US20070031479A1 - Bioadhesive gel based on hydroxyethycellulose - Google Patents

Bioadhesive gel based on hydroxyethycellulose Download PDF

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Publication number
US20070031479A1
US20070031479A1 US10/567,890 US56789004A US2007031479A1 US 20070031479 A1 US20070031479 A1 US 20070031479A1 US 56789004 A US56789004 A US 56789004A US 2007031479 A1 US2007031479 A1 US 2007031479A1
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United States
Prior art keywords
weight
sample
composition
hydroxyethylcellulose
bioadhesive
Prior art date
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Abandoned
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US10/567,890
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English (en)
Inventor
Massimo Prini
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Mitech Idea SRL
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Individual
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Filing date
Publication date
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Assigned to MIPHARM S.P.A. reassignment MIPHARM S.P.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PRINI, MASSIMO
Publication of US20070031479A1 publication Critical patent/US20070031479A1/en
Assigned to MITECH-IDEA S.R.L. reassignment MITECH-IDEA S.R.L. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MIPHARM S.P.A.
Priority to US13/293,484 priority Critical patent/US8790685B2/en
Abandoned legal-status Critical Current

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    • 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
    • A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • A61K9/0036—Devices retained in the vagina or cervix for a prolonged period, e.g. intravaginal rings, medicated tampons, medicated diaphragms
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • This invention relates to compositions in the form of a bioadhesive gel that adheres to the mucous membranes, in particular the vaginal mucosa, for the application of active ingredients and/or principles.
  • Bioadhesion is the property whereby some hydrogels adhere to biological tissues, in particular to mucous-coated epithelia such as the gastric, buccal, vaginal and rectal mucosae.
  • the most commonly used polymers that are capable of forming hydrogels and imparting bio- and/or muco-adhesion are acrylic or methacrylic acid polymers, possibly cross-linked, and chitosan, or its derivatives.
  • a bioadhesive gel able to ensure prolonged contact between the active ingredient and the vaginal mucosa, and gradual release of that ingredient over time, provides the ideal solution in terms of efficacy and compliance by patients.
  • Bioadhesive vaginal gels have consequently been disclosed, for example, in U.S. Pat. No. 6,159,491, US 2002012674, US 2003091642, WO 200047144, WO 200203896, WO 200143720 and WO 9610989.
  • an acrylic acid polymer (Carbomer or polycarbophil) is used as viscosity-controlling or bioadhesive agent.
  • WO 200015192 describes mucoadhesive formulations in which chitosan is used instead of the acrylic acid polymer.
  • bioadhesive gel formulations that adhere to the mucous membranes, in particular the vaginal mucosa, comprising hydroxyethylcellulose as the only bioadhesive polymer.
  • This gelling excipient has no acid groups and is therefore not dependent on the ionic strength of the medium; it also has a matrix effect which allows particularly slow, gradual release of the active ingredient, for up to 24 hours.
  • compositions in the form of an aqueous gel for the intravaginal delivery of active ingredients comprising hydroxyethylcellulose as the only gelling and bioadhesive agent.
  • compositions of the invention may also contain glycerol, diethylene glycol monoethyl ether, surfactants, preservatives, acidifiers and other excipients in common use for the form of delivery considered herein.
  • compositions of the invention will preferably contain 1 to 5% by weight of hydroxyethylcellulose, 25 to 90% by weight of water, 5 to 25% by weight of glycerol, 5 to 50% by weight of diethylene glycol monoethyl ether, 0.01 to 10% by weight of surfactants, 0.05 to 1% by weight of preservatives, and 0.01 to 1% by weight of acidifiers.
  • the hydroxyethylcellulose content is higher than 2% and less than 4%.
  • Hydroxyethylcellulose is commercially available from many sources: it is preferred an hydroxyethylcellulose having a degree of substitution of about 1.5 (corresponding to 3 hydroxyethyl groups every two saccharide units) and a molecular weight estimated from intrinsic viscosity measurements ranging from 1.0 to 1.3 ⁇ 10 6 . Hydroxyethylcellulose having said characteristic is available under the trade-mark Natrosol 250 HX by Hercules Inc. UK.
