CN102000043A - Flurbiprofen salt transdermal patch and preparation method thereof - Google Patents
Flurbiprofen salt transdermal patch and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of medicines and discloses a flurbiprofen salt transdermal patch and a preparation method thereof. The flurbiprofen salt transdermal patch comprises a backing layer, a medicine reservoir and an anti-adhesion layer, wherein the medicine reservoir comprises the following compositions in percentage by weight: 2-15 wt% of flurbiprofen salt as a principle agent, 70-90 wt% of pressure sensitive adhesive and 0-20 wt% of transdermal absorption accelerator, and an inert filler, a tackifier, an antioxidant and the like can also be added. The medicines are selected from flurbiprofen diethylamine, flurbiprofen triethylamine, flurbiprofen ethanolamine, flurbiprofen diethanolamine, flurbiprofen triethanolamine and flurbiprofen-(N-hydroxyethyl piperidine). The invention can enhance the transdermal absorption effect of the medicines to reach the action part by permeating through a skin barrier, wherein the curative effect of flurbiprofen is durable and stable; and if administration is needed to be interrupted, the patch can be only uncovered and is convenient to use. The patch also has the advantages of good adhesion ability, good flexibility and the like without pollution.
Description
Technical field:
The present invention relates to medical technical field, exactly is flurbiprofen salt transdermal patch and preparation method thereof.
Background technology:
Flurbiprofen is a class arylprop acid type NSAID (non-steroidal anti-inflammatory drug), relative molecular mass 244.26 g/mol, fusing point 114 oC～117 oC, p
KA 4.2, and the profit partition coefficient is 3.86, and dissolubility is 11mg/mL(25 oC), biological half-life is 3h～5 h in the body.Flurbiprofen is non-selectivity ring oxo enzyme inhibitor, by suppressing the effect of cyclooxygenase in the arachidonic acid metabolic, reduces the synthetic of prostaglandin, has analgesic, analgesia, antiinflammatory action.Zoopery confirms that the antiinflammatory and the analgesic activity of flurbiprofen are strong than ibuprofen, and toxicity is lower.Flurbiprofen has toleration preferably, and aspirin is invalid or can not the optional flurbiprofen of using of anti-receptor, and its analgesia, antiinflammatory and refrigeration function are respectively 250 times and 50 times of aspirin.
This type of medicine mainly contains oral and two kinds of dosage forms of external clinically at present.Oral administration is owing to need administration 3 times ~ 4 times shorter every day of half-life, and easily cause the gastrointestinal tract infringement to reach with cardiovascular risk, patient that need take medicine for a long time or gastric ulcer patient often can not tolerate, Shang Shi external preparation mainly contains patch etc. in recent years, and flurbiprofen is widely used in treatment of diseases such as arthralgia, arthritis clinically.Flurbiprofen transdermal administration patent in the disclosed patent all is to be principal agent with the flurbiprofen at present, as patent CN1387842, patent CN1205631, patent CN101119716, but the flurbiprofen dissolubility is little, fat-soluble stronger, transdermal effect is relatively poor, be difficult to see through skin barrier and arrive site of action, therefore, good flurbiprofen organic amine salt improves the Transdermal absorption effect of medicine to seek a kind of dissolubility, arriving site of action to see through skin barrier, is the direction that the pharmacy personnel are making great efforts always.
Summary of the invention:
Technical problem solved by the invention provides flurbiprofen salt transdermal patch and preparation method thereof.
