NAV

Gamithromycin

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

Identification

Generic Name
Gamithromycin
DrugBank Accession Number
DB11416
Background

Gamithromycin is an antibiotic used in cattle.

Type
Small Molecule
Groups
Vet approved
Structure
Similar Structures
Weight
Average: 777.05
Monoisotopic: 776.539825895
Chemical Formula
C40H76N2O12
Synonyms
  • Gamithromycin
External IDs
  • ML-1,709,460
  • ML-1709460
  • ML-460
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Gamithromycin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Gamithromycin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Gamithromycin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Gamithromycin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Gamithromycin is combined with Benzocaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid or derivatives / Aminoglycoside core / Azacycle / Carbonyl group / Carboxylic acid derivative
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ZE856183S0
CAS number
145435-72-9
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)(OC)[C@@H](O)[C@H](C)O1)O[C@H]1[C@H](C)[C@@H](O[C@]2([H])O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)N(CCC)C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]1C

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
ChemSpider
28530824
RxNav
1113697
ChEMBL
CHEMBL2107342
ZINC
ZINC000169292837

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability86.24 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/MSsplash10-004i-0000002900-904bd72ca7ee598c4d60
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000011900-4b66baef6f6560791a52
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kdi-2900004800-57d4b69ff04a8acd574a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-2900003600-ee54d16682bb743aee2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-4900003000-a26dd2036944b5e02230
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-1900002300-c7659a58932e579bf0d6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-245.38356
predicted
DeepCCS 1.0 (2019)
[M+H]+247.10728
predicted
DeepCCS 1.0 (2019)
[M+Na]+253.43623
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:35 / Updated at February 21, 2021 18:53