WO1992004029A1 - Composition contenant de la sulfadiazine d'argent et de la benzocaine utilisee dans le traitement de plaies apres une intervention chirurgicale au laser - Google Patents
Composition contenant de la sulfadiazine d'argent et de la benzocaine utilisee dans le traitement de plaies apres une intervention chirurgicale au laser Download PDFInfo
- Publication number
- WO1992004029A1 WO1992004029A1 PCT/CA1991/000307 CA9100307W WO9204029A1 WO 1992004029 A1 WO1992004029 A1 WO 1992004029A1 CA 9100307 W CA9100307 W CA 9100307W WO 9204029 A1 WO9204029 A1 WO 9204029A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- benzocaine
- silver sulfadiazine
- weight
- electrosurgery
- Prior art date
Links
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 title claims abstract description 68
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 229960003600 silver sulfadiazine Drugs 0.000 title claims abstract description 41
- 229960005274 benzocaine Drugs 0.000 title claims abstract description 34
- 208000027418 Wounds and injury Diseases 0.000 title claims abstract description 29
- 206010052428 Wound Diseases 0.000 title claims abstract description 28
- 238000011282 treatment Methods 0.000 title claims abstract description 20
- 238000002430 laser surgery Methods 0.000 title abstract description 5
- 230000036407 pain Effects 0.000 claims abstract description 15
- 230000003902 lesion Effects 0.000 claims abstract description 8
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 201000009030 Carcinoma Diseases 0.000 claims abstract description 5
- 231100000444 skin lesion Toxicity 0.000 claims abstract description 4
- 206010040882 skin lesion Diseases 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 26
- 239000006071 cream Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000001356 surgical procedure Methods 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003974 emollient agent Substances 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 8
- 238000002647 laser therapy Methods 0.000 claims description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 6
- 239000008213 purified water Substances 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 239000003906 humectant Substances 0.000 claims description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 3
- 229940075529 glyceryl stearate Drugs 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 3
- 229920000053 polysorbate 80 Polymers 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- 229940097789 heavy mineral oil Drugs 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 2
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 claims description 2
- 229940113124 polysorbate 60 Drugs 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- 208000032484 Accidental exposure to product Diseases 0.000 claims 2
- 231100000818 accidental exposure Toxicity 0.000 claims 2
- 230000003685 thermal hair damage Effects 0.000 claims 2
- 206010059313 Anogenital warts Diseases 0.000 abstract description 4
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 abstract description 4
- 201000004201 anogenital venereal wart Diseases 0.000 abstract description 4
- 230000000699 topical effect Effects 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 230000000845 anti-microbial effect Effects 0.000 description 12
- 229940048368 flamazine Drugs 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- 239000001569 carbon dioxide Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 238000000608 laser ablation Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 210000004392 genitalia Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 238000013532 laser treatment Methods 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- 239000004166 Lanolin Chemical class 0.000 description 2
- 241000186779 Listeria monocytogenes Species 0.000 description 2
- 241000192041 Micrococcus Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000002573 colposcopy Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010006797 Burns first degree Diseases 0.000 description 1
- 206010006802 Burns second degree Diseases 0.000 description 1
- 206010006803 Burns third degree Diseases 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 241000191936 Micrococcus sp. Species 0.000 description 1
- 101100440246 Mus musculus Ncaph gene Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- -1 against E.coli Chemical compound 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002962 histologic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940099261 silvadene Drugs 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000659 thermocoagulation Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100617 topical lotion Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- This invention relates to novel topical compositions containing as active ingredients silver sulfadiazine and benzocaine for use in the treatment of wounds and the relief of pain.
- Silver sulfadiazine in an emollient cream base is the treatment of choice in most brrn centers for treating and preventing infections in wour: > .
- Background information on silver sulfadiazine may be found in United States Patent No. 3,761,590 - Research Corporation, September 27, 1973.
- Silver sulfadiazine is merchandised in association with the trade marks FLAMAZINE and SILVADENE.