The present invention is achieved through the following technical solutions:
Flurbiprofen salt transdermal patch of the present invention comprises backing layer, medicine storing layer and anti-glutinous layer, and medicine storing layer is made up of medicine, pressure sensitive adhesive, transdermal absorption accelerator, and described medicine is a flurbiprofen salt, and consumption accounts for 2 wt %～15wt%.Selected pressure sensitive adhesive matrix material is one or more chemical compounds in silicone, isobutylene type, acrylic polymer or cellulose family and their derivant, and its consumption is 70 wt %～90wt%.Transdermal absorption accelerator is selected menthol and organic acid esters thereof for use, eucalyptole, australene, the d-limonene, the 3-carene, α-terpinol, Oleum Pini-4-alcohol, carveol, α-bisabolol, carvone, pulegone, piperitone, menthone, fenchone, cyclohexene oxide, the limonene oxide, the pinene oxide, cyclopentene oxide, ascaridole, 7-oxabicyclo [2,2,1] normal heptane, safrole, 1-ally-3,4-methy-lene dioxy benzene, nerolidol, geraniol, eucalyptus oil, chenopodium oil, cananga oil, Camphora, Borneolum Syntheticum, dimethyl sulfoxide, decyl methyl sulfone, oleic acid, isopropyl myristate, isopropyl palmitate, propylene glycol dipelargonate, ethyl sebacate, dibutyl sebacate, NexACT88, glycerol trioleate, polyethylene glycol monolaurate, polypropylene glycol monolaurate dehydrated sorbitol mono-fatty acid ester, dibutyl phthalate, sodium laurylsulfate, poloxamer, Transcutol P, polysorbas20, polysorbate40, polysorbate60, Tween 80, span 20, span 40, sorbester p18, sorbester p17, carbamide, dodecyl-N, N-dimethylamino acetamide, dimethyl acetylamide, aminoacid and ester thereof, lecithin, fabaceous lecithin, phosphatidyl glycerol, PHOSPHATIDYL ETHANOLAMINE, phosphatidylcholine, phosphatidylinositols, Phosphatidylserine, phosphatidic acid, sphingomyelins, among the SEPA etc. one or more are compound, and consumption is 0 wt %～20 wt %.
Described flurbiprofen salt is one or more in flurbiprofen diethylamine, flurbiprofen triethylamine, flurbiprofen ethanolamine, flurbiprofen diethanolamine, flurbiprofen triethanolamine, flurbiprofen-(the N-hydroxyethyl piperidine), and synthetic by the following method:
(1) flurbiprofen is dissolved in acetone or the chloroform;
(2) equimolar diethylamine, triethylamine are dissolved in respectively in the small amount of acetone, ethanolamine, diethanolamine,
Triethanolamine, pyrrolidine are dissolved in the minimum of chloroform respectively; Flurbiprofen acetone or chloroformic solution are mixed with above-mentioned corresponding organic amine acetone or chloroformic solution, and ultrasonic or backflow obtains target product.
The concrete synthesis technique of medicine involved in the present invention is as follows:
1. the synthesis technique of flurbiprofen diethylamine: get flurbiprofen 0.1mol, be dissolved in the 40mL acetone, ultrasonic 20min makes dissolving standby.Get diethylamine 0.1mol, be dissolved in the 10mL acetone, shake up, two kinds of solution are mixed, ultrasonic, rotary evaporation volatilizes solvent promptly.
2. the synthesis technique of flurbiprofen triethylamine: get flurbiprofen 0.1mol, be dissolved in the 40mL acetone, ultrasonic 20min makes dissolving standby.Get triethylamine 0.1mol, be dissolved in the 10mL acetone, shake up, two kinds of solution are mixed, ultrasonic, rotary evaporation volatilizes solvent promptly.
3. the synthesis technique of flurbiprofen ethanolamine: get flurbiprofen 0.1mol, be dissolved in the 40mL chloroform, ultrasonic 20min makes dissolving standby.Get ethanolamine 0.1mol, be dissolved in the 10mL chloroform, shake up, two kinds of solution are mixed, the ultrasonic precipitation of separating out filters and volatilizes solvent promptly.
4. the synthesis technique of flurbiprofen diethanolamine: get flurbiprofen 0.1mol, be dissolved in the 40mL chloroform, ultrasonic 20min makes dissolving standby.Get diethanolamine 0.1mol, be dissolved in the 10mL chloroform, shake up, two kinds of solution are mixed, ultrasonic, rotary evaporation volatilizes solvent promptly.
