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GB2394895A - Proton pump inhibitor composition in paste form - Google Patents

Proton pump inhibitor composition in paste form Download PDF

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Publication number
GB2394895A
GB2394895A GB0225926A GB0225926A GB2394895A GB 2394895 A GB2394895 A GB 2394895A GB 0225926 A GB0225926 A GB 0225926A GB 0225926 A GB0225926 A GB 0225926A GB 2394895 A GB2394895 A GB 2394895A
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United Kingdom
Prior art keywords
formulation according
pharmaceutical formulation
proton pump
pump inhibitor
plasticizer
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GB0225926A
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GB0225926D0 (en
Inventor
Amar Lulla
Geena Malhotra
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Cipla Ltd
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Cipla Ltd
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Priority to GB0225926A priority Critical patent/GB2394895A/en
Publication of GB0225926D0 publication Critical patent/GB0225926D0/en
Publication of GB2394895A publication Critical patent/GB2394895A/en
Withdrawn legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A pharmaceutical paste formulation for oral administration, which comprises a proton pump inhibitor, a surfactant, a plasticizer and an amphiphillic base.

Description

1 1 PHARMACEUTICAL PASTE FORMULATIONS
The present invention is concerned with improved pharmaceutical paste formulations containing proton pump inhibitors, and in particular improved pharmaceutical paste formulations containing omeprazole, and therapeutic uses thereof.
Omeprazole is described in U.S. patent 4,255,432. It is a potent inhibitor of gastric acid secretion that acts by inhibiting H+ K+ATPase, the enzyme involved in the final step of hydrogen ion production in the parietal cells, and has been used in the short term treatment of active duodenal and benign gastric ulcer and other gastric acid related diseases, in humans. Peptic ulcers are common also in some animals, particularly in horses. Although the etiology of gastro-
duodenal ulcers in horses has not been ascertained, it appears that stress plays important roles in some cases.
Omeprazole is highly acid labile and very slightly soluble in water and oral formulations have, therefore, been enteric-coated. Enteric coated formulations are expensive and time consuming to manufacture, and require elaborate technology and equipment. Another disadvantage of enteric-
coated formulations is the moisture sensitivity that can often be associated with such formulations. Various formulations have been reported for proton pump inhibitors, especially for omeprazole.
For example, W094/25070 discloses an oral composition containing a proton pump inhibitor in the form of enteric-coated dry particles mixed with a dry gelling agent, the mixture may then be made into a paste-like gel prior to administration. The composition, therefore, requires enteric coating, with the aforementioned disadvantages associated with such formulation. Furthermore, because such a moist gel is not stable during long-term storage at room temperature it cannot be
manufactured and sold as a ready-to-use formulation, rather it must be prepared ex tempore at the time of administration, making it inconvenient to use.
U.S. patents 5,708,017 and 6,316,481 describe paste formulations of proton-pump inhibitors comprising a proton-pump inhibitor, a thickening agent, a basifying agent and hydrophobic oily liquid vehicles. The thickening agent, along with a basifying agent, provides a non-acidic environment for the acid-labile omeprazole and thus has a stabilizing effect in the formulation.
The hydrophobic oily liquid vehicle comprises (i) a vegetable oil and (ii) triglycerides of medium chain fatty acids or propylene glycol diesters of medium chain fatty acids. The lubricant properties of the oil help the paste formulation to attain a desired degree of cohesiveness, plasticity, tenacity and ejectability. However, the common problem of syneresis, or separation of liquid from paste with time, has been reported with formulations as described in U.S. patents 5,708,017 and 6,316,481. Hence, there remains a need for pharmaceutical paste formulations having a blend of excipients that would alleviate the problems associated with prior art
formulations for thermolabile and moisture sensitive drugs.
The present invention now provides a stable, improved paste formulation for proton pump inhibitors. More particularly, there is provided by the present invention a pharmaceutical paste formulation for oral administration, which comprises a proton pump inhibitor, a surfactant, a plasticizer and an amphiphillic base.
