Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C80H106Cl2N11O27P.ClH |
Molecular Weight | 1792.096 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 18 / 18 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]1(C[C@](C)(NCCNCCCCCCCCCC)[C@H](O)[C@H](C)O1)O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC3=C4OC5=C(Cl)C=C(C=C5)[C@@H](O)[C@]6([H])NC(=O)[C@H](NC(=O)[C@@H]7NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](NC(=O)[C@@H](CC(C)C)NC)[C@H](O)C8=CC=C(OC3=CC7=C4)C(Cl)=C8)C9=CC=C(O)C(=C9)C%10=C(C=C(O)C(CNCP(O)(O)=O)=C%10O)[C@H](NC6=O)C(O)=O
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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C80H106Cl2N11O27P |
Molecular Weight | 1755.635 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 18 / 18 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
Originator
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VIBATIV Approved UseVIBATIV 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 Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Page: p.285Electrocardiogram QTc interval prolonged (1%) |
15 mg/kg single, intravenous Overdose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: Page: p.8 |
healthy Health Status: healthy Sources: Page: p.8 |
Other AEs: Dysgeusia, Nausea... Other AEs: Dysgeusia Sources: Page: p.8Nausea Vomiting Injection site erythema Headache Macular rash Red man syndrome |
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%) Sources: Page: p.9Rash (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.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) Sources: Page: p.1Electrocardiogram QTc interval prolonged |
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 Sources: Page: p.4Ototoxicity Superinfection |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 Health Status: healthy Sources: Page: p.8 |
|
Headache | 15 mg/kg single, intravenous Overdose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: Page: p.8 |
healthy Health Status: healthy Sources: Page: p.8 |
|
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 Health Status: healthy Sources: Page: p.8 |
|
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 Health Status: healthy Sources: Page: p.8 |
|
Nausea | 15 mg/kg single, intravenous Overdose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: Page: p.8 |
healthy Health Status: healthy Sources: Page: p.8 |
|
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 Health Status: healthy Sources: Page: p.8 |
|
Vomiting | 15 mg/kg single, intravenous Overdose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: Page: p.8 |
healthy Health Status: healthy Sources: Page: p.8 |
|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022110s000_ClinPharmR_P1.pdf#page=60 Page: 60.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29.0 |
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
Edited
Fri Dec 15 15:52:57 GMT 2023
by
admin
on
Fri Dec 15 15:52:57 GMT 2023
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Record UNII |
0701472ZG0
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C61101
Created by
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Code System | Code | Type | Description | ||
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DBSALT000170
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560130-42-9
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0701472ZG0
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864624
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SUB35005
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71226
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380636-75-9
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NON-SPECIFIC STOICHIOMETRY | |||
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9812715
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C87636
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0701472ZG0
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m10527
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admin on Fri Dec 15 15:52:57 GMT 2023 , Edited by admin on Fri Dec 15 15:52:57 GMT 2023
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PRIMARY | Merck Index | ||
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CHEMBL507870
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PP-64
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PRIMARY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |