Tulathromycin A
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MedKoo CAT#: 561476

CAS#: 217500-96-4

Description: Tulathromycin A, also known as Tulathromycin and CP-472295, is a macrolide antibiotic used to treat bovine respiratory disease (BRD) in cattle and swine respiratory disease in pigs.


Chemical Structure

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Tulathromycin A
CAS# 217500-96-4

Theoretical Analysis

MedKoo Cat#: 561476
Name: Tulathromycin A
CAS#: 217500-96-4
Chemical Formula: C41H79N3O12
Exact Mass: 805.5664
Molecular Weight: 806.09
Elemental Analysis: C, 61.09; H, 9.88; N, 5.21; O, 23.82

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 Ready to ship
2.0g USD 250.0 Ready to ship
5.0g USD 450.0 Ready to ship
10.0g USD 750.0 Ready to ship
20.0g USD 1250.0 Ready to ship
50.0g USD 2650.0 Ready to ship
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Synonym: Tulathromycin; Draxxin; Tulathromycin A; CP-472,295; CP-472295; CP 472295; CP472295;

IUPAC/Chemical Name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-(propylaminomethyl)oxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one

InChi Key: GUARTUJKFNAVIK-QPTWMBCESA-N

InChi Code: InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1

SMILES Code: O=C1[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@](CNCCC)(O)[C@](C)(OC)C2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@](C)(O)C[C@@H](C)CN[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)O1

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: >2 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

Biological target: Tulathromycin A (Tulathromycin), a macrolide antibiotic, inhibits protein synthesis (IC50=0.26 µM) by targeting bacterial ribosome.
In vitro activity: The immunomodulating mechanisms of the TUL activities were further analyzed in bovine cells in vitro. Tulathromycin inhibited the release of free fatty acids in bovine neutrophils stimulated with 10 μM melittin, an activator of PLA2. Furthermore, in both resting neutrophils and in those stimulated with 3 μM A23187, tulathromycin significantly reduced secreted levels of LTB4. The addition of 3 μM exogenous arachidonic acid partially restored the levels of LTB4 in tulathromycin-treated neutrophils. Reference: Antimicrob Agents Chemother. 2014 Aug;58(8):4298-307. https://pubmed.ncbi.nlm.nih.gov/24820086/
In vivo activity: To investigate the direct anti-inflammatory actions of tulathromycin in the absence of a bacterial stimulus, calves were challenged intratracheally with zymosan, a known Toll-like receptor 2 (TLR2) ligand that has been used as an inflammatory stimulus in vivo. Three hours postchallenge, BAL fluid LTB4 levels were significantly higher in zymosan-challenged sham-treated calves than in control calves (mean ± standard deviation, 209.9 ± 60.5 pg/ml and 51.1 ± 13.1 pg/ml, respectively); tulathromycin abolished this increase in BAL fluid LTB4 levels (63.9 ± 16.0 pg/ml). Twenty-four hours postchallenge, the BAL fluid levels of PGE2 were significantly higher in calves challenged with zymosan versus in the controls (594.6 ± 134.5 pg/ml and 142.5 ± 59.2 pg/ml, respectively); tulathromycin treatment inhibited the increase in BAL fluid PGE2 levels caused by zymosan (148.3 ± 34.7 pg/ml). Reference: Antimicrob Agents Chemother. 2014 Aug;58(8):4298-307. https://pubmed.ncbi.nlm.nih.gov/24820086/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 60.0 74.53

