OP-1118 | CAS# 1030825-28-5 | Biochemical

MedKoo Cat#: 574531 | Name: OP-1118

Featured

Description:

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

OP-1118 is a major metabolite of Fidaxomicin. Fidaxomicin and OP-1118 inhibited toxin A-mediated NF-kappaB phosphorylation in human and mouse intestinal mucosae.

Chemical Structure

OP-1118

CAS#1030825-28-5

Theoretical Analysis

MedKoo Cat#: 574531

Name: OP-1118

CAS#: 1030825-28-5

Chemical Formula: C48H68Cl2O17

Exact Mass: 986.3834

Molecular Weight: 987.96

Elemental Analysis: C, 58.36; H, 6.94; Cl, 7.18; O, 27.53

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks
50mg	USD 2,200.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

OP-1118

IUPAC/Chemical Name

(2S,3R,4R,5R,6S)-6-(((3E,5E,8S,9E,11S,12R,13E,15E,18S)-11-ethyl-8-hydroxy-18-((R)-1-hydroxyethyl)-9,13,15-trimethyl-2-oxo-12-(((2R,3S,4S,5S)-3,4,5-trihydroxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl)methoxy)-4-hydroxy-5-methoxy-2-methyltetrahydro-2H-pyran-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate

InChi Key

MWZWKUKATWMWGS-FXYIDGSOSA-N

InChi Code

InChI=1S/C48H68Cl2O17/c1-11-27-20-23(4)30(52)16-14-13-15-28(21-62-47-42(61-10)39(57)41(26(7)63-47)65-45(60)32-29(12-2)33(49)36(54)34(50)35(32)53)44(59)64-31(25(6)51)18-17-22(3)19-24(5)40(27)66-46-38(56)37(55)43(58)48(8,9)67-46/h13-15,17,19-20,25-27,30-31,37-43,46-47,51-58H,11-12,16,18,21H2,1-10H3/b14-13+,22-17+,23-20+,24-19+,28-15+/t25-,26+,27+,30+,31+,37-,38+,39-,40+,41+,42-,43+,46-,47+/m1/s1

SMILES Code

CC[C@H]1\C=C(/C)\[C@@H](O)C\C=C\C=C(/CO[C@H]2O[C@@H](C)[C@H](OC(=O)c3c(O)c(Cl)c(O)c(Cl)c3CC)[C@@H](O)[C@H]2OC)\C(=O)O[C@@H](C\C=C(/C)\C=C(/C)\[C@@H]1O[C@@H]4OC(C)(C)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](C)O

Appearance

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

Shelf Life

>3 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

Instruction

View handling instruction

Biological target:

OP-1118 is a major metabolite of Fidaxomicin.

In vitro activity:

This study used fresh human colonic explants, NCM460 human colonic epithelial cells, and RAW264.7 mouse macrophages to study the mechanism of the activity of fidaxomicin and OP-1118 against toxin A- and B-mediated cytokine expression and apoptosis. Fidaxomicin and OP-1118 dose-dependently inhibited toxin A- and B-induced TNF-α and interleukin-1β (IL-1β) mRNA expression and histological damage in human colonic explants. Fidaxomicin and OP-1118 inhibited toxin A-mediated NF-κB phosphorylation in human and mouse intestinal mucosae. Fidaxomicin and OP-1118 also inhibited toxin A-mediated NF-κB phosphorylation and TNF-α expression in macrophages, which was reversed by the NF-κB activator phorbol myristate acetate (PMA). Reference: Antimicrob Agents Chemother. 2017 Dec 21;62(1):e01513-17. https://pubmed.ncbi.nlm.nih.gov/29038278/

In vivo activity:

Based on the in vitro cytotoxicity and the responses of inhibiting the Notch signaling, the antitumor efficacy of fidaxomicin in 4T1-tumor-bearing mice was then evaluated. Fidaxomicin demonstrated potent anti-cancer activity, yielding 62.56% and 83.19% inhibitory efficacies on the growth of tumors at 25 and 25 mg/kg, respectively (Figure 9c). The average tumor weight of mice treated with fidaxomicin was significantly lower than that of mice treated with DAPT or 5-fluorouracil at a dose of 25 mg/kg, indicating the greatest anti-tumor ability among the three treatment groups. Reference: Pharmaceuticals (Basel). 2022 Apr 29;15(5):556. https://pubmed.ncbi.nlm.nih.gov/35631382/

