US3711602A - Compositions for topical application for enhancing tissue penetration of physiologically active agents with dmso - Google Patents
Compositions for topical application for enhancing tissue penetration of physiologically active agents with dmso Download PDFInfo
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- US3711602A US3711602A US00085697A US3711602DA US3711602A US 3711602 A US3711602 A US 3711602A US 00085697 A US00085697 A US 00085697A US 3711602D A US3711602D A US 3711602DA US 3711602 A US3711602 A US 3711602A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- compositions for topical application for enhancing tissue penetration of physiologically active agents with dime'thyl sulfoxide include physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients.
- physiologically active agents include physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients.
- Such compositions which may be in the form of lotions, ointments and suppositories, include the physiologically active agent, at least l0% by weight of DMSO and a pharmaceutically acceptable thickening agent.
- Liquid formulations for topical application of DMSO and the physiologically active agent in spray containers are also provided.
- Some agents are inactivated in the gastrointestinal tract or they are absorbed poorly into the body from the tract. Also, undesirable side effects may result which prevent effective oral administration.
- a local concentration for a local effect is often desired but a larger systemic dose must be given to achieve an effective concentration at the local area when the agent can only be injected or given orally, (but not topically). This higher dose often causes undesirable side effects, since dosage related side effects are very prevalent for many agents.
- Animal tissues comprise various membranes which are selectively permeable and which allow some substances to pass freely, while rejecting others or permitting only slight passage.
- Such membranes comprise the body coverings and externally communicating cavities, including the skin and mucous membranes ofthe body cavities, e.g. alimentary tract, respiratory tract, genitourinary tract, oral cavity, eyes, etc. (collectively defined herein as external membranes). They also include internal membranes such as the linings of the various organs and other internal body structures, e.g., peritoneum and pleura, and the membranes surrounding cellular and intracellular structures.
- Dimethyl sulfoxide is a water-white liquid at room temperature having a freezing point of approximately l8.5C and a specific gravity of approximately 1.1.
- Dimethyl sulfoxide is a well known industrial solvent and it has been available in commercial quantities for at least a decade (from Crown Zellerbach Corporation, San Francisco, Calif).
- DMSO was originally synthesized in 1866 and since that time it has been extensively investigated for possible industrial and biological utility and a considerable amount of literature has developed on its properties and uses. Over the last 25 years it has found widespread use as a solvent in industry and in the laboratory.
- DMSO has been investigated in the past for various biochemical uses, for example as a reaction solvent for preparing derivatives of various proteins, and antibiotics, as an extraction solvent for various proteins, as an analytical solvent and as a solvent'for various other laboratory uses. It has also been suggested as a solvent for certain pesticides.
- DMSO has been investigated as a preservative agent for in vitro storage of chilled or frozen tissue and it has also been determined to have a protective effect in experimentalanimals subjected to X-irradiation following injection of DMSO into such animals.
- DMSO has been listed along with various inert materials as bland, high boiling fluids to be used as carriers for the griseofulvin in applying it to the skin to control fungus growth in the skin.
- DMSO has been employed as a solvent for preparation of certain injectable formulations, namely chloramphenicol and an anthelminic preparation.
- DMSO when applied to animal tissue, increases the permeability of the tissue in a reversible manner to cause a much greater penetration rate for conjointly applied physiologically active agents.
- the mode of activity is still unclear, it is definitely not that of the simple vehicle" or carrier" since the effect may be obtained to some extent even when the DMSO is applied to the tissue separately and the enhanced penetrability of the tissue may last for as much as three hours after the DMSQ treatment.
- an agent such as a steroid
- a steroid When applied to the intact skin along with dimethyl sulfoxide, particularly at a DMSO concentration of 50 percent by weight and above, or to skin pretreated with the dimethyl sulfoxide, an agent such as a steroid, may penetrate rapidly to and saturate the stratum corneum (the highly resistant horny layer of the skin which is the major barrier to penetration). The steroid continues to penetrate through the skin from this reservoir" in the stratum corneum to the underlying tissue and into the circulatory system.
- stratum corneum the highly resistant horny layer of the skin which is the major barrier to penetration
- topical is intended to include application to all external membrane barriers including the cutaneous or epidermis regions and the mucous membranes including the gastrointestinal tract, the respiratory tract and the genitourinary tract.
