US20060240123A1 - Pharmaceutical composition - Google Patents
Pharmaceutical composition Download PDFInfo
- Publication number
- US20060240123A1 US20060240123A1 US10/525,208 US52520803A US2006240123A1 US 20060240123 A1 US20060240123 A1 US 20060240123A1 US 52520803 A US52520803 A US 52520803A US 2006240123 A1 US2006240123 A1 US 2006240123A1
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- topical composition
- metronidazole
- pharmacologically acceptable
- concentration
- application
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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Definitions
- the present invention relates to a pharmaceutical composition, in particular a topical composition comprising metronidazole or a pharmacologically acceptable derivative thereof.
- metronidazole is to be taken as including pharmaceutically acceptable derivatives thereof unless otherwise apparent from the context.
- Metronidazole (or “Flagyl”) is a synthetic antibacterial and antiprotozoan antibiotic having the formula 2-methyl-5-nitroimidazole-1-ethanol.
- the antibiotic has been used for many years in its oral or intravenous form, to treat inflammatory conditions of the colon, rectum, anal canal and perianal region.
- Oral metronidazole has been traditionally used to treat inflammatory bowel disease (including Crohn's disease and ulcerative colitis), idiopathic proctocolitis, or radiation proctitis.
- the oral form is used to treat inflammatory conditions of the perianal region or anal canal such as anal fissures, fistulas, abscess, ulcers or post-surgical wounds.
- Metronidazole is also used in an intravenous form to treat systemic sepsis resulting from several inflammatory conditions of the colon and rectum.
- Metronidazole possesses not only anti-bacterial properties, but also anti-inflammatory properties, which are less well understood.
- the medication is used for its anti-inflammatory properties in the treatment of several skin diseases.
- Metronidazole is frequently associated with a number of serious side effects, both in its oral and intravenous form. These include GI manifestations, such as nausea, vomiting, a metallic taste in the mouth, or inflammation of the oral cavity. Serious neurological side effects can occur which usually manifest as numbness or tingling of the extremities. These neurological side effects can be debilitating, are often irreversible, and necessitate stopping the Metronidazole. Serious hematological, cardiovascular, or renal complications are also common and can be life-threatening. In addition, the overgrowth of opportunistic organisms such as Candida can result from oral or intravenous metronidazole treatment. In addition, oral metronidazole can interact in an adverse manner with other medications, such as oral anticoagulants (e.g. coumadin), which can cause potentially fatal bleeding.
- oral anticoagulants e.g. coumadin
- Topical metronidazole has previously been used for a number of skin conditions (e.g. rosacea) or as a topical vaginal preparation in the treatment of vaginal infections (e.g. trichomonas). These preparations are contained in a medium containing alcohol, which would result in stinging and burning when used in the perianal region or in the anal canal. As far as the inventor is aware, there is no disclosure of the direct application of metronidazole into the rectum or distal colon (as for example a suppository, foam or enema) in the treatment of inflammatory disease and no such preparation of metronidazole is commercially available.
- a topical composition comprising metronidazole or a pharmacologically acceptable derivative thereof at a concentration of at least about 5 wt % in a pharmacologically acceptable non-aqueous vehicle.
- concentration of metronidazole is preferably between from about 5 wt % to about 50 wt %, more preferably between from about 5 wt % to about 15 wt % and most preferably about 10 wt %.
- the concentrations are based on the total weight of the composition.
- the vehicle is preferably an organic vehicle and, typically, comprises at least one hydrocarbon compound.
- the vehicle comprises a mixture of at least two semi-solid saturated hydrocarbon compounds.
- An example of a suitable vehicle is white petrolatum (USP), also known as white soft paraffin (BP).
- USP white petrolatum
- BP white soft paraffin
- Other suitable vehicles include zinc oxide, VaselineTM, Aquaphor (a combination of mineral oil, petrolatum ceresin and lanolin), lanolin or a petroleum-based carrier.
- the composition may consist essentially of metronidazole and the vehicle. However, a therapeutic amount of at least one other agent may be added to the composition to add to its effectiveness. Additional agents that may be added include steroids, e.g. hydrocortisone or a pharmacologically acceptable derivative thereof, analgesic agents, preferably from the amide or ester class such as pramoxine or benzocaine, antimicrobial agents (antibacterial or antiviral), e.g. ciprocfloxacin, amoxicillin-clavulonic acid, erythromycin, tetracyclin, clindamycin or doxycyclin, substances that either promote skin integrity or inhibits skin breakdown, e.g.
- vitamin E aloe, zinc oxide or other barrier cream
- anti-inflammatory agents e.g. a non-steroidal anti-inflammatory agent selected from aminosalicylic acid, ibuprofen, sulindac, piroxicam or diflunisal and antidiarrheal compounds such as a bismuth salt.
