JP6503627B2 - 医薬液体組成物 - Google Patents
医薬液体組成物 Download PDFInfo
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- JP6503627B2 JP6503627B2 JP2014061253A JP2014061253A JP6503627B2 JP 6503627 B2 JP6503627 B2 JP 6503627B2 JP 2014061253 A JP2014061253 A JP 2014061253A JP 2014061253 A JP2014061253 A JP 2014061253A JP 6503627 B2 JP6503627 B2 JP 6503627B2
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- luliconazole
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- 239000000203 mixture Substances 0.000 title description 30
- 239000007788 liquid Substances 0.000 title description 25
- YTAOBBFIOAEMLL-REQDGWNSSA-N Luliconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@H](CS\1)SC/1=C(\C#N)N1C=NC=C1 YTAOBBFIOAEMLL-REQDGWNSSA-N 0.000 claims description 34
- 229960000570 luliconazole Drugs 0.000 claims description 34
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 13
- 239000006071 cream Substances 0.000 claims description 12
- 229960004194 lidocaine Drugs 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000003429 antifungal agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 150000004667 medium chain fatty acids Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 4
- 201000004647 tinea pedis Diseases 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- -1 sodium hydroxide Chemical compound 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000002163 Mesapamea fractilinea Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DNTGGZPQPQTDQF-XBXARRHUSA-N crotamiton Chemical compound C/C=C/C(=O)N(CC)C1=CC=CC=C1C DNTGGZPQPQTDQF-XBXARRHUSA-N 0.000 description 1
- 229960003338 crotamiton Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 239000004318 erythorbic acid Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol 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
- 238000010438 heat treatment Methods 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Description
現在、治療効果の高い抗真菌剤として新規イミダゾール系抗真菌薬であるルリコナゾールが挙げられる。ルリコナゾールは強い抗真菌活性及び皮膚角層での高い薬物貯留性により、白癬、皮膚カンジダ症及び癜風に対し、既承認薬の臨床試験における薬剤塗布期間の半分の期間で優れた臨床効果を示すことが認められている(非特許文献1)。
今までに、ルリコナゾールとリドカインを含む軟膏剤が報告されている(特許文献1)。一般的に軟膏剤はべたつき感等の不快感を伴い、使用感の面で好ましくない場合がある。したがって、べたつきの少ない液体での医薬組成物が要望されている。
しかしながら、ルリコナゾールは外用剤に一般的に使用される基剤成分である水に対する溶解度が低い。また、光に対する安定性が低く、光によって着色する。これまでN−メチル−2−ピロリドン、炭酸プロピレンあるいはクロタミトンにルリコナゾールを溶解せしめることにより、ルリコナゾールの溶解性を向上させる技術が知られている(特許文献2)が、ルリコナゾールとリドカインを含有する医薬液体組成物の開示はない。
(1)ルリコナゾール及びリドカインを含有することを特徴とする医薬液体組成物、
(2)水を含有する(1)に記載の医薬液体組成物、
(3)液剤、ローション剤、エアゾール剤、水性ゲル剤、乳剤、クリーム剤である(1)
又は(2)に記載の医薬液体組成物、
(4)ルリコナゾールとリドカインを混合することを特徴とする、ルリコナゾールの溶解性向上方法、
(5)ルリコナゾールとリドカインを混合することを特徴とする、ルリコナゾールの着色防止方法、
である。
本発明の医薬液体組成物には、本発明の効果を妨げない範囲で、必要に応じて水溶性成分、油性成分、pH調整剤、抗酸化剤、界面活性剤、あるいは安定化剤などの公知の添加剤を配合することができる。
実施例1及び比較例1の製剤を室温で撹拌し、ルリコナゾールの性状を目視により評価した。結果を表3に示す。
実施例2及び比較例2の製剤を室温で撹拌して溶解後、3000luxの光を7日間照射し、外観性状及び波長400nmにて吸光度を測定した。結果を表4に示す。
実施例3〜4及び比較例3〜6の製剤を25℃で24時間以上撹拌した後、ろ過液中のルリコナゾールをHPLC法で定量し飽和溶解度を求めた。また、下記の式に従い溶解度向上倍率を算出した。
溶解度向上倍率(%)=各有効成分添加時のルリコナゾール飽和溶解度/ルリコナゾール単独の飽和溶解度
結果を表6に示した。
本発明の組成物は、ルリコナゾールの溶解度を向上することが分かった(実施例3〜4)。
実施例5及び比較例7の製剤を25℃で24時間以上撹拌した後、ろ過液中のルリコナゾールをHPLC法で定量し飽和溶解度を求めた。また、下記の式に従い溶解度向上倍率を算出した。
溶解度向上倍率(%)=各有効成分添加時のルリコナゾール飽和溶解度/ルリコナゾール単独の飽和溶解度
結果を表8に示した。
以下表9に示すクリーム剤を、常法に従い、調製した。なお、表9において、数値はすべて質量%を意味するものとする。
Claims (2)
- ルリコナゾール1%、リドカイン2.5%、及び水を含む液剤又はローション剤。
- ルリコナゾール1%、及びリドカイン1.5〜2.5%を含むクリーム剤。
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JP2014061253A JP6503627B2 (ja) | 2013-03-28 | 2014-03-25 | 医薬液体組成物 |
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JP2014208618A JP2014208618A (ja) | 2014-11-06 |
JP6503627B2 true JP6503627B2 (ja) | 2019-04-24 |
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Families Citing this family (2)
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CN107865825B (zh) * | 2016-09-28 | 2022-05-20 | 四川海思科制药有限公司 | 一种卢立康唑外用喷雾剂药物组合物及其制备方法 |
CN114259462A (zh) * | 2021-12-13 | 2022-04-01 | 海南海灵化学制药有限公司 | 一种含有卢立康唑的外用乳膏组合物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2645070C (en) * | 2006-03-08 | 2014-02-04 | Nihon Nohyaku Co., Ltd. | Pharmaceutical composition for external use |
JP5654497B2 (ja) * | 2009-02-13 | 2015-01-14 | トピカ ファーマシューティカルズ,インコーポレイテッド | 抗真菌製剤 |
JP5688406B2 (ja) * | 2009-04-09 | 2015-03-25 | 株式会社ポーラファルマ | 抗真菌医薬組成物 |
EP2416757A2 (en) * | 2009-04-09 | 2012-02-15 | Pola Pharma Inc. | Antimycotic pharmaceutical composition |
JP5665495B2 (ja) * | 2010-11-16 | 2015-02-04 | 三菱電機株式会社 | データ位相同期装置およびデータ位相同期方法 |
JP2012144449A (ja) * | 2011-01-07 | 2012-08-02 | Nippon Nohyaku Co Ltd | ルリコナゾールの皮膚浸透性を向上させる配合処方 |
JP5589927B2 (ja) * | 2011-03-28 | 2014-09-17 | コニカミノルタ株式会社 | クリーニング装置及び画像形成装置 |
JP6265624B2 (ja) * | 2012-05-11 | 2018-01-24 | ロート製薬株式会社 | ルリコナゾール含有外用医薬組成物 |
US20150238606A1 (en) * | 2012-09-14 | 2015-08-27 | Pola Pharma Inc., | Pharmaceutical composition containing luliconazole |
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