121080-63-5

Basic information

• Product Name: SN-38 GLUCURONIDE
• Synonyms: SN-38 GLUCURONIDE;(4S)-4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl β-D-Glucopyranosiduronic Acid;4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl β-D-Glucopyranosiduronic Acid
• CAS NO: 121080-63-5
• Molecular Formula: C28H28N2O11
• Molecular Weight: 568.53
• Product Categories: Chiral Reagents;Glucuronides;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 121080-63-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: >250°C (dec.)
• Appearance: /
• Refractive Index: 1.746
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: SN-38 GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SN-38 GLUCURONIDE(121080-63-5)
• EPA Substance Registry System: SN-38 GLUCURONIDE(121080-63-5)

Safety Data

• Hazardous Substances Data: 121080-63-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

A metabolite of Irinotecan

InChI:InChI=1/C28H28N2O11/c1-3-12-13-7-11(40-26-22(33)20(31)21(32)23(41-26)25(35)36)5-6-17(13)29-19-14(12)9-30-18(19)8-16-15(24(30)34)10-39-27(37)28(16,38)4-2/h5-8,20-23,26,31-33,38H,3-4,9-10H2,1-2H3,(H,35,36)/t20-,21-,22-,23?,26-,28-/m0/s1

Upstream product

• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 121098-77-9 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 2616-64-0 uridine diphosphoglucuronic acid 

Relevant articles and documents

Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin

1. The human liver UDP-glucuronosyltransferase (UGT) isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin (SN-38), the active metabolite of irinotecan (CPT-11), have been studied using microsomes from human liver and insect cells expressing human UGTs (1A1, 1A3, 1A4, 1A6, 1A9, 2B7, 2B15). 2. The glucuronidation of SN-38 was catalysed by UGT1A1, UGT1A3, UGT1A6 and UGT1A9 as well as by liver microsomes. Among these UGT isoforms, UGT1A1 showed the highest activity of SN-38 glucuronidation at both low (1 μM) and high (200 μM) substrate concentrations. The ranking in order of activity at low and high substrate concentrations was UGT1A1 > UGT1A9 > UGT1A6 > UGT1A3 and UGT1A1 > UGT1A3 > UGT1A6 ≥ UGT1A9, respectively. 3. The enzyme kinetics of SN-38 glucuronidation were examined by means of Lineweaver-Burk analysis. The activity of the glucuronidation in liver microsomes exhibits a monophasic kinetic pattern, with an apparent Km and Vmax of 35.9 μM and 134 pmol min-1 mg-1 protein, respectively. The UGT isoforms involved in SN-38 glucuronidation could be classified into two types: low-Km types such as UGT1A1 and UGT1A9, and high-Km types such as UGT1A3 and UGT1A6, in terms of affinity toward substrate. UGT1A1 had the highest Vmax followed by UGT1A3. Vmax of UGT1A6 and UGT1A9 were approximately 1/9 to 1/12 of that of UGT1A1. 4. The activity of SN-38 glucuronidation by liver microsomes and UGT1A1 was effectively inhibited by bilirubin. Planar and bulky phenols substantially inhibited the SN-38 glucuronidation activity of liver microsomes and UGT1A9, and/or UGT1A6. Although cholic acid derivatives strongly inhibited the activity of SN-38 glucuronidation by UGT1A3, the inhibition profile did not parallel that in liver microsomes. 5. These results demonstrate that at least four UGT1A isoforms are responsible for SN-38 glucuronidation in human livers, and suggest that the role and contribution of each differ substantially.