Details
Stereochemistry | ACHIRAL |
Molecular Formula | C33H36N4O6 |
Molecular Weight | 584.6621 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C=C)\C(NC1=O)=C\C2=C(C)C(CCC(O)=O)=C(CC3=C(CCC(O)=O)C(C)=C(N3)\C=C4/NC(=O)C(C=C)=C4C)N2
InChI
InChIKey=BPYKTIZUTYGOLE-IFADSCNNSA-N
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-
Molecular Formula | C33H36N4O6 |
Molecular Weight | 584.6621 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Optical Activity | NONE |
Bilirubin is an orange-yellow pigment made during the normal breakdown of red blood cells. Bilirubin passes through the liver and is excreted out of the body. Occasionally, higher bilirubin levels may indicate an increased rate of destruction of red blood cells (hemolysis). A high level of bilirubin in the blood is called hyperbilirubinemia. High bilirubin levels can cause jaundice. Jaundice makes the skin and the whites of the eyes appear yellow, due to the brown and yellow bilirubin in the blood. Phototherapy for neonatal is one of the treatment methods against hyperbilirubinemia. Light absorption by bilirubin in the skin transforms the native Z,Z-bilirubin to conformational photoisomers Z,E-bilirubin and E,Z-bilirubin and structural photoisomers E,Z-lumirubin and E,E-lumirubin. Formation and excretion of Z,E-bilirubin and E,Z-lumirubin are both important routes of elimination of bilirubin through bile and urine, although the precise contributions of the various photoisomers to the overall elimination of bilirubin are still unknown.
Approval Year
PubMed
Title | Date | PubMed |
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Fixed drug combinations and the displacement of bilirubin from albumin. | 1971 Jul |
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Papillary necrosis in the Gunn rat: rapid induction by analgesics. | 1972 Jul |
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[Apolipoprotein A in patients with alcoholic liver disease]. | 1990 Mar-Apr |
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[Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient]. | 1996 Dec |
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New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. | 1996 Nov |
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Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. | 1997 Aug |
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Effect of growth hormone or chromium picolinate on swine metabolism and inflammatory cytokine production after endotoxin challenge exposure. | 1997 Jun |
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Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. | 2005 Aug |
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In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. | 2005 Jan |
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Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the glucuronidation of 2-(4-chlorophenyl)- 5-(2-furyl)-4-oxazoleacetic acid (TA-1801A). | 2005 Jun |
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Inhibition of rat liver UDP-glucuronosyltransferase by silymarin and the metabolite silibinin-glucuronide. | 2005 Jun 24 |
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Modulation of intestinal transport of 2,4-dinitrophenyl-S-glutathione, a multidrug resistance-associated protein 2 substrate, by bilirubin treatment in rats. | 2005 May |
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Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5. | 2005 Nov 15 |
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Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer. | 2005 Sep |
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Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis. | 2006 |
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Heme oxygenase-1 protects tumor cells against photodynamic therapy-mediated cytotoxicity. | 2006 Jun 8 |
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Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes. | 2006 Jun 9 |
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Glutamate induces oxidative stress and apoptosis in cerebral vascular endothelial cells: contributions of HO-1 and HO-2 to cytoprotection. | 2006 May |
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Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. | 2007 Dec |
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The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. | 2007 Sep |
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Protective response of the Ah receptor to ANIT-induced biliary epithelial cell toxicity in see-through medaka. | 2008 Apr |
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Carbon monoxide donors or heme oxygenase-1 (HO-1) overexpression blocks interleukin-18-mediated NF-kappaB-PTEN-dependent human cardiac endothelial cell death. | 2008 Feb 1 |
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Protective effects of bilirubin against cyclophosphamide induced hemorrhagic cystitis in rats. | 2008 Mar |
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[Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?]. | 2008 May |
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Predictive factors associated with the progression to hepatic failure caused by lamivudine-resistant HBV. | 2008 Nov |
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Role of vitamin C transporters and biliverdin reductase in the dual pro-oxidant and anti-oxidant effect of biliary compounds on the placental-fetal unit in cholestasis during pregnancy. | 2008 Oct 15 |
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Interaction of porphyrins with human organic anion transporting polypeptide 1B1. | 2009 Nov 10 |
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Diagnostic performance of traditional hepatobiliary biomarkers of drug-induced liver injury in the rat. | 2010 Aug |
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Global changes in gene regulation demonstrate that unconjugated bilirubin is able to upregulate and activate select components of the endoplasmic reticulum stress response pathway. | 2010 Mar-Apr |
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Adiponectin-mediated heme oxygenase-1 induction protects against iron-induced liver injury via a PPARα dependent mechanism. | 2010 Oct |
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Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin. | 2011 |
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Differential oxidative stress responses to D-galactosamine-lipopolysaccharide hepatotoxicity based on real time PCR analysis of selected oxidant/antioxidant and apoptotic gene expressions in rat. | 2011 |
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In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins. | 2011 Apr |
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Displacement of bilirubin from albumin in plasma from jaundiced newborns. An in vitro study of purified Chinese herbal constituents and sulfisoxazole. | 2011 Jul |
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Inducible bilirubin oxidase: a novel function for the mouse cytochrome P450 2A5. | 2011 Nov 15 |
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Urinary excretion of bilirubin oxidative metabolites in arsenite-treated mice. | 2012 |
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Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012 Jan |
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Reduced expression of UGT1A1 in intestines of humanized UGT1 mice via inactivation of NF-κB leads to hyperbilirubinemia. | 2012 Jan |
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Metabolism of bilirubin by human cytochrome P450 2A6. | 2012 May 15 |
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Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2. | 2012 Nov |
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Cyclosporine A treated in vitro models induce cholestasis response through comparison of phenotype-directed gene expression analysis of in vivo Cyclosporine A-induced cholestasis. | 2013 Aug 29 |
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Cytochrome P450 2A5 and bilirubin: mechanisms of gene regulation and cytoprotection. | 2013 Jul 15 |
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Importance of UDP-glucuronosyltransferase 1A1 expression in skin and its induction by UVB in neonatal hyperbilirubinemia. | 2013 Nov |
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Epigenetic regulation is a crucial factor in the repression of UGT1A1 expression in the human kidney. | 2013 Oct |
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Mitochondrial Channel Opener Diazoxide Attenuates Hypoxia-Induced sFlt-1 Release in Human Choriocarcinoma Cells. | 2014 Apr |
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Physiological concentrations of unconjugated bilirubin prevent oxidative stress-induced hepatocanalicular dysfunction and cholestasis. | 2014 Feb |
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Developmental onset of bilirubin-induced neurotoxicity involves Toll-like receptor 2-dependent signaling in humanized UDP-glucuronosyltransferase1 mice. | 2014 Feb 21 |
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Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases. | 2014 Jul |
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Heme-regulated eIF2α kinase plays a crucial role in protecting erythroid cells against Pb-induced hemolytic stress. | 2015 Mar 16 |
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Role of brain cytochrome P450 mono-oxygenases in bilirubin oxidation-specific induction and activity. | 2016 Feb |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:11:07 GMT 2023
by
admin
on
Fri Dec 15 15:11:07 GMT 2023
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Record UNII |
RFM9X3LJ49
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Record Status |
Validated (UNII)
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Record Version |
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89871-8
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21 CFR 862.1113
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m2492
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BILIRUBIN
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211-239-7
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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
MINOR
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TRANSPORTER -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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