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    Chemistry

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    Also known as: Vibativ, Telavancin hcl, 560130-42-9, Td-6424, Td 6424, Telavancin hydrochloride [usan]
    Molecular Formula
    C80H107Cl3N11O27P
    Molecular Weight
    1792.1  g/mol
    InChI Key
    GSSIWSIRBWAZHG-ACOPVEIWSA-N
    FDA UNII
    0701472ZG0
    Telavancin Hydrochloride
    Telavancin Hydrochloride is the hydrochloride salt form of telavancin, a lipoglycopeptide and a semisynthetic derivative of vancomycin with antibacterial activity against gram-positive bacteria. Like vancomycin, telavancin binds tightly to the D-alanyl-D-alanine residue of cell wall precursors, thereby interfering with bacterial cell wall synthesis. In addition, the lipophilic moiety of telavancin may interact with the lipid bilayer in the bacterial cell membrane, thereby compromising the integrity of cell membrane and causing cell membrane depolarization. This novel mechanism of action may contribute to telavancin's rapid bactericidal activity and its improved activity over vancomycin against some antibiotic resistance gram-positive bacteria.
    1 2D Structure

    Telavancin Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-[2-(decylamino)ethylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-36-[(phosphonomethylamino)methyl]-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid;hydrochloride
    2.1.2 InChI
    InChI=1S/C80H106Cl2N11O27P.ClH/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39;/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114);1H/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-;/m0./s1
    2.1.3 InChI Key
    GSSIWSIRBWAZHG-ACOPVEIWSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCNCCNC1(CC(OC(C1O)C)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C(=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)CNCP(=O)(O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)C.Cl
    2.1.5 Isomeric SMILES
    CCCCCCCCCCNCCN[C@]1(C[C@@H](O[C@H]([C@H]1O)C)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C(=C(C=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)CNCP(=O)(O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)C.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    0701472ZG0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Td 6424

    2. Td-6424

    3. Td6424

    4. Telavancin

    5. Vibativ

    2.3.2 Depositor-Supplied Synonyms

    1. Vibativ

    2. Telavancin Hcl

    3. 560130-42-9

    4. Td-6424

    5. Td 6424

    6. Telavancin Hydrochloride [usan]

    7. Televancin Hydrochloride

    8. 0701472zg0

    9. Telavancin Hydrochloride (usan)

    10. Unii-0701472zg0

    11. Vibativ (tn)

    12. Chembl3301680

    13. Chebi:71226

    14. Telavancin Hydrochloride [mi]

    15. Telavancin Hydrochloride [mart.]

    16. Telavancin Hydrochloride [vandf]

    17. Televancin Hydrochloride [vandf]

    18. Telavancin Hydrochloride [who-dd]

    19. Telavancin Hydrochloride [orange Book]

    20. D06057

    21. Q47495786

    22. 380636-75-9

    23. Vancomycin, N(sup 3'')-(2-(decylamino)ethyl)-29-(((phosphonomethyl)amino)methyl)-, Monohydrochloride

    24. Vancomycin, N3'-(2-(decylamino)ethyl)-29-(((phosphonomethyl)amino)methyl)-, Monohydrochloride

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 1792.1 g/mol
    Molecular Formula C80H107Cl3N11O27P
    Hydrogen Bond Donor Count24
    Hydrogen Bond Acceptor Count31
    Rotatable Bond Count30
    Exact Mass1789.614107 g/mol
    Monoisotopic Mass1789.614107 g/mol
    Topological Polar Surface Area598 Ų
    Heavy Atom Count122
    Formal Charge0
    Complexity3490
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameVibativ
    PubMed HealthTelavancin (Injection)
    Drug ClassesAntibiotic
    Drug LabelVIBATIV contains telavancin hydrochloride, a lipoglycopeptide antibacterial that is a synthetic derivative of vancomycin. The chemical name of telavancin hydrochloride is vancomycin,N3''-[2-(decylamino)ethyl]-29-[[(phosphono-methyl)-amino]-methy
    Active IngredientTelavancin hydrochloride; Telavancin
    Dosage FormPowder; Injectable
    Routeinjection; Iv (infusion)
    Strengtheq 750mg base/vial; 250mg; 750mg; eq 250mg base/vial
    Market StatusPrescription
    CompanyTheravance; Theravance Biopharma

    2 of 2  
    Drug NameVibativ
    PubMed HealthTelavancin (Injection)
    Drug ClassesAntibiotic
    Drug LabelVIBATIV contains telavancin hydrochloride, a lipoglycopeptide antibacterial that is a synthetic derivative of vancomycin. The chemical name of telavancin hydrochloride is vancomycin,N3''-[2-(decylamino)ethyl]-29-[[(phosphono-methyl)-amino]-methy
    Active IngredientTelavancin hydrochloride; Telavancin
    Dosage FormPowder; Injectable
    Routeinjection; Iv (infusion)
    Strengtheq 750mg base/vial; 250mg; 750mg; eq 250mg base/vial
    Market StatusPrescription
    CompanyTheravance; Theravance Biopharma

    4.2 Drug Indication

    Vibativ is indicated for the treatment of adults with nosocomial pneumonia including ventilator-associated pneumonia, known or suspected to be caused by methicillin-resistant Staphylococcus aureus (MRSA).

    Vibativ should be used only in situations where it is known or suspected that other alternatives are not suitable.

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

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Lipoglycopeptides [EXT]; Lipoglycopeptide Antibacterial [EPC]
    5.3 ATC Code

    J01XA03

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - POWDER;INTRAVENOUS - EQ 250MG BASE/V...DOSAGE - POWDER;INTRAVENOUS - EQ 250MG BASE/VIAL

    USFDA APPLICATION NUMBER - 22110

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    DOSAGE - POWDER;INTRAVENOUS - EQ 750MG BASE/V...DOSAGE - POWDER;INTRAVENOUS - EQ 750MG BASE/VIAL

    USFDA APPLICATION NUMBER - 22110

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