JP4969050B2 - 皮膚外用剤 - Google Patents
皮膚外用剤 Download PDFInfo
- Publication number
- JP4969050B2 JP4969050B2 JP2005071145A JP2005071145A JP4969050B2 JP 4969050 B2 JP4969050 B2 JP 4969050B2 JP 2005071145 A JP2005071145 A JP 2005071145A JP 2005071145 A JP2005071145 A JP 2005071145A JP 4969050 B2 JP4969050 B2 JP 4969050B2
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- JP
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- Prior art keywords
- ether
- glycol
- skin
- weight
- acid
- 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.)
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- 230000000699 topical effect Effects 0.000 title description 2
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- 150000003904 phospholipids Chemical class 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 21
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 17
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- 229940045997 vitamin a Drugs 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
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- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 6
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 6
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
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- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 241000723346 Cinnamomum camphora Species 0.000 claims description 3
- 239000005770 Eugenol Substances 0.000 claims description 3
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 3
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- 230000000202 analgesic effect Effects 0.000 claims description 3
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229960001047 methyl salicylate Drugs 0.000 claims description 3
- CIVCELMLGDGMKZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC(Cl)=C(C(O)=O)C(Cl)=N1 CIVCELMLGDGMKZ-UHFFFAOYSA-N 0.000 claims description 2
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 claims description 2
- KYHQZNGJUGFTGR-LURJTMIESA-N 7-[(2s)-2-hydroxypropyl]-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C[C@@H](O)C KYHQZNGJUGFTGR-LURJTMIESA-N 0.000 claims description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