5. the synthesis technique of flurbiprofen triethanolamine: get flurbiprofen 0.1mol, be dissolved in the 40mL chloroform, ultrasonic 20min makes dissolving standby.Get triethanolamine 0.1mol, be dissolved in the 10mL chloroform, shake up, two kinds of solution are mixed, the ultrasonic precipitation of separating out filters and volatilizes solvent promptly.
6. the synthesis technique of flurbiprofen-(N-hydroxyethyl piperidine): get flurbiprofen 0.1mol, be dissolved in the 40mL chloroform, ultrasonic 20min makes dissolving standby.Get N-hydroxyethyl piperidine 0.1mol, be dissolved in the 10mL chloroform, shake up, two kinds of solution are mixed, ultrasonic, rotary evaporation volatilizes solvent promptly.
In the flurbiprofen salt of the present invention, flurbiprofen ethanolamine salt and flurbiprofen triethanolamine salt are the white powder solid, and other amine salt is thick liquid nano.
The present invention has measured the infrared spectrum of flurbiprofen, flurbiprofen diethyl amine salt, flurbiprofen triethylamine salt, flurbiprofen ethanolamine salt, flurbiprofen diethanolamine salt, flurbiprofen triethanolamine salt, flurbiprofen-(N-hydroxyethyl piperidine) salt, sees Fig. 1.The strong peak of stretching vibration of carbonyl has appearred belonging in flurbiprofen at the 1701.8cm-1 place.The carbonylic stretching vibration peak of flurbiprofen diethyl amine salt, flurbiprofen triethylamine salt, flurbiprofen ethanolamine salt, flurbiprofen diethanolamine salt, flurbiprofen triethanolamine salt, flurbiprofen-(N-hydroxyethyl piperidine) salt all moves to lower wave number, lays respectively at 1623.6 cm
-1, 1622.8 cm
-1, 1619.8 cm
-1, 1566.0 cm
-1, 1577.0 cm
-1, 1580.4 cm
-1, peak intensity all obviously reduces.This shows that the carboxylic group among the FP exists with the ionic form of carboxylic acid.
Flurbiprofen salt transdermal patch of the present invention can also add inert filler, tackifier and antioxidant etc. if needed, and its consumption is respectively 1 wt %～10 wt %.
Backing layer is selected for use and is contained the aluminumpolyethylene composite membrane, or elastic non-woven cloth.Anti-glutinous layer is that the surface is through anti-glutinous the processing or fluorine-containing polyester film or paper of silicone oil.
Preparation technology fully mixes principal agent flurbiprofen salt, pressure sensitive adhesive and transdermal absorption accelerator, transfer coated is on anti-glutinous layer, process is through 40 ° of C～80 ° C drying, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly make flurbiprofen salt transdermal patch.Bondline thickness is 100 μ m.
In the present invention, provide a kind of flurbiprofen salt transdermal patch and preparation method thereof clearly.Transdermal absorption accelerator has been selected the menthol organic acid esters derivant described in the patent CN101157612.Being applied to experiment in vitro skin model of the present invention is rat abdomen skin, and this skin model has obtained to use widely in scientific research, and its cuticle thickness is close with human body.
Nonsteroidal antiinflammatory drug transdermal patch of the present invention effectively improves its percutaneous transit dose by the flurbiprofen salify, can improve the percutaneous transit dose of flurbiprofen when not adding any promoter, can be reduction product administration area a kind of effective ways are provided.
The specific embodiment:
By the more explained in detail the present invention of following example, should be understood that: the present invention never only limits to embodiment, perhaps only shows as embodiment.
The Transdermal absorption test
The present invention adopts the horizontal diffusion cell of improved Franz, adopts rat abdomen skin as barrier, result of the test such as table 1.
