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MedKoo Cat#: 585240 | Name: Telavancin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Telavancin a semisynthetic lipoglycopeptide vancomycin-derivative and antimicrobial agent developed by Theravance for overcoming resistant Gram-positive bacterial infections, specifically methicillin-resistant Staphylococcus aureus (MRSA).

Chemical Structure

Telavancin
Telavancin
CAS#372151-71-8

Theoretical Analysis

MedKoo Cat#: 585240

Name: Telavancin

CAS#: 372151-71-8

Chemical Formula: C80H106Cl2N11O27P

Exact Mass: 1753.6374

Molecular Weight: 1755.65

Elemental Analysis: C, 54.73; H, 6.09; Cl, 4.04; N, 8.78; O, 24.60; P, 1.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Telavancin; TD-6424; TD6424; TD 6424
IUPAC/Chemical 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
InChi Key
ONUMZHGUFYIKPM-MXNFEBESSA-N
InChi Code
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
SMILES Code
O=C([C@@H](N1)C2=CC(O)=C(CNCP(O)(O)=O)C(O)=C2C3=C(O)C=CC([C@@]4([H])NC([C@](C5=CC(OC(C=C6)=C(Cl)C=C6[C@@H](O)[C@@](NC4=O)([H])C1=O)=C(O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]8O[C@@H](C)[C@@H](O)[C@@](C)(NCCNCCCCCCCCCC)C8)C(OC9=C(Cl)C=C(C=C9)[C@@H](O)[C@@H](NC([C@H](NC)CC(C)C)=O)C(N[C@H]%10CC(N)=O)=O)=C5)([H])NC%10=O)=O)=C3)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,755.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Schroeder CP, Van Anglen LJ, Dretler RH, Adams JS, Prokesch RC, Luu Q, Krinsky AH. Outpatient treatment of osteomyelitis with telavancin. Int J Antimicrob Agents. 2017 Jul;50(1):93-96. doi: 10.1016/j.ijantimicag.2017.01.034. Epub 2017 Apr 26. PubMed PMID: 28456704. 2: Das B, Sarkar C, Das D, Gupta A, Kalra A, Sahni S. Telavancin: a novel semisynthetic lipoglycopeptide agent to counter the challenge of resistant Gram-positive pathogens. Ther Adv Infect Dis. 2017 Mar;4(2):49-73. doi: 10.1177/2049936117690501. Epub 2017 Mar 8. Review. Erratum in: Ther Adv Infect Dis. 2017 Nov;4(6):193. PubMed PMID: 28634536; PubMed Central PMCID: PMC5467880. 3: Al Jalali V, Zeitlinger M. Clinical Pharmacokinetics and Pharmacodynamics of Telavancin Compared with the Other Glycopeptides. Clin Pharmacokinet. 2018 Jul;57(7):797-816. doi: 10.1007/s40262-017-0623-4. Review. PubMed PMID: 29332251; PubMed Central PMCID: PMC5999141. 4: Liu Y, Wang J. A comparison of telavancin and vancomycin for treatment of methicillin-resistant Staphylococcus aureus infections: A meta-analysis. Int J Clin Pharmacol Ther. 2017 Nov;55(11):839-845. doi: 10.5414/CP202996. Review. PubMed PMID: 28793957. 5: Britt NS, Tirmizi S, Ritchie DJ, Topal JE, McManus D, Nizet V, Casabar E, Sakoulas G. Telavancin for refractory MRSA bacteraemia in intermittent haemodialysis recipients. J Antimicrob Chemother. 2018 Mar 1;73(3):764-767. doi: 10.1093/jac/dkx437. PubMed PMID: 29244141; PubMed Central PMCID: PMC5890690. 6: Duncan LR, Sader HS, Smart JI, Flamm RK, Mendes RE. Telavancin activity in vitro tested against a worldwide collection of Gram-positive clinical isolates (2014). J Glob Antimicrob Resist. 2017 Sep;10:271-276. doi: 10.1016/j.jgar.2017.03.018. Epub 2017 Jul 19. PubMed PMID: 28735051. 7: Adamantia L, Antoni T. Pharmacodynamics, pharmacokinetics and clinical efficacy of telavancin in the treatment of pneumonia. Expert Opin Drug Metab Toxicol. 2016 Jul;12(7):803-12. doi: 10.1080/17425255.2016.1187599. Epub 2016 May 30. Review. PubMed PMID: 27158752. 