JPH03218308A - Composition for oral cavity - Google Patents
Composition for oral cavityInfo
- Publication number
- JPH03218308A JPH03218308A JP32800589A JP32800589A JPH03218308A JP H03218308 A JPH03218308 A JP H03218308A JP 32800589 A JP32800589 A JP 32800589A JP 32800589 A JP32800589 A JP 32800589A JP H03218308 A JPH03218308 A JP H03218308A
- Authority
- JP
- Japan
- Prior art keywords
- ethanol
- composition
- ibuprofen
- flurbiprofen
- ibufenac
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 210000000214 mouth Anatomy 0.000 title claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229960001680 ibuprofen Drugs 0.000 claims abstract description 21
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229960002390 flurbiprofen Drugs 0.000 claims abstract description 18
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229950009183 ibufenac Drugs 0.000 claims abstract description 17
- 229940079593 drug Drugs 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 14
- 239000000606 toothpaste Substances 0.000 abstract description 10
- 229940034610 toothpaste Drugs 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 239000002324 mouth wash Substances 0.000 abstract description 7
- 208000028169 periodontal disease Diseases 0.000 abstract description 7
- 229940051866 mouthwash Drugs 0.000 abstract description 6
- 208000002925 dental caries Diseases 0.000 abstract description 5
- 239000000796 flavoring agent Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 229960004756 ethanol Drugs 0.000 abstract description 4
- 235000019634 flavors Nutrition 0.000 abstract description 4
- 230000001580 bacterial effect Effects 0.000 abstract description 2
- 235000003599 food sweetener Nutrition 0.000 abstract description 2
- 239000002736 nonionic surfactant Substances 0.000 abstract description 2
- 239000003765 sweetening agent Substances 0.000 abstract description 2
- 239000002562 thickening agent Substances 0.000 abstract description 2
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 239000007767 bonding agent Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 238000005498 polishing Methods 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000007505 plaque formation Effects 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 230000002401 inhibitory effect Effects 0.000 description 12
- 239000000600 sorbitol Substances 0.000 description 9
- 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 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- -1 polyoxyethylene Polymers 0.000 description 8
- 208000002064 Dental Plaque Diseases 0.000 description 7
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229940085605 saccharin sodium Drugs 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000194019 Streptococcus mutans Species 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229940041616 menthol Drugs 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- XZAGBDSOKNXTDT-UHFFFAOYSA-N Sucrose monopalmitate Chemical compound CCCCCCCCCCCCCCCC(O)=O.OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(CO)O1 XZAGBDSOKNXTDT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000007621 bhi medium Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- FXPVUWKFNGVHIZ-UHFFFAOYSA-L disodium;dodecyl sulfate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O FXPVUWKFNGVHIZ-UHFFFAOYSA-L 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 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
- 239000005770 Eugenol Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- SAYJMCTYMUAYEN-UHFFFAOYSA-M [Na+].[F-].C(C)O Chemical compound [Na+].[F-].C(C)O SAYJMCTYMUAYEN-UHFFFAOYSA-M 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229940071145 lauroyl sarcosinate Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- AMCPECLBZPXAPB-UHFFFAOYSA-N propane-1,2,3-triol;sodium Chemical compound [Na].OCC(O)CO AMCPECLBZPXAPB-UHFFFAOYSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- WKMXOPXIVBEXRR-UHFFFAOYSA-H tricalcium;diphosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WKMXOPXIVBEXRR-UHFFFAOYSA-H 0.000 description 1
- 235000010493 xanthan gum Nutrition 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
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
産ｊＬＬ辺ＩＬ匁１■
本発明は、抗炎症効果に加え、歯垢形成抑制効果及び殺
菌効果に優れ、歯周疾患及びう蝕予防に有効な口腔用組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an oral composition that has anti-inflammatory effects, excellent plaque formation inhibiting effects and bactericidal effects, and is effective in preventing periodontal disease and dental caries. .