- DMSO acts by several mechanisms in enhancing penetration. DMSO is believed to act directly on tissue to alter the general permeability of the tissue membrane. More specifically, DMSO when applied thereto, is believed to decrease'the natural resistance of tissue membranes to penetration by foreign agents. DMSO is also believed to promote penetration by a direct transport effect, perhaps by the mechanism of complexing with the agent. This mechanism is believed more applicable to cationic and anionic agents.
- compositions which are uniquely suitable for the purpose of utilizing the penetration enhancement of DMSO, which compositions include the physiologically active agent, an amount of DMSO effective to enhance topical penetration of such agent and a pharmaceutically acceptable thickening agent.
- the DMSO concentration may be 10 percent by weight and higher.
- DMSO concentrations may be 50 percent or higher are suitable.
- the thickened composition forms of this invention permit more sustained contact of the composition with the treated surface and more accurate and controlled dosing. Accidental spilling, run off and undesired contact with the composition can also be minimized.
- Pharmaceutically acceptable hydrophillic diluents, particularly water may also be employed in these compositions to lessen the tissue irritation affects which may result from application of higher concentrations of DMSO.
- Liquid formulations for topical application comprising at least 10 percent by weight DMSO, the physiologically active agent and, optionally, diluents, thickening agents, etc. in spray containers are also provided.
- Such dosage forms are useful for topical application to prevent accidental spilling and undesired contact with the composition. They are particularly suitable for application to mucous membranes of various body orifices. They are also advantageous in providing a more uniform application to both dermal and mucous membrane surfaces.
- GENERAL DESCRlPTlON OF THE INVENTION This invention is applicable to the tissue or organisms of all animal phyla, DMSO having differing degrees of influence on penetration of various tissue types of a given animal.
- Animals of particular importance in the practice of the invention are the mammalians, especially man and veterinary animals.
- the invention may also be practiced with other vertebrates, as for example the amphibians, fishes, reptiles, etc., and with the lower species comprising the non-vertebrates.
- Penetration enhancement is generally non-selective in terms of the type of physiological effect or effects of agents to be transported across membrane barriers.
- the extent of penetration enhancement will depend upon' many factors, the predominant factors being the relative natural permeability of the particular membrane, the concentration of DMSO applied, the extent of solubility of the agent in DMSO and the chemical and physicalproperties of the agent.
- the thickened dosage forms of this invention for topical application include lotions, ointments (including creams and gels) and suppositories.
- These compositions comprise the physiologically active agent combined with the DMSO and a base comprising a thickening agent for the composition and such pharmaceutical diluents as may be indicated.
- Lotions and ointments may contain the usual ingredients to provide the thickening base, as for example cetyl alcohol, an emulsifier such as lauryl sulfate and water.
- Another base may be formulated by combining equal weight amounts of stearic acid, cetyl alcohol, triethanolamine and glycerol monostearate with water.
- Still other thickening bases may utilize polyethylene glycols of different viscosities, depending upon the desired consistency.
- DMSO may be added to the lotion or ointment base in varying amounts as desired, generally up to around 50 percent by weight or higher.
- a suppository form may be made from a high viscosity polyethylene glycol 4,000, water and DMSO, which may be present in an amount of about percent by weight.
- the spraying and misting dosage forms of the invention constitute nasal spray bottles, aspirators, misting devices, aerosol bombs and other dispensing containers having liquid spray or mist dispensing means, which containers are charged with fluid formulations comprising the physiologically active agent, at least l0 percent by weight DMSO and, optionally, water or diluent, thickening agents and the like.
- fluid formulations comprising the physiologically active agent, at least l0 percent by weight DMSO and, optionally, water or diluent, thickening agents and the like.
- the compositions for this purpose are sufficiently fluid to permit dispensing by spray or mist from the container.
- the DMSO component will provide adequate fluidity.
- the usual liquid diluents may be provided where desired to enhance sprayability.
- physiologically active in describing the agents contemplated herein is used in a broad sense to comprehend not only agents having a direct pharmacological effect on the host but also those having an indirect or observable effect which is useful in the medical arts, e.g., the screening of U.V. radiation from the tissues, etc.
- Agents, penetration of which across external membrane barriers may be beneficially enhanced upon direct application of the compositions of this invention include: physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients.
