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Identification
- Summary
Telavancin is an antibacterial agent used in the treatment of complicated skin and skin structure infections and types of hospital-acquired bacterial pneumonia.
- Brand Names
- Vibativ
- Generic Name
- Telavancin
- DrugBank Accession Number
- DB06402
- Background
Telavancin is a semi-synthetic derivative of vanocymycin that has bactericidal activity against Methicillin-resistant Staphylococcus aureus (MRSA) and other gram-positive bacteria. MRSA is an important pathogen capable of causing hospital-acquired pneumonia (HAP), ventilator-associated pneumonia (VAP), and skin and subcutaneous tissue infections among others.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Telavancin (DB06402)
- Weight
- Average: 1755.65
Monoisotopic: 1753.6374296 - Chemical Formula
- C80H106Cl2N11O27P
- Synonyms
- Telavancin
- Telavancina
- Télavancine
- Telavancinum
Pharmacology
- Indication
For the treatment of complicated skin and skin structure infections (cSSSI) caused by gram-positive bacteria like methicillin-susceptible or -resistant Staphylococcus aureus, vancomycin-susceptible Enterococcus faecalis, and Streptococcus pyogenes, Streptococcus agalactiae, or Streptococcus anginosus group. Also for the treatment of adult patients with hospital-acquired bacterial pneumonia (HAP) and ventilator-associated bacterial pneumonia (VAP), known or suspected to be caused by susceptible isolates of Staphylococcus aureus (including methicillin-susceptible and methicillin-resistant S. aureus).
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial infections •••••••••••• Treatment of Ventilator-associated bacterial pneumonia •••••••••••• Treatment of Complicated skin and subcutaneous tissue bacterial infections •••••••••••• Treatment of Hospital-acquired bacterial pneumonia •••••••••••• - Contraindications & Blackbox Warnings
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Telavancin is a semi-synthetic derivative of vancomycin, therefore the mode of bactericidal action is similar to vancomycin in which both antibiotics inhibit cell wall synthesis. Not only that, it displays concentration-dependent bactericidal action. Furthermore, telavancin is a more potent inhibitor (10-fold) of peptidoglycan synthesis and, unlike vancomycin, disrupts cell membrane integrity via its interaction with lipid II. AUC/MIC ratio best predicts the extent of in-vivo response in which the higher the ratio, the greater the bactericidal activity. The smallest ratio in which one would be able to observe no bacterial growth at 24 hours is 50. Maximal bactericidal activity is observed at a AUC/MIC ratio of 404.
- Mechanism of action
Telavancin is a bactericidal lipoglycopeptide that is active against a broad range of gram-positive bacteria. Telavancin prevents polymerization of N-acetylmuramic acid (NAM) and N-acetylglucosamine (NAG) and cross-linking of peptidoglycan by binding to D-Ala-D-Ala. As a result, inhibition of bacterial cell wall synthesis occurs. Furthermore, telavancin disrupts membrane potential and cell permeability as a result of the lipophillic side chain moiety. This additional bactericidal mechanism is what sets telavancin apart from vancomycin.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 agonistHumans ANeuronal acetylcholine receptor subunit alpha-3 agonistHumans ACorticotropin-releasing factor receptor 1 antagonistHumans - Absorption
Telavancin demonstrates linear pharmacokinetics at doses between 1 and 12.5 mg/kg. Furthermore, 24 hours post-infusion of a dose of 7.5 to 15 mg/kg, activity against MRSA and penicillin-resistant Streptococcus pneumonia can still be observed. The trough concentration at this point of time is approximately 10 μg/mL. Telavancin also has poor bioavailability and must be administered over 30-120 minutes IV. Cmax, healthy subjects, 10 mg/kg = 93.6 ± 14.2 μg/mL; AUC (0- ∞), healthy subjects, 10 mg/kg = 747 ± 129 μg · h/mL; AUC (0-24h), healthy subjects, 10 mg/kg = 666± 107 μg · h/mL; Time to steady state = 3 days;
- Volume of distribution
Vss, healthy subjects, 10 mg/kg = 0.14 L/kg
- Protein binding
>90% to serum albumin in a concentration independent manner (despite being highly protein bound, antimicrobial activity of telavancin is not affected)
- Metabolism
Metabolism of telavancin does not involve the cytochrome P450 enzyme system. Primary metabolite is called THRX-651540, but the metabolite pathway has not been identified.