の び が しようとする
従来、イブプロフェン、フルルビプロフェン、イブフェ
ナックは強い抗炎症効果を有しており、この薬剤の歯周
疾患への適用は治療促進のために有用であることが知ら
れている（特開昭５２一１一
３８０３０号公報、特開昭６０−６１５２４号公報）。Traditionally, ibuprofen, flurbiprofen, and ibufenac have strong anti-inflammatory effects, and the application of these drugs to periodontal disease is known to be useful for promoting treatment. (Japanese Patent Application Laid-open No. 52-11-38030, Japanese Patent Application Laid-open No. 60-61524).
しかしながら、歯周疾患は口腔内細菌の形成する歯垢が
原因であるので、単なる抗炎症剤の投与ではその治療効
果は十分とは言えない。即ち、歯周疾患をより有効に予
防、治療するためには、抗炎症効果に加え、歯垢の形成
を抑制あるいは阻止することが必要である。However, since periodontal diseases are caused by dental plaque formed by oral bacteria, mere administration of anti-inflammatory agents cannot be said to have a sufficient therapeutic effect. That is, in order to more effectively prevent and treat periodontal diseases, it is necessary to suppress or prevent the formation of dental plaque in addition to anti-inflammatory effects.
従って、イブプロフエン、フルルビプロフエン、イブフ
ェナックを含む口腔用組成物に更に歯垢形成阻止効果を
付与することができれば、歯周疾患の予防、治療促進に
非常に効果的である。Therefore, if oral compositions containing ibuprofen, flurbiprofen, and ibufenac can further have a plaque formation inhibiting effect, they will be very effective in preventing and promoting periodontal disease treatment.
この場合、歯垢はう蝕の原因ともなるため、歯垢形成を
抑制することはう蝕予防にも有効である。In this case, since dental plaque also causes dental caries, inhibiting dental plaque formation is also effective in preventing dental caries.
課 を するための び
本発明者は、イブプロフェン、フルルビプロフェン、イ
ブフェナックを含む口腔用組成物に歯垢形成抑制効果を
付与することについて鋭意検討を重ねた結果、これらの
薬剤を含む口腔用組成物に−２−
対しエタノールを組成物全体の５〜４０％（重量％、以
下同じ）配合することが効果的であることを知見した。As a result of intensive studies on imparting a plaque formation inhibiting effect to oral compositions containing ibuprofen, flurbiprofen, and ibufenac, the present inventor has developed oral compositions containing these drugs. It has been found that it is effective to incorporate 5 to 40% (weight %, same hereinafter) of ethanol into the composition based on the total composition.
即ち、イブプロフェン、フルルビプロフェン、イブフェ
ナックはそれぞれストレプトコッカス・ミュータンス菌
に由来する歯垢形成抑制能はなく、またエタノールもそ
れ自体２０％程度の濃度では歯垢形成抑制能がないもの
であるが、これらをエタノール５％以上の濃度において
併用した場合、イブプロフェン、フルルビプロフェン、
イブフェナックとエタノールとが相乗的に作用し、優れ
た歯垢形成阻止効果を与えることを知見した。That is, ibuprofen, flurbiprofen, and ibufenac each have no ability to inhibit plaque formation derived from Streptococcus mutans bacteria, and ethanol itself does not have the ability to inhibit plaque formation at a concentration of about 20%. , when these are used together at a concentration of 5% or more ethanol, ibuprofen, flurbiprofen,
It has been found that Ibufenac and ethanol act synergistically to provide an excellent plaque formation inhibiting effect.
