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United States Patent 19 11) 4,269,822 Pellico Et Al

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United States Patent 19 11) 4,269,822 Pellico Et Al United States Patent 19 11) 4,269,822 Pellico et al. 45 May 26, 1981 (54) ANTSEPTIC DENTIFRICE 2,773,801 12/1956 Fox ........................................ 424/49 (75) 2,891,868 6/1959 Heggie et al. ...... 424/50 X Inventors: Michael A. Pelico, Los Angeles; 3,574,824 4/1971 Echeandia et al. ... 424/50 Robert E. Montgomery, West Los 3,703,578 11/1972 Cella et al. ...... ... 424/49 Angeles, both of Calif. 3,934,000 1/1976 Barth ........... ... 424/49 (73) Assignee: Laclede Professional Products, Inc., 4,071,614 1/1978 Grimm ............ ... 424/49 4,132,771 1/1979 Schreiber et al. .. ... 424/52 Brooklyn, N.Y. 4,150,113 4/1979 Hoogendoorn et al. ... 424/50 21) Appl. No.: 182,384 4,159,316 6/1979 Janoszewski et al. ................. 424/49 22 Filed: Aug. 29, 1980 FOREIGN PATENT DOCUMENTS Related U.S. Application Data 4675M 1/1967 France ....................................... 424/50 Primary Examiner-Shep K. Rose (63) Continuation-in-part of Ser. No. 59,243, Jul. 20, 1979, abandoned. Attorney, Agent, or Firm-Donald Diamond (51) Int. Cl. ......................... A61K 7/22; A61K 7/28; 57 ABSTRACT A61K 37/50; A61K 31/195 An antiseptic dentifrice is provided which contains an (52) U.S. C. ........................................ 424/50; 424/54; enzyme system comprising an oxidizable amino acid 424/94; 424/319 substrate and an oxidoreductase enzyme specific to such 58 Field of Search ...................... 424/50, 54, 94,319 substrate for producing hydrogen peroxide and ammo (56) References Cited nia upon oral application of the dentifrice. In an illustra tive enzyme system for this purpose, the substrate is U.S. PATENT DOCUMENTS glycine and the oxidoreductase enzyme specific to this 85,166 -12/1868 Colburn ............................. 424/58 X substrate is glycine oxidase. 111,821 2/1871 Danforth ................................ 424/58 2, 124,971 7/1938 Eisenberg et al. ..................... 424/49 8 Claims, No Drawings 4,269,822 1. 2 development of dental plaque without inhibiting the ANTISEPTIC DENTIFRICE growth of these organisms. U.S. Pat. No. 3,137,634 (Schiraldi, 1964) discloses CROSS-REFERENCE TO RELATED that the oral application of a dentifrice composition APPLICATION containing, for example, potassium copper chlorophyl This application is a continuation-in-part of U.S. Pa lin, dicalcium phosphate dihydrate, and tetrasodium pyrophosphate is useful in the treatment of gum diseases tent Application Ser. No. 059,243 filed July 20, 1979 such as periodontal disorders like gingivitis, pyorrhea now abandoned, for Antiseptic Dentifrice. and trench mouth and, in addition, reduces undesirable BACKGROUND OF THE INVENTION 10 breath odors. U.S. Pat. No. 3,227,618 (Dunellen, 1966) in the back This invention relates to dentifrice compositions and, ground portion of the specification, recites that it has more particularly, to antiseptic dentifrice compositions been disclosed that treatment of tooth enamel with a wherein hydrogen peroxide and ammonia are produced mixture of stannous flouride, hydrogen peroxide and in situ during oral application of the dentifrice. 15 insoluble sodium metaphosphate increases the enamel Dentifrices, in powder, paste, cream and liquid forms, hardness as described in The Journal of the American are used for both cosmetic and therapeutic purposes. Dental Association, May, 1950, Vol. 40, pg. 513-519. Consistent with these purposes, dentifrices are formu Merck Index, 9th Edition, 1976, at page 633, discloses lated to contain active ingredients such as cleansing and that hydrogen peroxide solution 3% contains 2.5-3.5 polishing materials, as well as various antibacterial and 20 wt.% of hydrogen peroxide which is equivalent to 8-12 anticaries agents for use as aids in the prevention of volumes of oxygen, and that this solution is a topical tooth decay. anti-infective which is useful in pharmaceutical prepara It is generally understood in the dental art that certain tions such as mouthwashes, dentifrices, and sanitary kinds of tooth decay are initiated by acid etching of the lotions. tooth enamel with the source of the acid being a metab 25 U.S. Pat. No. 4,150,133 (Hoogendorn et al., 1979) olite resulting from bacterial and enzymatic action on discloses an enzymatic dentifrice containing glucose food particles in the oral cavity. It is hypothesized that oxidase which acts on glucose present in saliva and plaque-which is a soft accumulation on the tooth sur tooth plaque to produce hydrogen peroxide. faces consisting of an organized structure of microor Hydrogen peroxide is a fast acting, broad spectrum ganisms, proteinaceous and carbohydrate substances, 30 oral antiseptic. Unlike other anitbacterials which con epithelial cells, and food debris-is a contributory fac tinue into the digestive tract, hydrogen peroxide has the tor in the development of various pathological condi advantage of quickly breaking down into oxygen and tions of the teeth and soft tissue of the oral cavity. It has water in the oral cavity. Hydrogen peroxide is also been suggested that the saccharolytic organisms of the converted into oxygen and water in the oral cavity by oral cavity, which are associates with the plaque, cause 35 the enzymatic action of catalase which is present in decalcification beneath the plaque matrix through meto saliva. bolic activity which results in the accumulation and Previous attempts to incorporate hydrogen peroxide localized concentration of organic acids. The etching into dentifrices such as toothpaste have met with limited and decalcification of the enamel may continue until the success, due to the instability of hydrogen peroxide in pulp chamber of the tooth is reached. 