WO2013163714A1 - Formulation pharmaceutique de propolis verte à usage humain en odontologie - Google Patents

Formulation pharmaceutique de propolis verte à usage humain en odontologie Download PDF

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Publication number
WO2013163714A1
WO2013163714A1 PCT/BR2013/000151 BR2013000151W WO2013163714A1 WO 2013163714 A1 WO2013163714 A1 WO 2013163714A1 BR 2013000151 W BR2013000151 W BR 2013000151W WO 2013163714 A1 WO2013163714 A1 WO 2013163714A1
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Prior art keywords
propolis
containing green
green propolis
pharmaceutical composition
formulation
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PCT/BR2013/000151
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English (en)
Portuguese (pt)
Inventor
Esther Margarida ALVES FERREIRA BASTOS
Sílvia LIGÓRIO FIALHO
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Fundação Ezequiel Dias
Fundação de Amparo à Pesquisa do Estado de Minas Gerais
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Publication of WO2013163714A1 publication Critical patent/WO2013163714A1/fr

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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
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/63—Arthropods
    • A61K35/64—Insects, e.g. bees, wasps or fleas
    • A61K35/644—Beeswax; Propolis; Royal jelly; Honey
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/987—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of species other than mammals or birds
    • A61K8/988—Honey; Royal jelly, Propolis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • PATENT DESCRIPTION REPORT "PHARMACEUTICAL FORMULATION OF GREEN PROPOLIS FOR HUMAN USE IN DENTISTRY"
  • the present invention relates to the process of producing a green propolis pharmaceutical formulation derived from Baccharis dracunculifolia produced by Apis mellifera bees, with antimicrobial properties for the treatment of oral mucositis and peri-implantitis.
  • Said formulation comprises a colloidal dispersion of the glycolic propolis extract composed of nonionic surfactant and viscous agent capable of reducing the hydrophobia of the extract and its tendency to precipitate formation in aqueous medium.
  • the formulation is applicable to buccal administration.
  • Pliny refers to Propolis as a "medicine” capable of reducing swelling and relieving pain (Gonzalez AG, Mendez RB. Colmena products - Good practices for collection, storage and conservation. Lab de Reference for Investigations and Apicultural Health. Sancti Spiritus, Cuba).
  • propolis is derived from the Greek "pro” meaning defense and “polis” meaning city, ie “city defense of bees”. It is a natural resin produced by bees from secretions and exudates from various plants. These constituents are biotransformed, added with wax and then deposited in the hives where they play an important role in sealing cracks, immobilizing invasive agents and their role in protecting against the proliferation of microorganisms (Ghisalberti EL. Propolis: a review. Bee world, v. 60, pp.59-84, 1979).
  • propolis appeared in 1908 and described its chemical properties and composition. In 1968 came the abstract in Chemical Abstracts R patent using propolis (Romanian to produce bath lotions). The first Brazilian publication on propolis, in 1984, presented a comparative study of the effect of propolis and antibiotics on the inhibition of Staphylococcus aureus (Pereira AS, FRMS Seixas, Neto FRA Propolis: 100 years of research and their future perspectives. Quim. Nova, v. 25, pp. 321-326, 2002).
  • propolis is composed of a mixture of bioactive substances: 30% waxes, 55% resins and balms, 10% essential oils, 5% pollen and other compounds.
  • bioactive substances 30% waxes, 55% resins and balms, 10% essential oils, 5% pollen and other compounds.
  • Many natural products are effective in combating free radicals that cause cell oxidation, but so far none of them have been shown to be more effective than green propolis.
  • terpenes major aromatic acids (3-prenyl-4-hydroxycinnamic and 6-propenoic-2,2-dimethyl-2H-1-benzopyran), caffeic acid (potent hepatotoxic activity), fatty acids, amino acids, vitamins (A, B1, B2, B6, C, E, PP), minerals (Mn, Cu, Ca, Al, Si, V, Ni, Zn, Cr) , high molecular weight compounds, carbohydrates and Artepelin C (Pereira AS, Seixas FRMS, Neto FRA. Propolis: 100 years of research and your future prospects. Quim Nova, v. 25, p. 321-326, 2002).
  • propolis has received great attention from the scientific class. It has already been described for its antimicrobial, antimycotic properties (Brumfitt, Hamilton-Miller JMT, Franklin I. Antibiotics of natural products. Propolis Microbes, v. 62, p. 19-22, 1990; Aga H, Shibuya T, Sugimoto T, Kurimoto M, Naka i S. Isolation and identification of antimicrobial compounds in Brazilian propolis. Biosci Biotech Biochem, v.