The proton pump inhibitors used in the present invention are known compounds in the art, and methods for their preparation may be found in the literature. For example omeprazole is disclosed in EP 5129, lansoprazole in EP 174726, pantoprazole in EP 166287 and lemiprazole in GB 2,163,747. The preferred proton pump inhibitor used in the present invention is the compound known as omeprazole.
Many surfactants are reported in the literature, which can be used in formulations of the present invention, for example polyoxyethylenesorbitan monooleate, polyoxyethylene-sorbitan
l monopalmitate, polyoxyethylene-sorbitan monolaurate, polyoxyethylenesorbitan monostearate, polysorbates or the like. The more preferred surfactant for use in a formulation according to the present invention is polysorbate-60. The use of a surfactant in a formulation according to the present invention can aid emulsification of the fat and absorption of triglycerides, and thus can help to prepare a balanced paste formulation. A surfactant is typically present in a formulation according to the present invention at approximately 1% to 2 %w/w, based on the weight of the total formulation, depending on the amount of other ingredients present in a paste formulation according to the present invention. Preferably a surfactant is present in a formulation according to the present invention at approximately 0.5 to about 1.0 %w/w, based on the weight of the total formulation. Omeprazole is known to have poor intrinsic aqueous solubility and / or poor wetting capability, which has reduced the efficiency of its solubilisation within the gastrointestinal milieu when present in prior art pharmaceutical formulations. This reduction in solubility has led to poor
bioavailability of omeprazole in prior art formulations. We have now found that the use of
amphiphillic base in formulations according to the present invention can achieve improved bioavailability of a proton pump inhibitor present in a formulation according to the present invention. In particular, we have found that it is preferred to incorporate hard fats such as saturated polyglycolysed glycerides (also known in the art as Gelucire bases) to increase the bioavailability of the proton pump inhibitor present in a formulation according to the present invention. Examples of suitable gelucire bases include saturated polyglycolysed glycerides containing varying blends of (a) glycerides (mono-, di- and tri-), (b) mono- and allesters of such glycerides with polyethylene glycol and (c) low molecular weight polyethylene glycols.
Manipulation of the proportions of these blends has produced bases with a range of melting points (30 C to 50 C) and HLB values (for example 2 to 14), whereby the processing and release requirements can be selected.
A preferred amphiphillic base for use in a formulation according to the present invention is available under the trade mark Gelucire 33/01.
Suitable plasticizers for use in a formulation according to the present invention include for example adipates, epoxides, phosphates, phthalates, sebacates, azelates, citrates and the like.
Citrate plasticizer esters include triethyl citrate, acetyl triethyl citrate, tributyl citrate, acetyl tributyl citrate, tri-(2-ethylhexyl)citrate and the like. A preferred plasticizer is triethyl citrate.
These citrate plasticizers can be produced from citric acid and are commonly used as plasticizers in pharmaceutical formulations, where small amounts thereof can increase free volume in such formulations and thus allow increased movement of macromolecules, such as amphiphillic bases.
The combined use of a plasticizer and an amphiphillic base in a formulation according to the present invention can increase the solubility of a proton pump inhibitor, such as omeprazole, present in the formulation and can also provide a stable paste formulation therefor. The present invention achieves, therefore, a stable paste formulation for acid labile and poorly soluble proton pump inhibitors, such as omeprazole.
A particularly preferred pharmaceutical paste formulation for oral administration according to the present invention comprises a proton pump inhibitor which is omeprazole, a surfactant which is polysorbate-60, a plasticizer which is triethyl citrate and an amphiphillic base which is Gelucire 33/01.
A formulation according to the present invention may also include additional ingredients commonly used in the formulation of human and veterinary medicines. For example, flavouring agents such as caramel, carrot, apple, cinnamon and sausage flavours; and colouring agents such as iron oxide, titanium dioxide, aluminum lakes and the like, can be added.
The amount of a proton pump inhibitor employed in a formulation according to the present invention can vary, and suitably can be in the range of about 1 to 50%w/w, based on the weight of the total formulation. Preferably the amount is about 50%w/w or less, based on the weight of the total formulation, and more preferably in the range of about 30 to about 40%w/w, based on
