Gamithromycin | CAS#145435-72-9

MedKoo Cat#: 329858 | Name: Gamithromycin

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Description:

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

Gamithromycin is an animal used antibiotics. Gamithromycin is active in vitro against the bacterial agents most commonly associated with bronchopneumonia in older foals.

Chemical Structure

Gamithromycin

CAS#145435-72-9

Theoretical Analysis

MedKoo Cat#: 329858

Name: Gamithromycin

CAS#: 145435-72-9

Chemical Formula: C40H76N2O12

Exact Mass: 776.5398

Molecular Weight: 777.05

Elemental Analysis: C, 61.83; H, 9.86; N, 3.61; O, 24.71

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
200mg	USD 450.00	2 Weeks
500mg	USD 850.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Related CAS #

145435-72-9

Synonym

Gamithromycin; Gamitromicina; Zactran; Gamithromycinum; GAM; ML-1709460; ML 1709460; ML1709460;

IUPAC/Chemical Name

(2R,3S,4R,5S,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-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one

InChi Key

VWAMTBXLZPEDQO-UZSBJOJWSA-N

InChi Code

InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1

SMILES Code

O=C1[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](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)N(CCC)C[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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gamithromycin is an antimicrobial agent which can inhibit the growth of MmmSC strains B237 and Tan8 with MICs of 0.00012 and 0.00006 μg/mL, respectively.

In vitro activity:

TBD

In vivo activity:

The clinical scores, number of abscesses and the abscess scores after 1 and 2 weeks of treatment were significantly lower for foals treated with GAM (gamithromycin) or AZM‐RIF compared to control foals (Fig 1). The WBC count of foals treated with GAM was significantly higher than that of foals treated with AZM‐RIF on week 3 of treatment (Fig 1B). Reference: J Vet Intern Med. 2015 Jan;29(1):333-8. https://pubmed.ncbi.nlm.nih.gov/25619521/

	Solvent	mg/mL	mM
Solubility
	DMF	16.0	20.59
	DMSO	68.3	87.94
	Ethanol	58.0	74.64
	Ethanol:PBS (pH 7.2) (1:1)	0.5	0.64

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 777.05 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.

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. Hamel D, Richard-Mazet A, Voisin F, Böhne I, Fraisse F, Rauh R, Huang R, Kellermann M, Letendre L, Dumont P, Rehbein S. Gamithromycin in swine: Pharmacokinetics and clinical evaluation against swine respiratory disease. Vet Med Sci. 2021 Mar;7(2):455-464. doi: 10.1002/vms3.375. Epub 2020 Oct 15. PMID: 33058489; PMCID: PMC8025653. 2. Hildebrand F, Venner M, Giguère S. Efficacy of gamithromycin for the treatment of foals with mild to moderate bronchopneumonia. J Vet Intern Med. 2015 Jan;29(1):333-8. doi: 10.1111/jvim.12504. PMID: 25619521; PMCID: PMC4858060.

In vitro protocol:

TBD

In vivo protocol:

