Partitioning of Anti-inflammatory Steroid Drugs into Phosphatidylcholine and Phosphatidylcholine-Cholesterol Small Unilamellar Vesicles as Studied by Second-Derivative Spectrophotometry
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概要
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The partition coefficients (K_ps) of six anti-inflammatory steroid drugs, dexamethasone (DMS), betamethasone (BMS), triamcinolone acetonide (TCLA), fluocinolone acetonide (FCLA), betamethasone 17,21-dipropionate (BMSDP), and clobetasole propionate (CBSP), for phosphatidylcholine (PC), and PC-cholesterol small unilamellar vesicles (SUVs) were determined by a second-derivative spectrophotometric method. The K_p values were obtained with a relative standard deviation of below 10% and the following order was observed: BMS≤DMS<TCLA<FCLA≪BMSDP<CBSP. BMSDP which has a structure that the two hydroxyl groups of BMS are esterified with propionic acid showed a largely enhanced K_p value of 10.5 times that of BMS. Further, replacement of a propionate group in BMSDP with a chlorine atom resulted in the highest K_p value (CBSP) within the drugs examined, i.e., the K_p value of CBSP was 1.2 times that of BMSDP. The presence of 30mol% cholesterol in the SUV bilayers reduced these K_p values to approximately 35-50% of those values for the PC SUVs, although the order of the K_p values remained unchanged. The order of the K_p values agreed with that of the reported dermatological therapeutic potency of these drugs, although the order of their log P values for n-octanol/water systems showed a discrepancy. Our results indicate that the potency of steroid drugs in dermatological treatments depends to some extent on the K_p values of the drug, that is, the affinity of steroid drugs for PC bilayers influences their clinical potency, since potency is related to transdermal absorption.
- 公益社団法人日本薬学会の論文
- 2008-05-01
著者
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北村 和則
富山化学工業株式会社綜合研究所
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Kitamura Keisuke
Kyoto Pharmaceutical University
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KITADE Tatsuya
Kyoto Pharmaceutical University
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TAKEGAMI Shigehiko
Kyoto Pharmaceutical University
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Kitamura K
Kyoto Pharmaceutical University
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FUNAKOSHI Takako
Kyoto Pharmaceutical University
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北村 和則
Kyoto Pharmaceutical University
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Kitamura Keisuke
Kyoto College of Pharmacy
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