  • Propolis has also been successfully tested to combat protozoa by inhibiting the proliferation of Toxoplasma perenniali and Trichomonas vaginalis (Starzyk J, Scheller S, Szaflarski J, Moskwa M, Stojko A. Biological properties and clinical application of propolis II: activity of ethanol extract of propolis Arzneim Forsch, v. 27, pp. 1198-1199, 1997) and in the clinical treatment of giardiase (Mirayes C, Hollands I, Castaneda C. Therapeutic trials with the propolis-based product Propolisin in human giardiasis Acta Gastroent Latinoam, v. 18, pp. 195-202, 1988).
  • Higashi & Castro Higashi KO, Castro SLD. Propolis extracts are effective against Trypanosoma cruzi and have an impact on its interaction with host cells. J Ethnopharmacol, v. 43, p. 149-155, 1994) demonstrated that the extract ethanolic propolis was effective against Trypanossoma cruzi infection. Therefore, propolis cannot be relegated to a category of therapeutic fad, given that its virtues have been recognized for centuries, being reported in numerous works that demonstrate different types of biological activity and applications in various therapies.
  • the oral cavity is naturally colonized by several species of microorganisms, which when organized and structured constitute the oral microbiota (Seabra EJG, Lima IPC, Barbosa SV, Lima KC.
  • saliva contains about 10 bacteria / mL and this number reaches 10 11 in dental plaques, with quantitative and qualitative fluctuation (Trabulsi LR, Alterthum, F. Eds. Microbiota or normal flora of the human body.
  • Microbiology Sao Paulo: Atheneu , 4th ed, pp.
  • Streptococcus The predominant genus in the oral cavity is Streptococcus, being represented by the species: S. mutans, S. sanguis and S. salivarius, the latter being isolated mainly from the tongue, while the other species occur in association with the teeth (Moretti PE. Microbiota bacterial activity: oral microbiota Microorganisms Project, Section 1 - Bacteriology, Part 5 Microbial Associations, available at www: //. fam.br/microrganismos/bacteriologia_microbiota_human a_oral.htm. Accessed on 01.03.08).
  • Streptococcus mutans can colonize the surface of teeth and initiate dental plaque formation by being able to synthesize extracellular polysaccharides (such as insoluble glycans) from sucrose using the glycosyl transferase enzyme (Gibbons RJ, Houte J. Bacterial adherence in oral). microbial ecology Annu Rev Microbiol, v. 29, p.19-44, 1975). This adhesion polysaccharide allows other bacteria to adhere to this microenvironment, initiating the formation of microbial biofilms (Moretti PE. Human bacterial microbiota: oral microbiota. Project Microorganisms, Section 1- Bacteriology, Part 5-Microbial Associations, available at www: //. family / microorganisms / microbiology_microbiota_hum ana_oral.htm. Accessed on 01.03.08).
  • extracellular polysaccharides such as insoluble glycans
  • This adhesion polysaccharide allows other bacteria to
  • Cardiovascular infections bacterial endocarditis of oral origin. Pathogens and pophylaxis. J Clin Periodont, v.17, 494-496, 1990).
  • propolis A very effective antiseptic would be propolis.
  • propolis has already been described for its surface anesthetic action (Paintz M, Metzener J. Zur juanasthetician rial von propolis und Effhatsstofen. Pharmazie, v. 34, p.839 - 841, 1979) as a pre-oral mouthwash.
  • Shrock Son O Carvalho ACP. Application of propolis to dental sockets and skin wounds. J Nihon Uni Sch Dent, v.
  • US Patent 6,803,056 entitled “Methods and Composition for the Treatment of Viral Problems” describes a method and composition for treating lesions associated with viral infections, such as Herpes simplex, by applying an effective amount of a topical composition containing: propolis at a concentration of from 0.5 to 10%, preferably from 1 to 8%; a skin protector at a concentration of 0.5 to 50%, a penetration enhancer at a concentration of 5 to 30%, preferably 5 to 25% and a surfactant at a concentration of 1 to 20% (Dolak TM. Method and composition for treating viral outbreaks (US Patent 6,803,056; 2004). This patent further describes that the formulation exhibits better activity in the treatment of the described lesions, stopping their progression when applied and promoting complete healing, usually between 36 and 48 hours.
  • US Patent 6,153,226 entitled "Therapeutic composition containing a phenolic compound and propolis against viruses, especially herpes viruses” describes a therapeutic composition containing a phenolic compound and propolis against lipids, which contains (i) 100 to 650 parts by weight. of the phenolic component for (ii) one part by weight of propolis (Vachy R, Sauvager F, Amoros M. Therapeutic composition containing a phenol compound and propolis, which is useful against lipid capsid viruses, especially herpes viruses.
  • Patent US 6,153,226 / 2000 Said composition is suitable for the treatment of herpes.
  • US Patent 5,561,116 entitled “Solid Product Containing Propolis Components, Preparation and Use” describes a solid, water-dispersible composition containing propolis components (Nakamura S, Miyake T. Solid product containing propolis components, and preparation and uses thereof. 5,561,116; 1996).