- the concentration of physiologically active agent in the various dosage forms is, of course, commensurate with that normally utilized for the particular agent in conventional formulations for effective results for the intended route. Both the amount of physiologically active agent and the amount of DMSO will be influenced by the type of effect desired. If a more localized effect is required, lower amounts of physiologically active agents and lower concentrations of DMSO may be called for. Where deeper penetration is desired, as in the case of local anaesthesia, a higher concentration of DMSO may be desirable to promote adequate penetration. Where general systemic concentration of an agent is desired for a topical preparation, generally higher concentrations of DMSO are desirable and the amount of agent as, for example, a steroid, may be included in the composition sufficient to provide the blood level desired.
- the concentration of the DMSO in the compositions to enhance penetration may vary over wide limits.
- the concentration selected is desirably related to the route of administration to be employed.
- compositions including at least about 50 percent by weight DMSO are preferable in that they have been found to increase percutaneous penetration in a highly significant manner. Maximum cutaneous penetration is generally attained with DMSO concentrations closely approaching 100 percent (excluding the agent), but with concentrations much above 90 percent by weight the incremental increase in penetration rate over that achieved at 90 percent often is relatively small.
- concentrations much above 90 percent by weight the incremental increase in penetration rate over that achieved at 90 percent often is relatively small.
- above a percent concentration of dimethyl sulfoxide the side effects of a burning sensation and erythema increase significantly. Accordingly, for topical use, it may be desirable, consistent with physical stability of the composition, to formulate the DMSO in compositions containing a DMSO concentration of between about 50 and 90 percent by weight and containing water, preferably 10 percent by weight or greater.
- compositions of this invention may be included in the compositions of this invention as desirable for the particular route of administration and dosage form.
- amount and type of diluent or carrier used should, of course, be consistent with the compatability of the agent in DMSO and the diluent.
- a cosolvent or other standard adjuvant, such as a surfactant, may be called for to maintain the agent in solution or suspension at the desired concentration. Where stability of the agent in the presence of DMSO at the desired concentration is a problem, it may be desirable to prepare the formulation immediately before administration.
- the various pharmaceutical forms are desirably provided in determined amounts, as in containers of a given volume.
- Cotton tipped stick applicators, squeeze tubes may all be utilized for topical application of the thickened formulations.
- the amount of the composition, and thus of the physiologically active agent therein, to be administered will obviously be an effective amount for the desired result expected therefrom. This, of course, will be ascertained by the ordinary skill of the practitioner. Due to enhanced activity which may be achieved through better penetration, the dosage of agent may often be decreased from that generally applicable. In accordance with the usual prudent formulating practices, a dosage near the lower end of the useful range of the particular agent may be employed initially and the dosage increased as indicated from the observed response, as in the routine procedure of the physician.
- EXAMPLE 1 The following lotion formulation may be prepared containing about 0.01 to 1.0 percent, with preferably 0.1 percent fluocinolone acetonide:
- EXAMPLE 2 The following ointment (gel) formulation may be prepared containing about 0.2 to 1.0 percent, and preferably 0.6 percent triamcinilone acetonide:
- the corticosteroid is dissolved in a mixture of the first two ingredients, and the carboxy vinyl polymer gelling agent is sprinkled on the surface of the combined liquids and stirred until all the particles have been wetted and dispersed.
- the triethanolamine is then added dropwise to the mixture until it has gelled, care being taken to minimize the air entrapment.
- This gel is particularly effective in the treatment of seborrhea and other scalp and hair inflammatory conditions and may be applied in amount and frequency conventionally used for topical application of this steroid. Better penetration and thereby an increased anti-inflammatory active is obtained for the amount of steroid applied than results from its application in conventional formulations.
- EXAMPLE 3 The following ointment formulations may be prepared containing about 0.1 to 1.0 percent prednisone and preferably 0.5 percent:
- Prednisone gm 0.1-l Glyceryl monostearate, acid type gm I80 Stearyl alcohol gm 50 Polysorbate 80 cc 20 Water cc 450 Dimethyl sulfoxide cc 300 The product is prepared as described in Example 1.
- the ointment is a valuable base for application of the corticosteroid to inflammatory dermatological areas, particularly when they require inunction. Application is in accordance with that usual for topical application of this steroid in conventional bases.
- EXAMPLE 4 The following cream formulations may be prepared Water q.s. 1000 cc.
- Example l the product is prepared as directed in Example l and is useful in severe dermatoses requiring inunction.