Embodiment 1
Flurbiprofen 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 2
Flurbiprofen diethanolamine 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 3
Flurbiprofen diethylamine 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 4
Flurbiprofen ethanolamine 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 5
Flurbiprofen triethylamine 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 6
Flurbiprofen triethanolamine 0.1mmol is dissolved in the 2.0g dehydrated alcohol,, evenly coats on the anti-glutinous layer with the abundant mixing of polyacrylate pressure-sensitive, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 7
Flurbiprofen-(N-hydroxyethyl piperidine) 0.1mmol is dissolved in the 2.0g dehydrated alcohol, with the abundant mixing of polyacrylate pressure-sensitive, evenly coat on the anti-glutinous layer, through dry 15 minutes of 80 ° of C, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly.
Embodiment 8
Except that adding flurbiprofen triethanolamine 0.7mmol, with method similarly to Example 6
Embodiment 9
Except that adding isopropyl myristate 0.03g, with method similarly to Example 6.
Embodiment 10
Except that adding isopropyl myristate 0.2g, with method similarly to Example 6.
Embodiment 11
Except that adding isopropyl myristate 0.03g, menthol oleate 0.01g, Tween 80 0.02g, with method similarly to Example 6
Table 1 flurbiprofen (salt) patch percutaneous absorption parameter (`
X ± s, n=3)
| Permeants | Q 12h (μg/cm 2) | J?(μg/cm 2/h) | T lag(h) |
| 1 | 22.66±4.93 | 1.37±0.24 | 0 |
| 2 | 27.03±5.62 | 2.04±0.32 | 0.29±0.29 |
| 3 | 29.15±3.00 | 2.27±0.12 | 0.01±0.01 |
| 4 | 32.01±2.44 | 2.46±0.19 | 0.16±0.16 |
| 5 | 33.17±1.69 | 2.90±0.12 | 0.40±0.11 |
| 6 | 37.78±1.54 | 3.28±0.13 | 0.44±0.18 |
| 7 | 46.24±5.54 | 3.30±0.17 | 0 |
| 8 | 121.24±13.24 | 8.20±0.21 | 0 |
| 9 | 51.54±3.91 | 3.80±0.14 | 0 |
| 10 | 79.17±6.14 | 5.30±0.17 | 0 |
| 11 | 130.48±34.20 | 12.37±2.84 | 1.76±0.48 |
J: steady state flow
Q 12h: 12 hours accumulation transit doses
T Lag: time lag
As can be seen from Table 1, flurbiprofen salt patch has superior skin permeability, and, be selected from the transit dose that above-mentioned transdermal absorption accelerator can significantly improve active component if need to add one or more.
Claims (11)
1. flurbiprofen salt transdermal patch, constitute by backing layer, drug depot and anti-glutinous layer, it is characterized in that: described medicine storing layer is made up of medicine, pressure sensitive adhesive, transdermal absorption accelerator, drug dose accounts for 2 wt %～15wt%, the pressure sensitive adhesive consumption accounts for 70 wt %～90wt%, and the transdermal absorption accelerator consumption accounts for 0 wt %～20 wt %.
2. flurbiprofen salt transdermal patch according to claim 1 is characterized in that: can also add inert filler, tackifier and antioxidant, its consumption is respectively 1 wt %～10 wt %.
3. according to right 1 described flurbiprofen salt transdermal patch, it is characterized in that: described medicine comprises flurbiprofen diethylamine, flurbiprofen triethylamine, flurbiprofen ethanolamine, flurbiprofen diethanolamine, flurbiprofen triethanolamine, flurbiprofen-(N-hydroxyethyl piperidine).
4. flurbiprofen salt transdermal patch according to claim 1 is characterized in that: described transdermal absorption accelerator is one or more of alcohols, sulfoxide class, SEPA, fatty acid and esters thereof, surfactant-based, terpenes, amine, amide-type, amino acids and ester or phospholipids compounds.