- Benzocaine was selected because it is representative of some local anesthetics which are poorly soluble in water and consequently too slowly absorbed to be toxic. It can be applied directly to wounds and ulcerated surfaces where it remains localized for long periods of time to produce a sustained anesthetic action (reference Goodman and Gilman's "The Pharmacological Basis of Therapeutics", Seventh Edition, 1985, p.312) .
- Laser is one of the most effective surgical treatments for removing a great variety of skin lesions. Initially, the cost of the laser unit was a prohibitive factor; however, in recent years lasers became available at lower prices and in many practices their use is time shared. Another disadvantage of laser ablation was the extensive pain that patients experienced following surgical removal of
- SUBSTITUTE SHEET extensive lesions and those located in high pain intensity areas such as the lower genital skin.
- LEEP loop electrosurgical excision and fulguration procedure
- burns as defined herein refer to either accidentally or surgically caused burns and include first, second and third degree burns as discussed in the literature.
- a general object of the present invention is to provide a composition and a method for the treatment of wounds and the relief of pain involving the use of silver sulfadiazine/benzocaine formulations.
- a r'jre specific object of the invention is to establish a composition and an effective method of burn therapy involving the use of silver sulfadiazine/benzocaine formulations.
- Another object of the invention is the providing of a composition and a method for the treatment of wounds and the relief of pain resulting from surgical removal of lesions such as anogenital warts, carcinoma precursors, etc. , by the carbon dioxide laser and electrosurgical excision and fulguration procedure (LEEP) .
- the method comprises applying topically to the wound surface a novel composition containing as active ingredients silver sulfadiazine and benzocaine.
- Yet another object is to provide topical cream or lotion formulations containing up to 5% silver sulfadiazine and up to 20% benzocaine for the treatment of wounds and the relief of pain resulting from for example the surgical removal of lesions by carbon dioxide laser, as well as to provide a method of treatment using such formulations that will in all respects be superior to burn therapy treatment using silver sulfadiazine by itself.
- the present invention in general, provides a method
- SUBSTITUTE SHEET for the treatment of wounds and the relief of pain comprising applying topically to the wound surface a composition containing as active ingredients silver sulfadiazine and benzocaine.
- the present invention provides a composition for use in the treatment of wounds and the relief of pain, wherein said composition contains as active ingredients silver sulfadiazine and benzocaine.
- the active ingredients may, for example, be dispersed in an oil-in- water e olient cream emulsion.
- the composition may comprise, by weight, from about 1% to about 5% silver sulfadiazine and from about 5% to about 20% benzocaine; the composition may, in particular, contain from about 0.9% to about 1.1% silver sulfadiazine and from about 4.5% to about 5% benzocaine.
- a cream emulsion may include an emollient, a humectant and an emulsifier.
- SUBSTITUTE SHEET could compare the pain-relieving effect of Silcaine vs Flamazine on both laser treated and LEEP-ed regions in the same patient. Data on repair as well as post-treatment recurrences have also been obtained.
- the carbon dioxide laser and LEEP are among the most important and effective tools in a clinician's armamentarium for the removal of genital condylomata and carcinoma precursor lesions. Both genital warts and cancer precursors have reached epidemic proportions in current medical practice. Basic tissue interactions and technical aspects of laser treatment and LEEP have been published. The areas to undergo either laser treatment or LEEP are visualized at high magnification with the aid of a colposcope. The appropriate power to be used in a given case is set.
- the carbon dioxide laser light and the He-Ne guiding beam are aligned and the laser beam is moved horizontally and vertically across the treatment field. Vaporization of tissue is achieved because carbon dioxide laser energy is selectively absorbed by intracellular water; the over 100° heat generated by amplification of carbon dioxide photons instantaneously boils intracellular water, produces steam and results in cellular explosion by vaporization.
- the laser crater is cleaned from ashes (produced by thermo-coagulated water-free proteins in the
- thermo-coagulated tissue debris BSTITUTE SHEET cells
- the depth of lesional tissue vaporized is controlled by direct colposcopic visualization of the crater produced.
- appropriately chosen loop electrodes serve respectively to excise and fulgurate previously anesthetized anogenital condylomata.