  • Said composition is prepared by extracting the propolis components, which are further mixed with at least one saccharide selected from anhydrous saccharides and cyclodextrins.
  • the composition is suitable for use in different diseases by different application forms.
  • Dispersed systems are those with at least two phases, one of which (dispersed or internal phase) is finely distributed in the other (continuous or external phase) generally called dispersion medium or vehicle.
  • dispersed systems are termed coarse dispersion, colloidal dispersion or molecular dispersion (Morrison ID, Ross S. Colloidal dispersions - suspensions, emulsions, and foams. USA: Wiley-Interscience, 2002, 616 p.).
  • Colloidal dispersions are dispersed systems that are situated between molecular dispersion and coarse dispersion systems. Colloids are molecules or aggregates formed from 10 3 to 10 9 atoms, whose particle diameter is on the order of 10 4 to 10 ⁇ 7 cm, and the particles are distributed in a dispersing medium (Dispersiones colloidales. In: Remington - Pharmacy - 19th edition, AR Gennaro ed; wholesome Aires Pan Medica Editorial, 1998. p 366-425) Therefore, the colloidal dispersions are those with particle size ranging from 1 to 10 nm One property....
  • the characteristic feature of colloidal systems is the Tyndall effect, which occurs when a beam of light passes through the system and is scattered by the presence of suspended colloidal particles, promoting light scattering.
  • the extent of turbidity or opalescence of colloidal scatters depends on the nature, of the size and concentration of colloidal particles present (Russell B, Saville DA, Schowalter W. R. Colloidal dispersions. London: Cambridge university press, 1992, 544 p.).
  • One of the main challenges in the development of colloidal dispersions is to avoid the irreversible aggregation of suspended particles that would lead to internal phase sedimentation.
  • a stable colloidal dispersion has particles that remain suspended in the medium by Brownian mechanism.
  • solutes that modify the dielectric constant and raise the viscosity of the external phase may contribute to the reduction of particle aggregation (González-Caballero F., López-Durán JDG Suspension formulation. Eds Nielloud F., Marti-Masters G. New York: Mareei Dekker, 2000, Chapter 4, pp. 127-190).
  • Colloidal dispersion systems can be classified into colloid dispersion colloid and molecular association colloids (colloidal Dispersiones In: Remington - Pharmacy - 19th edition, AR Gennaro ed; wholesome Aires. Pan Medica Editorial, 1998. 366 p.. - 425).
  • a colloidal association colloid type dispersion has been developed.
  • Association colloids also called micellar colloids, comprise colloidal dispersed systems capable of forming micelles.
  • dispersed molecular substances such as surfactants
  • concentration a certain concentration
  • CMC Generally, hydrophobic or poorly soluble substances are found inside the micelle.
  • Surfactants play another important role in the formulation of colloidal dispersions. They are used as wetting agents, generally with the aim of increasing the miscibility of hydrophobic particles present in an aqueous vehicle (Muller RH, Bohm B, Benita S. Emulsions and nanosuspensions for the formulation of poorly soluble drugs. London: CRC Press. 1998 , 396 p.). These substances tend to accumulate at the interfaces due to their amphiphilic nature, reducing the surface tension of the present phases. The surfactant molecules orient themselves at the liquid-solid interface, so that the hydrocarbon chain is in contact with the solid particle surface, while the polar group is oriented towards the aqueous phase.
  • water-soluble nonionic surfactants are polyoxyethylated, with each molecule consisting of a lipophilic and a polyethylene glycol hydrophilic chain.
  • the surfactant adsorbs at the interface between a hydrophobic solid and water, with its hydrocarbon residue adhered to the solid surface and the water-facing polyethylene glycol residue. In this way, the particle surface is surrounded by a thin layer of. hydrated polyoxyethylene chains.
  • the hydrophilic layer forms a spherical barrier that prevents contact between the particles and hence aggregation (Russell WB, Saville DA, Schowalter W. Colloidal dispersions.
  • Poloxamers are copolymers composed of a polyoxypropylene hydrophobic central chain and two polyoxyethylene hydrophilic chains. Poloxamer is a nonionic surfactant and has the function of emulsifying, solubilizing and wetting agent (Ro and RC, Sheskey PJ, Weller PJ, Ro and R. Handbook of pharmaceutical excipients. 2003. 4 th ed., Washington: APhA Publications, 776p.). It is suitable for the production of aqueous liquid preparations containing hydrophobic substances.
  • Sorbitol is a hexahydric alcohol for mannose and mannitol isomer (Rowe RC, Sheskey PJ, Weller PJ, Rowe R. Handbook of pharmaceutical excipients. 2003.
  • the raw green propolis had its origin confirmed by microscopic laboratory analysis.
