U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C80H106Cl2N11O27P.ClH
Molecular Weight 1792.0988
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TELAVANCIN HYDROCHLORIDE

SMILES

CCCCCCCCCCNCCN[C@@]1(C)C[C@@]([H])(O[C@@]([H])(C)[C@@]1([H])O)O[C@]2([H])[C@]([H])([C@@]([H])([C@@]([H])(CO)O[C@@]2([H])Oc3c4cc5cc3Oc6ccc(cc6Cl)[C@]([H])([C@@]7([H])C(=N[C@@]([H])(c8cc(c(CNCP(=O)(O)O)c(c8-c9cc(ccc9O)[C@]([H])(C(=N7)O)N=C([C@]5([H])N=C([C@]([H])(CC(=N)O)N=C([C@@]([H])([C@@]([H])(c%10ccc(c(c%10)Cl)O4)O)N=C([C@@]([H])(CC(C)C)NC)O)O)O)O)O)O)C(=O)O)O)O)O)O.Cl

InChI

InChIKey=GSSIWSIRBWAZHG-ACOPVEIWSA-N
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

HIDE SMILES / InChI

Molecular Formula C80H106Cl2N11O27P
Molecular Weight 1755.6379
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

TELAVANCIN (VIBATIV®) is a lipoglycopeptide antibacterial that is a synthetic derivative of vancomycin. It exerts concentration-dependent, bactericidal activity against Gram-positive organisms in vitro. TELAVANCIN (VIBATIV®) inhibits cell wall biosynthesis by binding to late-stage peptidoglycan precursors, including lipid II. It also binds to the bacterial membrane and disrupts membrane barrier function. TELAVANCIN (VIBATIV®) is indicated for the treatment of adult patients with complicated skin and skin structure infections caused by susceptible isolates of the following Gram-positive microorganisms: Staphylococcus aureus (including methicillin-susceptible and -resistant isolates), Streptococcus pyogenes, Streptococcus agalactiae, Streptococcus anginosus group (includes S. anginosus, S. intermedius, and S. constellatus), or Enterococcus faecalis (vancomycin-susceptible isolates only). It is also indicated for the treatment of adult patients with hospital-acquired and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of Staphylococcus aureus (both methicillin-susceptible and -resistant isolates). It should be reserved for use when alternative treatments are not suitable.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIBATIV

Approved Use

VIBATIV is a lipoglycopeptide antibacterial drug indicated for the treatment of the following infections in adult patients caused by designated susceptible bacteria: Complicated skin and skin structure infections (cSSSI). Hospital-acquired and ventilator-associated bacterial pneumonia (HABP/VABP) caused by susceptible isolates of Staphylococcus aureus. VIBATIV should be reserved for use when alternative treatments are not suitable.

Launch Date

1.37177281E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
93.6 μg/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELAVANCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
747 μg × h/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELAVANCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELAVANCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELAVANCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.285
unhealthy, 62 ± 18.5
n = 751
Health Status: unhealthy
Condition: Nosocomial pneumonia
Age Group: 62 ± 18.5
Sex: M+F
Population Size: 751
Sources: Page: p.285
Disc. AE: Acute renal failure, Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Acute renal failure (1%)
Electrocardiogram QTc interval prolonged (1%)
Sources: Page: p.285
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Other AEs: Dysgeusia, Nausea...
Other AEs:
Dysgeusia
Nausea
Vomiting
Injection site erythema
Headache
Macular rash
Red man syndrome
Sources: Page: p.8
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.1,5
unhealthy
n = 929
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Population Size: 929
Sources: Page: p.1,5
Disc. AE: Nephrotoxicity...
AEs leading to
discontinuation/dose reduction:
Nephrotoxicity (1.29%)
Sources: Page: p.1,5
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.9
unhealthy
n = 929
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Population Size: 929
Sources: Page: p.9
Disc. AE: Nausea, Rash...
AEs leading to
discontinuation/dose reduction:
Nausea (1%)
Rash (1%)
Sources: Page: p.9
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Sources: Page: p.1
Disc. AE: Clostridium difficile colitis, Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Clostridium difficile colitis (all grades)
Electrocardiogram QTc interval prolonged
Sources: Page: p.1
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Nosocomial pneumonia
Sources: Page: p.4
Disc. AE: Hypersensitivity, Ototoxicity...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity
Ototoxicity
Superinfection
Sources: Page: p.4
AEs