しかも、イブプロフェン、フルルビプロフェン、イブフ
ェナックはそれぞれ殺菌効果が殆どなく、またエタノー
ルは従来より殺菌効果を有することが知られているが、
後述する実験例の結果からも認められるように５〜４０
％程度の濃度では十分な殺菌効果を与えないものである
にも拘らず、イブプロフェン、フルルビプロフェン、イ
ブフェナックとエタノールとをエタノール濃度５％以上
において併用することにより、ス１・レプトコッヵス・
ー３ー
ミュータンス菌等のダラム陽性菌及び大腸菌等のダラム
陰性菌に対して優れた殺菌効果を与えることを知見し、
本発明をなすに至ったものである。Moreover, ibuprofen, flurbiprofen, and ibufenac each have almost no bactericidal effect, and ethanol has been known to have a bactericidal effect, but
5 to 40 as seen from the results of the experimental examples described later.
% concentration does not provide a sufficient bactericidal effect, but by using ibuprofen, flurbiprofen, ibufenac and ethanol together at an ethanol concentration of 5% or more, S1, Leptococcus,
-3- It was discovered that it has an excellent bactericidal effect against Durham-positive bacteria such as Streptococcus mutans and Durham-negative bacteria such as Escherichia coli.
This is what led to the present invention.
以下、本発明につき更に詳述する。The present invention will be explained in more detail below.
本発明の口腔用組成物は、イブプロフエン、フルルビプ
ロフエン、イブフエナツクから選ばれる薬剤とエタノー
ルとを配合してなるもので、含漱剤、マウスウオッシュ
、練歯磨等の歯磨類などの剤型で使用される。The oral composition of the present invention is a composition containing ethanol and a drug selected from ibuprofen, flurbiprofen, and ibuprofen, and is available in the form of a mouthwash, mouthwash, toothpaste, and other dentifrices. used.
この場合、上記薬剤は１種を単独で使用してもよく、ま
た、２種以上を混合して使用してもよいが、その配合量
は、組成物全体の０．００１〜５％（重量％、以下同様
）、特に０．０５〜１％であることが好適である。In this case, the above-mentioned drugs may be used alone or in combination of two or more, but the blending amount is 0.001 to 5% (by weight) of the entire composition. %, hereinafter the same), particularly preferably from 0.05 to 1%.
また、エタノールの配合量は、組成物全体の５〜４０重
量％、好ましくは１０〜２５％、より好ましくは１０〜
１８％である。エタノールの配合量が５％より少ないと
、上記薬剤とエタノールとの併用による相乗効果が十分
に得られず、歯垢形成抑制効果及び殺菌効果に劣るもの
であり、４０４ー
％を越えるとそれ以上の効果は得られず、経済的に不利
になる上、使用感が低下し、得策でない。In addition, the amount of ethanol blended is 5 to 40% by weight of the entire composition, preferably 10 to 25%, more preferably 10 to 25%.
It is 18%. If the amount of ethanol is less than 5%, the synergistic effect of the combination of the above drug and ethanol will not be sufficiently obtained, and the plaque formation inhibiting effect and bactericidal effect will be inferior, and if it exceeds 404%, it will be more This is not a good idea because it does not have the same effect, is economically disadvantageous, and has a poor usability.
本発明の口腔用組成物には、上述した成分に加えて更に
その目的、組成物の種類等に応じた適宜な成分を配合す
ることができる。In addition to the above-mentioned components, the oral composition of the present invention may further contain appropriate components depending on the purpose, type of composition, etc.
例えば、含漱剤、マウスウオッシュの場合には、ボリオ
キシエチレン硬化ヒマシ油などのポリオキシエチレン脂
肪酸エステル，シヨ糖脂肪酸エステル，マルトース脂肪
酸エステル等の糖脂肪酸エステルなどの非イオン性界面
活性剤、ソルビツ１ヘ，グリセリン，エチレングリコー
ル，プロピレングリコール，ボリエチレングリコール，
ポリプロピレングリコール等の粘稠剤、サッカリンナト
リウム等の甘味剤、各種香料などを通常の配合量で添加
することができる。For example, in the case of rinses and mouthwashes, nonionic surfactants such as polyoxyethylene fatty acid esters such as polyoxyethylene hydrogenated castor oil, sugar fatty acid esters such as sucrose fatty acid esters, maltose fatty acid esters, sorbitol, etc. 1. Glycerin, ethylene glycol, propylene glycol, polyethylene glycol,
Thickening agents such as polypropylene glycol, sweeteners such as saccharin sodium, various flavoring agents, etc. can be added in usual amounts.