Preparing Stock Solutions

The following data is based on the product molecular weight 806.09 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
Formulation protocol: 1. Fischer CD, Duquette SC, Renaux BS, Feener TD, Morck DW, Hollenberg MD, Lucas MJ, Buret AG. Tulathromycin exerts proresolving effects in bovine neutrophils by inhibiting phospholipases and altering leukotriene B4, prostaglandin E2, and lipoxin A4 production. Antimicrob Agents Chemother. 2014 Aug;58(8):4298-307. doi: 10.1128/AAC.02813-14. Epub 2014 May 12. PMID: 24820086; PMCID: PMC4136062. 2. Fischer CD, Beatty JK, Zvaigzne CG, Morck DW, Lucas MJ, Buret AG. Anti-Inflammatory benefits of antibiotic-induced neutrophil apoptosis: tulathromycin induces caspase-3-dependent neutrophil programmed cell death and inhibits NF-kappaB signaling and CXCL8 transcription. Antimicrob Agents Chemother. 2011 Jan;55(1):338-48. doi: 10.1128/AAC.01052-10. Epub 2010 Oct 18. PMID: 20956586; PMCID: PMC3019645.
In vitro protocol: 1. Fischer CD, Duquette SC, Renaux BS, Feener TD, Morck DW, Hollenberg MD, Lucas MJ, Buret AG. Tulathromycin exerts proresolving effects in bovine neutrophils by inhibiting phospholipases and altering leukotriene B4, prostaglandin E2, and lipoxin A4 production. Antimicrob Agents Chemother. 2014 Aug;58(8):4298-307. doi: 10.1128/AAC.02813-14. Epub 2014 May 12. PMID: 24820086; PMCID: PMC4136062. 2. Fischer CD, Beatty JK, Zvaigzne CG, Morck DW, Lucas MJ, Buret AG. Anti-Inflammatory benefits of antibiotic-induced neutrophil apoptosis: tulathromycin induces caspase-3-dependent neutrophil programmed cell death and inhibits NF-kappaB signaling and CXCL8 transcription. Antimicrob Agents Chemother. 2011 Jan;55(1):338-48. doi: 10.1128/AAC.01052-10. Epub 2010 Oct 18. PMID: 20956586; PMCID: PMC3019645.
In vivo protocol: 1. Fischer CD, Duquette SC, Renaux BS, Feener TD, Morck DW, Hollenberg MD, Lucas MJ, Buret AG. Tulathromycin exerts proresolving effects in bovine neutrophils by inhibiting phospholipases and altering leukotriene B4, prostaglandin E2, and lipoxin A4 production. Antimicrob Agents Chemother. 2014 Aug;58(8):4298-307. doi: 10.1128/AAC.02813-14. Epub 2014 May 12. PMID: 24820086; PMCID: PMC4136062. 2. Fischer CD, Beatty JK, Zvaigzne CG, Morck DW, Lucas MJ, Buret AG. Anti-Inflammatory benefits of antibiotic-induced neutrophil apoptosis: tulathromycin induces caspase-3-dependent neutrophil programmed cell death and inhibits NF-kappaB signaling and CXCL8 transcription. Antimicrob Agents Chemother. 2011 Jan;55(1):338-48. doi: 10.1128/AAC.01052-10. Epub 2010 Oct 18. PMID: 20956586; PMCID: PMC3019645.

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1: Abell KM, Theurer ME, Larson RL, White BJ, Apley M. A mixed treatment comparison meta-analysis of metaphylaxis treatments for bovine respiratory disease in beef cattle. J Anim Sci. 2017 Feb;95(2):626-635. doi: 10.2527/jas.2016.1062. Review. PubMed PMID: 28380607.

2: O'Connor AM, Yuan C, Cullen JN, Coetzee JF, da Silva N, Wang C. A mixed treatment meta-analysis of antibiotic treatment options for bovine respiratory disease - An update. Prev Vet Med. 2016 Sep 15;132:130-139. doi: 10.1016/j.prevetmed.2016.07.003. Epub 2016 Aug 31. Review. PubMed PMID: 27612392.

3: Apley MD. Clinical evidence for individual animal therapy for papillomatous digital dermatitis (hairy heel wart) and infectious bovine pododermatitis (foot rot). Vet Clin North Am Food Anim Pract. 2015 Mar;31(1):81-95, vi. doi: 10.1016/j.cvfa.2014.11.009. Review. PubMed PMID: 25705026.

4: Villarino N, Brown SA, Martín-Jiménez T. The role of the macrolide tulathromycin in veterinary medicine. Vet J. 2013 Nov;198(2):352-7. doi: 10.1016/j.tvjl.2013.07.032. Epub 2013 Aug 6. Review. PubMed PMID: 24268476.

5: Villarino N, Brown SA, Martín-Jiménez T. Understanding the pharmacokinetics of tulathromycin: a pulmonary perspective. J Vet Pharmacol Ther. 2014 Jun;37(3):211-21. doi: 10.1111/jvp.12080. Epub 2013 Sep 30. Review. PubMed PMID: 24117832.

6: Villarino N, Martín-Jiménez T. Pharmacokinetics of macrolides in foals. J Vet Pharmacol Ther. 2013 Feb;36(1):1-13. doi: 10.1111/jvp.12010. Epub 2012 Oct 22. Review. PubMed PMID: 23082900.

7: Belanger AE, Shryock TR. Macrolide-resistant Campylobacter: the meat of the matter. J Antimicrob Chemother. 2007 Oct;60(4):715-23. Epub 2007 Aug 18. Review. PubMed PMID: 17704515.

8: Wellman NG, O'Connor AM. Meta-analysis of treatment of cattle with bovine respiratory disease with tulathromycin. J Vet Pharmacol Ther. 2007 Jun;30(3):234-41. Review. PubMed PMID: 17472655.

9: Evans NA. Tulathromycin: an overview of a new triamilide antibiotic for livestock respiratory disease. Vet Ther. 2005 Summer;6(2):83-95. Review. PubMed PMID: 16094557.