AEs

AESignificanceDosePopulation
Acute renal failure 1%
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.285
unhealthy, 62 ± 18.5
n = 751
Health Status: unhealthy
Condition: Nosocomial pneumonia
Age Group: 62 ± 18.5
Sex: M+F
Population Size: 751
Sources: Page: p.285
Electrocardiogram QTc interval prolonged 1%
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.285
unhealthy, 62 ± 18.5
n = 751
Health Status: unhealthy
Condition: Nosocomial pneumonia
Age Group: 62 ± 18.5
Sex: M+F
Population Size: 751
Sources: Page: p.285
Dysgeusia
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Headache
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Injection site erythema
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Macular rash
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Nausea
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Red man syndrome
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Vomiting
15 mg/kg single, intravenous
Overdose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources: Page: p.8
healthy
Nephrotoxicity 1.29%
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.1,5
unhealthy
n = 929
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Population Size: 929
Sources: Page: p.1,5
Nausea 1%
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.9
unhealthy
n = 929
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Population Size: 929
Sources: Page: p.9
Rash 1%
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.9
unhealthy
n = 929
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Population Size: 929
Sources: Page: p.9
Electrocardiogram QTc interval prolonged Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Sources: Page: p.1
Clostridium difficile colitis all grades
Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Skin and skin structure infections caused by susceptible Gram-positive bacteria
Sources: Page: p.1
Hypersensitivity Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Nosocomial pneumonia
Sources: Page: p.4
Ototoxicity Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Nosocomial pneumonia
Sources: Page: p.4
Superinfection Disc. AE
10 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 10 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/kg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Nosocomial pneumonia
Sources: Page: p.4
Overview

OverviewOther

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence

Sample Use Guides

Complicated skin and skin structure infections: 10 mg/kg VIBATIV® by IV infusion over 60 minutes every 24 hours for 7 to 14 days. Hospital-acquired and ventilator-associated bacterial pneumonia (HABP/VABP): 10 mg/kg VIBATIV® by IV infusion over 60 minutes every 24 hours for 7 to 21 days.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:28:45 UTC 2021
Edited
by admin
on Sat Jun 26 12:28:45 UTC 2021
Record UNII
0701472ZG0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TELAVANCIN HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
TELEVANCIN HYDROCHLORIDE
VANDF  
Common Name English
TELAVANCIN HCL
Common Name English
TELAVANCIN HYDROCHLORIDE [MI]
Common Name English
TELAVANCIN HYDROCHLORIDE [WHO-DD]
Common Name English
TD-6424
Code English
VIBATIV
Brand Name English
VANCOMYCIN, N(SUP 3'')-(2-(DECYLAMINO)ETHYL)-29-(((PHOSPHONOMETHYL)AMINO)METHYL)-, MONOHYDROCHLORIDE
Common Name English
TELAVANCIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
TELAVANCIN HYDROCHLORIDE [VANDF]
Common Name English
TELAVANCIN HYDROCHLORIDE [USAN]
Common Name English
TELEVANCIN HYDROCHLORIDE [VANDF]
Common Name English
TELAVANCIN HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C61101
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
Code System Code Type Description
DRUG BANK
DBSALT000170
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
CAS
560130-42-9
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
RXCUI
864624
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY RxNorm
EVMPD
SUB35005
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
CAS
380636-75-9
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
9812715
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
NCI_THESAURUS
C87636
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
FDA UNII
0701472ZG0
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
MERCK INDEX
M10527
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL507870
Created by admin on Sat Jun 26 12:28:45 UTC 2021 , Edited by admin on Sat Jun 26 12:28:45 UTC 2021
PRIMARY
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