更に、練歯磨等の歯磨類の場合には、上記の各種添加剤
に加え、第２リン酸カルシウム・２水和物及び無水和物
，炭酸カルシウム，ピロリン酸カルシウム，水酸化アル
ミニウム，アルミナ，無水ケイ酸，ケイ酸アルミニウム
等の沈降性シリカ，−５ー
ゲル化性シリカ等の研磨剤、カラゲナン，カルボキシメ
チルセルロースナトリウム，メチルセルロースなどのセ
ルロース誘導体、アルギン酸ナトリウムなどのアルカリ
金属アルギネート、キサンタンガム，トラガカントガム
，アラビアガムなどのガム類、ポリビニルアルコールな
どの合成粘結剤、シリカゲル，アルミニウムシルカゲル
などの無機粘結剤等の粘結剤などを配合することができ
る。Furthermore, in the case of toothpastes such as toothpaste, in addition to the various additives mentioned above, dibasic calcium phosphate dihydrate and anhydrate, calcium carbonate, calcium pyrophosphate, aluminum hydroxide, alumina, silicic anhydride, Precipitated silica such as aluminum silicate, abrasives such as -5-gelling silica, cellulose derivatives such as carrageenan, sodium carboxymethylcellulose, and methylcellulose, alkali metal alginates such as sodium alginate, gums such as xanthan gum, gum tragacanth, and gum arabic. , synthetic binders such as polyvinyl alcohol, and binders such as inorganic binders such as silica gel and aluminum silica gel.
なお、これら添加剤の配合量も通常の範囲とすることが
できる。Incidentally, the blending amount of these additives can also be within a normal range.
なお、組成物のｐ’ Ｈは５〜７とすることが好ましい
。In addition, it is preferable that p'H of a composition shall be 5-7.
允鷹■蟇か呆
本発明の口腔用組成物は、抗炎症効果を有する上、歯垢
形成抑制効果及び殺菌効果に優れているので、歯周疾患
及びう蝕の予防に有効である。The oral composition of the present invention not only has an anti-inflammatory effect, but also has excellent plaque formation inhibiting and bactericidal effects, and is therefore effective in preventing periodontal disease and dental caries.
次に、実験例により本発明の効果を具体的に示す。Next, the effects of the present invention will be specifically illustrated by experimental examples.
〔実験例１〕
イブプロフェンとエタノールを配合した第１表−６
に示す組成の被検サンプルを調製し、これらを試験試料
として使用し、下記の培養付着法により歯垢形成抑制に
及ぼす効果、及び、薬剤を短時間、細菌に作用させたと
きの殺菌効果を調べた。[Experimental Example 1] Test samples containing ibuprofen and ethanol with the composition shown in Table 1-6 were prepared, and these were used as test samples to determine the effect on inhibition of plaque formation by the following culture attachment method. We investigated the bactericidal effect when the drug was applied to bacteria for a short period of time.
１．歯垢形成抑制試験
１％のシヨ糖を含むＢＨＩ培地２ｍＱにストレプトコッ
カス・ミュータンス６７１５株を接種し、Ｎ２：ＣＯ２
：Ｈ２＝８０＝１０＝１０にガス置換されたアナエロボ
ックス内で、３７゜Ｃにおいて１６時間培養した。培養
後、生理食塩水で試験管壁に付着した歯垢を３回洗浄し
た。これに試験試料を３ｍｌｌｌ加え、１分間放置した
。その後試験試料を捨て、生理食塩水で３回洗浄し、１
％のシヨ糖を含むＢ Ｈ Ｉ培地３ｍＱを加え、再びア
ナエロボックス内で３７℃において１８時間培養した。1. Plaque formation inhibition test Streptococcus mutans strain 6715 was inoculated into 2 mQ of BHI medium containing 1% sucrose, and N2:CO2
Culture was carried out at 37°C for 16 hours in an Anaerobox with gas exchange such that: H2 = 80 = 10 = 10. After culturing, dental plaque adhering to the test tube wall was washed three times with physiological saline. 3 ml of the test sample was added to this and left to stand for 1 minute. The test sample was then discarded, washed three times with physiological saline, and
3 mQ of BHI medium containing % sucrose was added and cultured again in the Anaerobox at 37°C for 18 hours.
