Gamithromycin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Gamithromycin
Accession Number
DB11416
Type
Small Molecule
Groups
Vet approved
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
ZE856183S0
CAS number
Not Available
Weight
Average: 777.05
Monoisotopic: 776.539825895
Chemical Formula
C40H76N2O12
InChI Key
VWAMTBXLZPEDQO-UZSBJOJWSA-N
InChI
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
IUPAC 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
SMILES
[H][C@@]1(C)C[C@]([H])(N(C)C)[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(C)[C@]([H])(O[C@@]3([H])C[C@@](C)(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@@]([H])(C)C(=O)O[C@]([H])(CC)[C@@](C)(O)[C@]([H])(O)[C@@]([H])(C)CN(CCC)[C@]([H])(C)C[C@@]2(C)O)O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Gamithromycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Gamithromycin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Gamithromycin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Gamithromycin is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Gamithromycin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Gamithromycin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Gamithromycin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Gamithromycin.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Gamithromycin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Gamithromycin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Sargison ND, Scott PR: Metaphylactic gamithromycin treatment for the management of lameness in ewes putatively caused by Bacteroides melaninogenicus. Vet Rec. 2011 Nov 19;169(21):556. doi: 10.1136/vr.d4927. Epub 2011 Sep 22. [PubMed:21949059]
  2. Giguere 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:21355734]
  3. Berghaus LJ, Giguere 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:21443748]
  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:23687147]
  5. 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:23810743]
  6. 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. [PubMed:20557439]
  7. Baggott D, Casartelli A, Fraisse F, Manavella C, Marteau R, Rehbein S, Wiedemann M, Yoon S: Demonstration of the metaphylactic use of gamithromycin against bacterial pathogens associated with bovine respiratory disease in a multicentre farm trial. Vet Rec. 2011 Mar 5;168(9):241. doi: 10.1136/vr.c6776. Epub 2011 Feb 28. [PubMed:21493573]
  8. 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:21078926]
  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:26547885]
External Links
ChemSpider
28530824
ChEMBL
CHEMBL2107342

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.294 mg/mLALOGPS
logP3.74ALOGPS
logP2.98ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)9.95ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.08 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity203.55 m3·mol-1ChemAxon
Polarizability86.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / O-glycosyl compounds / Oxanes / Monosaccharides / Tertiary alcohols / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters
show 11 more
Substituents
Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on February 25, 2016 11:35 / Updated on June 04, 2019 07:21