8: Harting J, Fernandez F, Kelley R, Wiemken T, Peyrani P, Ramirez J. Telavancin for the treatment of methicillin-resistant Staphylococcus aureus bone and joint infections. Diagn Microbiol Infect Dis. 2017 Dec;89(4):294-299. doi: 10.1016/j.diagmicrobio.2017.09.004. Epub 2017 Sep 18. PubMed PMID: 29137718. 9: Masterton R, Cornaglia G, Courvalin P, Lode HM, Rello J, Torres A. The clinical positioning of telavancin in Europe. Int J Antimicrob Agents. 2015 Mar;45(3):213-20. doi: 10.1016/j.ijantimicag.2014.12.006. Epub 2014 Dec 24. Review. PubMed PMID: 25600892. 10: Zhanel GG, Calic D, Schweizer F, Zelenitsky S, Adam H, Lagacé-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. Review. Erratum in: Drugs. 2011 Mar 26;71(5):526. PubMed PMID: 20426497. 11: Chuan J, Zhang Y, He X, Zhu Y, Zhong L, Yu D, Xiao H. Systematic Review and Meta-Analysis of the Efficacy and Safety of Telavancin for Treatment of Infectious Disease: Are We Clearer? Front Pharmacol. 2016 Sep 23;7:330. eCollection 2016. Review. PubMed PMID: 27721793; PubMed Central PMCID: PMC5033967. 12: Matzneller P, Österreicher Z, Reiter B, Lackner E, Stimpfl T, Zeitlinger M. Tissue pharmacokinetics of telavancin in healthy volunteers: a microdialysis study. J Antimicrob Chemother. 2016 Nov;71(11):3179-3184. Epub 2016 Jul 11. PubMed PMID: 27494910. 13: Liapikou A, Dimakou K, Toumbis M. Telavancin in the treatment of Staphylococcus aureus hospital-acquired and ventilator-associated pneumonia: clinical evidence and experience. Ther Adv Respir Dis. 2016 Aug;10(4):368-78. doi: 10.1177/1753465816651594. Epub 2016 Jun 23. Review. PubMed PMID: 27340253; PubMed Central PMCID: PMC5933685. 14: Sandrock CE, Shorr AF. The role of telavancin in hospital-acquired pneumonia and ventilator-associated pneumonia. Clin Infect Dis. 2015 Sep 15;61 Suppl 2:S79-86. doi: 10.1093/cid/civ535. Review. PubMed PMID: 26316561. 15: Lepak AJ, Zhao M, Andes DR. Comparative Pharmacodynamics of Telavancin and Vancomycin in the Neutropenic Murine Thigh and Lung Infection Models against Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Jun 27;61(7). pii: e00281-17. doi: 10.1128/AAC.00281-17. Print 2017 Jul. PubMed PMID: 28416551; PubMed Central PMCID: PMC5487664. 16: Mendes RE, Sader HS, Smart JI, Castanheira M, Flamm RK. Update of the activity of telavancin against a global collection of Staphylococcus aureus causing bacteremia, including endocarditis (2011-2014). Eur J Clin Microbiol Infect Dis. 2017 Jun;36(6):1013-1017. doi: 10.1007/s10096-016-2865-8. Epub 2017 Jan 22. PubMed PMID: 28111724; PubMed Central PMCID: PMC5442220. 17: Mendes RE, Flamm RK, Farrell DJ, Sader HS, Jones RN. Telavancin activity tested against Gram-positive clinical isolates from European, Russian and Israeli hospitals (2011-2013) using a revised broth microdilution testing method: redefining the baseline activity of telavancin. J Chemother. 2016 Apr;28(2):83-8. doi: 10.1179/1973947815Y.0000000050. PubMed PMID: 26058844. 18: Jones RN, Flamm RK, Castanheira M, Sader HS, Smart JI, Mendes RE. Activity of telavancin against Gram-positive pathogens isolated from bone and joint infections in North American, Latin American, European and Asia-Pacific nations. Diagn Microbiol Infect Dis. 2017 Jun;88(2):184-187. doi: 10.1016/j.diagmicrobio.2017.03.003. Epub 2017 Mar 8. PubMed PMID: 28377166. 19: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500686/ PubMed PMID: 29999745. 20: Wenzler E, Rodvold KA. Telavancin: the long and winding road from discovery to food and drug administration approvals and future directions. Clin Infect Dis. 2015 Sep 15;61 Suppl 2:S38-47. doi: 10.1093/cid/civ522. Review. PubMed PMID: 26316557.