |
| NZ513991A (en) | 2001-09-28 |
| WO2000054593A1 (en) | 2000-09-21 |
| EP1158859B1 (en) | 2003-11-26 |
| ES2209862T3 (en) | 2004-07-01 |
| JP2002539140A (en) | 2002-11-19 |
| CA2364027A1 (en) | 2000-09-21 |
| AU766031B2 (en) | 2003-10-09 |
| US7014871B1 (en) | 2006-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20200313 |
|
| MKEX | Expiry |
Effective date: 20200313 |