5. flurbiprofen salt transdermal patch according to claim 4 is characterized in that: described alcohols transdermal absorption accelerator is one or both of ethanol, propylene glycol, isopropyl alcohol, isobutanol, n-dodecanol, n-octyl alcohol; Described sulfoxide class transdermal absorption accelerator is one or both of dimethyl sulfoxide, decyl methyl sulfone; Described fatty acid and esters transdermal absorption accelerator thereof are one or more of oleic acid, isopropyl myristate, isopropyl palmitate, propylene glycol dipelargonate, ethyl sebacate, dibutyl sebacate, NexACT88 glycerol trioleate, polyethylene glycol monolaurate, polypropylene glycol monolaurate; Described surfactant-based transdermal absorption accelerator is one or more of sodium laurylsulfate, poloxamer, Transcutol P, polysorbas20, polysorbate40, polysorbate60, Tween 80, span 20, span 40, sorbester p18, sorbester p17; Described terpenes transdermal absorption accelerator is menthol and organic acid esters thereof, eucalyptole, australene, d-limonene, 3-carene, α-terpinol, Oleum Pini-4-alcohol, carveol, α-bisabolol, carvone, pulegone, piperitone, menthone, fenchone, cyclohexene oxide, limonene oxide, pinene oxide, cyclopentene oxide, ascaridole, 7-oxabicyclo [2,2,1] one or more of normal heptane, safrole, 1-ally-3,4-methy-lene dioxy benzene, nerolidol, geraniol, eucalyptus oil, chenopodium oil, cananga oil, Camphora, Borneolum Syntheticum; Described amine transdermal absorption accelerator is carbamide, dodecyl-N, one or both of N-dimethylamino acetamide; Described phospholipid transdermal absorption accelerator is one or more of lecithin, fabaceous lecithin, phosphatidyl glycerol, PHOSPHATIDYL ETHANOLAMINE, phosphatidylcholine, phosphatidylinositols, Phosphatidylserine, phosphatidic acid, sphingomyelins.
6. flurbiprofen salt transdermal patch according to claim 5 is characterized in that: the organic acid in menthol and the organic acid esters transdermal absorption accelerator thereof is selected from acetic acid, propanoic acid, butanoic acid, valeric acid, caproic acid, enanthic acid, sad, n-nonanoic acid, lauric acid, myristic acid, Palmic acid, stearic acid, oleic acid, lactic acid, salicylic acid or cinnamic acid.
7. flurbiprofen salt transdermal patch according to claim 1 is characterized in that: pressure sensitive adhesive is one or more chemical compounds in silicone, isobutylene type, acrylic polymer or cellulose family and their derivant.
8. flurbiprofen salt transdermal patch according to claim 1, it is characterized in that: backing layer is selected the PVC film for use, or elastic non-woven cloth.
9. flurbiprofen salt transdermal patch according to claim 1 is characterized in that: anti-glutinous layer is that the surface is through anti-glutinous the processing or fluorine-containing polyester film or paper of silicone oil.
10. flurbiprofen salt transdermal patch according to claim 3 is characterized in that: described flurbiprofen salt is synthetic by the following method:
A. flurbiprofen is dissolved in acetone or the chloroform;
B. equimolar diethylamine, triethylamine are dissolved in respectively in the small amount of acetone, ethanolamine, diethanolamine, triethanolamine, pyrrolidine are dissolved in the minimum of chloroform respectively;
C. flurbiprofen acetone or chloroformic solution are mixed with above-mentioned corresponding organic amine acetone or chloroformic solution, ultrasonic or backflow obtains flurbiprofen salt.
11. preparation method as right 1 described flurbiprofen salt transdermal patch, it is characterized in that: principal agent flurbiprofen salt, pressure sensitive adhesive and transdermal absorption accelerator are fully mixed, transfer coated is on anti-glutinous layer, through 40 ° of C～80 ° C drying, then with comprise PVC or non-woven fabrics to mount the backing material compound, be die-cut into a certain size, specification, promptly make flurbiprofen salt transdermal patch.