Preparing Stock Solutions

The following data is based on the product molecular weight 987.96 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. Koon HW, Wang J, Mussatto CC, Ortiz C, Lee EC, Tran DH, Chen X, Kelly CP, Pothoulakis C. Fidaxomicin and OP-1118 Inhibit Clostridium difficile Toxin A- and B-Mediated Inflammatory Responses via Inhibition of NF-κB Activity. Antimicrob Agents Chemother. 2017 Dec 21;62(1):e01513-17. doi: 10.1128/AAC.01513-17. PMID: 29038278; PMCID: PMC5740352. 2. Babakhani F, Bouillaut L, Gomez A, Sears P, Nguyen L, Sonenshein AL. Fidaxomicin inhibits spore production in Clostridium difficile. Clin Infect Dis. 2012 Aug;55 Suppl 2(Suppl 2):S162-9. doi: 10.1093/cid/cis453. PMID: 22752866; PMCID: PMC3388029. 3. Rui M, Cai M, Zhou Y, Zhang W, Gao L, Mi K, Ji W, Wang D, Feng C. Identification of Potential RBPJ-Specific Inhibitors for Blocking Notch Signaling in Breast Cancer Using a Drug Repurposing Strategy. Pharmaceuticals (Basel). 2022 Apr 29;15(5):556. doi: 10.3390/ph15050556. PMID: 35631382; PMCID: PMC9146688. 4. Yuan J, Yu J, Huang Y, He Z, Luo J, Wu Y, Zheng Y, Wu J, Zhu X, Wang H, Li M. Antibiotic fidaxomicin is an RdRp inhibitor as a potential new therapeutic agent against Zika virus. BMC Med. 2020 Jul 31;18(1):204. doi: 10.1186/s12916-020-01663-1. PMID: 32731873; PMCID: PMC7392643.

In vitro protocol:

In vivo protocol:

1. Rui M, Cai M, Zhou Y, Zhang W, Gao L, Mi K, Ji W, Wang D, Feng C. Identification of Potential RBPJ-Specific Inhibitors for Blocking Notch Signaling in Breast Cancer Using a Drug Repurposing Strategy. Pharmaceuticals (Basel). 2022 Apr 29;15(5):556. doi: 10.3390/ph15050556. PMID: 35631382; PMCID: PMC9146688. 2. Yuan J, Yu J, Huang Y, He Z, Luo J, Wu Y, Zheng Y, Wu J, Zhu X, Wang H, Li M. Antibiotic fidaxomicin is an RdRp inhibitor as a potential new therapeutic agent against Zika virus. BMC Med. 2020 Jul 31;18(1):204. doi: 10.1186/s12916-020-01663-1. PMID: 32731873; PMCID: PMC7392643.

