Revision of monograph in the 4 th Edition of The International Pharmacopoeia (August 2008)

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1 August 2008 RESTRICTED MEBENDAZOLE Revision of monograph in the 4 th Edition of The International Pharmacopoeia (August 2008) REVISED DRAFT FOR ADOPTION This document was provided by a quality control expert. Previous comments received have been incorporated into this revised draft. Should you have any further comments, please send these to Dr S. Kopp with copies to Ms M.-L. Rabouhans and Ms C. Mendy, Medicines Quality Assurance Programme, Quality and Safety: Medicines, World Health Organization, 1211 Geneva 27, Switzerland; fax: (+41 22) or kopps@who.int, rabouhansm@who.int and mendyc@who.int by 20 October World Health Organization 2008 All rights reserved. This draft is intended for a restricted audience only, i.e. the individuals and organizations having received this draft. The draft may not be reviewed, abstracted, quoted, reproduced, transmitted, distributed, translated or adapted, in part or in whole, in any form or by any means outside these individuals and organizations (including the organizations concerned staff and member organizations) without the permission of WHO. The draft should not be displayed on any web site. Please send any request for permission to: Dr Sabine Kopp, Quality Assurance Programme, Medicines Quality Assurance Programme, Quality & Safety: Medicines (QSM), Department of Essential Medicines and Pharmaceutical Policies (EMP), World Health Organization, CH-1211 Geneva 27, Switzerland. Fax: (41-22) ; s: kopps@who.int. The designations employed and the presentation of the material in this draft do not imply the expression of any opinion whatsoever on the part of the World Health Organization concerning the legal status of any country, territory, city or area or of its authorities, or concerning the delimitation of its frontiers or boundaries. Dotted lines on maps represent approximate border lines for which there may not yet be full agreement. The mention of specific companies or of certain manufacturers products does not imply that they are endorsed or recommended by the World Health Organization in preference to others of a similar nature that are not mentioned. Errors and omissions excepted, the names of proprietary products are distinguished by initial capital letters. All reasonable precautions have been taken by the World Health Organization to verify the information contained in this draft. However, the printed material is being distributed without warranty of any kind, either expressed or implied. The responsibility for the interpretation and use of the material lies with the reader. In no event shall the World Health Organization be liable for damages arising from its use. This draft does not necessarily represent the decisions or the stated policy of the World Health Organization.

2 page 2 SCHEDULE FOR THE ADOPTION PROCESS OF DOCUMENT QAS/ International Pharmacopoeia monograph on Mebendazole Date Preparation of first draft by laboratory May 2008 Discussion in Consultation on Specifications for Medicines and Quality Control Laboratory Issues June 2008 First draft mailed out for comments June-July 2008 Collation of comments received August 2008 Revised draft sent out for comments September 2008 Collation of comments received October 2008 Presentation to WHO Expert Committee on Specifications for Pharmaceutical Preparations for possible adoption October 2008 Further action as required November

3 PROPOSED REVISION MEBENDAZOLE Working document QAS/08.272/Rev.1 page 3 Revision of monograph in the 4 th Edition of The International Pharmacopoeia (August 2008) [Note from secretariat: The proposed revision deals with the polymorphic form of the substance.] Monographs: Pharmaceutical substances: Mebendazolum - Mebendazole Molecular formula. C 16 H 13 N 3 O 3 Relative molecular mass Graphic formula. Chemical name. Methyl 5-benzoyl-2-benzimidazolecarbamate; methyl (5-benzoyl-1Hbenzimidazol-2-yl)carbamate; CAS Reg. No Description. A white to slightly yellow powder. Solubility. Practically insoluble in water, dilute mineral acids, ethanol (~750 g/l) TS and ether R ; freely soluble in formic acid (~1080 g/l) TS. Category. Anthelmintic drug. Storage. Mebendazole should be kept in a well-closed container, protected from light. Additional information. Mebendazole exhibits polymorphism. The polymorph specified in the monograph (form C) corresponds to the crystal form of mebendazole RS.

4 page 4 Requirements Definition. Mebendazole contains not less than 98.0% and not more than 102.0% of mebendazole (C 16 H 13 N 3 O 3 ), calculated with reference to the dried substance. Identity tests Either test A alone or tests B and C may be applied. A. Carry out the examination as described under 1.7 Spectrophotometry in the infrared region. The infrared absorption spectrum obtained from the solid state is concordant with the spectrum obtained from mebendazole RS or with the reference spectrum of mebendazole; (confirmation of polymorphic form C). [Note from Secretariat: For information, the sharp NH absorbance is characteristic for identification of the polymorphic form: polymorph A at about 3370 cm -1, polymorph B at about 3340 cm -1 and polymorph C at about 3410 cm -1 ] B. Shake 20 mg with 2.0 ml of sodium hydroxide (~80 g/l) TS, and heat the yellowish coloured suspension until it dissolves; the solution is yellow. Add a few drops of copper(ii) sulfate (160 g/l) TS; a greenish precipitate is produced. Add a few drops of ammonia (~100 g/l) TS; the colour turns to greenish blue. C. Dissolve 20 mg in 2 ml of sulfuric acid (~1760 g/l) TS; a yellow solution is produced. Carefully dilute with 3 ml of water; the yellow colour disappears. Then add 1.0 ml of silver nitrate (40 g/l) TS; a white precipitate is formed, which does not dissolve in an excess of ammonia (~100 g/l) TS. [Note from Secretariat: Since the polymorphic form is specified, the alternative tests are not applicable.] Heavy metals. Use 1.0 g for the preparation of the test solution as described under Limit test for heavy metals, Procedure 3; determine the heavy metals content according to Method A; not more than 20 µg/g. Sulfated ash (2.3). Not more than 1.0 mg/g. Loss on drying. Dry at 105 C under reduced pressure (not exceeding 0.6 kpa or about 5 mm of mercury) for 4 hours; it loses not more than 5.0 mg/g.

5 page 5 Related substances. Carry out the test as described under Thin-layer chromatography, using silica gel R6 as the coating substance and a mixture of 90 volumes of chloroform R, 5 volumes of methanol R, and 5 volumes of formic acid (~1080 g/l) TS as the mobile phase. Apply separately to the plate 10 µl of each of the following two solutions. For solution (A), dissolve 50 mg of the test substance in 1.0 ml of formic acid (~1080 g/l) TS in a 10-ml volumetric flask, dilute to volume with chloroform R, and mix. For solution (B), dilute 1.0 ml of solution A to 200 ml with a mixture of 9 volumes of chloroform R and 1 volume of formic acid (~1080 g/l) TS. After removing the plate from the chromatographic chamber, allow it to dry in air and examine the chromatogram in ultraviolet light (254 nm). Any spot obtained with solution A, other than the principal spot, is no larger or more intense than the principal spot obtained with solution B. Assay. Dissolve about 0.22 g, accurately weighed, in 30 ml of glacial acetic acid R1, and titrate with perchloric acid (0.1 mol/l) VS, determining the end-point potentiometrically as described under 2.6 Non-aqueous titration, Method A. Each ml of perchloric acid (0.1 mol/l) VS is equivalent to mg of C 16 H 13 N 3 O 3. ***

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