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MedKoo Cat#: 330027 | Name: Eravacycline free base
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Description:

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

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.

Chemical Structure

Eravacycline free base
Eravacycline free base
CAS#1207283-85-9 (free base)

Theoretical Analysis

MedKoo Cat#: 330027

Name: Eravacycline free base

CAS#: 1207283-85-9 (free base)

Chemical Formula: C27H31FN4O8

Exact Mass: 558.2126

Molecular Weight: 558.56

Elemental Analysis: C, 58.06; H, 5.59; F, 3.40; N, 10.03; O, 22.91

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
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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; TP 434; TP434; Eravacycline free base
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
InChi Key
HLFSMUUOKPBTSM-ISIOAQNYSA-N
InChi Code
InChI=1S/C27H31FN4O8/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)/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
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
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).

Preparing Stock Solutions

The following data is based on the product molecular weight 558.56 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: 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.