WO1991016068A1 - Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs - Google Patents

Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs Download PDF

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Publication number
WO1991016068A1
WO1991016068A1 PCT/US1991/002804 US9102804W WO9116068A1 WO 1991016068 A1 WO1991016068 A1 WO 1991016068A1 US 9102804 W US9102804 W US 9102804W WO 9116068 A1 WO9116068 A1 WO 9116068A1
Authority
WO
WIPO (PCT)
Prior art keywords
drug
water
lecithin
phospholipid
lipid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1991/002804
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English (en)
French (fr)
Inventor
Duncan H. Haynes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to DK91908933T priority Critical patent/DK0533690T3/da
Priority to RU9292016352A priority patent/RU2100030C1/ru
Priority to DE69131349T priority patent/DE69131349T2/de
Priority to CA002078990A priority patent/CA2078990C/en
Priority to EP91908933A priority patent/EP0533690B1/en
Publication of WO1991016068A1 publication Critical patent/WO1991016068A1/en
Anticipated expiration legal-status Critical
Priority to GR990401915T priority patent/GR3030825T3/el
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55555—Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers

Definitions

  • the formulation must allow injection of sufficient quantities of drug:
  • the formulation must carry the drug at high concentration. As an example, if the highest concentration available for a drug is 2% (w/v) or 20 mg/ml and the largest practical volume for an IM injection into man is 5 ml, then a single injection can supply only 100 mg of the drug. If the drug is sufficiently potent, this will present no problem. However, there are many examples in which 1-2 gm of drug must be introduced into the body. This would require either a 10- or 20-fold larger volume (impractical or impossible) or 10-20 times the concentration (heretofore unachievable).
  • diazepam (Valium ) is solublized to a concentration of 5 mg/ml (0.5%) in a solution of 40% propylene glycol, 10% ethyl alcohol, water and preservatives.
  • warnings are given to reduce the possibility of venous thrombosis, phlebitis, local irritation, etc. which are reported under adverse reaction.
  • the preparation is not stable to dilution in water (Roche, 1988 PDR, pp. 1764-1766.
  • a pre-anesthetic sedative product containing 2 mg/ml or 4 mg/ml lorazepam and 0.18 ml/ml polyethylene glycol 400 (non-ionic detergent) in propylene glycol is available for IM injection or IV injection after dilution. It is reported to cause pain and burning with 17% incidence with IM injection (Wyeth, 1988 PDR, pp. 2258-2259).
  • the data for days 1-7 post-injection are compared with results for the same quantity of OTC injected as a commercial 2-methyl-pyrolidone solution.
  • FIG. 4 shows the levels of OTC in central arterial blood in the experiment of Fig. 3.
  • FIG. 7 shows typical time courses of the level anesthesia in rats measured as vocalization threshold (mAmp) to intradermal electrical stimuli after intra-venous injection of lecithin-coated alphaxalone microcrystals.
  • mAmp vocalization threshold
  • my invention makes novel use of membrane -forming lipids as mechanical buffers, organizers of aqueous volume and retardants of recrystallization of the drug. This is achieved by excess phospholipid in the form of unilamellar and multi-lameliar phospholipid vesicles which form a secondary coating of the suspended microcrystal. Predominantly unilamellar vesicles are formed as a byproduct of the sonication and primary coating process. Their retention in the preparation was found to improve the long-term stability of the formulation.
  • the drug microcrystals exhibit only restricted Brownian Motion. Under microscopic observation they are not observed to change position in relation to eachother. They vibrate or "dance in place” about their central position. This partial restriction of motion is probably an important factor in the long-term stability of the preparation. When stored, concentrated preparations are diluted many thousand-fold into drug-saturated water, the microcrystals retain their micron or sub-micron size.
  • the aqueous suspension may show advantages for topical application, instillation into the eye.
  • the preparation can deliver drugs by the inhalation route, in the form of either an aqueous suspension or a lyophilized powder. It is also likely that the preparation will be useful for administration of pesticides and in creating high value biocompatible products, as exemplified by suspension of drugs in drinking water (Example 15).
  • OTC oxytetracycline
  • the lecithin-coated OTC microcrystal fraction had the following weight-averaged particle size distribution: 980+460 (SD) nm, 59%; 2,880+400 (SD) nm, 41%.
  • SD weight-averaged particle size distribution
  • Analysis of the preparation by electron microscopy using negative staining corroborated the above findings.
  • Several preparations were made as described above and were filled into rubber-stoppered glass ampules and glass bottles. With storage over a period of weeks some settling was observed, but the preparation could be rendered homogeneous with three inversions. The preparation retained its properties, including size distribution, OTC concentration, chemical integrity and syringability (20 gauge or narrower) for over 9 months.
  • lecithin-coated microparticles from a material with a melting point below the boiling point of water and above that of the intended temperature of use (37°C).
  • Pharmaceutically acceptable waxes and solids, of biological and synthetic origin include but not limited to hydrogenated castor oil, cetostearyl alcohol, cetyl alcohol, cetyl esters wax, myristyl alcohol, petrolatum, paraffin, and various waxes (emulsifying, microcrystalline, white, yellow, etc.). It is also possible to use these materials to provide a waxy coating for the drug microcrystals, which is in turn coated with phospholipid. The waxy coating will further slow the rate of release of the drug, thus prolonging its duration of action.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
PCT/US1991/002804 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs Ceased WO1991016068A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DK91908933T DK0533690T3 (da) 1990-04-26 1991-04-23 Phospholipid-coatede mikrokrystaller: injicerbare formuleringer af vanduopløselige lægemidler
RU9292016352A RU2100030C1 (ru) 1990-04-26 1991-04-23 Водная суспензия, содержащая микрокристаллы фармакологически активного водонерастворимого лекарственного вещества, покрытые мембранообразующим липидом (варианты), и лиофилизированный препарат водной суспензии
DE69131349T DE69131349T2 (de) 1990-04-26 1991-04-23 Phospholipid-beschichtete mikrokristalle: injizierbare formulierungen wasserlöslicher arzneimittel
CA002078990A CA2078990C (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
EP91908933A EP0533690B1 (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
GR990401915T GR3030825T3 (en) 1990-04-26 1999-07-20 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US514,012 1990-04-26
US07/514,012 US5091188A (en) 1990-04-26 1990-04-26 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Publications (1)

