Trivial names steroids

The common name vitamin D is used throughout the pharmaceutical kidustry for simplicity. The trivial name calciferol has also been used extensively with the prefix ergo- and chole-, which kidicate vitamin D2 (2) and vitamin (4), respectively (see Steroids). Vitamin D2 was originally named calciferol in 1931 by Angus and co-wotkets (2). Historically, a number of substances were referred to as vitamin D and were distinguished from one another by a subscript numeral, eg, vitamin D2, vitamin D, etc. 

Steroids are compounds possessing the tetracyclic skeleton of cyclopenta[a]phenan-threne (1) or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Natural steroids have trivial names. The nomenclature of steroids is not based on these trivial names, but on a few stereoparent hydrides that are common to many compounds. Substitutive nomenclature is used to designate characteristic groups and unsaturation. Structural modifications are expressed by appropriate non-detachable prefixes. 

Vitamins. The vitamins are natural organic compounds of considerable diversity that occur widely. The name derives from the Latin vita (life) and amin, a shortened form of amine. The name reflects the historical discovery of these substances, not all of which are amines. They are all of relatively low molecular weight, especially compared to peptides but in a range comparable to steroids. These substances are uniformly active and play various roles in biosynthesis and metabolism. The vitamins are too numerous to detail here but the most common examples are illustrated. They are classed using the common system, that is, water or fat soluble, depending on their approximate level of hydrophobicity or hydrophilicity. Their names are typically nonsystematic but the diversity of their structures requires that the trivial names be used. 

A question that will always require careful consideration, however, is whether introduction of a new trivial name is justified. Besides, replacing certain trivial names by more or less systematic ones can result in greatly improved surveyability of various highly specialized parts of organic chemistry and thus facilitate their further development. An example is the excellent report on the nomenclature of steroids published a short time ago in various languages (I) as a result of a conference of specialists in this field with the aid of a limited number of conventions, it appeared possible to replace the cumbersome trivial names of many compounds of well-known structure by systematic names of very reasonable length and form from which the structure can clearly and easily be deduced. 

The utility of the systematic name of a compound lies in the information that it provides about the parent compound, the position of bond unsaturation, and the nature, position, and orientation of substituents. The trivial name, as the term suggests, conveys little or no information about the chemical origin and characteristics of a compound (e.g., cortisol, progesterone, and testosterone). The trivial and systematic names of some of the important steroid hormones are given in Table 51-2. 

Bile acids contain hydroxyl groups, which are usually substituted at positions, C-3, C-7, or C-12 of the steroid nucleus. The three major bile acids found in man are 3a,7a,12a-trihydroxy-5P-cholan-24-oic acid 3a,7a-dihydroxy-5p-cholan-24-oic add and 3a,12a-dihydroxy-5p-cholan-24-oic acid. Because of the complexities of steroid nomenclature, bile acids are nearly always referred to by trivial names. 11108, the three major human bile acids are named cholic acid, chenodeoxycholic acid, and deoxycholic acid, respectively, and their chemical structures are shown in Fig. 1. Human bile does, however, contain small amounts of other bile acids, such as lithocholic acid (3a-hydroxy-5P-cholan-24-oic add) and ursodeoxycholic add (3a,7p-dihydroxy-5p-cholan-24-oic acid) (see Fig. 1). 

Throughout the text, full names have been used for steroids not referred to repetitively, but for the more common compounds mentioned, the trivial names in the table on pp. 144-146 are used throughout. 

As noted earlier, bile acids were among the first steroids to be obtained in pure crystalline form. These compounds played an important role in the effort devoted to divining the structure of steroids. Bile acids as a result acquired a sizeable number of trivial names, most of which gave little information as to their chemical structure. One approach to systematic names is based on the hypothetical cholanoic acid 8-1 (Scheme 8). Bile acids are then named as derivatives of this structure using the mles used for other classes of steroids. Note the cis A-B ring fusion in this series. The systematic name for 8-2, lithocholic acid, is then simply 3a-hydroxy-5/3-cholanic acid. Chenodeoxycholic acid, 8-3, becomes 3a,7a-dihydroxy-5/3-cholanic acid. The predominant acid in bile, 8-3, is cholic acid itself, or, 3a,7a,12a-trihydroxy-5 )8-cholanic acid. 

