WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H319695
CAS#: 1334714-66-7 (2HCl)
Description: Eravacycline, also known as TP-434, a novel antibiotics. Eravacycline showed potent broad-spectrum activity against 90% of the isolates (MIC90) in each panel at concentrations ranging from ≤0.008 to 2 μg/ml for all species panels except those of Pseudomonas aeruginosa and Burkholderia cenocepacia (MIC90 values of 32 μg/ml for both organisms). The antibacterial activity of eravacycline was minimally affected by expression of tetracycline-specific efflux and ribosomal protection mechanisms in clinical isolates. Furthermore, eravacycline was active against multidrug-resistant bacteria. Eravacycline has the potential to be a promising new intravenous (i.v.)/oral antibiotic for the empirical treatment of complicated hospital/health care infections and moderate-to-severe community-acquired infections.
Hodoodo Cat#: H319695
Name: Eravacycline HCl
CAS#: 1334714-66-7 (2HCl)
Chemical Formula: C27H33Cl2FN4O8
Exact Mass: 0.00
Molecular Weight: 631.480
Elemental Analysis: C, 51.36; H, 5.27; Cl, 11.23; F, 3.01; N, 8.87; O, 20.27
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Related CAS #: 1207283-85-9 (free base) 1334714-66-7 (2HCl)
Synonym: TP-434-046; TP 434-046; TP434-046; TP-434 2HCl; TP 434 2HCl; TP434 2HCl; TP-434 dihydrochloride; TP 434 dihydrochloride; TP434 dihydrochloride; Eravacycline HCl; Eravacycline 2HCl; Eravacycline dihydrochloride
IUPAC/Chemical Name: (4S,4aS,5aR,12aS)-4-(Dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-((pyrrolidin-1-ylacetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide dihydrochloride
InChi Key: JYCNMRVZELJVAW-RZVFYPHASA-N
InChi Code: InChI=1S/C27H31FN4O8.2ClH/c1-31(2)20-13-8-11-7-12-14(28)9-15(30-16(33)10-32-5-3-4-6-32)21(34)18(12)22(35)17(11)24(37)27(13,40)25(38)19(23(20)36)26(29)39;;/h9,11,13,20,34,36-37,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33);2*1H/t11-,13-,20-,27-;;/m0../s1
SMILES Code: O=C(C1=C(O)[C@@H](N(C)C)[C@@](C[C@@]2([H])C(C(C3=C(O)C(NC(CN4CCCC4)=O)=CC(F)=C3C2)=O)=C5O)([H])[C@@]5(O)C1=O)N.[H]Cl.[H]Cl
Appearance: Solid powder
Purity: >95% (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 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: Eravacycline (TP-434, Xerava) is a synthetic halogenated tetracycline class antibiotic by Tetraphase Pharmaceuticals. It is closely related to tigecycline. It has a broad spectrum of activity including many multi-drug resistant strains of bacteria. Phase III studies in complicated intra-abdominal infections (cIAI) and complicated urinary tract infections (cUTI) were recently completed with mixed results. Eravacycline was granted fast track designation by the FDA and is currently available in USA. (from https://en.wikipedia.org/wiki/Eravacycline).
