SN-38 | 10-hydroxy-7-ethyl-Camptothecin | CAS#86639-52-3

MedKoo Cat#: 406280 | Name: SN-38

Description:

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

SN-38 is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor); it is 1000 times more active than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN-38 is metabolized via glucoronidation by UGT1A1. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolization of irinotecan predicts irinotecan toxicity, as it cannot be excreted from the body in its SN-38 form. SN-38 is lost into the bile and feces. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.

Chemical Structure

SN-38

CAS#86639-52-3

Theoretical Analysis

MedKoo Cat#: 406280

Name: SN-38

CAS#: 86639-52-3

Chemical Formula: C22H20N2O5

Exact Mass: 392.1372

Molecular Weight: 392.40

Elemental Analysis: C, 67.34; H, 5.14; N, 7.14; O, 20.39

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	Ready to ship
10g	USD 1,650.00	Ready to Ship

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

SN38; SN-38; SN 38; 10-hydroxy-7-ethylcamptothecin; irinotecan metabolite.

IUPAC/Chemical Name

(S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

InChi Key

FJHBVJOVLFPMQE-QFIPXVFZSA-N

InChi Code

InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

SMILES Code

O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C(CC)C5=CC(O)=CC=C5N=C4C3=C2)=O

Appearance

Light yellow solid powder

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

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R06B25

QC Data

View QC data: current batch, Lot#C9R06B25

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

SN-38 inhibits DNA and RNA synthesis with IC50s of 0.077 and 1.3 μM, respectively.

In vitro activity:

SN-38 inhibits acute inflammation by blocking LPS-driven TLR4 signaling. Non-cytotoxic concentrations of SN-38 attenuated LPS (a TLR4 agonist)-driven cell activation without affecting peptidoglycan (a TLR2 agonist)-activating response. SN-38 abrogated LPS-dependent neutrophil migration and reduced TNF-α, IL-6, and keratinocyte chemoattractant levels in the air-pouch model, but failed to inhibit zymosan (a TLR2 agonist)-induced cell migration. Reference: Cancer Chemother Pharmacol. 2019 Aug;84(2):287-298. https://pubmed.ncbi.nlm.nih.gov/31011814/

In vivo activity:

The findings of this study suggest SN-38 as a potential adjunct to checkpoint inhibitor therapy in head and neck squamous cell carcinoma (HNSCC). In vivo, SN-38 enhanced anti-programmed cell death 1 efficacy, suppressing tumor growth and increasing immune cell infiltration. RNA-seq analysis indicated increased enrichment of immune-related genes. Reference: J Pathol. 2023 Apr;259(4):428-440. https://pubmed.ncbi.nlm.nih.gov/36641765/

	Solvent	mg/mL	mM
Solubility
	DMSO	24.2	61.57
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.76
	DMF	0.1	0.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 392.40 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:

1. Wong DVT, Ribeiro-Filho HV, Wanderley CWS, Leite CAVG, Lima JB, Assef ANB, Cajado AG, Batista GLP, González RH, Silva KO, Borges LPC, Alencar NMN, Wilke DV, Cunha TM, Figueira ACM, Cunha FQ, Lima-Júnior RCP. SN-38, the active metabolite of irinotecan, inhibits the acute inflammatory response by targeting toll-like receptor 4. Cancer Chemother Pharmacol. 2019 Aug;84(2):287-298. doi: 10.1007/s00280-019-03844-z. Epub 2019 Apr 22. PMID: 31011814. 2. Wallin A, Svanvik J, Holmlund B, Ferreud L, Sun XF. Anticancer effect of SN-38 on colon cancer cell lines with different metastatic potential. Oncol Rep. 2008 Jun;19(6):1493-8. PMID: 18497955. 3. Lee YM, Chen YH, Ou DL, Hsu CL, Liu JH, Ko JY, Hu MC, Tan CT. SN-38, an active metabolite of irinotecan, enhances anti-PD-1 treatment efficacy in head and neck squamous cell carcinoma. J Pathol. 2023 Apr;259(4):428-440. doi: 10.1002/path.6055. Epub 2023 Feb 24. PMID: 36641765. 4. Manzanares A, Restrepo-Perdomo CA, Botteri G, Castillo-Ecija H, Pascual-Pasto G, Cano F, Garcia-Alvarez L, Monterrubio C, Ruiz B, Vazquez-Carrera M, Suñol M, Mora J, Tornero JA, Sosnik A, Carcaboso AM. Tissue Compatibility of SN-38-Loaded Anticancer Nanofiber Matrices. Adv Healthc Mater. 2018 Aug;7(15):e1800255. doi: 10.1002/adhm.201800255. Epub 2018 Jun 11. PMID: 29892999.