The generxc witha steroids which has been proposed does not seem to have gained much popularity. For compounds with a modified carboxylic skeleton and or side chain, only CA names are being used, along with the trivial names. 

In medicine and biochemistry, the common or trivial names of compounds are used rather than the systematic nomenclature favored by chemists. Sometimes such names reflect functional groups, classes of compounds or the source from which the compound was first isolated. The compound testosterone provides an example. It was first isolated from monkey testis, the "ster" in its name denotes the steroid ring structure, and the "one" denotes a ketone group. 

Cytochrome P450 22A1 (the trivial name of which is cytochrome P450scc) was identified in human and bovine adrenal mitochondria. This enzyme mediates the cleavage of the cholesterol side chain to pregnenolone, which is the first stage in the biosynthesis of several steroidal hormones. 

Buxus steroid alkaloids. Steroid alkaloids with 9)8,19-cyclopregnane or 9(10- 19)-afeeo-pregnane structure, but with 1 to 3 additional methyl groups at C-4 and/or C-14 as well as amino functions at C-3 and/or C-20. They are isolated from numerous species of the Buxaceae genus Buxus. To date about 200 B.s. are known. In order to achieve transparency and especially to reduce the number of incomprehensible trivial names for new compounds it was proposed to ac-... 

TThe following systematic names are given to steroids and bile acids referred to by trivial names cholestanol, 5a-cholestan-3/5-ol cholic acid, 3a,7a,12a-trihydroxy-5j3-cholanoic acid hyocholic acid, 3a,6a,7a-trihydroxy-5/S-cholanoic acid a-muricholic acid, 3a,6/S,7a-trihydroxy-5/S-cholanoic acid /5-muricholic acid, 3a,6/S,7/S-trihydroxy-5/S-cholanoic acid allocholic acid, 3a,7a,12a-trihydroxy-5a-cholanoic acid chenodeoxycholic acid, 3a,7a-dihydroxy-5/5-cholanoic acid deoxycholic acid, 3a,12a-dihydroxy-5iS-cholanoic acid allochenodeoxycholic acid, 3a,7a-dihydroxy-5a-cholanoic acid allodeoxycholic acid, 3a,12a-dihydroxy-5a-cholanoic acid lithocholic acid, 3a-hydroxy-5/5-cholanoic acid. 

Little further was substantiated about cholic acid (or about bile acids generally) for nearly five decades. The name, cholic acid, had become well established, but trivial names based partly on imperfect characterization were common, so that consideration of nomenclature was a part of Wieland s first report on the bile acids in 1912 (56). A review of the evidence then available included that cholic acid was a trihydroxy, monocarboxylic acid and that two of the alcohols were secondary. The final presentation of the structure of cholic acid awaited the correct steroid formulation in 1932 (113, 114). By that time the structural relationship between the sterols and bile acids was well established. The preparation of cholanic acid from cholic acid had been reported in the paper by Wieland and Weil in 1912 (56). The preparation of cholanic acid from cholesterol (through coprostane) was reported in 1919 by Windaus and Neukirchen (55). 

Fig. 7.17 Unusual steroidal glycosides, unfortunately lacking trivial names, from two Cestmm species structural peculiarities are highlighted in grey...

Fig. 7.21 Unusual structural types of steroidal aLkamines. Wavy lines indicate unknown configuration. Highlighted in grey oxygen instead of nitrogen in other structural types. Dotted lines separate structures given together with their trivial names (above) from structurally related congeners (below)...

Three naming systems are in use for steroids trivial names (cholesterol, cholestanol, etc.), semisystematic names (use of trivial name such as cholesterol as a parent), and truly systematic names with commonly accepted saturated hydrocarbons as parents. The most often encountered steroids are derivatives of the parent, 5a-cholestane (2 lacking the HO-group) where 5a refers to the presence of an a-H-atom on C-5. Thus, cholestanol (2) is systematically 5a-cholestan-3yff-ol and cholesterol is cholest-5-en-3yff-ol. Cholestanol could also be described semi-systematically as 5a-dihydrocholesterol. 

Abbreviation Trivial name Origin of urinary steroid... 

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