Lumirubin

(Z)-isomer of lumirubin

Names
IUPAC name

3-[2-[[6-(2-carboxyethyl)-7,11-dimethyl-12-oxo-4,13-diazatricyclo[8.3.0.03,7]trideca-1,3,5,9-tetraen-5-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid

Identifiers

CAS Number

* 110617-57-7
* 83664-21-5

3D model (JSmol)

* Interactive image

ChemSpider |

* 4946083

PubChem CID

* 135754285

InChI

* InChI=1S/C33H36N4O6/c1-6-19-16(2)24(36-32(19)43)13-23-17(3)20(7-9-29(38)39)25(34-23)14-27-22(8-10-30(40)41)33(5)12-11-21-18(4)31(42)37-26(21)15-28(33)35-27/h6,11,13,15,18,34H,1,7-10,12,14H2,2-5H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b24-13+

Key: BYVDUQYJIIPFIB-ZMOGYAJESA-N

SMILES

* CC1C2=CCC3(C(=NC(=C3CCC(=O)O)CC4=C(C(=C(N4)/C=C/5\C(=C(C(=O)N5)C=C)C)C)CCC(=O)O)C=C2NC1=O)C

Properties

Chemical formula

| C33H36N4O6
Molar mass | 584.673 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Lumirubin is a structural isomer of bilirubin, which is formed during phototherapy used to treat neonatal jaundice. This polar isomer resulting from the blue-green lights of phototherapy has an active site to albumin, and its effects are considered less toxic than those of bilirubin.[1][2][3] Lumirubin is excreted into bile or urine. ZZ, ZE, EE and EZ are the four structural isomers of bilirubin. ZZ is the stable, more insoluble form. Other forms are relatively soluble and are known as lumirubins. Phototherapy converts the ZZ form into lumirubins. Monoglucuronylated lumirubins are easily excreted.[4]

## References

1. ↑ Dvořák, Aleš; Pospíšilová, Kateřina; Žížalová, Kateřina; Capková, Nikola; Muchová, Lucie; Vecka, Marek; Vrzáčková, Nikola; Křížová, Jana et al. (2021). "The Effects of Bilirubin and Lumirubin on Metabolic and Oxidative Stress Markers". Frontiers in Pharmacology 12: 567001. doi:10.3389/fphar.2021.567001. ISSN 1663-9812. PMID 33746746.
2. ↑ Jašprová, Jana; Dvořák, Aleš; Vecka, Marek; Leníček, Martin; Lacina, Ondřej; Valášková, Petra; Zapadlo, Miloš; Plavka, Richard et al. (2020-03-10). "A novel accurate LC-MS/MS method for quantitative determination of Z-lumirubin" (in en). Scientific Reports 10 (1): 4411. doi:10.1038/s41598-020-61280-z. ISSN 2045-2322. PMID 32157102. Bibcode: 2020NatSR..10.4411J.
3. ↑ Jasprova, Jana; Matteo Dal Ben; Eleonora Vianello; Iryna Goncharova; Marie Urbanova; Karolina Vyroubalova; Silvia Gazzin; Claudio Tiribelli et al. (1 February 2016). "The Biological Effects of Bilirubin Photoisomers". PLOS ONE 11 (2): e0148126. doi:10.1371/journal.pone.0148126. PMID 26829016. Bibcode: 2016PLoSO..1148126J.
4. ↑ "Phototherapy for neonatal jaundice: in vitro comparison of light sources". Pediatr. Res. 18 (7): 667–70. July 1984. doi:10.1203/00006450-198407000-00021. PMID 6540860.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Lumirubin. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Lumirubin&oldid=530299"
*[CID]: Compound ID