- the additional or supplemental antibiotic or antiviral medications may add to the anti-bacterial spectrum of activity (gram positive, gram negative aerobic or anaerobic, antiviral) of metronidazole.
- the topical composition is preferably in a form suitable for direct application to the colon, rectum, anorectum, perianal region or anal canal.
- suitable forms include an enema, suppository, ointment, lotion, gel, foam or cream.
- Preferred forms include ointment or enema.
- the ointment, lotion, gel or cream forms may be used to treat conditions affecting the perianal region and anorectum including perianal Crohn's disease and conditions arising following a hermorrhoidectomy.
- the suppository, foam or enema forms may be used to treat conditions affecting the colon or rectum including inflammatory bowel disease (Crohn's disease or ulcerative colitis), radiation proctitis, idiopathic proctocolitis or post-surgical pouchitis in a surgically constructed ileal J-pouch.
- inflammatory bowel disease Crohn's disease or ulcerative colitis
- radiation proctitis idiopathic proctocolitis or post-surgical pouchitis in a surgically constructed ileal J-pouch.
- Suitable vehicles for enema formulations include but are not limited to sodium chloride and 1% methylcellulose; propylene glycol and 2% methylcellulose gel; glycerin, 2% methylcellulose gel (retention enema); base C, glycerin, green soap; silica gel (micronized), 2% methylcellulose gel; 2% methylcellulose gel and purified water, sodium chloride, purified water, sodium hydroxide; xanthan gum, purified water, 2% methylcellulose gel; carbopol, xanthan gum; methocel 1%, polsorbate.
- a topical composition comprising metronidazole or a pharmacologically acceptable derivative thereof at a concentration of at least about 5 wt % in a pharmacologically acceptable non-aqueous vehicle for use in the treatment of the human or animal body.
- composition useful in the treatment of conditions of the colon, rectum, anorectum and perianal region but also that the composition assists in patient recovery following operations on the distal GI tract by relieving pain, reducing inflammation and edema, promoting wound healing and reversing tissue induration and granulation.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to relieve pain caused by conditions of the colon, rectum, anorectum or perianal region.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a medicament to relieve pain following a surgical operation to the colon, rectum, anorectum or perianal region.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to reduce inflammation following a surgical operation to the colon, rectum, anorectum or perianal region.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to promote healing following a surgical operation to the colon, rectum, anorectum or perianal region.
- a seventh aspect of the present invention there is provided use of metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to reduce edema following a surgical operation to the colon, rectum, anorectum or perianal region.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to reverse tissue induration and granulation following a surgical operation to the colon, rectum, anorectum or perianal region.
- the topical composition appears to be particularly effective where the surgical operation is an anorectal operation.
- operations in which the topical composition assists recovery include hemorrhoidectomy, fistulotomy, fissurectomy, sphincterotomy, sphincteroplasty or incision and drainage of an abscess.
- the invention has particular efficacy following a hemorrhoidectomy.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to treat conditions of the colon, rectum, anorectum or perianal region.
- treatable conditions include inflammatory bowel disease, ulcerative colitis, perianal Crohn's disease, radiation proctitis, idiopathic proctocolitis or pouchitis.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to treat anorectal or perianal ulcers or skin defects.
- the ulcers may be infective or inflammatory ulcers and may be induced by HIV or radiation.
- the ulcers may be erosive ulcers resulting from chronic diarrhea or anorectal incontinence.
- the ulcers may be associated with inflammatory bowel disease.
- metronidazole or a pharmacologically acceptable derivative thereof in the manufacture of a topical medicament to treat perianal infective or inflammatory processes.
- processes include perianal abscess, fissure in ano, hindradenitis, pilonidal abscess or sinus.
- the medicament may have any or all of the features of the topical composition of the first aspect in any appropriate combination.
- the invention also encompasses methods of treatment of the above-mentioned conditions and indications using the topical composition of the first aspect of the present invention.
- the dose of metronidazole for each application is preferably between from about 125 mg to about 1250 mg, more preferably between from about 125 mg to about 375 mg and most preferably about 250 mg.
- the most preferred dose is based on a single application of 2.5 cm 3 of a 10 wt % metronidazole ointment.
- the composition is usually applied between from 2 to 4 times daily and preferably 3 times daily.
- metronidazole in a topical form by direct application to the diseased or otherwise affected area results in a primarily local effect. Minimal systemic absorption is observed and therefore systemic side effects are effectively eliminated. In addition, a greater dose of metronidazole can be applied directly to the diseased or otherwise effected area, so increasing the efficacy of the medication.
- compositions comprising metronidazole in the form of a gel, cream, ointment, lotion, foam or suppository may be used to treat conditions in the lower parts of the anorectum, such as perianal Crohn's disease, postoperative incisions, ulcers, abscess, fissures, or fistulas.