培養後、水で３回洗浄し、３ｍＱの０．５ＮのＮａＯＨ
を加えて歯垢を均一に懸濁させた後、フオトメータを用
い５５０ｎｍで吸光度（濁度）を測定し、付着歯垢量を
求めた。結果を第２表に示す。なお、歯垢形成抑制率は
試験試料の代わりに生理食塩水＝７−
を用いたコントロールの抑制率をＯ％とした場合の百分
率で示した。After incubation, wash 3 times with water and add 3 mQ of 0.5N NaOH.
was added to uniformly suspend the dental plaque, and then the absorbance (turbidity) was measured at 550 nm using a photometer to determine the amount of attached dental plaque. The results are shown in Table 2. Note that the plaque formation inhibition rate was expressed as a percentage when the inhibition rate of a control using physiological saline = 7- instead of the test sample was taken as 0%.
２．殺菌力試験
ストレプトコッカス・ミュータンス６７１５株、または
、大腸菌Ｕ５／４１株をＴＨＥ培地で１６時間培養後、
遠心分離で集菌し、更に滅菌水で１回洗浄後、滅菌水に
懸濁した。各試験試料２．７艷に菌液０．３ｄを加え、
撹拌し、１分間放置した。その後、リン酸緩衝液にて希
釈し、ＳＣＤＬＰ寒天平板上に塗抹した。ストレプトコ
ッカス・ミュータンスは前述の嫌気的条件下で、大腸菌
は好気的に１８時間培養し、寒天平板上に生育したコロ
ニー数から各試験試料に作用させた後の残存生菌数を計
算した。結果を第３表に示す。2. Bactericidal activity test After culturing Streptococcus mutans strain 6715 or Escherichia coli U5/41 strain in THE medium for 16 hours,
Bacteria were collected by centrifugation, washed once with sterile water, and then suspended in sterile water. Add 0.3 d of bacterial solution to 2.7 liters of each test sample,
Stir and let stand for 1 minute. Thereafter, it was diluted with phosphate buffer and spread on an SCDLP agar plate. Streptococcus mutans was cultured under the above-mentioned anaerobic conditions, and E. coli was cultured aerobically for 18 hours, and the number of remaining viable bacteria after acting on each test sample was calculated from the number of colonies grown on the agar plate. The results are shown in Table 3.
−８−
第
１
表
−９
第
２
表
１０−
第
３
表
−１１一
第２，３表の結果より、エタノールの配合量が５％に満
たない場合（サンプルＮｏ． １ ）やイブプロフェン
無添加の場合（サンプルＮｏ．４．５）は歯垢形成抑制
効果及び殺菌効果が低いが、これらに比べ、イブプロフ
エンとエタノールとを併用した本発明品（サンプルＮｏ
．２．３）では、イブプロフェンとエタノールとの相乗
作用により、高い歯垢形成抑制効果及び殺菌効果が発揮
されることが確認された。-8- Table 1-9 2 Table 10- 3 Table-11 - From the results in Tables 2 and 3, it is clear that when the amount of ethanol is less than 5% (sample No. 1) and when no ibuprofen is added. (Sample No. 4.5) has low plaque formation inhibiting effect and bactericidal effect, but compared to these, the product of the present invention (Sample No.
