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Medical Term:

steroids

Pronunciation: ster'oydz, ster-

Definition: A large family of chemical substances, comprising many hormones, body constituents, and drugs, each containing the tetracyclic cyclopenta[a]phenanthrene skeleton. Stereoisomerism among steroids is not only common but of critical biologic significance. The nomenclature conventions are that the nucleus is presented as if projected onto the plane of the paper, with groups then lying above that plane being denoted by thickened bonds and called ß and those then lying below that plane being denoted by broken bonds and called a; the letter ? indicates unknown or unspecified orientation. The principal classes of steroids, with the names for the unsubstituted, saturated hydrocarbon forms that are clearly related to physiologic functions or sources are: 1) gonanes (in which the methyl groups C-18 and C-19, have been replaced by H), 2) estranes (in which the C-19 methyl groups have been replaced by H), 3) androstanes (equivalent to Formula II), 4) norandrostanes (in which one of the methyl groups, typically C-18, has been replaced by H), 5) cholanes (with —CH(CH3)(CH2)2CH3 bonded to C-17), 6) cholestanes (with —CH(CH3)(CH2)3CH(CH3)2 at C-17, 7) ergostanes (with —CH(CH3)(CH2)2CH(CH3)CH(CH3)2 at C-17), and 8) stigmastanes (with —CH(CH3)(CH2)2CH(CH2CHCH3)CH(CH3)2 at C-17). In addition, each of the classes can be in a 5a or 5ß series. The steroid derivatives known as cardanolides are androstanes with a 5-membered lactone linked to C-17. The squill-toad poisons known as the bufanolides are androstanes with a 6-membered lactone linked to C-17. Spirostans and furostans (the basic structures of many “genins,” including the sapogenins) are androstanes having certain cyclic ether moieties. The natural and synthetic derivatives are named by adding conventional chemical prefixes and suffixes for substituents; -ol for a hydroxyl group, -on(e) for a keto group, -al for an aldehyde group. “Nor” indicates loss of a –CH2— group; “homo,” the addition of a –CH2— group; each is preceded by the letter indicating which ring is contracted or expanded, respectively, or, in the case where the –CH2— is lost from a methyl group, the number of the carbon atom lost. “Seco” indicates fission of a ring with the addition of hydrogen atoms at the positions indicated by numerals preceding the term. Unsaturation is denoted, as usual, by substituting appropriate terms, -en(e), -yn(e), -adien(e), for the -ane or -an parts of the hydrocarbon or parent class names, with numerals indicating locations of the unsaturated bonds. The locations of double bonds are specified by the lower of the two (consecutive) numbers of the carbon atoms involved. When a double bond is formed between two nonconsecutive carbon atoms, the second is indicated in parentheses after the first; estriol and the estradiols possess three double bonds, between C-1 and C-2, between C-3 and C-4, and between C-5 and C-10, respectively. Steroid alkaloids may be named from the steroid parent, as above, or from trivial family names usually ending in -anine if the steroid is saturated or in -enine, -adienine, etc., if it is not saturated (conanine, tomatanine).

© Copyright 2016 Wolters Kluwer. All Rights Reserved. Review Date: Sep 19, 2016.
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