  • the extracts were obtained by maceration, centrifugation and sedimentation, for the concentration of phenolic and flavonoid compounds, active components of propolis (Table 1).
  • Antimicrobial activity tests were performed on the green propolis glycol extracts used (Table 1) against microorganisms of clinical interest in the oral cavity: Candida albicans ATCC 36802, Lactobacillus casei ATCC 7469, Porphyromonas gingivalis ATCC 49917, Prevotela melaninogenica ATCC 25845, Staphylococcus aureus ATCC 25923 and Streptococcus mutans ATCC 25175, all from the Reference Laboratory of Microorganisms of the National Institute for Health Quality Control, INCQS / FIOCRUZ, kept viable at 4 ° C in specific solid medium, with periodic subcultures every 20 days. .
  • the positive control was 0.12% (w / v) chlorhexidine hydrochloride salt, a concentration usually employed in clinical practice.
  • the concentrations of glycolic extracts evaluated were: 3, 4, 5 and 7% (v / v). It was evidenced that the concentration of 5% (v / v) of the Glycolic extracts were active against all evaluated microorganisms, inhibiting in 100% their development, similar to that observed for the positive control. This concentration, therefore, was that employed in preparing the formulation of said invention.
  • Example 4 pH measurement of colloidal dispersion containing glycol propolis extract
  • Example 5 Measurement of particle size of colloidal dispersion containing propolis glycolic extract
  • the particle size distribution of the colloidal dispersion was performed by dynamic light scattering at 90 ° optics at 25 ° C using the Zetasizer Model 3000HS (Malvern Instruments Ltd, UK). The result found, 136.5 nm, represents the average particle size. The particle size distribution had a polydispersion equivalent to 0.24.
  • Example 6 Measurement of the electrical charge of the particles of colloidal dispersion containing propolis glycolic extract
  • Colloidal particles are constantly under the influence of attractive forces, so repulsive forces prevent their aggregation (González-Caballero F., López-Durán JDG Suspension formulation. In: Pharmaceutical emulsions and suspensions. Eds. Nielloud F., Marti-Masters G. New York: Mareei Dekker, 2000, chap. 4, pp. 127-190). In most polar liquids, these forces come from particle charges. Potential Zeta is a measure of the intensity of the charge present and represents a clear indication of the stability of a dispersion, so that a value close to zero would indicate colloidal instability and may cause particle aggregation.
  • the viscosity of the developed dispersion was measured using the rotational viscosimeter set at a speed of 60rpm. Measurements were made in triplicate at a constant temperature of 25 ° C. The viscosity value obtained was 5.5 ⁇ 0.4 Cp.
  • Example 8 Measurement of the refractive index of colloidal dispersion containing propolis glycolic extract
  • the refractive index was determined using the refractometer without prior treatment of the formulation. Measurements were made in triplicate at a constant temperature of 25 ° C. The obtained result was 1,366 ⁇ 0,654. This value is close to the water refractive index, thus showing that the system is transparent.
  • Example 9 Evaluation of the stability of the colloidal dispersion containing glycol propolis extract
  • Colloidal dispersions containing propolis glycolic extract prepared for approximately twelve months and stored at 4 ° C, 25 ° C and 40 ° C showed no signs of loss of formulation stability such as: deposit formation, lump formation , crystal growth and phase separation.
  • Antimicrobial activity tests of colloidal dispersion containing green propolis glycolic extract were performed according to the methodology previously described in Example 2. This test was also used as control positive 0.12% (w / v) chlorhexidine digluconate oral solution.
  • FIG. 1 Evaluation of the present invention against Candida albicans yeast (A, B, C) and aerobic bacteria Staphylococcus aureus (D, E, F).
  • a and D Test plates containing formulation of the present invention,
  • B and E microorganism growth control,
  • C and F positive control: 0.12% chlorhexidine di luconate solution.
  • FIG. 3 Evaluation of the present invention against Lactobacillus casei (A, B, C) and Streptococcus mutans (D, E, F).
  • a and D Test plates containing formulation of the present invention,
  • B and E microorganism growth control,
  • C and F positive control: 0.12% chlorhexidine digluconate solution.
  • Porphyromonas gingivalis A, B, C
  • Prevotella melaninogenica D, E, F
  • a and D Test plates containing formulation of the present invention
  • B and E microorganism growth control
  • C and F positive control: 0.12% chlorhexidine digluconate solution.
  • the present invention demonstrated similar antimicrobial activity to that observed for chlorhexidine digluconate oral solution, currently the product of choice in dental offices.
  • the results presented show the therapeutic potential of the present invention as an easily formulated and low cost agent, in substitution for the product currently employed.

