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Also known as: 1207283-85-9, Tp-434, Xerava, Eravacycline [usan], Tp434, (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide
Molecular Formula
C27H31FN4O8
Molecular Weight
558.6  g/mol
InChI Key
AKLMFDDQCHURPW-ISIOAQNYSA-N
FDA UNII
07896928ZC

Eravacycline
Eravacycline, known as Xerava by Tetraphase Pharmaceuticals, is a fully synthetic fluorocycline antibiotic of the tetracycline class with activity against clinically significant gram-negative, gram-positive aerobic, and facultative bacteria. This includes most of those bacteria resistant to cephalosporins, fluoroquinolones, -lactam/-lactamase inhibitors, multidrug-resistant strains, and carbapenem-resistant Enterobacteriaceae, and the majority of anaerobic pathogens. It was first approved by the FDA on August 27, 2018. Eravacycline has demonstrated superior potency to that of antibiotics that are currently being marketed for intraabdominal infections.
Eravacycline is a Tetracycline-class Antibacterial.
1 2D Structure

Eravacycline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S,4aS,5aR,12aR)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
2.1.2 InChI
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/h9,11,13,20,34-35,38,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1
2.1.3 InChI Key
AKLMFDDQCHURPW-ISIOAQNYSA-N
2.1.4 Canonical SMILES
CN(C)C1C2CC3CC4=C(C=C(C(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F
2.1.5 Isomeric SMILES
CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F
2.2 Other Identifiers
2.2.1 UNII
07896928ZC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (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

2. (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

3. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline

4. Eravacycline Dihydrochloride

5. Tp-434

6. Tp-434-046

7. Tp-434046

8. Tp434

9. Xerava

2.3.2 Depositor-Supplied Synonyms

1. 1207283-85-9

2. Tp-434

3. Xerava

4. Eravacycline [usan]

5. Tp434

6. (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

7. Eravacycline (usan)

8. 07896928zc

9. 1-pyrrolidineacetamide, N-((5ar,6as,7s,10as)-9-(aminocarbonyl)-7-(dimethylamino)-4-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl)-

10. Eravacycline [usan:inn]

11. Unii-07896928zc

12. Yqm

13. Tp434;eravacycline

14. Eravacycline [mi]

15. Eravacycline [inn]

16. Eravacycline [who-dd]

17. Chembl1951095

18. Chembl4597183

19. Schembl10040430

20. Gtpl10805

21. Ex-a751

22. Chebi:177804

23. Dtxsid401026285

24. Mfcd31010183

25. Zinc200151468

26. Cs-7564

27. Db12329

28. Compound 17j [pmid: 2148514]

29. Hy-16980

30. D10369

31. J-690064

32. Q15410941

33. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline

34. (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[2-(pyrrolidin-1-yl)acetamido]-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide

35. (4s,4as,5ar,12ar)-4-(dimethylamino)-7-luoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

36. (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

37. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

38. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12atetrahydroxy-1,11-dioxo-9-(2-(pyrrolidin-1-yl)acetamido)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

39. 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

40. 7-[6-(2-hydroxy-2-propanyl)-3-pyridinyl]-1-(4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one

41. N-[(5ar,6as,7s,10as)-9-(aminocarbonyl)-7-(dimethylamino)-4-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl]-1-pyrrolidineacetamide

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 558.6 g/mol
Molecular Formula C27H31FN4O8
XLogP31
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count5
Exact Mass558.21259212 g/mol
Monoisotopic Mass558.21259212 g/mol
Topological Polar Surface Area194 Ų
Heavy Atom Count40
Formal Charge0
Complexity1200
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Eravacycline is a tetracycline class antibacterial indicated for the treatment of complicated intra-abdominal infections in patients 18 years of age and older.


FDA Label


Xerava is indicated for the treatment of complicated intra-abdominal infections (cIAI) in adults.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Eravacycline is an antibiotic that disrupts bacterial protein synthesis, treating complicated intraabdominal infections.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
ERAVACYCLINE
5.2.2 FDA UNII
07896928ZC
5.2.3 Pharmacological Classes
Tetracyclines [CS]; Tetracycline-class Antibacterial [EPC]
5.3 ATC Code

J01AA


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA13 - Eravacycline


5.4 Absorption, Distribution and Excretion

Absorption

Following single-dose intravenous administration, eravacycline AUC (area under the curve) and Cmax (maximum concentration) increase dose-proportionally for doses from 1 mg/kg - 3 mg/kg (3 times the approved dose). There is approximately 45% accumulation following intravenous dosing of 1 mg/kg every 12 hours.