- WJLVQTJZDCGNJN-UHFFFAOYSA-N Chlorhexidine hydrochloride Chemical compound Cl.Cl.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WJLVQTJZDCGNJN-UHFFFAOYSA-N 0.000 claims description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 claims description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 claims description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 claims description 2
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims description 2
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 2
- SQBWCQROZHGTAU-UHFFFAOYSA-N [1-[bis(2-methylpropyl)amino]-3-(1,3-dimethyl-2,6-dioxopurin-7-yl)propan-2-yl] benzoate Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CC(CN(CC(C)C)CC(C)C)OC(=O)C1=CC=CC=C1 SQBWCQROZHGTAU-UHFFFAOYSA-N 0.000 claims description 2
- 229960003556 aminophylline Drugs 0.000 claims description 2
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 claims description 2
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- 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 2
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- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 2
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- IVHBBMHQKZBJEU-UHFFFAOYSA-N cinchocaine hydrochloride Chemical compound [Cl-].C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCC[NH+](CC)CC)=C21 IVHBBMHQKZBJEU-UHFFFAOYSA-N 0.000 claims description 2
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Description
一方、リン脂質は大豆や卵黄など天然の動植物中に存在し、そのほとんどが食品にも使用できる安全性の高いもので、界面活性効果があること、保湿性を有すること、また外用剤に配合すると経皮吸収を促進することが知られている。しかし、リン脂質およびグリコールエーテルを組み合わせることによる効果については知られていない。
さらに、皮膚外用剤は適用部位に直接塗布して用いられることが多いため、製剤の経皮吸収性のみならず、製剤が長期的に安定であり、使用感がよいなどの優れた製剤が望まれている。
すなわち本発明は、下記(1)〜(9)に掲げる皮膚外用剤である。
(1)リン脂質0.01〜8重量%およびグリコールエーテル0.01〜6.5重量%を含有する皮膚外用剤。
(2)グリコールエーテルが、エチレングリコールモノエーテル、エチレングリコールジエーテル、プロピレングリコールモノエーテル、プロピレングリコールジエーテル、ブチレングリコールモノエーテル、ブチレングリコールジエーテル、ジエチレングリコールモノエーテル、ジエチレングリコールモノエーテル、ジエチレングリコールジエーテル、ジプロピレングリコールモノエーテル、ジプロピレングリコールジエーテル、ジブチレングリコールモノエーテルおよびジブチレングリコールジエーテルよりなる群から選択される1種または2種以上である(1)に記載の皮膚外用剤。
(3)リン脂質が水素添加リン脂質である(1)または(2)に記載の皮膚外用剤。
(4)リン脂質が非水素添加リン脂質である(1)または(2)に記載の皮膚外用剤。
(5)水素添加リン脂質のヨウ素価が10〜50である(1)〜(3)に記載の皮膚外用剤。
(6)さらに、有効成分を含有する(1)〜(5)に記載の皮膚外用剤。
(7)さらに、ビタミンA類、ビタミンC類、美白剤、抗シワ剤、消炎鎮痛剤、抗真菌剤、ステロイド剤、育毛剤、痩身剤を含有する(1)〜(5)に記載の皮膚外用剤。
(8)皮膚外用剤が液晶型皮膚外用剤である(1)〜(7)に記載の皮膚外用剤。
(9)皮膚外用剤がマイクロエマルジョン型皮膚外用剤である(1)〜(7)に記載の皮膚外用剤。
(10)皮膚外用剤がリポソーム型皮膚外用剤である(1)〜(7)に記載の皮膚外用剤。
(11)リン脂質およびグリコールエーテルからなる経皮吸収促進剤を、0.02〜14.5重量%含有する皮膚外用剤。