Abstract

La présente invention concerne un procédé de production d'une formulation pharmaceutique à base de propolis verte à propriétés antimicrobiennes, capable de traiter différentes maladies odontologiques, telles que la mucosite et la péri-implantite buccale. Ladite formulation comprend une dispersion colloïdale de l'extrait glycolique de propolis, constituée d'un tensioactif non ionique et d'un agent de viscosité capable de réduire l'hydrophobie de l'extrait et sa tendance à la formation de précipités en milieu aqueux. La formulation convient à une administration par voie buccale.
PCT/BR2013/000151 2012-05-03 2013-05-03 Formulation pharmaceutique de propolis verte à usage humain en odontologie WO2013163714A1 (fr)

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BR102012010441-5A BR102012010441A2 (pt) 2012-05-03 2012-05-03 Formulação farmacêutica de própolis verde para uso humano em odontologia

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9968548B2 (en) 2014-11-07 2018-05-15 Vets Plus, Inc. Dental hard chew supplements containing antimicrobial actives
RU2786136C1 (ru) * 2022-02-18 2022-12-19 Сергей Владимирович Сирак Паста для профилактики и лечения периимплантита
ES2850277R1 (es) * 2019-01-10 2023-07-07 Innovacorium Inc Composiciones de administración farmacéutica y usos de las mismas

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109993A1 (fr) * 1982-12-01 1984-06-13 Zenon M. Sosnowski Méthode d'extraction de la propolis, poudre sèche de propolis soluble dans l'eau ainsi obtenue et préparations cosmétiques et pharmaceutiques la contenant
KR20020076979A (ko) * 2001-03-28 2002-10-11 진승관 프로필렌글리콜을 용제로 사용한 수용성 프로폴리스의제조방법
BR0105471A (pt) * 2001-09-26 2003-09-23 Maria Cristina Marcucci Ribeir Formulações à base de própolis para uso odontológico
BRPI0800363A2 (pt) * 2008-03-10 2009-10-27 Univ Sao Paulo processo de obtenção de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis, formulações de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis, e o uso de formulações de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis como sanitizantes, anti-sépticos e/ou desinfetantes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109993A1 (fr) * 1982-12-01 1984-06-13 Zenon M. Sosnowski Méthode d'extraction de la propolis, poudre sèche de propolis soluble dans l'eau ainsi obtenue et préparations cosmétiques et pharmaceutiques la contenant
KR20020076979A (ko) * 2001-03-28 2002-10-11 진승관 프로필렌글리콜을 용제로 사용한 수용성 프로폴리스의제조방법
BR0105471A (pt) * 2001-09-26 2003-09-23 Maria Cristina Marcucci Ribeir Formulações à base de própolis para uso odontológico
BRPI0800363A2 (pt) * 2008-03-10 2009-10-27 Univ Sao Paulo processo de obtenção de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis, formulações de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis, e o uso de formulações de extratos padronizados, frações e substáncias isoladas de própolis ou espécies de baccharis como sanitizantes, anti-sépticos e/ou desinfetantes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9968548B2 (en) 2014-11-07 2018-05-15 Vets Plus, Inc. Dental hard chew supplements containing antimicrobial actives
ES2850277R1 (es) * 2019-01-10 2023-07-07 Innovacorium Inc Composiciones de administración farmacéutica y usos de las mismas
RU2786136C1 (ru) * 2022-02-18 2022-12-19 Сергей Владимирович Сирак Паста для профилактики и лечения периимплантита

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