40 the packaged product. A wide variety of materials have been considered for use as decay-preventative agents in dentifrice composi SUMMARY OF THE INVENTION tions. Some of the substances which have been so con In accordance with this invention, there is provided sidered include para-aminobenzoic acid, a combination an antiseptic dentifrice containing an enzyme system of urea and urease to produce ammonia during oral 45 comprising from about 0.01 to about 0.5 wt.% of an application of the dentifrice, chlorophyll, per oxidizable amino acid substrate and from about 50 IU to flourinated long chain organic compounds, complex about 1,000 IU of an oxidoreductase enzyme specific to iodine, penicillin, benzohydroxamic acid, and glucose the substrate wherein the enzyme system is activated in oxidase to produce hydrogen peroxide during oral ap the chemical environment of the oral cavity, upon oral plication of the dentifrice. 50 application of the dentifrice, to produce hydrogen per U.S. Pat. No. 2,526,614 (Butterfield, 1950) discloses oxide and ammonia. the incorporation into a dentifrice of an enzyme system comprising urea and urease which produces ammonia in DETALED DESCRIPTION the presence of moisture that is encountered during oral 55 The enzyme systems of this invention which can be application of the dentifrice. The patentee reports that incorporated into dentifrice compositions to produce the action of the ammonia together with residual urea is hydrogen peroxide and ammonia during oral applica bacterocidal to acidogenic organisms and antienzymatic tion of the dentifrice are illustrated by the substrate/en to the production of lactic acid by such organisms. In zyme combinations set forth in the following table: addition, it is pointed out that the action of ammonia 60 produced from this enzyme system dissolves mucin Oxidizable Oxidoreductase plaques. Substrate Enzyme U.S. Pat. No. 3,427,380 (Kirkland, 1969) discloses (a) D-amino acids D-amino acid oxidase that oral organisms produce a capsular material which (b) L-amino acids L-amino acid oxidase is a factor in holding plaque together and allowing its 65 (c) Glycine glycine oxidase further growth and that the oral application of a denti frice containing para-aminobenzoic acid inhibits capsule (a) D-amino acid oxidase catalyzes the interaction of formation by such organisms and thereby retards the D-amino acids such as the D isomers of proline, methio 4,269,822 3 4. nine, isoleucine, alanine, valine and phenylalanine to Where the products of the activated enzyme system ether with water and oxygen to produce hydrogen include a weak organic acid, it is advantageous to for roxide, ammonia and the corresponding alpha-keto mulate the dentifrice with a buffering agent to neutral acids; ize the organic acid. A suitable buffering agent is so (b) L-amino acid oxidase catalyzes the interaction of 5 dium bicarbonate which can be present in the dentifrice L-amino acids such as the L isomers of isoleucine, al in an amount up to about 6 wt.% as, for example, in an pha-amino butyric acid, citrulline, histidine, leucine, amount from about 4 to about 6 wt.%. methionine, norleucine, norvaline, phenylalanine, tryp Dentifrices, especially toothpaste, are preferred oral tophane and tyrosine together with water and oxygen compositions for the purpose of this invention. Denti to produce hydrogen peroxide, ammonia and the corre-10 frice compositions typically contain an abrasive polish sponding alpha-keto acids; and ing material and a surfactant as well as flavoring, sweet (c) Glycine oxidase catalyzes the interaction of gly ening and coloring agents. Toothpaste usually also con cine, water and oxygen to produce hydrogen peroxide, tains humectants and thickeners. ammonia and glyoxylic acid. Any abrasive polishing material which does not ex The characteristics of the enzymes from specific 15 cessively abrade dentin and is compatible with the oxi sources are as follows: doreductase enzymes described herein can be used in (a) D-Amino Acid Oxidase from Hog Kidney the compositions of this invention. These include, for (i) Molecular Weight: 90,000 (Antonini et al., 1966). example, calcium carbonate, calcium pyrophosphate, (ii) Composition: A glycoprotein containing two mol dicalcumium phosphate, zirconium oxide and aluminum ecules of flavine-adenine dinucleotide. 20 oxide. The abrasive polishing material is usually present (iii) Optinum pH: 9. in toothpaste in an amount from about 20 to about 60 (iv) Inhibitors: certain heavy metals.
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