．． In 2.3), it was confirmed that the synergistic effect of ibuprofen and ethanol exhibited a high plaque formation inhibiting effect and bactericidal effect.
〔実験例２〕
フルルビプロフェン又はイブフェナックとエタノールと
を配合した第４表に示す組成のサンプルを調製し、これ
らの歯垢形成抑制効果及び殺菌効果を実験例１と同様の
方法で調べた。結果を第５，６，７．８表に示す。[Experimental Example 2] Samples containing flurbiprofen or ibufenac and ethanol having the compositions shown in Table 4 were prepared, and their plaque formation inhibiting effects and bactericidal effects were examined in the same manner as Experimental Example 1. . The results are shown in Tables 5, 6, and 7.8.
−１２
第
４
表
−１３−
第
５
表
フルルビプロフェン配合品の歯垢形
成抑制効果
一１４一
第
６
表
フルルビプロフェン配合品の殺菌効果
第
７
表
イブフェナック配合品の歯垢形成抑制効果第
８
表
イブフェナック配合品の殺菌効果
− １７ー
上記結果から、フルルビプロフェン及びイブフェナック
の場合もイブプロフェンと同様の効果を有することが認
められた。-12 Table 4 -13- Table 5 Effect of inhibiting plaque formation on products containing flurbiprofen 14-6 Table 7 Sterilizing effect of products containing flurbiprofen Table 7 Effect on inhibiting plaque formation on products containing ibufenac Table 8: Bactericidal effect of ibufenac combination products - 17 - From the above results, it was confirmed that flurbiprofen and ibufenac had the same effect as ibuprofen.
以下、実施例を示して本発明を具体的に説明するが、本
発明は下記実施例に制限されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to examples, but the present invention is not limited to the following examples.
〔実施例１〕含轍剤
イブプロフェン ０．６％エタノー
ル １８．０％ポリエチレング
リコール４００ ２．０％グリセリン
１０．０％サッカリンナトリウム
０．０１％香 料
０．２％〔実施例２〕マウスウオッシュ
イブプロフェン
１ ．
Ｏ％
エタノール
２０．
０％
１８−
ソルビット
ショ糖モノパルミテート
サッカリンナトリウム
香 料
〔実施例３〕練歯磨
水酸化アルミニウム
ゲル化性シリカ
ソルビット
ショ糖モノバルミテート
ラウリル硫酸ナトリウム
サッカリンナトリウム
イブプロフェン
エタノーノレ
メントール
１０． ０％
１． ０％
０． ０１％
０．２％
４５． ０％
２． ０％
２５． ０％
０％
５％
２％
０５％
０％
２％
香
料
１ ．
Ｏ％
〔実施例４〕練歯磨
沈降性シリカ
ソルビット
グリセリン
ポリビニルピロリドン
ラウロイルボリグリセリンエステル
２ ５．
２５．
２５．
１ ．
１ ．
０％
０％
０％
０％
０％
サッカリンナトリウム
パラオキシ安息香酸エチル
イブプロフエン
エタノール
メントール
オイゲノール
香 料
水
計
０． ２％
０．１％
０． ０１％
１ ５． ０％
０．２％
０． １％
１．０％
残
１００．００％
〔実施例５〕練歯磨
第２リン酸カルシウム・２水和物
第２リン酸カルシウム・無水和物
ゲル化性シリカ
ソルビット
プロピレングリコール
２０． ０％
２０． ０％
２． ０％
２０．０％
２． ０％
ラウリルジエタノールアマイド
ラウリル硫酸ナトリウム
ラウロイルザルコシネート
サッカリンナトリウム
パラオキシ安息香酸エチル
イブプロフェン
エタノール
メントール
３−オクタノール
香 料
Ｏ％
５％
５％
１％
１％
１％
Ｏ％
１％
０５％
８％
−２１−
〔実施例６〕練歯磨
水酸化アルミニウム
ソルビット
４５．
２５．
Ｏ％
Ｏ％
ショ糖モノバルミテート
ラウリル硫酸ナトリウム
サッカリンナトリウム
フルルビプロフエン
エタノール
フッ化ナトリウム
メントール
香 料
０％
０％
２％
０５％
０％
２１％
１％
０％
〔実施例７〕練歯磨
第２リン酸カルシウム・２水和物
第２リン酸カルシウム・無水和物
ゲル化性シリカ
ソルビット
２０．
２０．
２．
２０．
０％
０％
０％
Ｏ％
ー２２ー
プロピレンゲリコール
ラウリル硫酸ナトリウム
イブフェナック
エタノール
デキストラナラーゼ
メントーノレ
香 料
０％
０％
０ ５
０％
０％
１％
０％
〔実施例８〕マウスウオッシュ
フルルビプロフェン
エタノール
ソルビット
２０．
１ ０．
Ｏ％
０％
０％
ショ糖モノパルミテート
サッカリンナトリウム