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- Route of elimination
Urine with >80% as unchanged drug and <20% as hydroxylated metabolites (with dose of 10mg/kg); Feces (<1%)
- Half-life
Terminal elimination half-life = 8 ± 1.5 hours (with normal renal function)
- Clearance
Cl, healthy subjects, 10 mg/kg = 13.9 ± 2.9 mL/h/kg
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Telavancin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Telavancin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Telavancin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Telavancin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Telavancin which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Telavancin hydrochloride 0701472ZG0 560130-42-9 GSSIWSIRBWAZHG-ACOPVEIWSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vibativ Injection, powder, lyophilized, for solution 15 mg/1mL Intravenous Theravance Biopharma R&d, Inc. 2009-11-05 2020-12-31 US 
Vibativ Injection, powder, lyophilized, for solution 250 mg/1 Intravenous Astellas Pharma Europe Bv 2009-11-05 2015-05-31 US Vibativ Injection, powder, for solution 250 mg Intravenous Theravance Biopharma Ireland Umited 2021-01-12 2018-05-16 EU 
Vibativ Powder, for solution 750 mg / vial Intravenous Pendopharm Division Of Pharmascience Inc 2016-01-06 Not applicable Canada 
Vibativ Injection, powder, lyophilized, for solution 15 mg/1mL Intravenous Theravance Biopharma R&d, Inc. 2009-11-05 Not applicable US
Categories
- ATC Codes
- J01XA03 — Telavancin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Carbohydrates
- Drugs that are Mainly Renally Excreted
- Glycoconjugates
- Glycopeptide Antibacterials
- Glycopeptides
- Glycosides
- Lipoglycopeptide Antibacterial
- Lipopeptides
- Moderate Risk QTc-Prolonging Agents
- Peptides
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / Aminoglycosides / Phenolic glycosides / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Diarylethers / Disaccharides / O-glycosyl compounds / 1-hydroxy-2-unsubstituted benzenoids show 25 more
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acetal / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid show 48 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- glycopeptide (CHEBI:71229)
- Affected organisms
- Streptococcus pyogenes
- Streptococcus agalactiae
- Staphylococcus aureus
- Enterococcus faecalis
- Streptococcus anginosus
Chemical Identifiers
- UNII
- XK134822Z0
- CAS number
- 372151-71-8
- InChI Key
- ONUMZHGUFYIKPM-MXNFEBESSA-N
- InChI
- InChI=1S/C80H106Cl2N11O27P/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)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1
- IUPAC Name
- (1S,2R,18R,19R,22S,25R,28R,40S)-22-(carbamoylmethyl)-5,47-dichloro-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-{[2-(decylamino)ethyl]amino}-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)pentanamido]-20,23,26,42,44-pentaoxo-36-{[(phosphonomethyl)amino]methyl}-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^{3,6}.2^{14,17}.1^{8,12}.1^{29,33}.0^{10,25}.0^{34,39}]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
- SMILES
- CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=C3OC4=CC=C(C=C4Cl)[C@@H](O)[C@@H](NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]4C(C=C2OC2=C(Cl)C=C(C=C2)[C@@H](O)[C@@H]2NC(=O)[C@H](NC4=O)C4=CC(=C(O)C=C4)C4=C(O)C(CNCP(O)(O)=O)=C(O)C=C4[C@H](NC2=O)C(O)=O)=C3)O[C@@H](C)[C@H]1O
References
- General References
- Laohavaleeson S, Kuti JL, Nicolau DP: Telavancin: a novel lipoglycopeptide for serious gram-positive infections. Expert Opin Investig Drugs. 2007 Mar;16(3):347-57. [Article]
- Rubinstein E, Corey GR, Stryjewski ME, Kanafani ZA: Telavancin for the treatment of serious gram-positive infections, including hospital acquired pneumonia. Expert Opin Pharmacother. 2011 Dec;12(17):2737-50. doi: 10.1517/14656566.2011.633511. [Article]
- Zhanel GG, Calic D, Schweizer F, Zelenitsky S, Adam H, Lagace-Wiens PR, Rubinstein E, Gin AS, Hoban DJ, Karlowsky JA: New lipoglycopeptides: a comparative review of dalbavancin, oritavancin and telavancin. Drugs. 2010 May 7;70(7):859-86. doi: 10.2165/11534440-000000000-00000. [Article]
- Wong SL, Goldberg MR, Ballow CH, Kitt MM, Barriere SL: Effect of Telavancin on the pharmacokinetics of the cytochrome P450 3A probe substrate midazolam: a randomized, double-blind, crossover study in healthy subjects. Pharmacotherapy. 2010 Feb;30(2):136-43. doi: 10.1592/phco.30.2.136. [Article]
- FDA Approved Drug Products: Vibativ (telavancin) for injection [Link]
- External Links
