Method of stabilizing imiquimod
DCFirst Claim
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1. A method of stabilizing 1-(2-methylpropyl)-1H imidazo[4,5-c]quinolin-4-amine (imiquimod) in a pharmaceutical cream formulated with the imiquimod and an oleic acid component during storage of the pharmaceutical cream prior to application of the pharmaceutical cream to a dermal or mucosal surface, said method comprising:
- formulating the pharmaceutical cream with a therapeutically effective amount of imiquimod and a pharmaceutically acceptable vehicle including an oleic acid component, wherein the oleic acid component contains at least about 80% oleic acid by weight as a fatty acid and has a peroxide value of no more than about 5 milliequivalents of oxygen per kilogram and contains less than about 1% by weight polar impurities at or prior to formulation of the pharmaceutical cream;
storing the formulated pharmaceutical cream prior to use of the pharmaceutical cream; and
maintaining a greater amount of the therapeutically effective amount of imiquimod in the pharmaceutical cream during said storing of the pharmaceutical cream, as compared to a reduced amount of imiquimod maintained in an identical pharmaceutical imiquimod cream but formulated with a compendial grade oleic acid component when the pharmaceutical cream and the identical pharmaceutical imiquimod cream are each stored under identical storage conditions for up to about six months after formulation.
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Abstract
Pharmaceutical formulations and methods including an immune response modifier (IRM) compound and an oleic acid component are provided where stability is improved by using oleic acid have low polar impurities such as peroxides.
150 Citations
20 Claims
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1. A method of stabilizing 1-(2-methylpropyl)-1H imidazo[4,5-c]quinolin-4-amine (imiquimod) in a pharmaceutical cream formulated with the imiquimod and an oleic acid component during storage of the pharmaceutical cream prior to application of the pharmaceutical cream to a dermal or mucosal surface, said method comprising:
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formulating the pharmaceutical cream with a therapeutically effective amount of imiquimod and a pharmaceutically acceptable vehicle including an oleic acid component, wherein the oleic acid component contains at least about 80% oleic acid by weight as a fatty acid and has a peroxide value of no more than about 5 milliequivalents of oxygen per kilogram and contains less than about 1% by weight polar impurities at or prior to formulation of the pharmaceutical cream; storing the formulated pharmaceutical cream prior to use of the pharmaceutical cream; and maintaining a greater amount of the therapeutically effective amount of imiquimod in the pharmaceutical cream during said storing of the pharmaceutical cream, as compared to a reduced amount of imiquimod maintained in an identical pharmaceutical imiquimod cream but formulated with a compendial grade oleic acid component when the pharmaceutical cream and the identical pharmaceutical imiquimod cream are each stored under identical storage conditions for up to about six months after formulation. - View Dependent Claims (2, 3, 4, 5, 6, 7, 11)
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8. A method of stabilizing 1-(2-methylpropyl)-1H imidazo[4,5-c]quinolin-4-amine (imiquimod) in a pharmaceutical cream formulated with the imiquimod and an oleic acid component during storage of the pharmaceutical cream prior to application of the pharmaceutical cream to a dermal or mucosal surface, said method comprising:
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formulating the pharmaceutical cream with a therapeutically effective amount of imiquimod and a pharmaceutically acceptable vehicle including an oleic acid component, wherein the oleic acid component contains at least about 80% oleic acid by weight as a fatty acid and has a peroxide value of no more than about 5 milliequivalents of oxygen per kilogram and contains less than about 1% by weight polar impurities at or prior to formulation of the pharmaceutical cream; storing the formulated pharmaceutical cream prior to use of the pharmaceutical cream; and maintaining a greater amount of the therapeutically effective amount of imiquimod in the pharmaceutical cream during said storing of the pharmaceutical cream, as compared to a reduced amount of imiquimod maintained in an identical pharmaceutical imiquimod cream but formulated with a compendial grade oleic acid component when the pharmaceutical cream and the identical pharmaceutical imiquimod cream are each stored under identical storage conditions for up to about four months after formulation. - View Dependent Claims (9, 10, 12, 13, 14)
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15. A method of stabilizing 1-(2-methylpropyl)-1H imidazo[4,5-c]quinolin-4-amine (imiquimod) in a pharmaceutical cream formulated with the imiquimod and an oleic acid component during storage of the pharmaceutical cream prior to application of the pharmaceutical cream to a dermal or mucosal surface, said method comprising:
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formulating the pharmaceutical cream with a therapeutically effective amount of imiquimod and a pharmaceutically acceptable vehicle including an oleic acid component, wherein the oleic acid component contains at least about 80% oleic acid by weight as a fatty acid and has a peroxide value of no more than about 5 milliequivalents of oxygen per kilogram and contains less than about 1% by weight polar impurities at or prior to formulation of the pharmaceutical cream; storing the formulated pharmaceutical cream prior to use of the pharmaceutical cream; and maintaining a greater amount of the therapeutically effective amount of imiquimod in the pharmaceutical cream during said storing of the pharmaceutical cream, as compared to a reduced amount of imiquimod maintained in an identical pharmaceutical imiquimod cream but formulated with a compendial grade oleic acid component when the pharmaceutical cream and the identical pharmaceutical imiquimod cream are each stored under identical storage conditions for up to about two months. - View Dependent Claims (16, 17, 18, 19, 20)
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Specification