CN100462075C - Nanometer miconazole nitrate emulsion medicine and its prepn process - Google Patents
Nanometer miconazole nitrate emulsion medicine and its prepn process Download PDFInfo
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- CN100462075C CN100462075C CNB2006101046101A CN200610104610A CN100462075C CN 100462075 C CN100462075 C CN 100462075C CN B2006101046101 A CNB2006101046101 A CN B2006101046101A CN 200610104610 A CN200610104610 A CN 200610104610A CN 100462075 C CN100462075 C CN 100462075C
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Abstract
The nanometer miconazole nitrate emulsion medicine consists of surfactant, oil, miconazole nitrate and distilled water. Its preparation process includes the following steps: weighing surfactant with or without co-surfactant; calculating HLB value and selecting oil phase for reaching emulsifying HLB value near that of the surfactant phase; changing the ratio between the surfactant phase and the oil phase regularly; adding dimethyl sulphoxide with dissolved miconazole nitrate into surfactant through stirring at 20-25 deg.c; adding distilled water slowly to form clear and flowing O/W type nanometer emulsion liquid. The nanometer miconazole nitrate emulsion has high skin permeability, no contamination to clothing, high dissolubility of miconazole nitrate, raised bioavailability of miconazole nitrate, delayed metabolism time and wide medicine market foreground.
Description
Technical field
The invention belongs to drug world, relate to a kind of novel form of external broad-spectrum antifungal pharmaceutical miconazole nitrate, particularly a kind of nanometer miconazole nitrate emulsion medicine and preparation method thereof.
Background technology
Miconazole nitrate belongs to imidazole derivative, is a kind of broad-spectrum antifungal agent.Dermatophytes, candidiasis, yeast and other algae, ascomycetes, cryptococcus etc. are had inhibition and killing action, simultaneously gram-positive cocci and bacillus are also had good antibacterial effect.Therefore be commonly used for vaginal infection and the secondary infection that causes by dermatophytes, yeast and other fungus-caused skin, fingernail, toenail infection and angular cheilitis, external otitis and candidiasis, gram positive bacteria clinically.The exterior-applied formulation of miconazole nitrate has ointment and suppository etc. clinically at present.When preparation ointment, because miconazole nitrate is insoluble to oil phase, so influenced its bioavailability.The present method that adopts: the one, principal agent is mixed with relatively large glycerol, be heated to 120 ℃ jointly, make it to dissolve, be added to immediately while hot in other composition of water then.The weak point of this method is that temperature is wayward, and emulsification times is long slightly, separate out crystallization again easily, and technology is loaded down with trivial details, is unsuitable for producing in enormous quantities; The 2nd, principal agent and PEG40 are made suspension, to add in the ointment base, the ointment principal agent granularity that this method is prepared out is thick excessively, does not reach requirement; The 3rd, principal agent is carried out controlled micro crystallization earlier, be made into ointment with substrate again.This method increases treatment process, and increase equipment increases production cost, is difficult for promoting in production in enormous quantities.
Summary of the invention
Shortcoming and deficiency at above-mentioned prior art the object of the present invention is to provide a kind of dissolubility height, bioavailability height, the good and simple nanometer miconazole nitrate emulsion medicine of production technology to percutaneous permeability.
The technical scheme that realizes the foregoing invention purpose is the water nanometer miconazole nitrate emulsion medicine, and it is made up of the following weight proportion raw material:
Surfactant 35.0%～45.0%
Oil 5.0%～10.0%
Miconazole nitrate 0.1%～2.0%
Dimethyl sulfoxide 5.0%～10.0%
Distilled water 44%～52%
Total component is 100%.