- metronidazole can be used in an enema form to treat conditions of the more proximal rectum and colon, such as inflammatory bowel disease, radiation proctitis, idiopathic proctocolitis or post-surgical “pouchitis” in a surgically constructed ileal J pouch.
- the flat blade of the Harmonic Scalpel was utilized to cauterize the fissure, and a left lateral internal sphincterotomy was performed, extending to the proximal extent of the fissure.
- Postoperative pain was evaluated using a visual analog score (VAS), which was recorded by the patient on days 1, 2, 7, 14, and 28. Patients in both groups ranked the level of pain from 0 (no pain) to 10 (very severe pain). The number of analgesics required (number of hydrocodone pills) per 24 hours, was also recorded by the patient on days 1, 2, 7, 14, and 28. Patients were evaluated at two and four weeks postoperatively, and the completed data sheets were collected at the four-week visit. The mean pain scores for each group were compared using Wilcoxin's Rank sum test. The number of narcotic analgesics required in each group was compared using a two-sample t-test.
- VAS visual analog score
- Wound healing was evaluated at two weeks, by taking a high quality color digital photograph of the surgical site.
- three surgeons independently ranked the 20 surgical incisions in a blinded manner. Incisions were graded in three different categories: A, postoperative incisional edema: B, primary versus secondary wound healing; and C, overall wound healing.
- A, B and C For each category (A, B and C), each of the three surgeons ranked the twenty photographs and a mean rank for each photograph was calculated. Thus all twenty photographs had three mean ranks for categories A, B and C.
- Mean ranking in categories A, B and C were then compared between metronidazole and control groups, using the Mann-Whitney U test.
- a prospective pilot study of topical 10 wt % metronidazole according to Example 1 in the treatment of refractory anorectal Crohn's disease was undertaken. Three patients are described: one patient was suspected to have the disease on initial examination (Patient 1), and two unsuspected cases were diagnosed after undergoing routine anorectal surgery. Granulomata were identified histologically in all three patients.
- Patient 3 a 78 year-old female, presented with rectal bleeding and fissure-type symptoms. A posterior midline fissure was noted in association with a sentinel tag. The patient was treated with fiber supplements and copious liquids but failed to respond after two weeks. Intraoperative colonoscopy and examination under anesthesia were performed, which showed a normal appearing colon and a deep posterior midline fissure and a left postero-lateral trans-sphincteric fistula. The fissure was cauterized, the postero-lateral internal sphincter was divided, and a seton placed through the remaining fistula.
- Histopathology of the debrided tissue reported the presence of non-caseating granulomata, consistent with anorectal Crohn's disease. The patient experienced excessive postoperative pain associated with induration, bleeding, and non-healing of the surgical site. Topical 10 wt % metronidazole according to Example 1 was initiated in an attempt to promote healing and control pain.
- Patient 1 had anterior anal fissure. After two weeks of topical metronidazole, the patient reported a significant improvement in his pain and anorectal discharge. Repeat examination under anesthesia was performed three weeks later, and the tissue edema and granulomation tissue had resolved dramatically. In addition, the granulomata noted on the initial biopsy had resolved, and none was seen in the second biopsy specimen, performed after 3 weeks of topical metronidazole.
- Patient 2 reported dramatic pain relief and healing of her incisions had progressed significantly after 2 weeks of topical metronidazole treatment. Four weeks later, the patient was asymptomatic from her anorectal disease.
- Patient 3 experienced dramatic pain relief within two weeks treatment with topical metronidazole and the incisions appeared much improved. At 4 weeks, the granulation tissue and induration had resolved and the seton was therefore removed. At 6 weeks, the incisions were healed, there was no evidence of a persistent fistula, and the patient had no anorectal symptoms.