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Cited By (10)
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| CN102940618A (en) * | 2012-11-29 | 2013-02-27 | 沈阳药科大学 | Loxoprofen organic amine salt transdermal patch and preparation method thereof |
| CN103211799A (en) * | 2013-03-11 | 2013-07-24 | 无锡艾德美特生物科技有限公司 | Flurbiprofen paracetamol ester external use slow release transdermal patch and preparation method thereof |
| CN105073102A (en) * | 2012-10-01 | 2015-11-18 | 香港科技大学 | Design and manufacture of nonelectronic, active-infusion patch and device for transdermal delivery across skin |
| CN105232496A (en) * | 2015-09-23 | 2016-01-13 | 成都艾比科生物科技有限公司 | Flurbiprofen coating agent and preparation method thereof |
| CN106822065A (en) * | 2016-12-06 | 2017-06-13 | 北京茗泽中和药物研究有限公司 | A kind of flurbiprofen cataplasms |
| CN108143772A (en) * | 2018-01-18 | 2018-06-12 | 河南羚锐制药股份有限公司 | A kind of transdermal patch for alleviating nasal obstruction |
| CN108721253A (en) * | 2017-04-17 | 2018-11-02 | 北京泰德制药股份有限公司 | A kind of warming gel ointment |
| CN109432061A (en) * | 2018-11-09 | 2019-03-08 | 北京德默高科医药技术有限公司 | Multilayer transdermal delivery system containing brufen or its analogue |
| CN110694036A (en) * | 2019-08-21 | 2020-01-17 | 云南中医药大学 | Sanfu plaster with slow release function and preparation method thereof |
| CN113648297A (en) * | 2021-08-16 | 2021-11-16 | 乐明药业(苏州)有限公司 | Pharmaceutical composition and patch containing flurbiprofen |
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| CN105073102A (en) * | 2012-10-01 | 2015-11-18 | 香港科技大学 | Design and manufacture of nonelectronic, active-infusion patch and device for transdermal delivery across skin |
| CN102940618A (en) * | 2012-11-29 | 2013-02-27 | 沈阳药科大学 | Loxoprofen organic amine salt transdermal patch and preparation method thereof |
| CN103211799A (en) * | 2013-03-11 | 2013-07-24 | 无锡艾德美特生物科技有限公司 | Flurbiprofen paracetamol ester external use slow release transdermal patch and preparation method thereof |
| CN105232496A (en) * | 2015-09-23 | 2016-01-13 | 成都艾比科生物科技有限公司 | Flurbiprofen coating agent and preparation method thereof |
| CN106822065A (en) * | 2016-12-06 | 2017-06-13 | 北京茗泽中和药物研究有限公司 | A kind of flurbiprofen cataplasms |
| CN108721253A (en) * | 2017-04-17 | 2018-11-02 | 北京泰德制药股份有限公司 | A kind of warming gel ointment |
| CN108143772A (en) * | 2018-01-18 | 2018-06-12 | 河南羚锐制药股份有限公司 | A kind of transdermal patch for alleviating nasal obstruction |
| CN109432061A (en) * | 2018-11-09 | 2019-03-08 | 北京德默高科医药技术有限公司 | Multilayer transdermal delivery system containing brufen or its analogue |
| CN112206222A (en) * | 2018-11-09 | 2021-01-12 | 北京德默高科医药技术有限公司 | Multi-layer transdermal drug delivery system containing ibuprofen structural analogs |
| JP2022507102A (en) * | 2018-11-09 | 2022-01-18 | 北京▲徳▼默高科医▲薬▼技▲術▼有限公司 | Multilayer transdermal drug delivery system containing ibuprofen or its structural analogs |
| EP3900710A4 (en) * | 2018-11-09 | 2022-10-12 | Demotech. Inc. | Multi-layer transdermal drug delivery system containing ibuprofen or structural analogue thereof |
| JP7354242B2 (en) | 2018-11-09 | 2023-10-02 | 北京▲徳▼默高科医▲薬▼技▲術▼有限公司 | Multilayer transdermal drug delivery system containing ibuprofen or its structural analogs |
| CN110694036A (en) * | 2019-08-21 | 2020-01-17 | 云南中医药大学 | Sanfu plaster with slow release function and preparation method thereof |
| CN113648297A (en) * | 2021-08-16 | 2021-11-16 | 乐明药业(苏州)有限公司 | Pharmaceutical composition and patch containing flurbiprofen |
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