| Biological target: | Eravacycline HCl is a potent and broad-spectrum antibacterial agent. |
| In vitro activity: | This study provides evidence, including a novel X-ray structure, that SF2312 is a highly potent, low-nanomolar inhibitor of enolase. It demonstrated that SF2312 is active against a range of bacteria, with strong activity against Salmonella and Staphylococcus, weak activity against E. coli, and no activity against fungi. Reference: Nat Chem Biol. 2016 Dec;12(12):1053-1058. https://pubmed.ncbi.nlm.nih.gov/27723749/ |
| In vivo activity: | Eravacycline was active in multiple murine models of infection against clinically important Gram-positive and Gram-negative pathogens. Eravacycline showed effectiveness against Staphylococcus aureus and Streptococcus pyogenes, including resistant strains, as well as Escherichia coli. In lung and kidney infection models, it reduced bacterial burden significantly, outperforming other antibiotics in some cases. Reference: Antimicrob Agents Chemother. 2015 May;59(5):2567-71. https://pubmed.ncbi.nlm.nih.gov/25691636/ |
The following data is based on the product molecular weight 631.48 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. Krucinska J, Lombardo MN, Erlandsen H, Hazeen A, Duay SS, Pattis JG, Robinson VL, May ER, Wright DL. Functional and structural basis of E. coli enolase inhibition by SF2312: a mimic of the carbanion intermediate. Sci Rep. 2019 Nov 19;9(1):17106. doi: 10.1038/s41598-019-53301-3. PMID: 31745118; PMCID: PMC6863902. 2. Leonard PG, Satani N, Maxwell D, Lin YH, Hammoudi N, Peng Z, Pisaneschi F, Link TM, Lee GR 4th, Sun D, Prasad BAB, Di Francesco ME, Czako B, Asara JM, Wang YA, Bornmann W, DePinho RA, Muller FL. SF2312 is a natural phosphonate inhibitor of enolase. Nat Chem Biol. 2016 Dec;12(12):1053-1058. doi: 10.1038/nchembio.2195. Epub 2016 Oct 10. PMID: 27723749; PMCID: PMC5110371. 3. Özel Y, Çavuş İ, Ünlü M, Özbilgin A. Sıtma Modelinde Cinnamaldehyde, Cannabidiol ve Eravacycline’in Etkinliğinin Araştırılması [Investigation of the Efficacy of Cinnamaldehyde, Cannabidiol and Eravacycline in a Malaria Model]. Mikrobiyol Bul. 2023 Oct;57(4):608-624. Turkish. doi: 10.5578/mb.20239949. PMID: 37885389. 4. Grossman TH, Murphy TM, Slee AM, Lofland D, Sutcliffe JA. Eravacycline (TP-434) is efficacious in animal models of infection. Antimicrob Agents Chemother. 2015 May;59(5):2567-71. doi: 10.1128/AAC.04354-14. Epub 2015 Feb 17. PMID: 25691636; PMCID: PMC4394802. |
| In vitro protocol: | 1. Krucinska J, Lombardo MN, Erlandsen H, Hazeen A, Duay SS, Pattis JG, Robinson VL, May ER, Wright DL. Functional and structural basis of E. coli enolase inhibition by SF2312: a mimic of the carbanion intermediate. Sci Rep. 2019 Nov 19;9(1):17106. doi: 10.1038/s41598-019-53301-3. PMID: 31745118; PMCID: PMC6863902. 2. Leonard PG, Satani N, Maxwell D, Lin YH, Hammoudi N, Peng Z, Pisaneschi F, Link TM, Lee GR 4th, Sun D, Prasad BAB, Di Francesco ME, Czako B, Asara JM, Wang YA, Bornmann W, DePinho RA, Muller FL. SF2312 is a natural phosphonate inhibitor of enolase. Nat Chem Biol. 2016 Dec;12(12):1053-1058. doi: 10.1038/nchembio.2195. Epub 2016 Oct 10. PMID: 27723749; PMCID: PMC5110371. |
| In vivo protocol: | 1. Özel Y, Çavuş İ, Ünlü M, Özbilgin A. Sıtma Modelinde Cinnamaldehyde, Cannabidiol ve Eravacycline’in Etkinliğinin Araştırılması [Investigation of the Efficacy of Cinnamaldehyde, Cannabidiol and Eravacycline in a Malaria Model]. Mikrobiyol Bul. 2023 Oct;57(4):608-624. Turkish. doi: 10.5578/mb.20239949. PMID: 37885389. 2. Grossman TH, Murphy TM, Slee AM, Lofland D, Sutcliffe JA. Eravacycline (TP-434) is efficacious in animal models of infection. Antimicrob Agents Chemother. 2015 May;59(5):2567-71. doi: 10.1128/AAC.04354-14. Epub 2015 Feb 17. PMID: 25691636; PMCID: PMC4394802. |
1: Jackson MNW, Wei W, Mang NS, Prokesch BC, Ortwine JK. Combination eravacycline therapy for ventilator-associated pneumonia due to carbapenem- resistant Acinetobacter baumannii in patients with COVID-19: A case series. Pharmacotherapy. 2024 Jan 25. doi: 10.1002/phar.2908. Epub ahead of print. PMID: 38270447.
