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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


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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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