WHO Expert Committee on Specifications for Pharmaceutical Preparations - WHO Technical Report Series, No. 863 - Thirty-fourth Report
(1996; 200 pages) Voir le document au format PDF
Table des matières
Afficher le document1. Introduction
Ouvrir ce répertoire et afficher son contenu2. The international pharmacopoeia and related activities
Afficher le document3. Simple test methodology
Ouvrir ce répertoire et afficher son contenu4. Stability of dosage forms
Ouvrir ce répertoire et afficher son contenu5. Good manufacturing practices for pharmaceutical products
Ouvrir ce répertoire et afficher son contenu6. Legal and administrative aspects of the functioning of national drug regulatory authorities
Ouvrir ce répertoire et afficher son contenu7. Quality assurance in the supply system
Afficher le document8. Terminology
Afficher le documentAcknowledgements
Afficher le documentReferences
Fermer ce répertoireAnnex 1 - Guidelines for the graphic representation of chemical formulae
Afficher le document1. Introduction
Afficher le document2. Acyclic structures
Afficher le document3. Cyclic structures
Afficher le document4. Ionic structures
Afficher le document5. Isotopically modified compounds
Afficher le document6. Coordination compounds
Afficher le document7. Stereochemistry
Afficher le document8. Carbohydrates
Afficher le document9. Steroids
Afficher le document10. Terpenoids
Afficher le document11. Prostanoids
Afficher le document12. Alkaloids
Afficher le document13. Antibiotics
Afficher le document14. Polypeptides
Afficher le document15. Polymers
Afficher le documentAcknowledgements
Afficher le documentReferences
Afficher le documentAnnex 2 - List of available International Chemical Reference Substances1
Afficher le documentAnnex 3 - List of available International Infrared Reference Spectra
Ouvrir ce répertoire et afficher son contenuAnnex 4 - General recommendations for the preparation and use of infrared spectra in pharmaceutical analysis
Ouvrir ce répertoire et afficher son contenuAnnex 5 - Guidelines for stability testing of pharmaceutical products containing well established drug substances in conventional dosage forms
Ouvrir ce répertoire et afficher son contenuAnnex 6 - Good manufacturing practices: guidelines on the validation of manufacturing processes
Ouvrir ce répertoire et afficher son contenuAnnex 7 - Good manufacturing practices: supplementary guidelines for the manufacture of investigational pharmaceutical products for clinical trials in humans
Ouvrir ce répertoire et afficher son contenuAnnex 8 - Good manufacturing practices: supplementary guidelines for the manufacture of herbal medicinal products1
Ouvrir ce répertoire et afficher son contenuAnnex 9 - Multisource (generic) pharmaceutical products: guidelines on registration requirements to establish interchangeability
Ouvrir ce répertoire et afficher son contenuAnnex 10 - Guidelines for implementation of the WHO Certification Scheme on the Quality of Pharmaceutical Products Moving in International Commerce
Ouvrir ce répertoire et afficher son contenuAnnex 11 - Guidelines for the assessment of herbal medicines1,2
Ouvrir ce répertoire et afficher son contenuAnnex 12 - Guidelines on import procedures for pharmaceutical products
Afficher le documentBack Cover
 

3. Cyclic structures

3.1 Rings are shown in full as polygons. The symbols of the carbon atoms that form the ring are not shown, but are represented by the vertices of the rings. The hydrogen atoms attached to them are not represented unless they are needed to show stereochemistry. The symbols of atoms other than carbon are shown with all the hydrogen atoms attached to them but without linking dashes. Single, double or triple bonds are indicated thus:

3.2 In aromatic systems a circle should not be used to depict delocalized electrons; instead, alternating single and double bonds are shown (Kekulé representation):

In monocyclic aromatic compounds, double bonds should be arranged to have the lowest possible numbering:

3.3 In fused polycyclic systems a double bond should form the fusion bond nearest to the right-hand side:

3.4 Six-membered rings should be represented with a vertex at the base rather than a horizontal bond when the chains linked to them are represented in the form of lines at an angle to one another (as is preferred for acyclic chains - see section 2.3):

3.5 Depiction of the ring with a horizontal bond at the base is, however, preferred when the chains are shown in the compact form:

3.6 Rings are shown as regular polygons when they consist of up to eight atoms:

3.7 Wherever possible, the regularity of the polygons is maintained in the drawing of fused cyclic compounds:

3.8 However, in fused polycyclic systems the polygons may often be distorted in order to maintain the symmetry of the structure:

3.9 Rings with more than eight vertices are often shown with re-entrant angles. It is recommended by Chemical Abstracts Service (CAS) that they should be drawn like amalgamated rings with five, six or seven vertices:

3.10 These recommendations need not always be followed. In particular, the shape of such large rings as those of macrolide antibiotics is often determined by the presence of more or less bulky substituents and the need to indicate stereochemical conformations:

3.11 When a substituent is attached to an atom occupying a position in a ring (carbon or heteroatom), the direction to be taken by the dash linking it to that atom can be found by extending the line bisecting the cycle:

3.12 Where two substituents are attached to the same ring atom, they should generally both be at the same angle to the bisector, and preferably at a right angle to the adjacent side:

However, for the graphic representation of certain structures, such as steroids, other considerations may have priority.

3.13 Substituents are normally placed outside rings, except in steroids, terpenes and alkaloids (see sections 9, 10 and 12) and where substituents attached at bridgeheads can only be displayed inside the rings of polycyclic structures:

3.14 In bridged structures, a non-atomic bridge (direct bond) is represented by a straight line, an atomic bridge by lines at an angle to one another. The symbols for carbon atoms are not shown; however, if the bridge contains one or more heteroatoms, the atomic symbols for those atoms are shown. To give some perspective to the figure or to represent stereochemical features, wedges, thickened lines or broken lines can be used (see p. 19):

3.15 Sometimes a three-dimensional approach is possible, if a planar representation is considered not clear enough:

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Dernière mise à jour: le 3 mai 2013