the weight of the total formulation. Suitably a surfactant is included in a formulation according to the present invention in the range of about 1 to 2%w/w, based on the weight of the total formulation; preferably in the range of about 0.5 to 1%w/w, based on the weight of the total formulation. Suitably a plasticizer is included in a formulation according to the present invention in the range of about 2 to 6%w/w, based on the weight of the total formulation; preferably in the range of about 3 to 5%w/w, based on the weight of the total formulation. An amphiphillic base is suitably included in a formulation according to the present invention in the range of about 50 to 70%w/w, based on the weight of the total formulation, depending on the amount of other excipients present in a paste formulation according to the present invention.
The incorporation of an acid labile drug substance, namely a proton pump inhibitor, in a formulation according to the present invention, results in an orally palatable and pharmaceutically stable paste. A paste formulation according to the present invention, and a pharmacologically active proton pump inhibitor contained therein, exhibit good stability.
Formulations according to the present invention are useful in the treatment of peptic ulcer diseases in humans or animals and can be used to deliver acid labile proton pump inhibitors orally for systemic activity in animals. The formulations of the present invention may be administered directly into the mouth of an animal, such as a horse, in need of anti-ulcer therapy; preferably a paste-dosing syringe can be used to facilitate drug administration. The consistency of a paste formulation according to the present invention is preferably such that it cannot easily drip out or be expelled once it is deposited on the dorsal part of an animal's tongue. The paste is essentially free of air bubbles, which enhances dosing accuracy.
There is also provided by the present invention a method of treating a human or animal patient suffering from or susceptible to a peptic ulcer or related disease, which method comprises administering to the human or animal patient a therapeutically effective amount of a formulation according to the present invention. The term "treatment" as used herein refers to prophylaxis in
susceptible patients, as well as the treatment of established symptoms of peptic ulcer or related disease. The present invention also provides a process of preparing a stable, improved paste formulation for a proton pump inhibitor, such as omeprazole, substantially as hereinbefore described, which process comprises admixing the proton pump inhibitor, a surfactant, a plasticizer and an amphiphillic base substantially as hereinbefore described, so as to yield a formulation according to the present invention, which formulation can suitably be coloured and / or flavoured.
More particularly, a formulation according to the present invention can be prepared by dispersing the proton pump inhibitor, in powder form, in a melted amphiphillic base (Gelucire) containing surfactant, plasticizer and optionally colouring agents, at a controlled temperature below about 30 C. A flavouring agent may then be added and mixed and homogenized to achieve desired consistency. A paste formulation thus obtained may be used to fill dosing syringes, which may be used directly to administer proton pump inhibitors to an animal in need of such treatment.
The present invention will now be further illustrated by the following Examples, which do not limit the scope of the invention in any way.
EXAMPLE 1
Sr No. Ingredients Standard quantity (%w/w) Omeprazole 37.0 2. Polysorbate-60 I.0 3. Triethyl citrate 4.0 4. Hard Fat (Gelucire 33/01) 57.7 5. Yellow oxide of iron 0.1 6. Cinnamon flavor 0.2
Polysorbate 60 and triethyl citrate were added to melted Gelucire base at 30-35 C, under stirring.
Colour dispersion was then added with mixing to the mass. The resulting mixture was cooled to below 30 C and omeprazole was added while mixing. Finally flavour was added, and mixing continued until a homogeneous mass was obtained.
EXAMPLE 2
Sr No. Ingredients Standard quantity (%w/w) Omeprazole 37.0 2. Polysorbate- 80 1.5 Tributyl citrate 4.5 4. Hard Fat (Gelucire 37/02) 57. 0 5. Yellow oxide of iron 0.1 Cinnamon flavor 0.2 Following the procedure of Example 1, omeprazole paste of the above composition was prepared. EXAMPLE 3
Sr No. ingredients Standard quantity (%w/w) 1. Omeprazole 37.0 2. Polysorbate - 60 1.0 3. Tributyl citrate 5.0 4. Hard Fat (Gelucire 39/01) 56.7 5. Yellow oxide of iron 0.1 Cinnamon flavor 0.2
Following the procedure of Example 1, omeprazole paste of the above composition was prepared. EXAMPLE 4
Sr No. Ingredients Standard quantity (%w/w) 1. Omeprazole 37.0 2. Polysorbate- 80 0.6 3. Triethyl citrate 3.8 4. Hard Fat (Gelucire 37/06) 58.3 5. Yellow oxide of iron 0.1 6. Cinnamon flavor 0.2 Following the procedure of Example 1, omeprazole paste of the above composition was prepared.