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/525,208 US20060240123A1 (en) | 2002-08-26 | 2003-08-22 | Pharmaceutical composition |
US12/834,198 US9655883B2 (en) | 2002-08-26 | 2010-07-12 | Pharmaceutical composition |
US13/834,281 US10653671B2 (en) | 2002-08-26 | 2013-03-15 | Topical pharmaceutical compositions for treatment of skin damage |
US14/288,686 US10709689B2 (en) | 2002-08-26 | 2014-05-28 | Pharmaceutical composition |
US15/234,084 US10881640B2 (en) | 2002-08-26 | 2016-08-11 | Topical pharmaceutical compositions for treatment of pilonidal sinus wounds |
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US40635102P | 2002-08-26 | 2002-08-26 | |
US10/525,208 US20060240123A1 (en) | 2002-08-26 | 2003-08-22 | Pharmaceutical composition |
PCT/GB2003/003692 WO2004017962A2 (en) | 2002-08-26 | 2003-08-22 | Tropical formulation comprising at least 5% of metronidazole in white petrolatum and its use in the anal and rectal region |
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PCT/GB2003/003692 A-371-Of-International WO2004017962A2 (en) | 2002-08-26 | 2003-08-22 | Tropical formulation comprising at least 5% of metronidazole in white petrolatum and its use in the anal and rectal region |
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US12/834,198 Continuation US9655883B2 (en) | 2002-08-26 | 2010-07-12 | Pharmaceutical composition |
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US10/525,208 Abandoned US20060240123A1 (en) | 2002-08-26 | 2003-08-22 | Pharmaceutical composition |
US12/834,198 Active 2026-03-25 US9655883B2 (en) | 2002-08-26 | 2010-07-12 | Pharmaceutical composition |
US13/834,281 Expired - Fee Related US10653671B2 (en) | 2002-08-26 | 2013-03-15 | Topical pharmaceutical compositions for treatment of skin damage |
US14/288,686 Expired - Fee Related US10709689B2 (en) | 2002-08-26 | 2014-05-28 | Pharmaceutical composition |
US15/234,084 Active 2024-10-22 US10881640B2 (en) | 2002-08-26 | 2016-08-11 | Topical pharmaceutical compositions for treatment of pilonidal sinus wounds |
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US12/834,198 Active 2026-03-25 US9655883B2 (en) | 2002-08-26 | 2010-07-12 | Pharmaceutical composition |
US13/834,281 Expired - Fee Related US10653671B2 (en) | 2002-08-26 | 2013-03-15 | Topical pharmaceutical compositions for treatment of skin damage |
US14/288,686 Expired - Fee Related US10709689B2 (en) | 2002-08-26 | 2014-05-28 | Pharmaceutical composition |
US15/234,084 Active 2024-10-22 US10881640B2 (en) | 2002-08-26 | 2016-08-11 | Topical pharmaceutical compositions for treatment of pilonidal sinus wounds |
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US (5) | US20060240123A1 (zh) |
EP (1) | EP1545516B1 (zh) |
KR (1) | KR100991054B1 (zh) |
CN (2) | CN1678309A (zh) |
AT (1) | ATE406890T1 (zh) |
AU (1) | AU2003260736B8 (zh) |
BR (1) | BR0313824A (zh) |
CA (1) | CA2496864C (zh) |
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CU (1) | CU23436B6 (zh) |
CY (1) | CY1108601T1 (zh) |
DE (1) | DE60323380D1 (zh) |
DK (1) | DK1545516T3 (zh) |
EA (1) | EA008150B1 (zh) |
ES (1) | ES2312847T3 (zh) |
HK (1) | HK1077758A1 (zh) |
HR (1) | HRP20050258A2 (zh) |
IL (1) | IL167069A (zh) |
IS (1) | IS7761A (zh) |
MA (1) | MA27520A1 (zh) |
MX (1) | MXPA05002033A (zh) |
NO (1) | NO333670B1 (zh) |
NZ (1) | NZ538998A (zh) |
PL (1) | PL375560A1 (zh) |
PT (1) | PT1545516E (zh) |
RS (1) | RS20050170A (zh) |
UA (1) | UA81638C2 (zh) |
WO (1) | WO2004017962A2 (zh) |
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US20120177582A1 (en) * | 2011-01-11 | 2012-07-12 | Ramirez Jose E | Compositions for anorectal use and methods for treating anorectal disorders |
US20120177583A1 (en) * | 2011-01-11 | 2012-07-12 | Ramirez Jose E | Compositions for anorectal use and methods for treating anorectal disorders |
US20140256661A1 (en) * | 2011-07-15 | 2014-09-11 | David Nigel Armstrong | Pharmaceutical compositions for rectal administration |
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US20060211752A1 (en) | 2004-03-16 | 2006-09-21 | Kohn Leonard D | Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression |
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- 2013-03-15 US US13/834,281 patent/US10653671B2/en not_active Expired - Fee Related
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US4957918A (en) * | 1988-06-09 | 1990-09-18 | Leonard Bloom | Topical treatment of blepharitis |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITRM20090618A1 (it) * | 2009-11-25 | 2011-05-26 | Bruno Masci | "composizione farmaceutica a base di metronidazolo ed ossido di zinco per il trattamento topico di patologie anali acute e croniche distrofiche e post-operatorie" |
US20120177582A1 (en) * | 2011-01-11 | 2012-07-12 | Ramirez Jose E | Compositions for anorectal use and methods for treating anorectal disorders |
US20120177583A1 (en) * | 2011-01-11 | 2012-07-12 | Ramirez Jose E | Compositions for anorectal use and methods for treating anorectal disorders |
US8952057B2 (en) * | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
US20140256661A1 (en) * | 2011-07-15 | 2014-09-11 | David Nigel Armstrong | Pharmaceutical compositions for rectal administration |
US10588864B2 (en) | 2016-03-11 | 2020-03-17 | Gateway Pharmaceuticals LLC | Pharmaceutical compositions for colon-specific delivery |
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