In the selection of surfactant, the present invention selects the nonionic surfactant of avirulence and good biocompatibility for use.Nonionic surfactant is more stable in solution, is not subject to the influence of strong electrolyte, inorganic salts, also is not subject to the influence of soda acid, and good with the compatibility of other surfactants, and haemolysis is less.In theory, the preparation of 0/W type micro emulsion needs the HLB value of surfactant between 8～18, consider preparation technology's simplicity, be the stability of the easy formation of microemulsion and the microemulsion for preparing, the present invention selects the liquid nonionic surfactant of HLB between 10～15 for use, and is perhaps composite with the non-ionic surface active agent of a kind of HLB＜10.Available surfactant has: lauric acid polyoxyethylene ether, castor oil polyoxyethylene ether (as EL-40), alkylphenol polyoxyethylene are (as TX-8, TX-10), any or several mixture in the castor oil hydrogenated polyoxyethylene ether (as RH-40).
The present invention is according to when the HLB of the required surfactant of emulsifying oil phase is close with surfactant, the principle that formed emulsion is stable, the oils and fats of selecting for use have any or several mixture in isopropyl myristate, isopropyl palmitate, Adeps Serpentis, almond oil, olive oil, the Oleum Ricini.Be in a liquid state, do not have bad abnormal smells from the patient under these oily room temperature.
Another object of the present invention provides a kind of preparation method of nanometer miconazole nitrate emulsion medicine, and step is as follows:
(1) preparation of surfactant phase takes by weighing surfactant by formula proportion, use separately or with help surface activity composite in proportion, calculate the HLB value of this system, stir.The HLB value of common emulsifying agent can be found in some chemical industry handbooks, as " the chemical products handbook of chemical industry publishing house.Because hydrophile-lipophile balance (HLB) value of surfactant has additive properties, the available quality averaging method is obtained the HLB value of surfactant.For example, after two kinds of surfactant A, B mixed, the hydrophile-lipophile balance HLBAB value of its mixed surfactant was
HLBAB＝(WAHLBA+WBHLBB)/(WA+WB)
WA in the formula, WB---the quality of blend surfactants A, B;
HLBA, the HLB value of HLBB---surfactant A, B.
(2) preparation of oil phase is selected one or more oil according to the HLB value of surfactant phase, transfers its ratio, makes the required HLB value of its emulsifying close with surfactant HLB mutually.
(3) in the rule change surfactant phase of 9:1～1:9 and the ratio of oil phase, fully stir at 20 ℃～25 ℃, slowly add the dimethyl sulfoxide that is dissolved with miconazole nitrate then, fully stir, slowly add distilled water again and stir, until forming clear, viscosity is little and has mobile faint yellow or colourless O/W type nanometer miconazole nitrate emulsion medicine.
The present invention detects through transmission electron microscope, and droplet diameter distribution is between 10～100nm, and outward appearance is transparent faint yellow or colourless liquid, has good stability:
1, ageing stability
Ageing stability is meant when nanoemulsion medicine liquid is preserved under room temperature nature change condition, and the nanoemulsions outward appearance prolongs and the degree that changes in time.This nanometer miconazole nitrate emulsion medicine is transparent lastingly, does not find muddy or precipitation, illustrates that then ageing stability is good.This is an important indicator estimating nanoemulsions.
2, heat storage stability
This nanometer miconazole nitrate emulsion medicine places test tube, and sealing places 37 ℃ of constant water bath box to store 14 days, and this liquid heat storage back outward appearance is still transparent.
3, anti-freeze-stable
With this nanometer miconazole nitrate emulsion medicine in refrigerator-4 ℃ preserve a week after.Return to room temperature.If nanoemulsions becomes solids at-4 ℃, return to room temperature, return to transparent, and place one week the back continue transparently, think that then freezing-resistance is good.
4, accelerated stability
Nanometer miconazole nitrate emulsion medicine of the present invention is placed test tube, and sealing under the rotating speed of 15000r/min centrifugal 20 minutes, does not have layering, still clear.