In vitro protocol:

In vivo protocol:

1. Lee YM, Chen YH, Ou DL, Hsu CL, Liu JH, Ko JY, Hu MC, Tan CT. SN-38, an active metabolite of irinotecan, enhances anti-PD-1 treatment efficacy in head and neck squamous cell carcinoma. J Pathol. 2023 Apr;259(4):428-440. doi: 10.1002/path.6055. Epub 2023 Feb 24. PMID: 36641765. 2. Manzanares A, Restrepo-Perdomo CA, Botteri G, Castillo-Ecija H, Pascual-Pasto G, Cano F, Garcia-Alvarez L, Monterrubio C, Ruiz B, Vazquez-Carrera M, Suñol M, Mora J, Tornero JA, Sosnik A, Carcaboso AM. Tissue Compatibility of SN-38-Loaded Anticancer Nanofiber Matrices. Adv Healthc Mater. 2018 Aug;7(15):e1800255. doi: 10.1002/adhm.201800255. Epub 2018 Jun 11. PMID: 29892999.

1: Xiao S, Yin H, Lv X, Wang Z, Jiang L, Xia Y, Liu Y. Inhibition of human UDP- glucuronosyltransferase (UGT) enzymes by darolutamide: Prediction of in vivo drug-drug interactions. Chem Biol Interact. 2024 Sep 13;403:111246. doi: 10.1016/j.cbi.2024.111246. Epub ahead of print. PMID: 39278459. 2: McConville C, Lastakchi S, Al Amri A, Ngoga D, Fayeye O, Cruickshank G. Local Delivery of Irinotecan to Recurrent GBM Patients at Reoperation Offers a Safe Route of Administration. Cancers (Basel). 2024 Aug 29;16(17):3008. doi: 10.3390/cancers16173008. PMID: 39272866; PMCID: PMC11393903. 3: Hou X, Wei Z, Qi X, Liu D, Sun Y, Jiang Y, Liu C, Zhou W, Yang L, Liu K. Biomimetic modification of macrophage membrane-coated prussian blue nanoparticles loaded with SN-38 to treat colorectal cancer by photothermal- chemotherapy. Drug Deliv Transl Res. 2024 Sep 9. doi: 10.1007/s13346-024-01689-5. Epub ahead of print. PMID: 39251553. 4: Wang J, Tong Z, Tan Y, Shi Y, Wu Y, Zhou Q, Xing X, Chen X, Qiu F, Ma F. Phase 1a study of ESG401, a Trop2 antibody-drug conjugate, in patients with locally advanced/metastatic solid tumors. Cell Rep Med. 2024 Sep 17;5(9):101707. doi: 10.1016/j.xcrm.2024.101707. Epub 2024 Aug 30. PMID: 39216478. 5: Petrylak DP, Tagawa ST, Jain RK, Bupathi M, Balar A, Kalebasty AR, George S, Palmbos P, Nordquist L, Davis N, Ramamurthy C, Sternberg CN, Loriot Y, Agarwal N, Park C, Tonelli J, Vance M, Zhou H, Grivas P. TROPHY-U-01 Cohort 2: A Phase II Study of Sacituzumab Govitecan in Cisplatin-Ineligible Patients With Metastatic Urothelial Cancer Progressing After Previous Checkpoint Inhibitor Therapy. J Clin Oncol. 2024 Aug 26:JCO2301720. doi: 10.1200/JCO.23.01720. Epub ahead of print. PMID: 39186707. 6: Tian JR, Qiao YH, Zhuang QB, Fan R, Li Z, Zhang XM, Zhang FM, Tu YQ. Organo- cation catalyzed enantioselective α-hydroxylation of pyridinone-fused lactones: asymmetric synthesis of SN-38 and irinotecan. Chem Commun (Camb). 2024 Sep 10;60(73):9954-9957. doi: 10.1039/d4cc03580a. PMID: 39177032. 7: Wong MH, Jones VC, Yu W, Bosserman LD, Lavasani SM, Patel N, Sedrak MS, Stewart DB, Waisman JR, Yuan Y, Mortimer JE. UGT1A1*28 polymorphism and the risk of toxicity and disease progression in patients with breast cancer receiving sacituzumab govitecan. Cancer Med. 2024 Aug;13(16):e70096. doi: 10.1002/cam4.70096. PMID: 39157928; PMCID: PMC11331244. 8: Nair S, Selvo NS, Stolarski A, Klee B, Federico SM, Stewart CF. Quantitative determination of liposomal irinotecan and SN-38 concentrations in plasma samples from children with solid tumors: Use of a cryoprotectant solution to enhance liposome stability. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Sep 15;1245:124273. doi: 10.1016/j.jchromb.2024.124273. Epub 2024 Aug 14. PMID: 39146822. 9: Zheng Z, Šaponjac VT, Singh R, Chen J, Srinual S, Yin T, Sun R, Hu M. Fecal SN-38 Content as a Surrogate Predictor of Intestinal SN-38 Exposure and Associated Irinotecan-induced Severe Delayed-Onset Diarrhea by a Novel Use of the Spectrofluorimetric Method. Pharm Res. 2024 Aug 13. doi: 10.1007/s11095-024-03755-6. Epub ahead of print. PMID: 39138788. 