JP4683835B2 - 防腐剤及びこれを含有する水性組成物 - Google Patents
防腐剤及びこれを含有する水性組成物 Download PDFInfo
- Publication number
- JP4683835B2 JP4683835B2 JP2003402179A JP2003402179A JP4683835B2 JP 4683835 B2 JP4683835 B2 JP 4683835B2 JP 2003402179 A JP2003402179 A JP 2003402179A JP 2003402179 A JP2003402179 A JP 2003402179A JP 4683835 B2 JP4683835 B2 JP 4683835B2
- Authority
- JP
- Japan
- Prior art keywords
- preservative
- aqueous composition
- sodium
- salt
- hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003755 preservative agent Substances 0.000 title claims description 67
- 239000000203 mixture Substances 0.000 title claims description 57
- 230000002335 preservative effect Effects 0.000 title claims description 55
- 150000003839 salts Chemical class 0.000 claims description 36
- 230000002421 anti-septic effect Effects 0.000 claims description 33
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims description 27
- 229960004958 ketotifen Drugs 0.000 claims description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 18
- 239000004327 boric acid Substances 0.000 claims description 15
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 12
- 235000010199 sorbic acid Nutrition 0.000 claims description 12
- 239000004334 sorbic acid Substances 0.000 claims description 12
- 229940075582 sorbic acid Drugs 0.000 claims description 12
- 235000011187 glycerol Nutrition 0.000 claims description 11
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 6
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 6
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 5
- 229960001950 benzethonium chloride Drugs 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000003889 eye drop Substances 0.000 description 17
- 241000894006 Bacteria Species 0.000 description 14
- 229940012356 eye drops Drugs 0.000 description 13
- -1 organic acid salt Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
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- YNQQEYBLVYAWNX-WLHGVMLRSA-N ketotifen fumarate Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 YNQQEYBLVYAWNX-WLHGVMLRSA-N 0.000 description 11
- 150000003505 terpenes Chemical class 0.000 description 10
- 239000012085 test solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 239000004615 ingredient Substances 0.000 description 9
- 229960003630 ketotifen fumarate Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000003732 agents acting on the eye Substances 0.000 description 8
- 229940125702 ophthalmic agent Drugs 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 6
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229940083542 sodium Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 229910021538 borax Inorganic materials 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 235000010339 sodium tetraborate Nutrition 0.000 description 5
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 230000003266 anti-allergic effect Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 235000010241 potassium sorbate Nutrition 0.000 description 4
- 239000004302 potassium sorbate Substances 0.000 description 4
- 229940069338 potassium sorbate Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 4
- 239000000341 volatile oil Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 235000006679 Mentha X verticillata Nutrition 0.000 description 3
- 235000002899 Mentha suaveolens Nutrition 0.000 description 3
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
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- 235000019438 castor oil Nutrition 0.000 description 3
- KXKPYJOVDUMHGS-OSRGNVMNSA-N chondroitin sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 KXKPYJOVDUMHGS-OSRGNVMNSA-N 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