- EXAMPLE 5 The following ointment formulation may be prepared containing about 0.5 to 2.5 percent preferably 1.0 percent, desoxycorticosterone acetate:
- the product is prepared as specified in Example 1.
- the product may be employed in treatment of pigmentation in Addisons disease by topical application to the affected area. Penetration may be increased sufficiently so that effective results may be obtained. In conventional bases this steroid has had very limited effectiveness topically and injection usually must be resorted to.
- a suppository formulation may be prepared as follows containing about 1 to 5 percent, preferably 2 per- The solid constituents are melted, added to the solution of the steroid in DMSO and poured into an appropriate mold. The product is recommended for rectal application as replacement therapy.
- a suppository formulation may be prepared as follows containing about 1 to 5 percent, preferably 2 percent, l7-methyl testosterone:
- a cream formulation may be prepared as follows containing about'l to 10 percent, preferably 3 percent, 1 7a-ethyll 9-nortestosterone:
- This cream may be prepared as noted in Example 1. It may be applied topically for stimulation of epithelization and connective tissue regeneration.
- EXAMPLE 9 The following cream may be formulated with the following composition containing about 1 to 10 percent, and preferably 3%, 2a-methyl-dihydrotestosterone The cream is prepared as directed in Example I. The product is useful in the treatment of muscle wasting l5 and weakness followed breast cancer surgery and may be applied topically to the affected area. Penetration of the steroid is greatly improved over that obtained in conventional formulations.
- gel may be formulated containing about 1 to 5 percent, preferably 2 percent, steroid:
- the product is prepared as specified in Example 2.
- the product is useful in topical anabolic treatment, particularly in preventing thinning of the skin and in inducing blood vessel thickening.
- EXAMPLE 1 l The following lotion may be formulated as follows containing about 0.1 to 1.0 percent, preferably 0.4 percent, estradiol valerate:
- This product is prepared as noted in Example '1.
- the product is designed as a means of establishing systemic replacement therapy for estrogens during menopause by simple topical application to the skin or mucous membrane.
- the DMSO enhances penetration of the estrogen sufficiently to obtain a systemic effect. This has not been possible in conventional formulations.
- a suppository may be formulated as follows to contain 0.1 to 1.0 percent, preferably 0.5 percent, of 3- methyl ether of ethynylestradiol:
- EXAMPLE 13 The following ointment (gel) may be formulated containing 0. 1 percent diethylstilbesterol:
- This gel is prepared as detailed in Example 2.
- the preparation is particularly suitable for topical application in the treatment of adolescent acne.
- EXAMPLE 14 A cream may be formulated as follows to contain about 0.72 percent norethynodrel and about 0.0286 percent mestranol:
- a suppository formulation may be prepared as follows:
- Example 7 Chlormadinone mg 5 Stilbesterol mg l Polyethylene glycol 4000 gm 400 Propylene glycol monostearate gm Dimethyl sulfoxide cc 500 The suppositories are formed as in Example 7. The product may be employed for treatment of irregular or prolonged bleeding.
- EXAMPLE 16 The following ophthalmic formulation may be prepared containing about 0.1 to 0.75 percent, preferably 0.3 percent, spironolactone:
- the formulation is prepared by melting the polyethylene glycol 4000, dissolving the steroid in the DMSO, mixing the two liquids together and diluting to volume with water while stirring.
- the preparation is applied topically to the eye by eye dropper, or similar applicator, for treatment of glaucoma.
- a 5-fluorouracil formulation may be prepared by blending the following:
- the formulation is particularly useful in topical treatment of skin tumors or other localized superficial tumors. A typical dose is grams. lt is also useful intreating viral disorders such as warts.
- a suppository formulation may be prepared by melting together the following:
- EXAMPLE 19 A topical ointment formulation of tripelennamine base particularly suitable for treatment of itching dermatoses (applied to the affected area several times daily), may be formulated as follows:
- a chloral hydrate suppository formulation may be prepared by blending together:
- the melt is poured into a suppository mold and cooled to form l0 suppositories each supplying a l gram dose.
- l0 suppositories each supplying a l gram dose.
- One or two suppositories, as indicated, may be administered as a general sedative.
- a unit dose suppository form of imipramine can be prepared by melting together:
- This dosage may be administered rectally T.l.D. to relieve depression.