10: Balinda HU, Kelly WJ, Kaklamani VG, Lathrop KI, Canola MM, Ghamasaee P, Sareddy GR, Michalek J, Gilbert AR, Surapaneni P, Tiziani S, Pandey R, Chiou J, Lodi A, Floyd JR 2nd, Brenner AJ. Sacituzumab Govitecan in patients with breast cancer brain metastases and recurrent glioblastoma: a phase 0 window-of- opportunity trial. Nat Commun. 2024 Aug 7;15(1):6707. doi: 10.1038/s41467-024-50558-9. PMID: 39112464; PMCID: PMC11306739. 11: Loriot Y, Balar AV, Petrylak DP, Kalebasty AR, Grivas P, Fléchon A, Jain RK, Swami U, Bupathi M, Barthélémy P, Beuzeboc P, Palmbos P, Kyriakopoulos CE, Pouessel D, Sternberg CN, Tonelli J, Sierecki M, Zavodovskaya M, Elboudwarej E, Diehl L, Jürgensmeier JM, Tagawa ST. Sacituzumab Govitecan Demonstrates Efficacy across Tumor Trop-2 Expression Levels in Patients with Advanced Urothelial Cancer. Clin Cancer Res. 2024 Aug 1;30(15):3179-3188. doi: 10.1158/1078-0432.CCR-23-3924. PMID: 39086310. 12: Tanita K, Koseki Y, Kumar S, Taemaitree F, Mizutani A, Nakatsuji H, Suzuki R, Dao ATN, Fujishima F, Tada H, Ishida T, Saijo K, Ishioka C, Kasai H. Carrier- free nano-prodrugs for minimally invasive cancer therapy. Nanoscale. 2024 Aug 15;16(32):15256-15264. doi: 10.1039/d4nr01763c. PMID: 39073351. 13: Schmutz C, Plaza C, Steiger F, Stoirer N, Gufler J, Pahlke G, Will F, Berger W, Marko D. Anthocyanin-Rich Berry Extracts Affect SN-38-Induced Response: A Comparison of Non-Tumorigenic HCEC-1CT and HCT116 Colon Carcinoma Cells. Antioxidants (Basel). 2024 Jul 15;13(7):846. doi: 10.3390/antiox13070846. PMID: 39061915; PMCID: PMC11273996. 14: Jiang Y, Xu X, Fan D, Liu P, Zhou M, Cheng M, Huang J, Luo Y, Guo Y, Yang T. Advancing Tumor-Targeted Chemo-Immunotherapy: Development of the CAR-M-derived Exosome-Drug Conjugate. J Med Chem. 2024 Aug 22;67(16):13959-13974. doi: 10.1021/acs.jmedchem.4c00753. Epub 2024 Jul 23. PMID: 39041307. 15: Ji D, Shen W, Li T, Wang H, Bai J, Cao J, Hu X. Liposomal irinotecan (HR070803) in combination with 5-fluorouracil and leucovorin in patients with advanced solid tumors: a phase 1b dose-escalation and expansion study. Invest New Drugs. 2024 Aug;42(4):462-470. doi: 10.1007/s10637-024-01442-2. Epub 2024 Jul 22. PMID: 39037543; PMCID: PMC11327190. 16: Sabljo K, Ischyropoulou M, Napp J, Alves F, Feldmann C. High-load nanoparticles with a chemotherapeutic SN-38/FdUMP drug cocktail. Nanoscale. 2024 Aug 13;16(31):14853-14860. doi: 10.1039/d4nr01403k. PMID: 39034735. 17: Leylek O, Honeywell ME, Lee MJ, Hemann MT, Ozcan G. Functional genomics reveals an off-target dependency of drug synergy in gastric cancer therapy. Gastric Cancer. 2024 Jul 20. doi: 10.1007/s10120-024-01537-y. Epub ahead of print. PMID: 39033209. 18: Zarnoosheh Farahani T, Nejadmoghaddam MR, Sari S, Ghahremanzadeh R, Minai- Tehrani A. Generation of anti-SN38 antibody for loading efficacy and therapeutic monitoring of SN38-containing therapeutics. Heliyon. 2024 Jun 18;10(12):e33232. doi: 10.1016/j.heliyon.2024.e33232. PMID: 39021912; PMCID: PMC11253049. 19: Marsh DT, Smid SD. Selected phytocannabinoids inhibit SN-38- and cytokine- evoked increases in epithelial permeability and improve intestinal barrier function in vitro. Toxicol In Vitro. 2024 Aug;99:105888. doi: 10.1016/j.tiv.2024.105888. Epub 2024 Jun 29. PMID: 38950639. 20: Nakayama Y, Ino A, Yamamoto K, Takara K. Down-regulation of ABCB1 in Everolimus-resistant Renal Cell Carcinoma Cells. Anticancer Res. 2024 Jul;44(7):2871-2876. doi: 10.21873/anticanres.17099. PMID: 38925842.

1. Yang Y, Wu ZX, Wang JQ, Teng QX, Lei ZN, Lusvarghi S, Ambudkar SV, Chen ZS, Yang DH. OTS964, a TOPK Inhibitor, Is Susceptible to ABCG2-Mediated Drug Resistance. Front Pharmacol. 2021 Feb 15;12:620874. doi: 10.3389/fphar.2021.620874. PMID: 33658942; PMCID: PMC7917255.