  • the percentage of active ingredient will obviously depend on the characteristics of the selected drug, and may vary within a wide range, for example from 0.01 to 10% by weight.
  • Active ingredients which can be advantageously formulated according to the invention include antifungals, antiseptics and antimicrobials, antibiotics, analgesics, local anaesthetics, antihistamines, anti-inflammatory agents, contraceptives, hormones, and combinations thereof.
  • active ingredients include, in particular, econazole, miconazole, fluconazole, ciclopiroxolamine, nifuratel, nystatin, chlorhexidine, ibuprofen, ketoprofen, naproxen, benzydamine, benzalkonium chloride or other quaternary ammonium antiseptics, nonoxynol-9 and all other active ingredients of interest for gynaecological applications.
  • composition Percentage Purified water 81.9% Glycerol 12.9% Chlorhexidine digluconate, 20% solution w/v 2.7% Hydroxyethylcellulose (Natrosol 250 HX) 2.5%
  • Bioadhesion was measured in vitro using a suitably modified Lloyd dynamometer.
  • the measurement substrate (rabbit gastric mucosa or polypropylene) was fixed with an adhesive to the upper support, which in turn was connected to the mobile crossbar, and 200 mg of the test formulation were placed on the lower support so as to cover the surface evenly. After effecting close contact between the formulation and the substrate (30 s), the crossbar was raised at a defined, constant speed until the two surfaces separated.
  • Diffusion medium lactate buffer, pH 4.0
  • Release membrane cellulose acetate 0.45 ⁇ m.
  • the test for release of the drug from the gel was performed using diffusion cells, with cellulose acetate membranes having a 4.5 cm 2 surface.
  • the quantity of gel applied was 1.5 g.
  • an automated system took predetermined sample aliquots, with immediate UV spectrophotometer at 254 nm.
  • FIG. 1 shows the diffusion profile of chlorhexidine as the mean of 8 ⁇ standard deviation.
  • FIG. 2 shows the diffusion profile of chlorhexidine from the 8 samples.
  • Table 2 shows the percentages released for the 8 chlorhexidine samples. TABLE 2 time sample 1 sample 2 sample 3 sample 4 sample 5 sample 6 sample 7 sample 8 mean SD 0 0 0 0 0 0 0 0 0 0 0 10 12.89 8.532 11.94 10.37 11.54 4.473 12.28 9.514 10.19 2.74 20 20.05 19.09 19.92 19.39 18.9 17.3 20.35 18.51 19.19 0.98 30 25.29 23.73 26.29 24.53 23.49 22.86 25.73 24.65 24.57 1.17 40 29.94 28.16 31.35 29.54 27.11 27.24 29.5 27.47 28.79 1.53 60 37.63 33.33 39.02 38.09 34.48 35.99 37.73 35.43 36.46 1.97 90 48.43 45.46 51.11 50.36 42.11 40.69 45.84 43.93 45.99 3.76 120 57.25 53.77 59.81 60.04 49.54 51.69 53.37 51.09 54.57 4.
  • FIG. 3 shows the diffusion profile of ibuprofen as the mean of 8 samples ⁇ standard deviation.
  • Table 3 shows the percentages released for the 8 ibuprofen samples. TABLE 3 time (min) sample 1 sample 2 sample 3 sample 4 sample 5 sample 6 sample 7 sample 8 mean SD 0 0 0 0 0 0 0 0 0 0 0 0 30 15.56 17.83 18.96 18.96 4.18 3.22 17.06 11.26 13.38 6.05 60 24.34 26.60 26.88 19.53 33.15 24.14 26.71 19.95 25.16 4.06 90 30.56 28.02 32.26 28.02 34.44 36.37 30.57 37.01 32.16 3.28 120 40.19 33.39 45.28 30.56 36.05 44.74 42.16 39.59 38.99 4.94 150 47.26 47.54 45.56 56.60 47.63 44.74 43.77 43.77 47.11 3.89 180 57.45 41.60 53.49 46.69 47.31 44.74 44.09 44.41 47.47 4.99 240 57.73 54.62 54.62 59.71 52.
  • FIG. 4 shows the diffusion profile of econazole as the mean of 8 samples ⁇ standard deviation.
  • Table 4 shows the percentages released of the 8 econazole samples. TABLE 4 time sample 1 sample 2 sample 3 sample 4 sample 5 sample 6 sample 7 sample 8 mean SD 1 8.9 8.9 10.7 11.7 9.1 8.8 10.3 12 10.1 1.3 2 12.3 15.5 18.4 19.1 14.4 15 17.3 19.5 16.4 2.5 3 24.1 21.6 24 25 22.1 25.3 21.1 23.6 23.4 1.6 4 29 26.2 28.8 30.1 30.4 28.2 25.8 32.1 28.8 2.1 5 34.1 30.4 32.8 34.5 36 33.4 30.2 33.7 33.1 2.0 6 40 34.2 35.4 37.6 38.4 36.5 34 36.3 36.6 2.1 7 40.5 36.8 37.4 39.9 41 39.2 37 38.4 38.8 1.6 8 44.4 39.3 38.6 41.3 43.2 40.2 39.6 41.2 41.0 2.0 9 45.2 40.6 40 43 45.8 42.1 42.3 44.2 42.9 2.1 10 46.1 41.8 40.9 44 47.3 44 45 45.4 44.3 2.1 11 47.2 42.8 41.4

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Reproductive Health (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Urology & Nephrology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Immunology (AREA)
  • Medicinal Preparation (AREA)
  • Materials For Medical Uses (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Adhesives Or Adhesive Processes (AREA)
US10/567,890 2003-08-08 2004-07-30 Bioadhesive gel based on hydroxyethycellulose Abandoned US20070031479A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/293,484 US8790685B2 (en) 2003-08-08 2011-11-10 Bioadhesive gel based on hydroxyethylcellulose