- PubChem Compound
- 3081362
- PubChem Substance
- 175427069
- ChemSpider
- 2338980
- 473837
- ChEBI
- 71229
- ChEMBL
- CHEMBL507870
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Telavancin
- FDA label
- Download (6.45 MB)
- MSDS
- Download (479 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Complicated Skin and Skin Structure Infection / Hospital-Acquired Pneumonia / Infections due to Gram-positive pathogens / Ventilator Associated Bacterial Pneumonia (VABP) 1 somestatus stop reason just information to hide Not Available Withdrawn Not Available Pregnancy 1 somestatus stop reason just information to hide 4 Completed Other Cystic Fibrosis (CF) 1 somestatus stop reason just information to hide 4 Completed Other End Stage Renal Disease (ESRD) / Stage 5 Chronic Kidney Disease (CKD) 1 somestatus stop reason just information to hide 4 Recruiting Treatment Aneurysmal Subarachnoid Hemorrhage (A-sah) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous Injection, powder, for solution Intravenous 250 mg Injection, powder, for solution Intravenous 750 mg Injection, powder, lyophilized, for solution Intravenous 15 mg/1mL Injection, powder, lyophilized, for solution Intravenous 250 mg/1 Injection, powder, lyophilized, for solution Intravenous 750 mg/1 Powder, for solution Intravenous 250 mg / vial Powder, for solution Intravenous 750 mg / vial - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6635618 No 2003-10-21 2023-09-11 US US7008923 No 2006-03-07 2021-05-06 US US7351691 No 2008-04-01 2021-05-01 US US7700550 No 2010-04-20 2021-05-01 US US6858584 No 2005-02-22 2022-08-24 US US7531623 No 2009-05-12 2027-01-01 US US7544364 No 2009-06-09 2021-05-01 US US7208471 No 2007-04-24 2021-05-01 US US6872701 No 2005-03-29 2021-06-05 US US8101575 No 2012-01-24 2021-05-01 US US8158580 No 2012-04-17 2021-05-01 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0148 mg/mL ALOGPS logP 2.32 ALOGPS logP -6.2 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 1.55 Chemaxon pKa (Strongest Basic) 9.99 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 29 Chemaxon Hydrogen Donor Count 23 Chemaxon Polar Surface Area 598.09 Å2 Chemaxon Rotatable Bond Count 30 Chemaxon Refractivity 429.41 m3·mol-1 Chemaxon Polarizability 175.85 Å3 Chemaxon Number of Rings 10 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9186 Blood Brain Barrier - 0.9691 Caco-2 permeable - 0.6403 P-glycoprotein substrate Substrate 0.9318 P-glycoprotein inhibitor I Non-inhibitor 0.6459 P-glycoprotein inhibitor II Non-inhibitor 0.9898 Renal organic cation transporter Non-inhibitor 0.946 CYP450 2C9 substrate Non-substrate 0.877 CYP450 2D6 substrate Non-substrate 0.8047 CYP450 3A4 substrate Substrate 0.665 CYP450 1A2 substrate Non-inhibitor 0.7471 CYP450 2C9 inhibitor Non-inhibitor 0.7401 CYP450 2D6 inhibitor Non-inhibitor 0.8259 CYP450 2C19 inhibitor Non-inhibitor 0.6898 CYP450 3A4 inhibitor Inhibitor 0.5291 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8482 Ames test Non AMES toxic 0.5605 Carcinogenicity Non-carcinogens 0.8098 Biodegradation Not ready biodegradable 0.9966 Rat acute toxicity 2.7064 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9196 hERG inhibition (predictor II) Inhibitor 0.6147
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
- Specific Function
- acetylcholine receptor activity
- Gene Name
- CHRNA2
- Uniprot ID
- Q15822
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-2
- Molecular Weight
- 59764.82 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
- Specific Function
- acetylcholine binding
- Gene Name
- CHRNA3
- Uniprot ID
- P32297
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-3
- Molecular Weight
- 57479.54 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for CRH (corticotropin-releasing factor) and UCN (urocortin). Has high affinity for CRH and UCN. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and down-stream effectors, such as adenylate cyclase. Promotes the activation of adenylate cyclase, leading to increased intracellular cAMP levels. Inhibits the activity of the calcium channel CACNA1H. Required for normal embryonic development of the adrenal gland and for normal hormonal responses to stress. Plays a role in the response to anxiogenic stimuli
- Specific Function
- corticotrophin-releasing factor receptor activity
- Gene Name
- CRHR1
- Uniprot ID
- P34998
- Uniprot Name
- Corticotropin-releasing factor receptor 1
- Molecular Weight
- 47670.42 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at March 19, 2008 16:29 / Updated at October 10, 2024 12:49