Nanometer miconazole nitrate emulsion medicine of the present invention has better percutaneous permeability, can strengthen the dissolubility of miconazole nitrate, improve the bioavailability of miconazole nitrate, and have slow-releasing, prolonged the medicine metabolism time in vivo, made the drug effect performance fully.Nanometer miconazole nitrate emulsion medicine is a kind of broad-spectrum antifungal agent, dermatophytes, candidiasis, yeast and other algae, ascomycetes, cryptococcus etc. are had inhibition and killing action, simultaneously gram-positive cocci and bacillus are also had good antibacterial effect.Therefore be commonly used for the vaginal infection that causes by dermatophytes, yeast and other fungus-caused skin, fingernail, toenail infection and angular cheilitis, external otitis and candidiasis, gram positive bacteria and the treatment of secondary infection clinically.Sooner or later each was applied in the affected part 1 time on 1st; Tinea versicolor 1 time on the one, should continue medication 5 days, in case recurrence behind the transference cure.
Nanometer miconazole nitrate emulsion medicine of the present invention compared with prior art has the following advantages:
1) thermodynamic stability height, during preparation operation fairly simple, not phase-splitting, do not precipitate, bin stability improves;
2) light transmission is good, and any inhomogeneities or sedimentary existence easily are found, and sensible quality is carried;
3) antiseptic property improves, because decentralized photo liquid is smaller, can prevent the intrusion of antibacterial, increases the dissolubility of some active ingredients simultaneously;
4) have good solubilization, can improve the dissolubility of miconazole nitrate, delay the regression time of miconazole nitrate, thereby improved the bioavailability of miconazole nitrate:
5) salubrious clean, pollution clothes not;
6) method technology is simple, is fit to large-scale production.
Below further set forth the better quality and the beneficial effect of miconazole nitrate nanoemulsion medicine of the present invention by testing example, these are tested examples and have comprised that medicine of the present invention tests and the comparative efficacy test animal irritation test, antibacterial activity.
Test example 1 animal irritation test
8 of New Zealand tower rabbits, divide 2 groups, one group is carried out the skin irritation test, adopt 0.5% respectively, 1%, 1.5%, each 0.3ml of 2% nanometer miconazole nitrate emulsion medicine observes one group eye dripping, tangible zest does not appear behind the 24h, adopt 0.5% respectively again, 1%, 1.5%, each 3ml of 2% nanometer miconazole nitrate emulsion medicine carries out the skin irritation test to another group, 24h sloughs back part of animal spinal column diamond wool before test, the depilation scope is 3cm * 3cm, one side is tested, one side tangible zest do not occur with control sides for contrast behind the 24h.
The test of test example 2 antibacterial activities
Get the New Zealand tower rabbit of 6 body weight no significant differences, on skin, infect achorion, Candida albicans, malassezia furfur, Pilus Caprae seu Ovis sample sporidiole bacteria, staphylococcus aureus and Listeria monocytogenes (above strain provides by my school Microbiological Lab) respectively, nanometer miconazole nitrate emulsion medicine with 0.5%, 1%, 1.5%, 2% carries out external antibacterial activity contrast test, and result of the test is as shown in table 1:
The test of table 1 antibacterial activity in vitro
The result of table 1 clearlys show effective Mlc of miconazole nitrate 1%～2%, and above bacterium all is antibiotic preferably vigor, and the high more antibacterial effect of concentration is good more.
The pharmacodynamics contrast test of test example 3 nanometer miconazole nitrate emulsion medicines and other preparations
Choose patient's 24 examples that have toenail to infect clinically, be equally divided into three groups, first group with miconazole nitrate nanoemulsion medicine treatment of the present invention, and external is coated with the affected part of putting on the skin in cleaning, respectively 1 time sooner or later on the one; Second group of the accurate word H19983185 of traditional Chinese medicines miconazole nitrate ointment with 2% (containing miconazole nitrate 0.2g) of Changshu Xing Hai pharmaceutical Co. Ltd production, external is coated with the affected part of putting on the skin in cleaning, each 1 time sooner or later on the one; The 3rd group of accurate word H31022700 of the traditional Chinese medicines husband who produces with Shanghai Shikangte Pharmaceutical Co., Ltd. is health (miconazole nitrate solution), and the affected part is cleaned in external, dries spraying, 2--3 time on the one.Through the treatment of time of one identical period, first group of cure rate is that to be 62%, the three group be 75% to 88%, the second group of cure rate.Obviously visible miconazole nitrate nano-emulsion curative effect is better than miconazole nitrate ointment and the husband is a health.
The concrete experimental example and the embodiment that provide below in conjunction with the applicant describe in further detail.
Embodiment 1
Accurately take by weighing castor oil hydrogenated polyoxyethylene ether 4.5g, Adeps Serpentis 0.5g, dimethyl sulfoxide 0.5g (wherein dissolving miconazole nitrate 0.01g), under 20 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is O/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.0g.
Embodiment 2
Accurately take by weighing castor oil polyoxyethylene ether 4.0g, iso-octyl palmitate 1.0g, dimethyl sulfoxide 0.6 (wherein dissolving miconazole nitrate 0.05), under 22 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is the faint yellow transparent nanometer miconazole nitrate emulsion medicine of O/W type, claims that its weight is 10.00g.
Embodiment 3
Accurately take by weighing castor oil hydrogenated polyoxyethylene ether 4.5g, Fructus Canarii albi 0.5g, dimethyl sulfoxide 0.7g (wherein dissolving miconazole nitrate 0.1g), under 24 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is O/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.0g.
Embodiment 4
Accurately take by weighing castor oil hydrogenated polyoxyethylene ether 4.5g, Semen Myristicae isopropyl ester 0.5g, dimethyl sulfoxide 1.0g (wherein dissolving miconazole nitrate 0.15g), under 22 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is O/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.00g.
Embodiment 5
Accurately take by weighing castor oil hydrogenated polyoxyethylene ether 4.0g, Oleum Ricini 1.0g, dimethyl sulfoxide 1.0g (wherein dissolving miconazole nitrate 0.18g), under 24 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is O/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.0g.
Embodiment 6
Accurately take by weighing alkylphenol polyoxyethylene 4.0g, almond oil 1.0g, dimethyl sulfoxide 0.3g (wherein dissolving miconazole nitrate 0.08g), under 23 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, amount of water is for then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is O/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.00g.
Embodiment 7
Accurately take by weighing castor oil polyoxyethylene ether 4.0g, isopropyl palmitate 1.0g, dimethyl sulfoxide 1.0g (wherein dissolving miconazole nitrate 0.2g), under 25 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is the faint yellow transparent nanometer miconazole nitrate emulsion medicine of O/W type, claims that its weight is 10.0g.
Embodiment 8
Accurately take by weighing lauric acid polyoxyethylene ether 4.0g, almond oil 1.0g, dimethyl sulfoxide 0.8g (wherein dissolving miconazole nitrate 0.13g), under 23 ℃ of room temperature conditions, manually stir its abundant mix homogeneously, then to wherein slowly adding distilled water, the limit adds the waterside manually stirs, and the system viscosity is less during beginning, with the increase of rate of water added, it is sticky that system can become, this moment, liquid crystal state or water-in-oil type nanoemulsion may appear in system, continue to drip and constantly stir, when system unexpected when thinning, what produced this moment promptly is 0/W type water white transparency nanometer miconazole nitrate emulsion medicine, claims that its weight is 10.00g.
Claims (2)
1. oil-in-water type nanometer miconazole nitrate emulsion medicine, it is characterized in that it is made up of the following weight proportion raw material: 35.0%～45.0% surfactant, 5.0%～10.0% oil, 0.1%～2.0% miconazole nitrate, 5.0%～10.0% dimethyl sulfoxide, 44%～52% distilled water, total component is 100%;
Described surfactant is any or several mixture in lauric acid polyoxyethylene ether, castor oil polyoxyethylene ether, castor oil hydrogenated polyoxyethylene ether, the alkylphenol polyoxyethylene;
Described oil is any or several mixture of isopropyl myristate, isopropyl palmitate, iso-octyl palmitate, Adeps Serpentis, almond oil, olive oil, Oleum Ricini.
2. oil-in-water type nanometer miconazole nitrate emulsion medicine according to claim 1 is characterized in that: the particle diameter of described nanometer miconazole nitrate emulsion medicine is 10nm～100nm.
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