- EXAMPLE 23 The following formulation maybe melted together, placed in a suppository mold and cooled to form a unit dose for rectal application as a monoamine oxidase inhibitor for treatment of depressive states:
- Mecamylamine is representative of agents having a site of activity at the autonomic ganglia (ganglionic stimulating and blocking agents). It may be formulated as follows to provide a single dose in suppository form for rectal application in treatment of hypertension:
- a glycerol trinitrate ointment may be prepared by blending the following ingredients:
- EXAMPLE 26 A male subject had a skin markedly sensitive to ultraviolet light.
- a test solution was made containing 1 percent ultraviolet absorber in percent dimethyl sulfoxide.
- a control solution was made containing the ultraviolet-absorber in 100 percent ethanol, and both solutions were similarly thickened with Carbowax 4000 to provide lotion forms.
- the ultraviolet absorber was 2,2-dihydroxy-4,4'-dimethoxy benzophenone.
- the two lotions were applied to different sides of the subjects face. After one day of severe sun exposure, the subject was examined. The side with the control application showed marked redness. The side with the test application showed only slight redness. Two days later, the control side was blistered, whereas the test side was normal and free of redness.
- EXAMPLE 27 An ointment base may be prepared from the follow. ing:
- a composition suitable for topical application to external membranes of a human or animal subject for enhanced penetration of a physiologically active agent in said composition which comprises an amount of a physiologically active agent effective to produce the desired physiological effect on topical application of the composition to an external membrane of the subject, said agent being selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients, an amount of DMSO effective to enhance external membrane penetration of said agent and comprising at least about percent by weight of said composition, and a pharmaceutically acceptable thickening agent in an amount sufficient to materially increase the viscosity of said composition, whereby to facilitate controlled topical application thereof.
- a physiologically active agent effective to produce the desired physiological effect on topical application of the composition to an external membrane of the subject
- said agent being selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents
- composition as in claim 2 and wherein said agent is selected from the group consisting of physiologically active steroids, antineoplastic agents, and
- antigens antihistaminic agents, analgesics, local anaesthetics and antiinflammatory agents;
- composition as in claim 1 and wherein said composition is in the form of a lotion.
- composition as in claim 1 and wherein said composition is in the form of an ointment.
- composition as in claim 1 and wherein said composition is in the form of a suppository.
- a container provided with liquid spray dispensing means and containing a fluid, sprayable composition which comprises an amount of a physiologically active agent effective to produce the desired physiological effeet on topical application of the composition to an external membrane of a human or animal, said agent being selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients, and an amount of DMSO effective to enhance external membrane penetration of said agent and comprising at least about 10 percent by weight of said composition.
- a physiologically active agent effective to produce the desired physiological effeet on topical application of the composition to an external membrane of a human or animal
- said agent being selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients, and an
- a container as in claim 7 and wherein said DMSO in the composition charged therein comprises at least about 50 percent by weight of said composition.
Abstract
Description
Claims (10)
- 2. A composition as in claim 1 for dermal application and wherein said DMSO comprises at least about 50 percent by weight of said composition.
- 3. A composition as in claim 2 and wherein said agent is selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, analgesics, local anaesthetics and antiinflammatory agents.
- 4. A composition as in claim 1 and wherein said composition is in the form of a lotion.
- 5. A composition as in claim 1 and wherein said composition is in the form of an ointment.
- 6. A composition as in claim 1 and wherein said composition is in the form of a suppository.
- 7. A container provided with liquid spray dispensing means and containing a fluid, sprayable composition which comprises an amount of a physiologically active agent effective to produce the desired physiological effect on topical application of the composition to an external membrane of a human or animal, said agent being selected from the group consisting of physiologically active steroids, antineoplastic agents, antigens, antihistaminic agents, neuropharmacologic agents, antiinflammatory agents, anticoagulants, vasodilators, ultra-violet screening agents and nutrients, and an amount of DMSO effective to enhance external membrane penetration of said agent and comprising at least about 10 percent by weight of said composition.
- 8. A container as in claim 7 and wherein said DMSO in the composition charged therein comprises at least about 50 percent by weight of said composition.
- 9. A container as in claim 7 and wherein said container is an aerosol bomb containing a halocarbon propellant.
- 10. A container as in claim 7 and wherein said container is a squeeze bottle.
- 11. A container as in claim 7 and wherein the composition therein contains a substantial amount of water as a diluent.
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US8569770A | 1970-10-30 | 1970-10-30 |
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