(12)さらに、有効成分を含有する(11)に記載の皮膚外用剤。
また、本発明は以下の方法をも包含する。
(13)リン脂質0.01〜8重量%およびグリコールエーテル0.01〜6.5重量%を皮膚外用剤に含有することによる、有効成分の経皮吸収促進方法。
(14)リン脂質0.01〜8重量%およびグリコールエーテル0.01〜6.5重量%を含有する皮膚外用剤に、ビタミンA類またはキサンチン類を配合することによる、ビタミンA類またはキサンチン類の経皮吸収促進方法。
(15)リン脂質およびグリコールエーテルからなる経皮吸収促進剤を、皮膚外用剤中に0.02〜14.5重量%含有することによる、有効成分の経皮吸収促進方法。
グリセロリン脂質は、グリセロリン酸骨格を有する物質で、親油基として脂肪酸エステル、長鎖アルキルエーテル、ビニルエーテルなどを有している。具体的には、ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルセリン、ホスファジイルイノシトール、ホスファチジルイノシトールポリリン酸、ホスファチジルグリセロール、ジホスファチジルグリセロール(カルジオリピン)、ホスファチジン酸、リゾホスファチジルコリン、リゾホスファチジルエタノールアミン、リゾホスファチジルセリン、リゾホスファチジルイノシトール、リゾホスファチジルグリセロール、リゾホスファチジン酸などが挙げられる。
スフィンゴリン脂質は、スフィンゴシン、フィトスフィンゴシンなどの長鎖塩基または長鎖脂肪酸と、リン酸またはホスホン酸を有しており、セラミド1−リン酸誘導体(スフィンゴミエリンなど)、セラミド1−ホスホン酸誘導体(セラミドアミノエチルホスホン酸など)が挙げられる。
これらのリン脂質のうち、好ましくはグリセロリン脂質であり、特に好ましくはホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルグリセロールである。
レシチンは、非水素添加レシチン、水素添加レシチン、水酸化レシチンなどであっても良く、非水素添加レシチン、水素添加レシチンが好ましい。また、レシチンのヨウ素価は、通常10〜50、好ましくは20〜45、特に好ましくは30〜45であると良い。
これらの成分は1種または2種以上を組み合わせて用いることができる。
具体的には次の成分が例示できる。
中でも、好ましくはd-δ-トコフェリルレチノエートなどのビタミンA類、テトライソパルミチン酸アスコルビル、アスコルビン酸、アスコルビン酸グルコシドなどのビタミンC類であり、特に好ましくはアスコルビン酸、アスコルビン酸グルコシドなどの水溶性ビタミンC類である。
鎮痒剤:クロタミトン、クロルフェニラミン、マレイン酸クロルフェニラミン、ジフェンヒドラミン、塩酸ジフェンヒドラミン、サリチル酸ジフェンヒドラミン、サリチル酸、ノニル酸ワニリルアミド、メキタジン、カンフル、チモール、オイゲノール、ポリオキシエチレンラウリルエーテル、コンフリーエキス、シソエキスなど。
抗ウイルス剤:アシクロビル、ペンシクロビルなど。
抗酸化剤:ジブチルヒドロキシトルエン、ブチルヒドロキシアニソール、エチレンジアミン四酢酸二ナトリウム・二水和物(以下、エデト酸ナトリウムとも言う)、ソルビン酸、亜硫酸ナトリウムなど。
液晶は生体二重膜や細胞間脂質と構造が類似しているため、皮膚になじみやすく、また有用な成分の経皮吸収を促進できるという利点がある。
本発明において、皮膚外用剤中に液晶を含有していると好ましい。
マイクロエマルジョンは、光学的な透明性を有するほど分散しているミセルが小さいため、通常のエマルジョンよりも製剤が角質層から皮膚に吸収されやすいという利点を持つ。
リポソームは生体二重膜と構造が類似しているため、皮膚になじみやすく、また有用な成分の経皮吸収を促進できるという利点がある。
本発明の皮膚外用剤が液晶型皮膚外用剤である場合、グリコールエーテルにリン脂質、水溶性化合物、少量の水などを投入・撹拌し、油分および油溶性化合物などを適宜投入・撹拌して調製することができる。また、本発明の液晶型皮膚外用剤は、少量の水を配合することができるが、水を別途配合せずに実質的に無水の製剤としても調製することができる。
本発明の皮膚外用剤がマイクロエマルジョン型皮膚外用剤である場合、グリコールエーテルにリン脂質などを投入・撹拌し、油分および油溶性化合物などを適宜投入・撹拌した後、水溶性化合物、水を加えて高圧ホモミキサーを使用して乳化、調製することができる。
本発明の皮膚外用剤がリポソーム型皮膚外用剤である場合、調製方法には特に制限はなく、これまで知られている種々の調製方法が利用できるが、例えば、グリコールエーテルにリン脂質、水溶性化合物、水などを投入・撹拌し、油分および油溶性化合物などを適宜投入・撹拌して調製することができる。
前記経皮吸収促進剤を含有する皮膚外用剤において、リン脂質、グリコールエーテル、およびこれらの配合比は、前記皮膚外用剤で用いたものと同様である。また、前記経皮吸収促進剤の配合量は、本発明の効果を奏すれば特に制限されず、皮膚への使用感や効果を考慮して適宜選択して用いることができるが、皮膚外用剤全体として、通常0.02〜14.5重量%、好ましくは0.2〜13.5重量%、特に好ましくは2〜12重量%であれば良い。
