Topical delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH)

Susruta Majumdar; K. B. Sloan

doi:10.1016/j.ijpharm.2006.09.034

Topical delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH)

Susruta Majumdar
, K. B. Sloan

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

N⁷-(N-Alkyl-N-alkyloxycarbonyl) aminomethyl (NANAOCAM) prodrugs of theophylline (ThH) have been synthesized and characterized by their solubilities in isopropyl myristate (S_IPM), solubilities in water (S_AQ), partition coefficients between IPM and pH 4.0 buffer (K_IPM:4.0) and by their ability to penetrate hairless mouse skin from IPM (J_MIPM). The most lipid soluble and water soluble member, N-methyl-N-ethyloxy-carbonylaminomethyltheophylline, gave the highest flux through hairless mouse skin from IPM compared to ThH. The flux of NANAOCAM prodrugs of ThH can be accurately predicted by the Roberts-Sloan (RS) equation.

Original language	English
Pages (from-to)	64-71
Number of pages	8
Journal	International Journal of Pharmaceutics
Volume	332
Issue number	1-2
DOIs	https://doi.org/10.1016/j.ijpharm.2006.09.034
State	Published - Mar 6 2007

Keywords

Lipid solubility
NANAOCAM
Permeation
Prodrugs
Roberts-Sloan equation
Theophylline
Water solubility

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10.1016/j.ijpharm.2006.09.034

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title = "Topical delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH)",

abstract = "N7-(N-Alkyl-N-alkyloxycarbonyl) aminomethyl (NANAOCAM) prodrugs of theophylline (ThH) have been synthesized and characterized by their solubilities in isopropyl myristate (SIPM), solubilities in water (SAQ), partition coefficients between IPM and pH 4.0 buffer (KIPM:4.0) and by their ability to penetrate hairless mouse skin from IPM (JMIPM). The most lipid soluble and water soluble member, N-methyl-N-ethyloxy-carbonylaminomethyltheophylline, gave the highest flux through hairless mouse skin from IPM compared to ThH. The flux of NANAOCAM prodrugs of ThH can be accurately predicted by the Roberts-Sloan (RS) equation.",

keywords = "Lipid solubility, NANAOCAM, Permeation, Prodrugs, Roberts-Sloan equation, Theophylline, Water solubility",

author = "Susruta Majumdar and Sloan, \{K. B.\}",

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journal = "International Journal of Pharmaceutics",

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T1 - Topical delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH)

AU - Majumdar, Susruta

AU - Sloan, K. B.

PY - 2007/3/6

Y1 - 2007/3/6

N2 - N7-(N-Alkyl-N-alkyloxycarbonyl) aminomethyl (NANAOCAM) prodrugs of theophylline (ThH) have been synthesized and characterized by their solubilities in isopropyl myristate (SIPM), solubilities in water (SAQ), partition coefficients between IPM and pH 4.0 buffer (KIPM:4.0) and by their ability to penetrate hairless mouse skin from IPM (JMIPM). The most lipid soluble and water soluble member, N-methyl-N-ethyloxy-carbonylaminomethyltheophylline, gave the highest flux through hairless mouse skin from IPM compared to ThH. The flux of NANAOCAM prodrugs of ThH can be accurately predicted by the Roberts-Sloan (RS) equation.

AB - N7-(N-Alkyl-N-alkyloxycarbonyl) aminomethyl (NANAOCAM) prodrugs of theophylline (ThH) have been synthesized and characterized by their solubilities in isopropyl myristate (SIPM), solubilities in water (SAQ), partition coefficients between IPM and pH 4.0 buffer (KIPM:4.0) and by their ability to penetrate hairless mouse skin from IPM (JMIPM). The most lipid soluble and water soluble member, N-methyl-N-ethyloxy-carbonylaminomethyltheophylline, gave the highest flux through hairless mouse skin from IPM compared to ThH. The flux of NANAOCAM prodrugs of ThH can be accurately predicted by the Roberts-Sloan (RS) equation.

KW - Lipid solubility

KW - NANAOCAM

KW - Permeation

KW - Prodrugs

KW - Roberts-Sloan equation

KW - Theophylline

KW - Water solubility

UR - https://www.scopus.com/pages/publications/33846851514

U2 - 10.1016/j.ijpharm.2006.09.034

DO - 10.1016/j.ijpharm.2006.09.034

M3 - Article

C2 - 17064862

AN - SCOPUS:33846851514

SN - 0378-5173

VL - 332

SP - 64

EP - 71

JO - International Journal of Pharmaceutics

JF - International Journal of Pharmaceutics

IS - 1-2

ER -

Topical delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH)

Abstract

Keywords

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