`PHARMACEUTICAL
`EXCIPIENTS
`
`American Pharmaceutical Association
`2215 Constitution Avenue, NW
`Washington, DC 20037 USA
`
`The Pharmaceutical Society of Great Britain
`1 Lambeth High Street
`London SE1 7JN, England
`
`Published by
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`Cosmo Ex 2029-p. 1
`Mylan v Cosmo
`IPR2017-01035
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`American Pharmaceutical Association Production Staff
`James C. Boylan
`Jack Cooper
`Zak T. Chowhan
`
`The Pharmaceutical Society of Great Britain Production Staff
`Walter Lund
`Ainley Wade
`Robert F. Weir
`Bernard J. Yates
`
`Publication Production Staff
`Marlene Povich, Art and Production Manager
`Carol Niedzialek, Production Coordinator
`John Covert, Director of Publications
`
`Library of Congress Data
`
`The use of portions of the text of USP XXI/NF XVI is by permission of the USP Convention,
`Inc. The Convention is not responsible for any inaccuracy of quotation or for any false or mis
`leading implication that may arise from separation of an excerpt from the original context or
`by obsolescence resulting from publication of a supplement.
`
`Selected structural formulas from The Merck Index, Tenth Edition, 1983, published by Merck
`& Co., Rahway, New Jersey, are reprinted with permission.
`
`© Copyright 1986 by the American Pharmaceutical Association, 2215 Constitution Avenue,
`N.W., Washington, D.C. 20037 USA, and The PharmaceuticalSociety of Great Britain, 1 Lam
`beth High Street, London SE1 7JN, England. No part of this publication may be reproduced or
`transmitted in any form or by any means, electronic or imechanical, including photocopy, re
`cording,.or any information storage or retrieval system,without prior written permission from
`the joint publishers.
`
`ISBN (U.S.): 0-917330-56-0
`ISBN (U.K.): 0-85369-164-9
`
`Printed in the USA
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`Lecithin
`
`1. Nonproprietary Name
`NF: Lecithin
`
`2. Functional Categories
`USP: Emulsifying and/or solubilizing agent.
`Others: wetting and dispersing agent; emollient; digestible
`surfactant; moisturizer
`
`3. Synonyms
`Soybean phospholipids; mixed soybean phosphatides; soy
`bean lecithin; vegetable lecithin; egg lecithin; ovolecithin.
`
`4. Chemical Name and CAS Registry Number
`Phosphatidylcholine—commercially, a mixture of phos
`phatidylcholine, phosphatidylethanolamine, phosphatidyl-
`inositol, phytoglycolipids, other phosphatides, carbohy
`drates, triglycerides and other components. [8002-43-SJ
`
`3. Empirical Formula
`
`. Molecular Weight
`
`0—phosphatidylcholine
`
`6. Structural Formula
`CHnOCOR
`I CHOCOR
`,0"
`+
`/
`I
`CH20 —P — OCH2CH2N (CH3) 3
`o
`a—phosphatidylcholine
`7. Commercial Availability
`USA
`•
`American Lecithin
`Central Soya Co.
`Spencer-Kellogg
`UK
`Alembic (Lovelock) Products
`Steetley Chemicals, Ltd.
`8. Method of Manufacture
`Crude soybean lipids are obtained by the solvent extraction
`of soybeans. Lecithin is obtained as a water extract of these
`crude soybean lipids. This crude lecithin is then upgraded by
`various techniques. Lecithin can also be made from corn,
`' peanut, cottonseed, castor seed and coffee beans. It has
`been made from egg, known as egg lecithin. Synthetic
`lecithins are also made.
`9. Description
`Lecithin is brown to light yellow, depending on whether it is
`unbleached or bleached. It has practically no odor and a
`bland to nut-like taste, similar to soybean oil. In consistency,
`it may vary from plastic to fluid depending on the free fatty
`acid content.
`10. Pharmacopeial Specifications
`Test
`Water (method 1)
`Arsenic
`Lead
`Heavy metals (method II)
`Acid value
`
`.
`
`.
`
`NF
`<1.5%
`<3 ppm
`<0.001%
`<0.004%
`<36
`
`lecithin 165
`
`NF
`<0.3%
`<50.0%
`
`Test
`Hexane-insoluble matter
`Acetane-insoluble matter
`11. Typical Properties
`Isoelectric point: Approximately 3.5
`Miscibility: When mixed with water, lecithin hydrates to
`form an emulsion. It readily forms imbibitions (taking up
`liquid without a measurable increase in volume) with almost
`any solvent.
`pH: Approx. 6.6 (soybean phosphatides)
`Solubility.' Soluble in aliphatic and aromatic hydrocarbons,
`halogenated hydrocarbons, mineral oil and fatty acid. Insol
`uble in polar solvents and water. Practically insoluble in cold
`vegetable and animal oils.
`Physical form: Liquid or granule (oil-free lecithin)
`Density: Liquid lecithin, 0.97 g/cm3; granule lecithin, 0.5 g/
`cm3
`Iodine value: Liquid lecithin, 95-100; granule lecithin, 82-88
`Saponification value: 196
`12. Stability and Storage Conditions
`Fluid lecithin grades should be stored at room temperature
`or above (22°-49°C) in well-closed containers. Tempera
`tures of 160-180°C will cause degradation within 24 hours.
`Temperatures below 10°C may cause separation. Lecithins
`are hygroscopic; keep containers closed to prevent moisture
`pickup. Lecithin is subject to microbial degradation. Expo
`sure to light should be avoided. A shelf life of several years
`can be expected when stored at ambient temperatures.
`13. Incompatibilities
`Lecithin decomposes at extreme pH. When heated, it oxi
`dizes, darkens and decomposes. It is hydrolyzed by ester
`ases.
`14. Safety
`Lecithin is recognized as a multiple purpose food substance
`by the FDA.
`15. Handling Precautions
`
`16. Regulatory Status
`NF XVI
`17. Applications in Pharmaceutical Formulation or
`Technology
`Lecithins are used as dispersing and emulsifying agents for
`intramuscular injections. They are used in creams and
`ointments as dispersing, wetting, emulsifying and emollient
`agents.
`18. Related Substances
`
`19. Comments
`Since lecithin contains a variety of unspecified materials,
`care should be exercised in the use of unpurified lecithin in
`injectable or topical dosage forms, as interaction with the
`active ingredient or formulation excipients may occur.
`20. Specific References
`1. P. Sartoretto, Lecithin. In "Encyclopedia of Chemical
`Technology," 2nd Ed., Kirk &r Othmer eds., Vol. 12,
`John Wiley and Sons, Inc., 1967, New York, p. 343.
`2. G. B. Ansell and J. N. Hawthorne, "Phospholipids," El
`sevier, New York, 1964.
`
`USA: W. Han*; A. Palmieri**; A. L. Monaco**
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`Cosmo Ex 2029-p. 3
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`IPR2017-01035
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