香 料
水
計
Ｏ％
０２％
２％
１ ００．
００％
〔実施例９〕マウスウオッシュ
イブフェナック
エタノール
ソルビット
１． ５％
２０．０％
１０． ０％
シ目糖モノパルミテート
サッカリンナトリウム
香 料
１．０％
０． ０２％
０． ２％
〔実施例１０〕含漱剤
フルルビプロフェン
エタノール
０．５％
２０． ０％
ポリエチレングリコール
グリセリン
サッカリンナトリウム
香 料
０％
Ｏ％
０２％
２％
水
〔実施例１１〕含漱剤
イブフェナック
エタノール
０． ５％
２０． ０％
ポリエチレングリコール
グリセリン
サッカリンナトリウム
香 料
Ｏ％
０％
０２％
２％[Example 1] Rutting agent ibuprofen 0.6% ethanol 18.0% polyethylene glycol 400 2.0% glycerin
10.0% saccharin sodium
0.01% fragrance
0.2% [Example 2] Mouthwash Ibuprofen 1. O% ethanol20. 0% 18-Sorbitol Sucrose Monopalmitate Sodium Saccharin Flavor [Example 3] Toothpaste Aluminum Hydroxide Gellable Silica Sorbitol Sucrose Monobalmitate Sodium Lauryl Sulfate Sodium Saccharin Ibuprofen Ethanol Menthol 10. 0% 1. 0% 0. 01% 0.2% 45. 0% 2. 0% 25. 0% 0% 5% 2% 05% 0% 2% Fragrance 1. O% [Example 4] Toothpaste precipitated silica sorbitol glycerin polyvinylpyrrolidone lauroylboriglycerin ester 2 5. 25. 25. 1. 1. 0% 0% 0% 0% 0% Sodium saccharin Ethyl paraoxybenzoate Ibuprofen Ethanol Menthol Eugenol Flavored water Total 0. 2% 0.1% 0. 01% 1 5. 0% 0.2% 0. 1% 1.0% Remaining 100.00% [Example 5] Toothpaste dicalcium phosphate/dihydrate dicalcium phosphate/anhydrate gelling silica sorbitol propylene glycol 20. 0% 20. 0% 2. 0% 20.0% 2. 0% lauryl diethanolamide sodium lauryl sulfate lauroyl sarcosinate saccharin sodium paraoxybenzoate ethyl ibuprofen ethanol menthol 3-octanol fragrance O% 5% 5% 1% 1% 1% O% 1% 05% 8% -21- [Implementation] Example 6] Toothpaste aluminum hydroxide sorbitol 45. 25. O% O% Sucrose monobalmitate Sodium lauryl sulfate Sodium saccharin Flurbiprofen Ethanol Sodium fluoride Menthol Flavor 0% 0% 2% 05% 0% 21% 1% 0% [Example 7] Toothpaste No. 2 Calcium phosphate dihydrate dicalcium phosphate anhydrate gelling silica sorbitol 20. 20. 2. 20. 0% 0% 0% O% -22-Propylene Gelicol Sodium Lauryl Sulfate Ibufenac Ethanol Dextranalase Mentorol Fragrance 0% 0% 0 5 0% 0% 1% 0% [Example 8] Mouthwash Flurbiprofen ethanol sorbitol 20. 1 0. O% 0% 0% Sucrose monopalmitate saccharin sodium flavored water meter O% 02% 2% 1 00. 00% [Example 9] Mouthwash Ibufenac ethanol sorbitol 1. 5% 20.0% 10. 0% Citrus sugar monopalmitate saccharin sodium flavoring 1.0% 0. 02% 0. 2% [Example 10] Rough agent flurbiprofen ethanol 0.5% 20. 0% Polyethylene glycol glycerin Sodium saccharin Flavor 0% O% 02% 2% Water [Example 11] Rough agent Ibufenac ethanol 0. 5% 20. 0% Polyethylene glycol glycerin saccharin sodium flavoring O% 0% 02% 2%
Claims (1)
ナックから選ばれる１種又は２種以上の薬剤を含有する
口腔用組成物に、エタノールを組成物全体の５〜４０重