Publication Number Publication Date
WO1991016068A1 true WO1991016068A1 (en) 1991-10-31

Family

ID=24045456

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/002804 Ceased WO1991016068A1 (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Country Status (16)

Country Link
US (2) US5091188A (https=)
EP (1) EP0533690B1 (https=)
JP (1) JP3261129B2 (https=)
KR (1) KR0159114B1 (https=)
AT (1) ATE181234T1 (https=)
AU (1) AU7852891A (https=)
CA (1) CA2078990C (https=)
DE (1) DE69131349T2 (https=)
DK (1) DK0533690T3 (https=)
ES (1) ES2134776T3 (https=)
GR (1) GR3030825T3 (https=)
MX (1) MX25532A (https=)
RU (1) RU2100030C1 (https=)
TW (1) TW203559B (https=)
WO (1) WO1991016068A1 (https=)
ZA (1) ZA913122B (https=)

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EP0533690A1 (en) 1993-03-31
GR3030825T3 (en) 1999-11-30
JPH05507685A (ja) 1993-11-04
DE69131349T2 (de) 1999-11-18
DE69131349D1 (de) 1999-07-22
TW203559B (https=) 1993-04-11
ATE181234T1 (de) 1999-07-15
MX25532A (es) 1993-10-01
JP3261129B2 (ja) 2002-02-25
US5091188A (en) 1992-02-25
CA2078990A1 (en) 1991-10-27
ZA913122B (en) 1992-04-29
USRE35338E (en) 1996-09-24
CA2078990C (en) 2002-06-04
AU7852891A (en) 1991-11-11
ES2134776T3 (es) 1999-10-16
RU2100030C1 (ru) 1997-12-27
DK0533690T3 (da) 1999-11-22
KR0159114B1 (ko) 1998-12-01
EP0533690A4 (en) 1993-04-14
EP0533690B1 (en) 1999-06-16

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