2: Kunz Coyne AJ, Alosaimy S, Lucas K, Lagnf AM, Morrisette T, Molina KC, DeKerlegand A, Schrack MR, Kang-Birken SL, Hobbs AL, Agee J, Perkins NB 3rd, Biagi M, Pierce M, Truong J, Andrade J, Bouchard J, Gore T, King MA, Pullinger BM, Claeys KC, Herbin S, Cosimi R, Tart S, Veve MP, Jones BM, Rojas LM, Feehan AK, Scipione MR, Zhao JJ, Witucki P, Rybak MJ. Eravacycline, the first four years: health outcomes and tolerability data for 19 hospitals in 5 U.S. regions from 2018 to 2022. Microbiol Spectr. 2024 Jan 11;12(1):e0235123. doi: 10.1128/spectrum.02351-23. Epub 2023 Nov 29. PMID: 38018984; PMCID: PMC10782980.
3: Alexander C, Hill D. A retrospective case-control study of eravacycline for the treatment of carbapenem-resistant Acinetobacter infections in patients with burn injuries. J Burn Care Res. 2023 Nov 16:irad183. doi: 10.1093/jbcr/irad183. Epub ahead of print. PMID: 37971422.
4: Özel Y, Çavuş İ, Ünlü M, Özbilgin A. Sıtma Modelinde Cinnamaldehyde, Cannabidiol ve Eravacycline’in Etkinliğinin Araştırılması [Investigation of the Efficacy of Cinnamaldehyde, Cannabidiol and Eravacycline in a Malaria Model]. Mikrobiyol Bul. 2023 Oct;57(4):608-624. Turkish. doi: 10.5578/mb.20239949. PMID: 37885389.
5: Li X, Yang H, Duan X, Cui M, Xing W, Zheng S. Synergistic effect of eravacycline combined with fluconazole against resistant Candida albicans in vitro and in vivo. Expert Rev Anti Infect Ther. 2023 Jul-Dec;21(11):1259-1267. doi: 10.1080/14787210.2023.2270160. Epub 2023 Nov 8. PMID: 37818633.
6: Stefanos SS, Davis L, Panwala A, Gelfand MS, Animalu CN, Cutshall BT. Prolonged course of eravacycline leading to acute pancreatitis. Am J Med Sci. 2023 Dec;366(6):464-467. doi: 10.1016/j.amjms.2023.09.012. Epub 2023 Sep 15. PMID: 37716601.
7: Buckley V, Tran M, Price T, Singh S, Stramel S. Use of Eravacycline for Acinetobacter baumannii Infections: A Case Series. J Pharm Pract. 2023 Sep 16:8971900231196076. doi: 10.1177/08971900231196076. Epub ahead of print. PMID: 37715948.
8: Wu J, Zhang G, Zhao Q, Wang L, Yang J, Cui J. In vitro Antimicrobial Activity and Dose Optimization of Eravacycline and Other Tetracycline Derivatives Against Levofloxacin-Non-Susceptible and/or Trimethoprim-Sulfamethoxazole-Resistant Stenotrophomonas maltophilia. Infect Drug Resist. 2023 Sep 8;16:6005-6015. doi: 10.2147/IDR.S425061. PMID: 37705512; PMCID: PMC10497097.
9: Rahul R, Maheswary D, Damodaran N, Leela KV. Eravacycline -Synergistic activity with other antimicrobials in carbapenem resistant isolates of Escherichia coli and Acinetobacter baumannii. Diagn Microbiol Infect Dis. 2023 Nov;107(3):116006. doi: 10.1016/j.diagmicrobio.2023.116006. Epub 2023 Jun 14. PMID: 37604046.
10: Brauncajs M, Bielec F, Macieja A, Pastuszak-Lewandoska D. In Vitro Activity of Eravacycline against Carbapenemase-Producing Gram-Negative Bacilli Clinical Isolates in Central Poland. Biomedicines. 2023 Jun 21;11(7):1784. doi: 10.3390/biomedicines11071784. PMID: 37509424; PMCID: PMC10376096.
11: Özer B, Özbek Çelık B. Comparative in vitro activities of eravacycline in combination with colistin, meropenem, or ceftazidime against various Achromobacter spp. strains isolated from patients with cystic fibrosis. J Chemother. 2023 Dec;35(8):700-706. doi: 10.1080/1120009X.2023.2213600. Epub 2023 May 21. PMID: 37211830.
