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MedKoo Cat#: 556186 | Name: SN-38 Glucuronide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SN-38 Glucuronide is a phase II metabolite of irinotecan. It is formed via glucuronidation of the irinotecan phase I metabolite SN-38 by the UDP-glucuronosyltransferase (UGT) isoform UGT1A1. Irinotecan (CPT-11) is chemotherapy used mainly in the metastatic colorectal cancer. CPT-11 is converted to its active metabolite, SN-38, which is conjugated to SN-38 glucuronide (SN-38G). SN-38G excreted in the intestinal lumen is extensively deconjugated by bacterial β-glucuronidase, resulting in the regeneration of SN-38, which causes diarrhea.

Chemical Structure

SN-38 Glucuronide
SN-38 Glucuronide
CAS#121080-63-5

Theoretical Analysis

MedKoo Cat#: 556186

Name: SN-38 Glucuronide

CAS#: 121080-63-5

Chemical Formula: C28H28N2O11

Exact Mass: 568.1693

Molecular Weight: 568.54

Elemental Analysis: C, 59.15; H, 4.96; N, 4.93; O, 30.95

Price and Availability

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1mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
SN-38 Glucuronide; SN38 Glucuronide
IUPAC/Chemical Name
(2S,3S,4S,5R,6S)-6-(((S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
InChi Key
SSJQVDUAKDRWTA-CAYKMONMSA-N
InChi Code
InChI=1S/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
SMILES Code
CCC1=C2C(C(N3C2)=CC([C@](O)(C(OC4)=O)CC)=C4C3=O)=NC5=CC=C(O[C@@H]6O[C@@H]([C@H]([C@@H]([C@H]6O)O)O)C(O)=O)C=C51
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 568.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gasthuys E, van Ovost J, Vande Casteele S, Cosyns S, Ceelen W, Van Bocxlaer J, Vermeulen A. Development and validation of an UPLC-MS/MS method for the determination of irinotecan (CPT-11), SN-38 and SN-38 glucuronide in human plasma and peritoneal tumor tissue from patients with peritoneal carcinomatosis. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Feb 1;1233:123980. doi: 10.1016/j.jchromb.2023.123980. Epub 2024 Jan 6. PMID: 38215697. 2: Meng J, Abu YF, Zhang Y, Zhou Y, Xie Y, Yan Y, Tao J, Ramakrishnan S, Chen C, Roy S. Opioid-induced microbial dysbiosis disrupts irinotecan (CPT-11) metabolism and increases gastrointestinal toxicity in a murine model. Br J Pharmacol. 2023 May;180(10):1362-1378. doi: 10.1111/bph.16020. Epub 2023 Jan 9. PMID: 36562107; PMCID: PMC10089971. 3: Crane RA, Grubb ES, Coward LU, Gorman GS. In vitro metabolic biomodulation of irinotecan to increase potency and reduce dose-limiting toxicity by inhibition of SN-38 glucuronide formation. Drug Metab Pers Ther. 2022 Mar 7;37(3):295-303. doi: 10.1515/dmpt-2021-0178. PMID: 35257538. 4: Aoullay Z, Van Wijk XMR, Yanhui M, Meddah B, Lynch KL, Cherrah Y, Wu AHB. Development of an LC-MS/MS Method for Measurement of Irinotecan and Its Major Metabolites in Plasma: Technical Considerations. Lab Med. 2022 Jan 6;53(1):47-52. doi: 10.1093/labmed/lmab059. PMID: 34351422. 5: Yokokawa A, Kaneko S, Endo S, Minowa Y, Ayukawa H, Hirano R, Nagashima F, Naruge D, Okano N, Kobayashi T, Kawai K, Furuse J, Furuta T, Shibasaki H. Effect of UGT1A1, CYP3A and CES Activities on the Pharmacokinetics of Irinotecan and its Metabolites in Patients with UGT1A1 Gene Polymorphisms. Eur J Drug Metab Pharmacokinet. 2021 Mar;46(2):317-324. doi: 10.1007/s13318-021-00675-3. Epub 2021 Feb 23. PMID: 33619631. 6: Kalthoff S, Paulusch S, Rupp A, Holdenrieder S, Hartmann G, Strassburg CP. The coffee ingredients caffeic acid and caffeic acid phenylethyl ester protect against irinotecan-induced leukopenia and oxidative stress response. Br J Pharmacol. 2020 Sep;177(18):4193-4208. doi: 10.1111/bph.15162. Epub 2020 Jul 16. PMID: 32548889; PMCID: PMC7443465. 7: Collins SL, Patterson AD. The gut microbiome: an orchestrator of xenobiotic metabolism. Acta Pharm Sin B. 2020 Jan;10(1):19-32. doi: 10.1016/j.apsb.2019.12.001. Epub 2019 Dec 10. PMID: 31998605; PMCID: PMC6984741. 8: Cheng KW, Tseng CH, Tzeng CC, Leu YL, Cheng TC, Wang JY, Chang JM, Lu YC, Cheng CM, Chen IJ, Cheng YA, Chen YL, Cheng TL. Pharmacological inhibition of bacterial β-glucuronidase prevents irinotecan-induced diarrhea without impairing its antitumor efficacy in vivo. Pharmacol Res. 2019 Jan;139:41-49. doi: 10.1016/j.phrs.2018.10.029. Epub 2018 Nov 1. PMID: 30391354. 