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

SN-38 Glucuronide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 556186

CAS#: 121080-63-5

Description: 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

CAS# 121080-63-5

Instruction

Theoretical Analysis

MedKoo Cat#: 556186
Name: SN-38 Glucuronide
CAS#: 121080-63-5
Chemical Formula: C28H28N2O11
Exact Mass: 568.17
Molecular Weight: 568.540
Elemental Analysis: C, 59.15; H, 4.96; N, 4.93; O, 30.95

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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.

2: 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.

3: 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.

4: Satoh T, Yasui H, Muro K, Komatsu Y, Sameshima S, Yamaguchi K, Sugihara K. Pharmacokinetic assessment of irinotecan, SN-38, and SN-38-glucuronide: a substudy of the FIRIS study. Anticancer Res. 2013 Sep;33(9):3845-53. PMID: 24023318.

5: Hirose K, Kozu C, Yamashita K, Maruo E, Kitamura M, Hasegawa J, Omoda K, Murakami T, Maeda Y. Correlation between plasma concentration ratios of SN-38 glucuronide and SN-38 and neutropenia induction in patients with colorectal cancer and wild-type UGT1A1 gene. Oncol Lett. 2012 Mar;3(3):694-698. doi: 10.3892/ol.2011.533. Epub 2011 Dec 22. PMID: 22740978; PMCID: PMC3362497.

6: Takakura A, Kurita A, Asahara T, Yokoba M, Yamamoto M, Ryuge S, Igawa S, Yasuzawa Y, Sasaki J, Kobayashi H, Masuda N. Rapid deconjugation of SN-38 glucuronide and adsorption of released free SN-38 by intestinal microorganisms in rat. Oncol Lett. 2012 Mar;3(3):520-524. doi: 10.3892/ol.2011.519. Epub 2011 Dec 9. PMID: 22740943; PMCID: PMC3362476.

7: Kato A, Ueyama J, Abe F, Hotta K, Tsukiyama I, Oshima T, Kondo F, Saito H, Hasegawa T. Panipenem does not alter the pharmacokinetics of the active metabolite of irinotecan SN-38 and inactive metabolite SN-38 glucuronide (SN-38G) in rats. Anticancer Res. 2011 Sep;31(9):2915-22. PMID: 21868538.

8: Klein CE, Gupta E, Reid JM, Atherton PJ, Sloan JA, Pitot HC, Ratain MJ, Kastrissios H. Population pharmacokinetic model for irinotecan and two of its metabolites, SN-38 and SN-38 glucuronide. Clin Pharmacol Ther. 2002 Dec;72(6):638-47. doi: 10.1067/mcp.2002.129502. PMID: 12496745.

9: Natsui S, Maruyama M, Ochiai T, Hasegawa K, Takashima I, Nagahama T, Ebuchi M. [Pharmacokinetic study of CPT-11, SN-38 and SN-38 glucuronide in the ascites, plasma and bile after intraperitoneal administration of CPT-11]. Gan To Kagaku Ryoho. 2002 Nov;29(12):2188-90. Japanese. PMID: 12484033.

10: Sloan JA, Atherton P, Reid J, Pitot HC, Erlichman C, Schaaf L. Limited sampling models for CPT-11, SN-38, and SN-38 glucuronide. Cancer Chemother Pharmacol. 2001 Sep;48(3):241-9. doi: 10.1007/s002800100296. PMID: 11592347.

11: Kurita A, Kaneda N. High-performance liquid chromatographic method for the simultaneous determination of the camptothecin derivative irinotecan hydrochloride, CPT-11, and its metabolites SN-38 and SN-38 glucuronide in rat plasma with a fully automated on-line solid-phase extraction system, PROSPEKT. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):335-44. doi: 10.1016/s0378-4347(98)00554-4. PMID: 10219676.

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