Route of Elimination

Following a single intravenous dose of radiolabeled eravacycline 60 mg, approximately 34% of the dose is excreted in urine and 47% in feces as unchanged eravacycline (20% in urine and 17% in feces) and metabolites.


Volume of Distribution

The volume of distribution at steady-state is approximately 321 L.


Clearance

17.82 L/min (standard deviation of 3.4).


5.5 Metabolism/Metabolites

Eravacycline is metabolized primarily by CYP3A4- and FMO-mediated oxidation.


5.6 Biological Half-Life

The mean elimination half-life is 20 hours.


5.7 Mechanism of Action

Eravacycline is a fluorocycline antibacterial of the tetracycline class of antibacterial drugs. Eravacycline disrupts bacterial protein synthesis by binding to the 30S ribosomal subunit, preventing the incorporation of amino acid residues into elongating peptide chains. In general, eravacycline is bacteriostatic against gram-positive bacteria (e.g., Staphylococcus aureus and Enterococcus faecalis); however, in vitro bactericidal activity has been shown against certain strains of Escherichia coli and Klebsiella pneumoniae.


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ABOUT THIS PAGE

Looking for 1207283-85-9 / TP-434 API manufacturers, exporters & distributors?

TP-434 manufacturers, exporters & distributors 1

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PharmaCompass offers a list of TP-434 API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right TP-434 manufacturer or TP-434 supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred TP-434 manufacturer or TP-434 supplier.

PharmaCompass also assists you with knowing the TP-434 API Price utilized in the formulation of products. TP-434 API Price is not always fixed or binding as the TP-434 Price is obtained through a variety of data sources. The TP-434 Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

TP-434

Synonyms

1207283-85-9, Xerava, Eravacycline [usan], Tp434, (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide, Eravacycline (usan)

Cas Number

1207283-85-9

Unique Ingredient Identifier (UNII)

07896928ZC

About TP-434

Eravacycline, known as Xerava by Tetraphase Pharmaceuticals, is a fully synthetic fluorocycline antibiotic of the tetracycline class with activity against clinically significant gram-negative, gram-positive aerobic, and facultative bacteria. This includes most of those bacteria resistant to cephalosporins, fluoroquinolones, -lactam/-lactamase inhibitors, multidrug-resistant strains, and carbapenem-resistant Enterobacteriaceae, and the majority of anaerobic pathogens. It was first approved by the FDA on August 27, 2018. Eravacycline has demonstrated superior potency to that of antibiotics that are currently being marketed for intraabdominal infections.

Eravacycline Manufacturers

A Eravacycline manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Eravacycline, including repackagers and relabelers. The FDA regulates Eravacycline manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Eravacycline API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Eravacycline manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Eravacycline Suppliers

A Eravacycline supplier is an individual or a company that provides Eravacycline active pharmaceutical ingredient (API) or Eravacycline finished formulations upon request. The Eravacycline suppliers may include Eravacycline API manufacturers, exporters, distributors and traders.

click here to find a list of Eravacycline suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Eravacycline NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Eravacycline as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Eravacycline API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Eravacycline as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Eravacycline and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Eravacycline NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Eravacycline suppliers with NDC on PharmaCompass.

Eravacycline GMP

Eravacycline Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Eravacycline GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Eravacycline GMP manufacturer or Eravacycline GMP API supplier for your needs.

Eravacycline CoA

A Eravacycline CoA (Certificate of Analysis) is a formal document that attests to Eravacycline's compliance with Eravacycline specifications and serves as a tool for batch-level quality control.

Eravacycline CoA mostly includes findings from lab analyses of a specific batch. For each Eravacycline CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Eravacycline may be tested according to a variety of international standards, such as European Pharmacopoeia (Eravacycline EP), Eravacycline JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Eravacycline USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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