これらの有効成分や各種の成分の配合量、配合比については、前記皮膚外用剤で用いたものと同様である。また、これらの有効成分や各種の成分は1種単独で、または2種以上を任意に組み合わせて配合することができる。
さらに本発明は、リン脂質およびグリコールエーテルからなる経皮吸収促進剤を、皮膚外用剤中に含有することによる、有効成分の経皮吸収促進方法をも包含する。本発明の方法において、有効成分の経皮吸収促進は、リン脂質およびグリコールエーテルからなる経皮吸収促進剤0.02〜14.5重量%を皮膚外用剤中に含有させることによって達成できる。
リン脂質、グリコールエーテルおよび有効成分の配合量、並びにリン脂質およびグリコールエーテルの配合比は、前記皮膚外用剤で用いたものと同様である。
表1に示す処方に従い、リン脂質、d-δ-トコフェリルレチノエートのトリ(カプリル・カプリン酸)グリセリル溶液をグリコールエーテル及び多価アルコールに溶解し、別途加温した精製水と混合して調製したリポソーム型製剤について、縦型のFranzセルのリザーバー側にリン酸緩衝液(pH 7.4)10mLを入れ、へアレスマウス(系統:HR-1、7週令、雄)の脂肪を除去した全層皮膚をセルの間に固定した後、ドナー側に試験薬剤を1mL添加した。試験薬剤添加24時間後に全層皮膚をセルからはずし、角層表面を水と酢酸エチルで洗浄した後、全層皮膚をホモジネートして酢酸エチル抽出し、HPLCにてd-δ-トコフェリルレチノエートを定量した。
結果を表1に示す。
d-δ-トコフェリルレチノエートはリン酸緩衝液には難溶であるため、本試験では角層を透過し皮内貯留した量を経皮吸収量とした。
このように、実施例1は経皮吸収性に優れた皮膚外用剤であり、有効成分の薬理効果を十分に期待することができることから、特に有用である。
表2に示す全ての実施例において、配合した有効成分の経皮吸収性が優れていた。
表3、4に示す全ての実施例において、配合した有効成分の経皮吸収性が優れていた。
表5に示す処方に従い、リン脂質をグリコールエーテルもしくは多価アルコールに加温溶解し、別途加温したカフェイン水溶液に添加して調製したリポソーム型製剤について、縦型のFranzセルのリザーバー側にリン酸緩衝液(pH 7.4)10mLを入れ、へアレスマウス(系統:HR-1、7週令、雄)の脂肪を除去した全層皮膚をセルの間に固定した後、ドナー側に試験薬剤を1mL添加した。添加30時間後にリザーバー側からサンプリングし、直ちにHPLCにてカフェインを定量した。
結果を表5に示す。
このように、実施例19は経皮吸収性に優れた皮膚外用剤であり、有効成分の薬理効果を十分に期待することができることから、特に有用である。
Claims (7)
- (A)リン脂質0.01〜8重量%、
(B)ジエチレングリコールモノエチルエーテル0.01〜6.5重量%、および
(C)ビタミンA類、消炎鎮痛剤、痩身剤、鎮痒剤、局所麻酔剤、および抗菌剤よりなる群から選択される1種または2種以上、
を含有する皮膚外用ゲル剤。 - ビタミンA類が、レチノール、酢酸レチノール、レチナール、レチノイン酸、レチノイン酸メチル、レチノイン酸エチル、レチノイン酸レチノール、ビタミンA油、ビタミンA脂肪酸エステル、d-δ-トコフェリルレチノエート、α-トコフェリルレチノエート、β-トコフェリルレチノエートよりなる群から選択される1種または2種以上であり、
消炎鎮痛剤が、サリチル酸メチル、サリチル酸グリコール、アラントイン又はその誘導体よりなる群から選択される1種または2種以上であり、
痩身剤が、カフェイン、アミノフィリン、テオフィリン、オクストリフィリン、ダイフィリン、ジイソブチルアミノベンゾイルオキシプロピルテオフィリン、テオブロミン、ジプロフィリン、プロキシフィリン、ペントキシフィリン、カプサイシンよりなる群から選択される1種または2種以上であり、
鎮痒剤が、ジフェンヒドラミン、塩酸ジフェンヒドラミンよりなる群から選択される1種または2種であり、
局所麻酔剤が、リドカイン、塩酸リドカイン、ジブカイン、塩酸ジブカイン、アミノ安息香酸エチル、ユーカリ油、オイゲノール、カンフル、ハッカ油よりなる群から選択される1種または2種以上であり、
抗菌剤が、イソプロピルメチルフェノール、グルコン酸クロルヘキシジン、塩酸クロルヘキシジン、塩化ベンザルコニウム、塩化ベンゼトニウム、臭化セチルトリメチルアンモニウム、塩化デカリニウム、トリクロサン、トリクロロカルバニリドよりなる群から選択される1種または2種以上である、
請求項1に記載の皮膚外用ゲル剤。 - ビタミンA類の配合量が、0.1〜30重量%であり、
消炎鎮痛剤の配合量が、0.1〜30重量%であり、
痩身剤の配合量が、0.1〜30重量%であり、
鎮痒剤の配合量が、0.001〜20重量%であり、
局所麻酔剤の配合量が、0.001〜20重量%であり、
抗菌剤の配合量が、0.001〜20重量%である、
請求項1又は2に記載の皮膚外用ゲル剤。 - リン脂質が水素添加リン脂質である請求項1〜3のいずれかに記載の皮膚外用ゲル剤。
- リン脂質が非水素添加リン脂質である請求項1〜3のいずれかに記載の皮膚外用ゲル剤。
- 水素添加リン脂質のヨウ素価が10〜50である請求項1〜4のいずれかに記載の皮膚外用ゲル剤。
- ゲル剤が、液晶、マイクロエマルジョンおよびリポソームのいずれかの形態である、請求項1〜6のいずれかに記載の皮膚外用ゲル剤。
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