9: Pellock SJ, Walton WG, Biernat KA, Torres-Rivera D, Creekmore BC, Xu Y, Liu J, Tripathy A, Stewart LJ, Redinbo MR. Three structurally and functionally distinct β-glucuronidases from the human gut microbe Bacteroides uniformis. J Biol Chem. 2018 Nov 30;293(48):18559-18573. doi: 10.1074/jbc.RA118.005414. Epub 2018 Oct 9. PMID: 30301767; PMCID: PMC6290157. 10: Toth EL, Li H, Dzierlenga AL, Clarke JD, Vildhede A, Goedken M, Cherrington NJ. Gene-by-Environment Interaction of Bcrp-/- and Methionine- and Choline-Deficient Diet-Induced Nonalcoholic Steatohepatitis Alters SN-38 Disposition. Drug Metab Dispos. 2018 Nov;46(11):1478-1486. doi: 10.1124/dmd.118.082081. Epub 2018 Aug 30. PMID: 30166404; PMCID: PMC6193212. 11: Park JB, Kim D, Min JS, Jeong S, Cho DY, Zheng YF, Yoon KD, Bae SK. Identification and characterization of in vitro inhibitors against UDP- glucuronosyltransferase 1A1 in uva-ursi extracts and evaluation of in vivo uva- ursi-drug interactions. Food Chem Toxicol. 2018 Oct;120:651-661. doi: 10.1016/j.fct.2018.07.058. Epub 2018 Jul 31. PMID: 30075316. 12: Hahn RZ, Antunes MV, Verza SG, Perassolo MS, Suyenaga ES, Schwartsmann G, Linden R. Pharmacokinetic and Pharmacogenetic Markers of Irinotecan Toxicity. Curr Med Chem. 2019;26(12):2085-2107. doi: 10.2174/0929867325666180622141101. PMID: 29932028. 13: Chandrawati R, Olesen MTJ, Marini TCC, Bisra G, Guex AG, de Oliveira MG, Zelikin AN, Stevens MM. Enzyme Prodrug Therapy Engineered into Electrospun Fibers with Embedded Liposomes for Controlled, Localized Synthesis of Therapeutics. Adv Healthc Mater. 2017 Sep;6(17):10.1002/adhm.201700385. doi: 10.1002/adhm.201700385. Epub 2017 Jul 12. PMID: 28699219; PMCID: PMC5590711. 14: Lu W, Rettenmeier E, Paszek M, Yueh MF, Tukey RH, Trottier J, Barbier O, Chen S. Crypt Organoid Culture as an in Vitro Model in Drug Metabolism and Cytotoxicity Studies. Drug Metab Dispos. 2017 Jul;45(7):748-754. doi: 10.1124/dmd.117.075945. Epub 2017 May 3. PMID: 28468837; PMCID: PMC5478905. 15: Atasilp C, Chansriwong P, Sirachainan E, Reungwetwattana T, Puangpetch A, Prommas S, Sirilerttrakul S, Rerkarmnuaychoke B, Wongwaisayawan S, Sukasem C. Determination of irinotecan, SN-38 and SN-38 glucuronide using HPLC/MS/MS: Application in a clinical pharmacokinetic and personalized medicine in colorectal cancer patients. J Clin Lab Anal. 2018 Jan;32(1):e22217. doi: 10.1002/jcla.22217. Epub 2017 Apr 10. PMID: 28393405; PMCID: PMC6817234. 16: Mallick P, Basu S, Moorthy B, Ghose R. Role of Toll-like receptor 4 in drug- drug interaction between paclitaxel and irinotecan in vitro. Toxicol In Vitro. 2017 Jun;41:75-82. doi: 10.1016/j.tiv.2017.02.019. Epub 2017 Feb 27. PMID: 28242239; PMCID: PMC5479719. 17: Wang L, Chan CEL, Wong AL, Wong FC, Lim SW, Chinnathambi A, Alharbi SA, Lee LS, Soo R, Yong WP, Lee SC, Ho PC, Sethi G, Goh BC. Combined use of irinotecan with histone deacetylase inhibitor belinostat could cause severe toxicity by inhibiting SN-38 glucuronidation via UGT1A1. Oncotarget. 2017 Jun 20;8(25):41572-41581. doi: 10.18632/oncotarget.15017. PMID: 28157715; PMCID: PMC5522258. 18: Guillen KP, Ruben EA, Virani N, Harrison RG. Annexin-directed β-glucuronidase for the targeted treatment of solid tumors. Protein Eng Des Sel. 2017 Feb;30(2):85-94. doi: 10.1093/protein/gzw063. Epub 2016 Dec 15. PMID: 27986920; PMCID: PMC5241760. 19: Coriat R, Faivre SJ, Mir O, Dreyer C, Ropert S, Bouattour M, Desjardins R, Goldwasser F, Raymond E. Pharmacokinetics and safety of DTS-108, a human oligopeptide bound to SN-38 with an esterase-sensitive cross-linker in patients with advanced malignancies: a Phase I study. Int J Nanomedicine. 2016 Nov 21;11:6207-6216. doi: 10.2147/IJN.S110274. PMID: 27920527; PMCID: PMC5123727. 20: Basu S, Zeng M, Yin T, Gao S, Hu M. Development and validation of an UPLC- MS/MS method for the quantification of irinotecan, SN-38 and SN-38 glucuronide in plasma, urine, feces, liver and kidney: Application to a pharmacokinetic study of irinotecan in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 15;1015-1016:34-41. doi: 10.1016/j.jchromb.2016.02.012. Epub 2016 Feb 9. PMID: 26894853; PMCID: PMC5215916.