JP2008184444A - アダパレン含有外用剤組成物 - Google Patents
アダパレン含有外用剤組成物 Download PDFInfo
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- JP2008184444A JP2008184444A JP2007020289A JP2007020289A JP2008184444A JP 2008184444 A JP2008184444 A JP 2008184444A JP 2007020289 A JP2007020289 A JP 2007020289A JP 2007020289 A JP2007020289 A JP 2007020289A JP 2008184444 A JP2008184444 A JP 2008184444A
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- adapalene
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- isopropylmethylphenol
- Prior art date
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- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 229960002916 adapalene Drugs 0.000 title claims abstract description 80
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 claims abstract description 27
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 17
- 239000006071 cream Substances 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 3
- 230000035699 permeability Effects 0.000 abstract description 14
- 102000011782 Keratins Human genes 0.000 abstract description 10
- 108010076876 Keratins Proteins 0.000 abstract description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 19
- 229910052710 silicon Inorganic materials 0.000 description 19
- 239000010703 silicon Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 16
- 210000003491 skin Anatomy 0.000 description 15
- 230000005012 migration Effects 0.000 description 12
- 238000013508 migration Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MRAMPOPITCOOIN-VIFPVBQESA-N (2r)-n-(3-ethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide Chemical compound CCOCCCNC(=O)[C@H](O)C(C)(C)CO MRAMPOPITCOOIN-VIFPVBQESA-N 0.000 description 6
- 206010000496 acne Diseases 0.000 description 6
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- 208000002874 Acne Vulgaris Diseases 0.000 description 5
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- -1 oxygen scavengers Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 206010020649 Hyperkeratosis Diseases 0.000 description 3
- 208000001126 Keratosis Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 206010040954 Skin wrinkling Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
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- 208000003322 Coinfection Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
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- 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 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 206010006784 Burning sensation Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 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 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003908 antipruritic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
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- 206010037844 rash Diseases 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 238000002834 transmittance Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
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- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
【解決手段】アダパレン及びイソプロピルメチルフェノールを含有することを特徴とする外用剤組成物。
【選択図】なし
Description
前提:Tanakaらによれば、開放系でのシリコン膜を用いた移行性試験は局所投与製剤の経皮吸収性の評価に適しているとされている(S.Tanaka, et al., International Journal of Pharmaceutics, 27:29-38(1985))ことから、角質への浸透性をシリコン膜移行性試験により評価した。また、シリコン膜にすることで、アダパレンが浸透しやすい毛穴の影響を排除することができるので、単純にアダパレンの角質への移行性を評価できると考えられる。