12: Hawser S, Kothari N, Monti F, Morrissey I, Siegert S, Hodges T. In vitro activity of eravacycline and comparators against Gram-negative and Gram-positive bacterial isolates collected from patients globally between 2017 and 2020. J Glob Antimicrob Resist. 2023 Jun;33:304-320. doi: 10.1016/j.jgar.2023.04.017. Epub 2023 May 18. PMID: 37207925.
13: Chen J, Liu Y, Jia W, Xu X, Sun G, Wang T, Li J, Zhang G, Jing R, Sun H, Xu Y, Liu Y. In Vitro Activities of Aztreonam-Avibactam, Eravacycline, Cefoselis, and Other Comparators against Clinical Enterobacterales Isolates: a Multicenter Study in China, 2019. Microbiol Spectr. 2023 Jun 15;11(3):e0487322. doi: 10.1128/spectrum.04873-22. Epub 2023 May 15. PMID: 37184411; PMCID: PMC10269566.
14: Li A, He S, Li J, Zhang Z, Li B, Chu H. Omadacycline, Eravacycline, and Tigecycline Express Anti-Mycobacterium abscessus Activity In Vitro. Microbiol Spectr. 2023 Jun 15;11(3):e0071823. doi: 10.1128/spectrum.00718-23. Epub 2023 May 4. PMID: 37140428; PMCID: PMC10269442.
15: Galani I, Papoutsaki V, Karaiskos I, Moustakas N, Galani L, Maraki S, Mavromanolaki VE, Legga O, Fountoulis K, Platsouka ED, Giannopoulou P, Papadogeorgaki H, Damala M, Chinou E, Pasxali A, Deliolanis I, Vagiakou H, Petinaki E, Chli A, Vagdatli E, Kazila P, Papaioannou V, Kontopoulou K, Ferke AN, Moraitou E, Antoniadou A, Giamarellou H. In vitro activities of omadacycline, eravacycline, cefiderocol, apramycin, and comparator antibiotics against Acinetobacter baumannii causing bloodstream infections in Greece, 2020-2021: a multicenter study. Eur J Clin Microbiol Infect Dis. 2023 Jul;42(7):843-852. doi: 10.1007/s10096-023-04616-7. Epub 2023 May 3. PMID: 37133639; PMCID: PMC10155660.
16: Baumann AJ, Cleveland KO, Gelfand MS, Perkins Iii NB, Covington AD, Hobbs ALV. Residual Infusion Performance Evaluation (RIPE): A Single-Center Evaluation of Residual Volume Post-Intravenous Eravacycline Infusion. Pharmacy (Basel). 2023 Apr 13;11(2):75. doi: 10.3390/pharmacy11020075. PMID: 37104081; PMCID: PMC10142521.
17: Zou X, Jin S, Chen L, Li J, Zhang X, Zhou H, Li X, Huang H. Antibacterial Activity of Eravacycline Against Carbapenem-Resistant Gram-Negative Isolates in China: An in vitro Study. Infect Drug Resist. 2023 Apr 17;16:2271-2279. doi: 10.2147/IDR.S396910. PMID: 37090037; PMCID: PMC10120866.
18: Correction to: Eravacycline Associated Hypofibrinogenemia: A Case Series of Transplant Patients With Mycobacterium Abscessus Infections and Review of Literature. Open Forum Infect Dis. 2023 Apr 11;10(4):ofad053. doi: 10.1093/ofid/ofad053. Erratum for: Open Forum Infect Dis. 2022 Dec 15;9(12):ofac591. PMID: 37056982; PMCID: PMC10086305.
19: Blanchard LS, Armstrong TP, Kresken M, Emery CL, Ying YX, Sauvonnet V, Zambardi G. Multicenter Clinical Evaluation of ETEST Eravacycline for Susceptibility Testing of Enterobacteriaceae and Enterococci. J Clin Microbiol. 2023 Mar 23;61(3):e0165022. doi: 10.1128/jcm.01650-22. Epub 2023 Mar 6. PMID: 36877080; PMCID: PMC10035295.
20: Rolston K, Gerges B, Nesher L, Shelburne SA, Prince R, Raad I. In vitro activity of eravacycline and comparator agents against bacterial pathogens isolated from patients with cancer. JAC Antimicrob Resist. 2023 Mar 2;5(2):dlad020. doi: 10.1093/jacamr/dlad020. PMID: 36875177; PMCID: PMC9981869.