1: Sambol SP, Skinner AM, Serna-Perez F, Owen B, Gerding DN, Johnson S. Effective Colonization by Nontoxigenic Clostridioides difficile REA Strain M3 (NTCD-M3) Spores following Treatment with Either Fidaxomicin or Vancomycin. Microbiol Spectr. 2023 Mar 28;11(2):e0051723. doi: 10.1128/spectrum.00517-23. Epub ahead of print. PMID: 36975811; PMCID: PMC10100807. 2: Cao YR, Li YF, Wang JJ, Yang HJ, Wei Q, Yu JC, Cao GY, Gao J, Zhang J, Li XN, Yu SY. Pharmacokinetic evaluation and relative bioavailability pilot study of fidaxomicin in healthy Chinese subjects: An open, randomized, single-dose, cross-over study. Int J Clin Pharmacol Ther. 2022 Oct;60(10):448-458. doi: 10.5414/CP204263. PMID: 35979900. 3: Guery B, Georgopali A, Karas A, Kazeem G, Michon I, Wilcox MH, Cornely OA. Pharmacokinetic analysis of an extended-pulsed fidaxomicin regimen for the treatment of Clostridioides (Clostridium) difficile infection in patients aged 60 years and older in the EXTEND randomized controlled trial. J Antimicrob Chemother. 2020 Apr 1;75(4):1014-1018. doi: 10.1093/jac/dkz549. PMID: 31960058. 4: Wolf J, Kalocsai K, Fortuny C, Lazar S, Bosis S, Korczowski B, Petit A, Bradford D, Croos-Dabrera R, Incera E, Melis J, van Maanen R. Safety and Efficacy of Fidaxomicin and Vancomycin in Children and Adolescents with Clostridioides (Clostridium) difficile Infection: A Phase 3, Multicenter, Randomized, Single-blind Clinical Trial (SUNSHINE). Clin Infect Dis. 2020 Dec 17;71(10):2581-2588. doi: 10.1093/cid/ciz1149. PMID: 31773143; PMCID: PMC7744996. 5: Högenauer C, Mahida Y, Stallmach A, Marteau P, Rydzewska G, Ivashkin V, Gargalianos-Kakolyris P, Michon I, Adomakoh N, Georgopali A, Tretter R, Karas A, Reinisch W. Pharmacokinetics and safety of fidaxomicin in patients with inflammatory bowel disease and Clostridium difficile infection: an open-label Phase IIIb/IV study (PROFILE). J Antimicrob Chemother. 2018 Dec 1;73(12):3430-3441. doi: 10.1093/jac/dky368. PMID: 30260412. 6: Yanagihara K, Akamatsu N, Matsuda J, Kaku N, Katsumata K, Kosai K. Susceptibility of Clostridium species isolated in Japan to fidaxomicin and its major metabolite OP-1118. J Infect Chemother. 2018 Jun;24(6):492-495. doi: 10.1016/j.jiac.2017.12.006. Epub 2018 Jan 17. PMID: 29373265. 7: Koon HW, Wang J, Mussatto CC, Ortiz C, Lee EC, Tran DH, Chen X, Kelly CP, Pothoulakis C. Fidaxomicin and OP-1118 Inhibit Clostridium difficile Toxin A- and B-Mediated Inflammatory Responses via Inhibition of NF-κB Activity. Antimicrob Agents Chemother. 2017 Dec 21;62(1):e01513-17. doi: 10.1128/AAC.01513-17. PMID: 29038278; PMCID: PMC5740352. 8: Cataldo MA, Granata G, Petrosillo N. Clostridium difficile infection: new approaches to prevention, non-antimicrobial treatment, and stewardship. Expert Rev Anti Infect Ther. 2017 Nov;15(11):1027-1040. doi: 10.1080/14787210.2017.1387535. Epub 2017 Oct 9. PMID: 28980505. 9: O'Gorman MA, Michaels MG, Kaplan SL, Otley A, Kociolek LK, Hoffenberg EJ, Kim KS, Nachman S, Pfefferkorn MD, Sentongo T, Sullivan JE, Sears P. Safety and Pharmacokinetic Study of Fidaxomicin in Children With Clostridium difficile- Associated Diarrhea: A Phase 2a Multicenter Clinical Trial. J Pediatric Infect Dis Soc. 2018 Aug 17;7(3):210-218. doi: 10.1093/jpids/pix037. PMID: 28575523. 10: Zhanel GG, Walkty AJ, Karlowsky JA. Fidaxomicin: A novel agent for the treatment of Clostridium difficile infection. Can J Infect Dis Med Microbiol. 2015 Nov-Dec;26(6):305-12. doi: 10.1155/2015/934594. PMID: 26744587; PMCID: PMC4692299. 11: Srinivas NR. Fidaxomicin Pharmacokinetics in Humans: Is There a Role of Biliary Excretion? Clin Drug Investig. 2015 Aug;35(8):531-2. doi: 10.1007/s40261-015-0305-7. PMID: 26135594. 12: Chahine EB, Sucher AJ, Mantei K. Fidaxomicin: a novel macrolide antibiotic for Clostridium difficile infection. Consult Pharm. 2014 Sep;29(9):614-24. doi: 10.4140/TCP.n.2014.614.. PMID: 25203410. 13: Koon HW, Ho S, Hing TC, Cheng M, Chen X, Ichikawa Y, Kelly CP, Pothoulakis C. Fidaxomicin inhibits Clostridium difficile toxin A-mediated enteritis in the mouse ileum. Antimicrob Agents Chemother. 2014 Aug;58(8):4642-50. doi: 10.1128/AAC.02783-14. Epub 2014 Jun 2. PMID: 24890583; PMCID: PMC4135997. 14: Babakhani F, Bouillaut L, Sears P, Sims C, Gomez A, Sonenshein AL. Fidaxomicin inhibits toxin production in Clostridium difficile. J Antimicrob Chemother. 2013 Mar;68(3):515-22. doi: 10.1093/jac/dks450. Epub 2012 Dec 2. PMID: 23208832. 15: Allen CA, Babakhani F, Sears P, Nguyen L, Sorg JA. Both fidaxomicin and vancomycin inhibit outgrowth of Clostridium difficile spores. Antimicrob Agents Chemother. 2013 Jan;57(1):664-7. doi: 10.1128/AAC.01611-12. Epub 2012 Nov 12. PMID: 23147724; PMCID: PMC3535933. 16: Babakhani F, Bouillaut L, Gomez A, Sears P, Nguyen L, Sonenshein AL. Fidaxomicin inhibits spore production in Clostridium difficile. Clin Infect Dis. 2012 Aug;55 Suppl 2(Suppl 2):S162-9. doi: 10.1093/cid/cis453. PMID: 22752866; PMCID: PMC3388029. 17: Goldstein EJ, Babakhani F, Citron DM. Antimicrobial activities of fidaxomicin. Clin Infect Dis. 2012 Aug;55 Suppl 2(Suppl 2):S143-8. doi: 10.1093/cid/cis339. PMID: 22752863; PMCID: PMC3388021. 18: Sears P, Crook DW, Louie TJ, Miller MA, Weiss K. Fidaxomicin attains high fecal concentrations with minimal plasma concentrations following oral administration in patients with Clostridium difficile infection. Clin Infect Dis. 2012 Aug;55 Suppl 2(Suppl 2):S116-20. doi: 10.1093/cid/cis337. PMID: 22752859; PMCID: PMC3388019. 19: Babakhani F, Gomez A, Robert N, Sears P. Postantibiotic effect of fidaxomicin and its major metabolite, OP-1118, against Clostridium difficile. Antimicrob Agents Chemother. 2011 Sep;55(9):4427-9. doi: 10.1128/AAC.00104-11. Epub 2011 Jun 27. PMID: 21709084; PMCID: PMC3165303. 20: Babakhani F, Gomez A, Robert N, Sears P. Killing kinetics of fidaxomicin and its major metabolite, OP-1118, against Clostridium difficile. J Med Microbiol. 2011 Aug;60(Pt 8):1213-1217. doi: 10.1099/jmm.0.029470-0. Epub 2011 Feb 24. PMID: 21349983; PMCID: PMC3167880.