1: Hildebrand F, Venner M, Giguère S. Efficacy of gamithromycin for the treatment of foals with mild to moderate bronchopneumonia. J Vet Intern Med. 2015 Jan;29(1):333-8. doi: 10.1111/jvim.12504. PubMed PMID: 25619521; PubMed Central PMCID: PMC4858060. 2: Kellermann M, Huang RA, Forbes AB, Rehbein S. Gamithromycin plasma and skin pharmacokinetics in sheep. Res Vet Sci. 2014 Oct;97(2):199-203. doi: 10.1016/j.rvsc.2014.08.008. Epub 2014 Sep 4. PubMed PMID: 25241389. 3: Mitchell JD, Goh S, McKellar QA, McKeever DJ. In vitro pharmacodynamics of gamithromycin against Mycoplasma mycoides subspecies mycoides Small Colony. Vet J. 2013 Sep;197(3):806-11. doi: 10.1016/j.tvjl.2013.05.025. Epub 2013 Jun 28. PubMed PMID: 23810743. 4: Watteyn A, Plessers E, Wyns H, De Baere S, De Backer P, Croubels S. Pharmacokinetics of gamithromycin after intravenous and subcutaneous administration in broiler chickens. Poult Sci. 2013 Jun;92(6):1516-22. doi: 10.3382/ps.2012-02932. PubMed PMID: 23687147. 5: Berghaus LJ, Giguère S, Sturgill TL, Bade D, Malinski TJ, Huang R. Plasma pharmacokinetics, pulmonary distribution, and in vitro activity of gamithromycin in foals. J Vet Pharmacol Ther. 2012 Feb;35(1):59-66. doi: 10.1111/j.1365-2885.2011.01292.x. Epub 2011 Mar 28. PubMed PMID: 21443748. 6: Torres S, Thomson DU, Bello NM, Nosky BJ, Reinhardt CD. Field study of the comparative efficacy of gamithromycin and tulathromycin for the control of undifferentiated bovine respiratory disease complex in beef feedlot calves at high risk of developing respiratory tract disease. Am J Vet Res. 2013 Jun;74(6):839-46. doi: 10.2460/ajvr.74.6.839. PubMed PMID: 23718651. 7: DeDonder KD, Apley MD, Li M, Gehring R, Harhay DM, Lubbers BV, White BJ, Capik SF, KuKanich B, Riviere JE, Tessman RK. Pharmacokinetics and pharmacodynamics of gamithromycin in pulmonary epithelial lining fluid in naturally occurring bovine respiratory disease in multisource commingled feedlot cattle. J Vet Pharmacol Ther. 2016 Apr;39(2):157-66. doi: 10.1111/jvp.12267. Epub 2015 Oct 6. PubMed PMID: 26441021. 8: Strobel H, Lauseker M, Forbes AB. Targeted antibiotic treatment of lame sheep with footrot using either oxytetracycline or gamithromycin. Vet Rec. 2014 Jan 11;174(2):46. doi: 10.1136/vr.101840. Epub 2013 Dec 20. PubMed PMID: 24362004. 9: Wyns H, Meyer E, Plessers E, Watteyn A, van Bergen T, Schauvliege S, De Baere S, Devreese M, De Backer P, Croubels S. Modulation by gamithromycin and ketoprofen of in vitro and in vivo porcine lipopolysaccharide-induced inflammation. Vet Immunol Immunopathol. 2015 Dec 15;168(3-4):211-22. doi: 10.1016/j.vetimm.2015.09.014. Epub 2015 Sep 28. PubMed PMID: 26547885. 10: Torres S, Thomson DU, Bello NM, Nosky BJ, Reinhardt CD. Field study of the comparative efficacy of gamithromycin and tulathromycin for the treatment of undifferentiated bovine respiratory disease complex in beef feedlot calves. Am J Vet Res. 2013 Jun;74(6):847-53. doi: 10.2460/ajvr.74.6.847. PubMed PMID: 23718652. 11: Wyns H, Meyer E, Plessers E, Watteyn A, De Baere S, De Backer P, Croubels S. Pharmacokinetics of gamithromycin after intravenous and subcutaneous administration in pigs. Res Vet Sci. 2014 Feb;96(1):160-3. doi: 10.1016/j.rvsc.2013.11.012. Epub 2013 Dec 1. PubMed PMID: 24331716. 12: Forbes AB, Strobel H, Stamphoj I. Field studies on the elimination of footrot in sheep through whole flock treatments with gamithromycin. Vet Rec. 2014 Feb 8;174(6):146. doi: 10.1136/vr.102028. Epub 2014 Jan 29. PubMed PMID: 24477473. 13: Giguère S, Huang R, Malinski TJ, Dorr PM, Tessman RK, Somerville BA. Disposition of gamithromycin in plasma, pulmonary epithelial lining fluid, bronchoalveolar cells, and lung tissue in cattle. Am J Vet Res. 2011 Mar;72(3):326-30. doi: 10.2460/ajvr.72.3.326. PubMed PMID: 21355734. 14: Jones ML, Washburn KE, Fajt VR, Rice S, Coetzee JF. Synovial fluid pharmacokinetics of tulathromycin, gamithromycin and florfenicol after a single subcutaneous dose in cattle. BMC Vet Res. 2015 Feb 7;11:26. doi: 10.1186/s12917-015-0346-4. PubMed PMID: 25886555; PubMed Central PMCID: PMC4332912. 15: Plessers E, Watteyn A, Wyns H, Pardon B, De Backer P, Croubels S. Study of the immunomodulatory properties of gamithromycin and dexamethasone in a lipopolysaccharide inflammation model in calves. Res Vet Sci. 2015 Dec;103:218-23. doi: 10.1016/j.rvsc.2015.10.014. Epub 2015 Oct 28. PubMed PMID: 26679821. 16: Watteyn A, Devreese M, De Baere S, Wyns H, Plessers E, Boyen F, Haesebrouck F, De Backer P, Croubels S. Pharmacokinetic and pharmacodynamic properties of gamithromycin in turkey poults with respect to Ornithobacterium rhinotracheale. Poult Sci. 2015 Sep;94(9):2066-74. doi: 10.3382/ps/pev217. Epub 2015 Jul 20. PubMed PMID: 26195808. 17: Huang RA, Letendre LT, Banav N, Fischer J, Somerville B. Pharmacokinetics of gamithromycin in cattle with comparison of plasma and lung tissue concentrations and plasma antibacterial activity. J Vet Pharmacol Ther. 2010 Jun 1;33(3):227-37. doi: 10.1111/j.1365-2885.2009.01125.x. Erratum in: J Vet Pharmacol Ther. 2010 Dec;33(6):622. PubMed PMID: 20557439. 18: De Baere S, Devreese M, Watteyn A, Wyns H, Plessers E, De Backer P, Croubels S. Development and validation of a liquid chromatography-tandem mass spectrometry method for the quantitative determination of gamithromycin in animal plasma, lung tissue and pulmonary epithelial lining fluid. J Chromatogr A. 2015 Jun 12;1398:73-82. doi: 10.1016/j.chroma.2015.04.022. Epub 2015 Apr 17. PubMed PMID: 25937131. 19: Plessers E, Wyns H, Watteyn A, Pardon B, De Baere S, Sys SU, De Backer P, Croubels S. Immunomodulatory properties of gamithromycin and ketoprofen in lipopolysaccharide-challenged calves with emphasis on the acute-phase response. Vet Immunol Immunopathol. 2016 Mar;171:28-37. doi: 10.1016/j.vetimm.2016.01.007. Epub 2016 Jan 29. PubMed PMID: 26964715. 20: Forbes AB, Ramage C, Sales J, Baggott D, Donachie W. Determination of the duration of antibacterial efficacy following administration of gamithromycin using a bovine Mannheimia haemolytica challenge model. Antimicrob Agents Chemother. 2011 Feb;55(2):831-5. doi: 10.1128/AAC.00552-10. Epub 2010 Nov 15. PubMed PMID: 21078926; PubMed Central PMCID: PMC3028799.