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Prodrug strategies aimed at improvin...
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Majumdar, Susruta.
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Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety./
作者:
Majumdar, Susruta.
面頁冊數:
159 p.
附註:
Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3730.
Contained By:
Dissertation Abstracts International67-07B.
標題:
Chemistry, Organic. -
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3228780
ISBN:
9780542806926
Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety.
Majumdar, Susruta.
Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety.
- 159 p.
Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3730.
Thesis (Ph.D.)--University of Florida, 2006.
Topical delivery is an attractive route to deliver drugs into systemic circulation; however the poor biphasic solubility of drug molecules limits delivery across the skin. N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM)-drug conjugates were designed as prodrugs with good biphasic solubilities to increase the topical delivery of phenol and imide containing drugs.
ISBN: 9780542806926Subjects--Topical Terms:
516206
Chemistry, Organic.
Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety.
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Prodrug strategies aimed at improving topical delivery of drugs using the N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) promoiety.
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Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3730.
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Thesis (Ph.D.)--University of Florida, 2006.
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Topical delivery is an attractive route to deliver drugs into systemic circulation; however the poor biphasic solubility of drug molecules limits delivery across the skin. N-Alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM)-drug conjugates were designed as prodrugs with good biphasic solubilities to increase the topical delivery of phenol and imide containing drugs.
520
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Prodrugs are biological inactive derivatives of a drug which hydrolyse in vivo to the parent drug molecule. These derivatives mask polar functional groups present in a drug molecule which, in this case, leads to increased solubility of the drug in the skin.
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Prodrugs must hydrolyse to exhibit their pharmacological activity. To elucidate the mechanism of chemical hydrolysis, a series of NANAOCAM conjugates of phenols, thiols and carboxylic acids were synthesized and their rates of hydrolysis determined in aqueous buffers. The hydrolysis followed pseudo-unimolecular first order kinetics and was dependent on the nucleofugacity of the leaving group. The hydrolysis was also independent of the pH of buffers. To further elucidate the mechanism of hydrolysis, N-aryl-N-alkyloxycarbonylaminomethyl (NArNAOCAM) conjugates of phenols and carboxylic acids were also synthesized and their rates of hydrolysis determined. Since the hydrolysis of NArNAOCAM conjugates were slower than NANOCAM conjugates, the NANAOCAM conjugates are proposed to hydrolyse by a SN1 type of pathway with the lone pair on the nitrogen stabilizing the carbocation formed as an intermediate.
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To investigate if the NANAOCAM promoiety increases the dermal delivery of phenolic drugs and imide containing drugs, a homologous series of NANAOCAM-acetaminophen and NANAOCAM-theophylline were synthesized. These derivatives were characterized by determination of their solubilities in IPM and water, partition coefficients between IPM and pH 4.0 buffer and flux through hairless mouse skins from IPM.
520
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Only two prodrugs of acetaminophen, C1 alkyloxy and C2 alkyloxy, increased flux through the skin. These derivatives were the most water soluble prodrugs in the series of more lipophilic prodrugs. In the theophylline series, only one derivative, C2 alkyloxy, increased delivery through the skin. This derivative was the most lipid and most water soluble member of the series. The flux of NANAOCAM prodrugs from IPM was accurately predicted by the Roberts-Sloan equation.
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http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3228780
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