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT001640A ITMI20031640A1 (it) 2003-08-08 2003-08-08 Base per gel bioadesivi.
ITMI2003A001640 2003-08-08
PCT/EP2004/008577 WO2005014047A1 (en) 2003-08-08 2004-07-30 Bioadhesive gel based on hydroxyethylcellulose

Related Parent Applications (1)

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PCT/EP2004/008577 A-371-Of-International WO2005014047A1 (en) 2003-08-08 2004-07-30 Bioadhesive gel based on hydroxyethylcellulose

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US13/293,484 Continuation US8790685B2 (en) 2003-08-08 2011-11-10 Bioadhesive gel based on hydroxyethylcellulose

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US13/293,484 Expired - Lifetime US8790685B2 (en) 2003-08-08 2011-11-10 Bioadhesive gel based on hydroxyethylcellulose

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US (2) US20070031479A1 (da)
EP (1) EP1651274B1 (da)
JP (1) JP4855935B2 (da)
CN (1) CN1832760B (da)
AT (1) ATE395084T1 (da)
BR (1) BRPI0413446A (da)
CA (1) CA2535123C (da)
CY (1) CY1108548T1 (da)
DE (1) DE602004013787D1 (da)
DK (1) DK1651274T3 (da)
ES (1) ES2305818T3 (da)
IT (1) ITMI20031640A1 (da)
PL (1) PL1651274T3 (da)
PT (1) PT1651274E (da)
SI (1) SI1651274T1 (da)
WO (1) WO2005014047A1 (da)

Cited By (2)

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WO2018007288A1 (en) * 2016-07-08 2018-01-11 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Pharmaceutical composition comprising benzydamine
CN111557897A (zh) * 2020-07-07 2020-08-21 温州海鹤药业有限公司 一种含有硝呋太尔的药物组合物及其制备方法

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CN100394919C (zh) * 2006-03-01 2008-06-18 杨军 一种用于治疗阴道疾病的药物组合物
US8433851B2 (en) 2007-08-16 2013-04-30 International Business Machines Corporation Reducing wiring congestion in a cache subsystem utilizing sectored caches with discontiguous addressing
US8778365B1 (en) 2013-01-31 2014-07-15 Merz Pharmaceuticals, Llc Topical compositions and methods for making and using same
US9446131B2 (en) 2013-01-31 2016-09-20 Merz Pharmaceuticals, Llc Topical compositions and methods for making and using same
US9452173B2 (en) 2013-01-31 2016-09-27 Merz Pharmaceuticals, Llc Topical compositions and methods for making and using same
US9433680B2 (en) * 2013-01-31 2016-09-06 Merz Pharmaceuticals, Llc Topical compositions and methods for making and using same
CN106310266A (zh) * 2015-07-09 2017-01-11 王强 一种预防或治疗粘膜疾病的组合物及制备方法
CN106109398A (zh) * 2016-06-14 2016-11-16 上海通用药业股份有限公司 一种含有噻康唑的阴道用凝胶
CN106038477A (zh) * 2016-06-14 2016-10-26 上海通用药业股份有限公司 一种含有噻康唑的阴道用凝胶的制备方法
IT201900000388A1 (it) * 2019-01-10 2020-07-10 L N Age S R L Composizione per l'uso nel trattamento di lesioni vaginali, del glande ed anali
EP3986378A1 (en) * 2019-06-21 2022-04-27 Alfasigma S.p.A. Pharmaceutical compositions in the form of gel containing xyloglucan and alcohols for the controlled release of active ingredients
EP4389228A1 (en) 2022-12-21 2024-06-26 Lacer, S.A.U. Oral care composition containing cellulosic polymers

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018007288A1 (en) * 2016-07-08 2018-01-11 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Pharmaceutical composition comprising benzydamine
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CN111557897A (zh) * 2020-07-07 2020-08-21 温州海鹤药业有限公司 一种含有硝呋太尔的药物组合物及其制备方法

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PL1651274T3 (pl) 2008-10-31
CA2535123A1 (en) 2005-02-17
CN1832760A (zh) 2006-09-13
WO2005014047A1 (en) 2005-02-17
EP1651274A1 (en) 2006-05-03
CN1832760B (zh) 2010-06-23
EP1651274B1 (en) 2008-05-14
BRPI0413446A (pt) 2006-10-17
PT1651274E (pt) 2008-08-11
CA2535123C (en) 2012-06-26
US8790685B2 (en) 2014-07-29
JP2007533604A (ja) 2007-11-22
DE602004013787D1 (de) 2008-06-26
ITMI20031640A1 (it) 2005-02-09
US20120083515A1 (en) 2012-04-05
CY1108548T1 (el) 2014-04-09
ATE395084T1 (de) 2008-05-15
JP4855935B2 (ja) 2012-01-18
SI1651274T1 (sl) 2008-10-31
DK1651274T3 (da) 2008-09-08
ES2305818T3 (es) 2008-11-01

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