- 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 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
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- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 2
- 229930182837 (R)-adrenaline Natural products 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine chloride (TN) Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 VKJGBAJNNALVAV-UHFFFAOYSA-M 0.000 description 2
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Description
即ち、本発明は、下記に掲げる防腐剤である:
項1. ケトチフェン又はその塩を有効成分とする防腐剤。
項2. 更に、有効成分としてグリセリン、ソルビン酸、ソルビン酸の塩、テルペノイド、ホウ酸及びホウ酸の塩よりなる群から選択される少なくとも1種の成分を組み合わせてなる、項1に記載の防腐剤。
項3. 項1又は2に記載の防腐剤を含有する、水性組成物。
項4. 項1又は2に記載の防腐剤を含有する、マルチドーズ型の水性組成物。
項5. 項1又は2に記載の防腐剤を含有する、pHが4.5〜7.5である水性組成物。
以下、本発明を詳細に説明する。なお、本発明でいう「防腐」とは、微生物の繁殖を防止し、腐敗を防ぐことを意味する。該「微生物」には、細菌、真菌等が含まれる。また、本明細書中、特に言及しない限り、%はw/v%(g/100mL)を意味するものとする。また、コンタクトレンズという語句は、特記しない限り、ハード、酸素透過性ハード、ソフト等のあらゆるタイプのコンタクトレンズを包含する意味で用いる。また、水性組成物とは、組成物中に水を少なくとも5重量%以上、好ましくは20重量%以上、更に好ましくは50重量%以上含有するものを意味する。
本発明の防腐剤の配合割合の一例として、水性組成物中に、ケトチフェン又はその塩が、通常0.001〜0.3%、好ましくは0.001〜0.1%、更に好ましくは0.01〜0.07%となる割合が挙げられる。上記範囲内で、ケトチフェン又はその塩単独からなる防腐剤を使用すると、水性組成物に優れた防腐作用を備えさせることができる。また、上記範囲内で、ケトチフェン又はその塩単独と第二有効成分からなる防腐剤を使用すると、より一層優れた防腐作用を発揮することができる。
など。
これらはd体、l体又はdl体のいずれでもよい。
試験例1 フマル酸ケトチフェンの保存効力試験(1)
表1及び2に記載の処方に従い、各成分を精製水に溶解して全量を100mLとして試験液(実施例1−7及び比較例1−4)を調製し、これを濾過滅菌した。これらの試験液について、第十四改正日本薬局方参考情報 保存効力試験方法に従って、防腐作用を評価した。具体的には、グラム陰性細菌(Escherichia coli)及び真菌(Candida albicans)を用いて、それぞれの菌液を調製した。各菌液を、105〜106CFU/mLになるよう試験液に接種し、23℃で保管した。接種7日後の試験液をサンプリングし、メンブランフィルター法にて試験液中の菌数を測定した。また、測定した試験液中の菌数から、下記評価基準に基づいて、試験液の防腐効果を評価した。
<評価基準>
◎:7日後の菌数が接種菌数の0.1%以下である
○:7日後の菌数が接種菌数の0.1%より多く1%以下である
△:7日後の菌数が接種菌数の1より多く10%以下である
×:7日後の菌数が接種菌数の10%より多い
表5に記載の処方に従い、各成分を精製水に溶解して全量を100mLとして試験液(実施例8)を調製し、これを濾過滅菌した。これらの試験液を用いて、試験例1と同様の方法で、グラム陽性細菌(Staphyrococcus aureus)、グラム陰性細菌(Pseudmonas aeruginosa、及びEscherichia coli)及び真菌(Aspergilus niger)に対する防腐作用を評価した。
常法により、以下の表7〜9に記載の処方の点眼剤(実施例9〜26)、洗眼剤(実施例27)、コンタクトレンズ装着液(表中、CL装着液と記す)(実施例28)コンタクトレンズ用消毒剤(表中、CL消毒剤と記す)(実施例29)、及び点鼻剤(実施例30)を調製した。
Claims (8)
- ケトチフェン又はその塩を有効成分とする、マルチドーズ型水性組成物用の防腐剤。
- 更に、有効成分としてグリセリン、テルペノイド、ホウ酸及びホウ酸の塩よりなる群から選択される少なくとも1種の成分を組み合わせてなる、請求項1に記載の防腐剤。
- pHが4.5〜7.5であるマルチドーズ型水性組成物において用いられる、請求項1又は2に記載の防腐剤。
- コンタクトレンズ装用者用のマルチドーズ型水性組成物において用いられる、請求項1〜3のいずれかに記載の防腐剤。
- ケトチフェン又はその塩を含有し、且つ、塩化ベンザルコニウム、塩化ベンゼトニウム、パラベン、ソルビン酸及びソルビン酸の塩のいずれも含有しないことを特徴とする、マルチドーズ型水性組成物。
- 更に、グリセリン、テルペノイド、ホウ酸及びホウ酸の塩よりなる群から選択される少なくとも1種の成分を含有する、請求項5に記載のマルチドーズ型水性組成物。
- pHが4.5〜7.5である、請求項5又は6に記載のマルチドーズ型水性組成物。
- コンタクトレンズ装用者用である、請求項5〜7のいずれかに記載のマルチドーズ型水性組成物。
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WO2007074904A1 (ja) * | 2005-12-28 | 2007-07-05 | Wakamoto Pharmaceutical Co., Ltd. | 水性医薬組成物 |
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KR20220161379A (ko) * | 2020-03-31 | 2022-12-06 | 산텐 세이야꾸 가부시키가이샤 | 수지제 용기에 충전된 은염 함유 안과용 수성 조성물 |
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JP2001187728A (ja) * | 1999-12-28 | 2001-07-10 | Lion Corp | 眼科用組成物 |
JP2003026565A (ja) * | 2001-07-10 | 2003-01-29 | Senju Pharmaceut Co Ltd | ケトチフェン含有結膜移行性促進水性点眼剤 |
JP2003518498A (ja) * | 1999-12-23 | 2003-06-10 | ノバルティス アクチエンゲゼルシャフト | 点眼薬としてのケトチフェンの使用 |
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JPH07324034A (ja) * | 1994-05-30 | 1995-12-12 | Toa Yakuhin Kk | フマル酸ケトチフェン含有の点眼剤 |
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JP2003518498A (ja) * | 1999-12-23 | 2003-06-10 | ノバルティス アクチエンゲゼルシャフト | 点眼薬としてのケトチフェンの使用 |
JP2001187728A (ja) * | 1999-12-28 | 2001-07-10 | Lion Corp | 眼科用組成物 |
JP2003026565A (ja) * | 2001-07-10 | 2003-01-29 | Senju Pharmaceut Co Ltd | ケトチフェン含有結膜移行性促進水性点眼剤 |
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