- the cutting and coagulation power outputs are 36 and 50 watts respectively.
- the heat generated by rapid sparks of alternating current is absorbed by intracellular water as is laser generated energy, and the resulting steam explodes cells when cutting and superficially thermocoagulates them when fulguration is applied.
- the depths of excision and fulguration is controlled under the guidance of high magnification colposcopy and the escar produced after fulguration is wiped off with a wet cotton- tipped applicator.
- the depth of laser and LEEP craters ranges between 1mm and 2mm and extends into the papillary to superficial reticular dermis of the external anogenital skin. As such, a second degree surgical and a third degree histologic burn is produced.
- formulations of our novel product consisting of active ingredients in the specific amounts of 5% benzocaine and 1% silver sulfadiazine.
- active ingredients may, for example, be utilized in the following ranges:
- a preferred formulation is as follows:
- Mineral oil is an emollient and may be exchanged for other suitable emollients such as isopropyl myristate, pal itate or stearate; lanolin or lanolin derivatives; petrolatum, etc.
- Glycerine is a humectant, but others such as propylene glycol or sorbitol may also be used.
- Polysorbates and glyceryl stearate + PEG 100 distearate are emulsifiers but numerous others may be substituted.
- Stearyl alcohol is an emulsion stabilizer and thickener but others such as cetyl alcohol, stearic acid, xanthan gum, carbomers, cellulose gums, etc. can be also used in such formulations.
- Any suitable base cream or lotion could be used such as water-in-oil emulsions. Those described above are creams and of an oil-in-water type.
- the foregoing formulation has provided an unexpected bonus in that the antimicrobial property of the silver sulfadiazine plus benzocaine combination displays slightly enhanced antimicrobial properties to that of Flamazine.
- the results of the preliminary study and a more recent study involving clinical strain micro-organisms are tabulated below.
- the holes are completely filled with agar and the overlay evenly distributed. After solidification, the plates were inverted and incubated at 37°C for 24 hours. Clear zones around test wells was evidence that the formulation was active against the bacteria being evaluated while a hazy appearance around the well was indicative of bacteriostatic action. The diameters of the zones of inhibition reflected the degree of antimicrobial activity.
- the zones of inhibition values (mm) above represent single determinations. This study was repeated using the 1% silver sulfadiazine + 5% benzocaine and Flamazine formulations, twelve millimeter diameter wells instead of seven, and an average of " 125mg formulation per well.
- the micro-organisms used were obtained from American Type Culture Collection (ATCC) as well as from strains isolated and characterized from patients in clinical burn centers. The values below represent the average values of six determinations.
- the results demonstrate the enhancement effect of benzocaine on antimicrobial activity of silver sulfadiazine particularly against E.coli, Enterobacter cloacae, Listeria monocytogenes and MIcrococcus SP.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002024220A CA2024220A1 (fr) | 1990-08-29 | 1990-08-29 | Compose contenant de la sulfadiazine d'argent et de la benzocaine pour le traitement des plaies apres une chirurgie au laser |
CA2,024,220 | 1990-08-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992004029A1 true WO1992004029A1 (fr) | 1992-03-19 |
Family
ID=4145839
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CA1991/000307 WO1992004029A1 (fr) | 1990-08-29 | 1991-08-28 | Composition contenant de la sulfadiazine d'argent et de la benzocaine utilisee dans le traitement de plaies apres une intervention chirurgicale au laser |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0549606A1 (fr) |
AU (1) | AU8411391A (fr) |
CA (1) | CA2024220A1 (fr) |
