TRS 1060-附件9：国际非专利名称和国际药典出版物中药物化学结构的图形表示指南

Guidance for the graphic representation of chemicalstructures of pharmaceutical substances in thepublications of International Nonproprietary Names andThe International Pharmacopoeia This guide is intended to describe rules for drawing structures and to supersedethe previous version, entitledGuidelines for the graphic representation of chemicalformulae, published in the report of the thirty-fourth meeting of the ExpertCommittee on Specifications for Pharmaceutical Preparations, WHO TechnicalReport Series No. 863, Annex 1, 1996, concerning conventions for chemicalstructure representation of pharmaceutical substances.For any further information or request, please send an email to the Norms and Standards for Pharmaceuticals (NSP) Team at WHO, at email nsp@who.int Background During the fiftieth meeting of the World Health Organization (WHO) ExpertCommitteeon Specifications for Pharmaceutical Preparations(ECSPP),apossible revision of the general guidance on how to represent graphic formulaewas discussed. The revision of guidance on how to represent graphic formulaeinThe International Pharmacopoeia and within the list of InternationalNonproprietary Names (INNs) list was developed and adopted by the ExpertCommittee at its thirty-fourth meeting (Technical Report Series No. 863, Annex1, 1996). A discussion took place on whether an update of the guidance would beuseful to bring it into line with current practices. Such updated guidance couldpromote convergence in this area. The Expert Committee supported the proposaland recommended that work should start promptly to update WHO guidance onrepresentation of graphic formulae.During the fifty-first ECSPP meeting, an update was given on the revision of this general guidance. Different approaches for graphic representation used bydifferent pharmacopoeias may result in a risk of confusion and mistakes. There isa need to identify a harmonized approach that can be recommended for use by allorganizations. The Expert Committee expressed its support for ongoing work inthis regard, which would enable an update of WHO guidance on representationof graphic formulae.The work on the general guidance was resumed in March 2024, and the outcomes are published in the present annex to the report of the fifty-eighthmeeting of the ECSPP. Contents Background 467 WHO Technical Report Series, No. 1060, 2025Introduction4761.General issues4771.1Bond types4771.2Atomic symbols and structural abbreviations4781.3Chemical groups4801.3.1Expanded form4801.3.2Representation of N-oxides4811.3.3Representation of functional groups containing elements withvariable valences4811.4Structures4821.4.1General aspects4821.4.1.1Distinctive aspects of acyclic structures4861.4.1.2Distinctive aspects of cyclic structures4881.4.2Ionic structures4951.4.2.1General aspects4951.4.2.2Distinctive aspects of inorganic metal salts4971.4.2.3Distinctive aspects of organic metal salts4971.4.2.4Distinctive aspects of amine salts4991.4.2.5Distinctive aspects of zwitterions5001.4.3Coordination compounds5001.4.3.1Linear formulae of non-cyclic coordination compounds5001.4.3.2Structural formulae of coordination complexes5011.4.3.3Stereochemistry of coordination complexes5011.4.4Isotopically modified compounds5041.4.5Tautomeric compounds5051.5Stereochemistry5081.5.1General aspects5081.5.2Cis- and trans-isomerism5091.5.2.1(EZ) isomerism: carbon-carbon double bonds and imines5091.5.2.2Cis- and trans-isomerism of rings5121.5.3Compounds with one centre of chirality5121.5.3.1Specified configuration5121.5.3.2Unspecified configuration5131.5.4Compounds with several centres of chirality5141.5.4.1Mixtures of two diastereoisomers5141.5.4.2Cis- andtrans-isomerism of rings5151.5.4.3Mixtures of more than two diastereoisomers5161.5.4.4Fully depicted mixtures of stereoisomers5181.5.4.5Unspecified configuration5181.5.4.6Distinctive aspects of stereogenic centres at fusion atoms andat bridgehead atoms5181.6Unbound substituents or radicals5191.6.1Attachment points5191.6.2Orientation5211.6.3Depiction style521 1.7Generic structures5231.7.1General aspects5231.7.2Symbols for substituent groups and repeating units5241.7.3Mixtures of complicated structures5261.7.4Structural differences versus common features527 2.Main structural classes 2.1Structure representation of amino acids and peptides5282.1.1General aspects5282.1.2Full depiction5282.1.3Standard three-letter code5292.1.3.1Stereochemical features5292.1.3.2Amino acid modifications5302.1.3.3Homodetic cyclic peptides5312.1.3.4Heterodetic cyclic peptides5322.1.3.5Amino acid one-letter code5332.2Structure representation of carbohydrates and derivatives535 2.2.1Haworth depictions5352.2.1.1Stereochemical considerations5362.2.2Mills depictions5382.2.3Conformations of acyclic chains: Fischer projections5392.2.4Oligosaccharides and saccharide derivatives5402.3Structure representation of nucleosides and polynucleotides5412.3.1Nucleosides and small derivatives5412.3.2Nucleic acids and derivatives5422.4Str