量％配合したことを特徴とする口腔用組成物。1. An oral cavity composition containing one or more drugs selected from ibuprofen, flurbiprofen, and ibufenac, containing 5 to 40% by weight of ethanol based on the total composition. Composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32800589A JP2738092B2 (en) | 1989-11-17 | 1989-12-18 | Oral composition |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29913889 | 1989-11-17 | ||
| JP1-299138 | 1989-11-17 | ||
| JP32800589A JP2738092B2 (en) | 1989-11-17 | 1989-12-18 | Oral composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03218308A true JPH03218308A (en) | 1991-09-25 |
| JP2738092B2 JP2738092B2 (en) | 1998-04-08 |
Family
ID=26561805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32800589A Expired - Fee Related JP2738092B2 (en) | 1989-11-17 | 1989-12-18 | Oral composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2738092B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464609A (en) * | 1990-03-16 | 1995-11-07 | The Procter & Gamble Company | Use of ketorolac for treatment of oral diseases and conditions |
| WO1997018802A1 (en) * | 1995-11-22 | 1997-05-29 | The Boots Company Plc | Pharmaceutical compositions comprising flurbiprofen |
| KR100395974B1 (en) * | 2001-04-13 | 2003-08-27 | 부광약품 주식회사 | Toothpaste composition for prevention and/or treatment of sensitive teeth |
| WO2017029710A1 (en) * | 2015-08-18 | 2017-02-23 | 合同会社Ｐｈａｒｍａ Ｓｅｅｄｓ Ｃｒｅａｔｅ | Oral composition containing nsaid or heparin compound |
-
1989
- 1989-12-18 JP JP32800589A patent/JP2738092B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464609A (en) * | 1990-03-16 | 1995-11-07 | The Procter & Gamble Company | Use of ketorolac for treatment of oral diseases and conditions |
| US5646174A (en) * | 1990-03-16 | 1997-07-08 | Kelm; Gary Robert | Use of ketorolac for treatment of oral diseases and conditions |
| US5785951A (en) * | 1990-03-16 | 1998-07-28 | The Procter & Gamble Company | Use of ketorolac for treatment of oral diseases and conditions |
| WO1997018802A1 (en) * | 1995-11-22 | 1997-05-29 | The Boots Company Plc | Pharmaceutical compositions comprising flurbiprofen |
| KR100395974B1 (en) * | 2001-04-13 | 2003-08-27 | 부광약품 주식회사 | Toothpaste composition for prevention and/or treatment of sensitive teeth |
| WO2017029710A1 (en) * | 2015-08-18 | 2017-02-23 | 合同会社Ｐｈａｒｍａ Ｓｅｅｄｓ Ｃｒｅａｔｅ | Oral composition containing nsaid or heparin compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2738092B2 (en) | 1998-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |