Skip to Main Content

++

In the human fetus, as in the adult, biliverdin-IXα and any small amounts of non-IXα isomers that are formed are reduced to the corresponding bilirubins. Of these, bilirubin-IXα is uniquely hydrophobic and lipophilic, and ready to cross the placenta for elimination by the mother. In utero, residual non-IXα isomers too polar to cross the placenta, particularly the IXβ isomer, accumulate and are detectable in bile and meconium by 15 weeks gestation.1 This observation has led some to conclude erroneously that heme catabolism in the fetus yields predominantly the IXβ isomer. The major form of bilirubin generated in infants and adults alike is bilirubin-IXα, and can be measured in various forms (Table 3-1).

++
Table Graphic Jump Location
Table 3-1. Bilirubin Nomenclature and Chemical Behavior
++

The poor solubility of bilirubin can be explained by considering its chemical three-dimensional structure.2 Although often represented as a linear structure for convenience (Figure 3-1, structure 5), bilirubin has a folded flexible structure in which the weakly acidic propionic acid side chains can stretch and form internal hydrogen bonds with spatially proximate nitrogen and oxygen groups. This results in a compact structure in which the surface is lipophilic and the polar parts of the molecule are protected from interactions with solvent water. The stereochemical configuration of the two double bonds between the rings in bilirubin is the same as in heme from which the bilirubin was derived and is designated unambiguously in current organic chemistry nomenclature as Z (from zusammen, German: together) (in contradistinction to E [entgegen: opposite], the other possible configuration). Because of its low solubility in water at physiologic pH, bilirubin requires a carrier molecule for transport from the reticuloendothelial system to the liver for excretion.3 In blood and ...

Want remote access to your institution's subscription?

Sign in to your MyAccess profile while you are actively authenticated on this site via your institution (you will be able to verify this by looking at the top right corner of the screen - if you see your institution's name, you are authenticated). Once logged in to your MyAccess profile, you will be able to access your institution's subscription for 90 days from any location. You must be logged in while authenticated at least once every 90 days to maintain this remote access.

Ok

About MyAccess

If your institution subscribes to this resource, and you don't have a MyAccess profile, please contact your library's reference desk for information on how to gain access to this resource from off-campus.

Subscription Options

AccessPediatrics Full Site: One-Year Subscription

Connect to the full suite of AccessPediatrics content and resources including 20+ textbooks such as Rudolph’s Pediatrics and The Pediatric Practice series, high-quality procedural videos, images, and animations, interactive board review, an integrated pediatric drug database, and more.

$595 USD
Buy Now

Pay Per View: Timed Access to all of AccessPediatrics

24 Hour Subscription $34.95

Buy Now

48 Hour Subscription $54.95

Buy Now

Pop-up div Successfully Displayed

This div only appears when the trigger link is hovered over. Otherwise it is hidden from view.