WO (1) | WO1992004029A1 (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014161891A1 (fr) * | 2013-04-02 | 2014-10-09 | Leo Pharma A/S | Mébutate d'ingénol combiné à la thérapie laser pour le traitement de lésions cutanées hyperkératotiques |
US8932624B2 (en) | 2007-06-20 | 2015-01-13 | The Trustees Of Columbia University In The City Of New York | Bio-film resistant surfaces |
US9497975B2 (en) | 2011-12-06 | 2016-11-22 | The Trustees Of Columbia University In The City Of New York | Broad spectrum natural preservative composition |
US9511040B2 (en) | 2007-06-20 | 2016-12-06 | The Trustees Of Columbia University In The City Of New York | Skin and surface disinfectant compositions containing botanicals |
US9687429B2 (en) | 2007-06-20 | 2017-06-27 | The Trustees Of Columbia University In The City Of New York | Antimicrobial compositions containing low concentrations of botanicals |
US9968101B2 (en) | 2011-11-03 | 2018-05-15 | The Trustees Of Columbia University In The City Of New York | Botanical antimicrobial compositions |
US9981069B2 (en) | 2007-06-20 | 2018-05-29 | The Trustees Of Columbia University In The City Of New York | Bio-film resistant surfaces |
EP2552440B1 (fr) * | 2010-03-30 | 2018-10-10 | Helperby Therapeutics Limited | Nouveau traitement combiné et utilisation associée |
US10806144B2 (en) | 2011-11-03 | 2020-10-20 | The Trustees Of Columbia University In The City Of New York | Composition with sustained antimicrobial activity |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1240545A (en) * | 1967-07-17 | 1971-07-28 | Research Corp | Silver-containing therapeutic agents |
WO1989006962A1 (fr) * | 1988-01-29 | 1989-08-10 | Konrad Minninger | Agent contenant de la sulfadiazine d'argent pour traitement topique externe |
-
1990
- 1990-08-29 CA CA002024220A patent/CA2024220A1/fr not_active Abandoned
-
1991
- 1991-08-28 AU AU84113/91A patent/AU8411391A/en not_active Abandoned
- 1991-08-28 WO PCT/CA1991/000307 patent/WO1992004029A1/fr not_active Application Discontinuation
- 1991-08-28 EP EP91914895A patent/EP0549606A1/fr not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1240545A (en) * | 1967-07-17 | 1971-07-28 | Research Corp | Silver-containing therapeutic agents |
WO1989006962A1 (fr) * | 1988-01-29 | 1989-08-10 | Konrad Minninger | Agent contenant de la sulfadiazine d'argent pour traitement topique externe |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8932624B2 (en) | 2007-06-20 | 2015-01-13 | The Trustees Of Columbia University In The City Of New York | Bio-film resistant surfaces |
US9511040B2 (en) | 2007-06-20 | 2016-12-06 | The Trustees Of Columbia University In The City Of New York | Skin and surface disinfectant compositions containing botanicals |
US9687429B2 (en) | 2007-06-20 | 2017-06-27 | The Trustees Of Columbia University In The City Of New York | Antimicrobial compositions containing low concentrations of botanicals |
US9981069B2 (en) | 2007-06-20 | 2018-05-29 | The Trustees Of Columbia University In The City Of New York | Bio-film resistant surfaces |
US10542760B2 (en) | 2007-06-20 | 2020-01-28 | The Trustees Of Columbia University In The City Of New York | Skin and surface disinfectant compositions containing botanicals |
EP2552440B1 (fr) * | 2010-03-30 | 2018-10-10 | Helperby Therapeutics Limited | Nouveau traitement combiné et utilisation associée |
US9968101B2 (en) | 2011-11-03 | 2018-05-15 | The Trustees Of Columbia University In The City Of New York | Botanical antimicrobial compositions |
US10806144B2 (en) | 2011-11-03 | 2020-10-20 | The Trustees Of Columbia University In The City Of New York | Composition with sustained antimicrobial activity |
US9497975B2 (en) | 2011-12-06 | 2016-11-22 | The Trustees Of Columbia University In The City Of New York | Broad spectrum natural preservative composition |
WO2014161891A1 (fr) * | 2013-04-02 | 2014-10-09 | Leo Pharma A/S | Mébutate d'ingénol combiné à la thérapie laser pour le traitement de lésions cutanées hyperkératotiques |
Also Published As
Publication number | Publication date |
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CA2024220A1 (fr) | 1992-03-01 |
AU8411391A (en) | 1992-03-30 |
EP0549606A1 (fr) | 1993-07-07 |
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