Claims (19)

1. A pharmaceutical paste formulation for oral administration, which comprises a proton pump inhibitor, a surfactant, a plasticizer and an amphiphillic base.
2. A pharmaceutical formulation according to claim 1, wherein the proton pump inhibitor is selected from the group consisting of omeprazole, lansoprazole, pantoprazole and lemiprazole.
3. A pharmaceutical formulation according to claim 2, wherein the proton pump inhibitor is omeprazole.
4. A pharmaceutical formulation according to any of claims 1 to 3, wherein the surfactant is selected from the group consisting of polyoxyethylene-sorbitan monooleate, polyoxyethylene-
sorbitan monopalmitate, polyoxyethylene-sorbitan monolaurate, polyoxyethylene-sorbitan monostearate and polysorbates.
5. A pharmaceutical formulation according to claim 4, wherein the surfactant is polysorbate-60.
6. A pharmaceutical formulation according to any of claims I to 5, wherein the amphiphillic base is a saturated polyglycolysed glyceride.
7. A pharmaceutical formulation according to claim 6, wherein the polyglycolysed glyceride is Gelucire 33/01.
8. A pharmaceutical formulation according to any of claims 1 to 7, wherein the plasticizer is selected from the group consisting of adipates, epoxides, phosphates, phthalates, sebacates, azelates and citrates.
9. A pharmaceutical formulation according to claim 8, wherein the citrate plasticizer is selected from the group consisting of triethyl citrate, acetyl triethyl citrate, tributyl citrate, acetyl tributyl citrate and tri-(2-ethylhexyl)-citrate.
10. A pharmaceutical formulation according to claim 9, wherein the plasticizer is triethyl citrate.
11. A pharmaceutical paste formulation for oral administration, which comprises a proton pump inhibitor which is omeprazole, a surfactant which is polysorbate-60, a plasticizer which is triethyl citrate and an amphiphillic base which is Gelucire 33/01.
12. A pharmaceutical formulation according to any of claims 1 to 11, wherein the proton pump inhibitor is present in an amount in the range of about 1 to 50%w/w, based on the weight of the total formulation.
13. A pharmaceutical formulation according to claim 12, wherein the proton pump inhibitor is present in an amount in the range of about 30 to about 40%w/w, based on the weight of the total formulation.
14. A pharmaceutical formulation according to any of claims 1 to 13, wherein the surfactant is present in an amount in the range of about 1 to 2%w/w, based on the weight of the total formulation.
15. A pharmaceutical formulation according to any of claims I to 14, wherein the plasticizer is present in an amount in the range of about 2 to 6%w/w, based on the weight of the total formulation.
16. A pharmaceutical formulation according to any of claims I to 15, wherein the amphiphillic base is present in an amount in the range of about 50 to 70%w/w, based on the weight of the total formulation.
17. A method of treating a human or animal patient suffering from or susceptible to a peptic ulcer or related disease, which method comprises administering to the human or animal patient a therapeutically effective amount of a formulation according to any of claims I to 16.
18. A process of preparing a pharmaceutical formulation according to any of claims I to 16, which process comprises admixing a proton pump inhibitor, a surfactant, a plasticizer and an amphiphillic base, so as to yield a formulation according to any of claims I to 16.
19. A process according to claim 18, which comprises dispersing the proton pump inhibitor, in powder form, in a melted amphiphillic base containing surfactant, plasticizer and optionally colouring agents, at a controlled temperature below about 30 C.
GB0225926A 2002-11-06 2002-11-06 Proton pump inhibitor composition in paste form Withdrawn GB2394895A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2046334A4 (en) * 2006-07-25 2009-11-25 Vecta Ltd Compositions and meth0ds for inhibiting gastric acide secretion using derivatives of small dicarboxylic acids in combination with ppi
US7803817B2 (en) 2005-05-11 2010-09-28 Vecta, Ltd. Composition and methods for inhibiting gastric acid secretion
US7981908B2 (en) 2005-05-11 2011-07-19 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
WO2020200586A1 (en) 2019-04-05 2020-10-08 Arcelik Anonim Sirketi A robot vacuum cleaner and the control method thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5708017A (en) * 1995-04-04 1998-01-13 Merck & Co., Inc. Stable, ready-to-use pharmaceutical paste composition containing proton pump inhibitors
WO2000050038A1 (en) * 1999-02-23 2000-08-31 Merck & Co., Inc. Pharmaceutical composition containing proton pump inhibitors
DE10061135C1 (en) * 2000-12-07 2002-11-07 Byk Gulden Lomberg Chem Fab Stable gel preparation for oral administration of acid-labile drug, especially proton pump inhibitor, comprises multiple drug units dispersed in gel base

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5708017A (en) * 1995-04-04 1998-01-13 Merck & Co., Inc. Stable, ready-to-use pharmaceutical paste composition containing proton pump inhibitors
WO2000050038A1 (en) * 1999-02-23 2000-08-31 Merck & Co., Inc. Pharmaceutical composition containing proton pump inhibitors
DE10061135C1 (en) * 2000-12-07 2002-11-07 Byk Gulden Lomberg Chem Fab Stable gel preparation for oral administration of acid-labile drug, especially proton pump inhibitor, comprises multiple drug units dispersed in gel base

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WPI ABSTRACT, Acc. Nr. 2002-714526/78; & DE 10061135 C1 (BYK GULDEN LOMBERG CHEM FAB) (07-11-2002) *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7803817B2 (en) 2005-05-11 2010-09-28 Vecta, Ltd. Composition and methods for inhibiting gastric acid secretion
US7981908B2 (en) 2005-05-11 2011-07-19 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
US9132082B2 (en) 2005-05-11 2015-09-15 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
US9278080B2 (en) 2005-05-11 2016-03-08 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
US9370481B2 (en) 2005-05-11 2016-06-21 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
EP2046334A4 (en) * 2006-07-25 2009-11-25 Vecta Ltd Compositions and meth0ds for inhibiting gastric acide secretion using derivatives of small dicarboxylic acids in combination with ppi
US9233092B2 (en) 2006-07-25 2016-01-12 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion using derivatives of small dicarboxylic acids in combination with PPI
WO2020200586A1 (en) 2019-04-05 2020-10-08 Arcelik Anonim Sirketi A robot vacuum cleaner and the control method thereof

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