表1記載の各液剤中に溶解しているアダパレン量に依存してアダパレンのシリコン膜移行性が増大しているとも考えられることから、各液剤のアダパレンの溶解度とシリコン膜移行性との関係を調べるため、各液剤中のアダパレンの飽和溶解度を測定した。
比較例2(アダパレンの1質量部に対して2.5質量部のパントテニルエチルエーテル)では1.5倍、比較例4(アダパレンの1質量部に対して25質量部のパントテニルエチルエーテル)では約3倍、実施例2(アダパレンの1質量部に対して2.5質量部のイソプロピルメチルフェノール)では1.3倍、実施例3(アダパレンの1質量部に対して5質量部のイソプロピルメチルフェノール)では約1.7倍、実施例4(アダパレンの1質量部に対して25質量部のイソプロピルメチルフェノール)では約6倍とパントテニルエチルエーテルとイソプロピルメチルフェノールの濃度依存的にアダパレンの溶解度比率は増大した。
Claims (4)
- アダパレン及びイソプロピルメチルフェノールを含有することを特徴とする外用剤組成物。
- アダパレンの含有量が外用剤組成物全体に対して0.01〜1.0質量%である請求項1記載の外用剤組成物。
- イソプロピルメチルフェノールの含有量がアダパレンの1質量部に対して0.5〜25質量部である請求項1記載の外用剤組成物。
- 液剤、ローション剤、ゲル剤、エアゾール剤、クリーム剤又は水性軟膏剤である請求項1〜3の何れか1項に記載の外用剤組成物。
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JP2007020289A JP5109383B2 (ja) | 2007-01-31 | 2007-01-31 | アダパレン含有外用剤組成物 |
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JP2007020289A JP5109383B2 (ja) | 2007-01-31 | 2007-01-31 | アダパレン含有外用剤組成物 |
Publications (2)
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JP2008184444A true JP2008184444A (ja) | 2008-08-14 |
JP5109383B2 JP5109383B2 (ja) | 2012-12-26 |
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JP2007020289A Expired - Fee Related JP5109383B2 (ja) | 2007-01-31 | 2007-01-31 | アダパレン含有外用剤組成物 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019218345A (ja) * | 2018-06-16 | 2019-12-26 | ロート製薬株式会社 | 外用組成物 |
JPWO2019240290A1 (ja) * | 2018-06-16 | 2021-06-24 | ロート製薬株式会社 | 外用組成物 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002241279A (ja) * | 2001-02-16 | 2002-08-28 | Kanebo Ltd | 包装体入り製品及び吸着防止方法 |
JP2002265313A (ja) * | 2001-03-06 | 2002-09-18 | Kose Corp | 皮膚外用剤 |
JP2004189656A (ja) * | 2002-12-10 | 2004-07-08 | Kao Corp | 抗アクネ菌組成物 |
JP2004307372A (ja) * | 2003-04-04 | 2004-11-04 | Choya Umeshu Co Ltd | ニキビ用外用剤およびウメ抽出物の使用方法ならびに殺菌・抗菌剤 |
JP2005517649A (ja) * | 2001-12-07 | 2005-06-16 | ジョンソン・アンド・ジョンソン・コンシューマー・カンパニーズ・インコーポレイテッド | アクネ減少法または皮膚の色合い改善法 |
JP2006022101A (ja) * | 2004-07-07 | 2006-01-26 | Johnson & Johnson Consumer Co Inc | 抗アクネ剤を含む組成物及びその使用方法 |
WO2006122883A1 (en) * | 2005-05-20 | 2006-11-23 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Use of adamantyl methoxydi phenyl propenoic acid for the treatment of acne |
-
2007
- 2007-01-31 JP JP2007020289A patent/JP5109383B2/ja not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002241279A (ja) * | 2001-02-16 | 2002-08-28 | Kanebo Ltd | 包装体入り製品及び吸着防止方法 |
JP2002265313A (ja) * | 2001-03-06 | 2002-09-18 | Kose Corp | 皮膚外用剤 |
JP2005517649A (ja) * | 2001-12-07 | 2005-06-16 | ジョンソン・アンド・ジョンソン・コンシューマー・カンパニーズ・インコーポレイテッド | アクネ減少法または皮膚の色合い改善法 |
JP2004189656A (ja) * | 2002-12-10 | 2004-07-08 | Kao Corp | 抗アクネ菌組成物 |
JP2004307372A (ja) * | 2003-04-04 | 2004-11-04 | Choya Umeshu Co Ltd | ニキビ用外用剤およびウメ抽出物の使用方法ならびに殺菌・抗菌剤 |
JP2006022101A (ja) * | 2004-07-07 | 2006-01-26 | Johnson & Johnson Consumer Co Inc | 抗アクネ剤を含む組成物及びその使用方法 |
WO2006122883A1 (en) * | 2005-05-20 | 2006-11-23 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Use of adamantyl methoxydi phenyl propenoic acid for the treatment of acne |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019218345A (ja) * | 2018-06-16 | 2019-12-26 | ロート製薬株式会社 | 外用組成物 |
JPWO2019240290A1 (ja) * | 2018-06-16 | 2021-06-24 | ロート製薬株式会社 | 外用組成物 |
JP7299766B2 (ja) | 2018-06-16 | 2023-06-28 | ロート製薬株式会社 | 外用組成物 |
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