GENTAMICIN C1A

Identification

Name
GENTAMICIN C1A
Accession Number
DB04729
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Gentamicin c1a sulfateS7K05PO15737713-04-5HNCAOLPMSASREN-UCMBPTNBSA-N
Categories
UNII
AV4A72IATD
CAS number
Not Available
Weight
Average: 449.5423
Monoisotopic: 449.284948627
Chemical Formula
C19H39N5O7
InChI Key
VEGXETMJINRLTH-BOZYPMBZSA-N
InChI
InChI=1S/C19H39N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1
IUPAC Name
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
SMILES
CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H]2O)OC[C@]1(C)O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
A30S ribosomal protein S12
adduct
Escherichia coli (strain K12)
A16S rRNA
adduct
Enteric bacteria and other eubacteria
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
(4R)-limonene(4R)-limonene may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.
AcetaminophenGENTAMICIN C1A may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with GENTAMICIN C1A.
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with GENTAMICIN C1A.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with GENTAMICIN C1A.
AlclofenacAlclofenac may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.
AlcuroniumGENTAMICIN C1A may increase the respiratory depressant activities of Alcuronium.
Alendronic acidGENTAMICIN C1A may increase the hypocalcemic activities of Alendronic acid.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C00908
PubChem Compound
72396
PubChem Substance
46505724
ChemSpider
65329
ChEBI
27784
ChEMBL
CHEMBL194126
HET
LLL
PDB Entries
2et3 / 3ham / 4lf4 / 4lf9 / 4v53 / 4v55 / 5obm

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
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility20.5 mg/mLALOGPS
logP-2.2ALOGPS
logP-4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area213.72 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.83 m3·mol-1ChemAxon
Polarizability47.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9691
Blood Brain Barrier-0.9812
Caco-2 permeable-0.7232
P-glycoprotein substrateSubstrate0.7767
P-glycoprotein inhibitor INon-inhibitor0.659
P-glycoprotein inhibitor IINon-inhibitor0.873
Renal organic cation transporterNon-inhibitor0.8371
CYP450 2C9 substrateNon-substrate0.8321
CYP450 2D6 substrateNon-substrate0.7952
CYP450 3A4 substrateSubstrate0.5286
CYP450 1A2 substrateNon-inhibitor0.9169
CYP450 2C9 inhibitorNon-inhibitor0.9187
CYP450 2D6 inhibitorNon-inhibitor0.9049
CYP450 2C19 inhibitorNon-inhibitor0.8876
CYP450 3A4 inhibitorNon-inhibitor0.9756
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9421
Ames testNon AMES toxic0.7877
CarcinogenicityNon-carcinogens0.96
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity1.8005 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.978
hERG inhibition (predictor II)Non-inhibitor0.6741
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
2-deoxystreptamine aminoglycosides / O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tertiary alcohols / 1,2-aminoalcohols / Oxacyclic compounds
show 5 more
Substituents
Amino cyclitol glycoside / 2-deoxystreptamine aminoglycoside / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Monosaccharide / Oxane
show 18 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
gentamycin C (CHEBI:27784)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Gill AE, Amyes SG: The contribution of a novel ribosomal S12 mutation to aminoglycoside resistance of Escherichia coli mutants. J Chemother. 2004 Aug;16(4):347-9. [PubMed:15332709]
  4. Tamehiro N, Hosaka T, Xu J, Hu H, Otake N, Ochi K: Innovative approach for improvement of an antibiotic-overproducing industrial strain of Streptomyces albus. Appl Environ Microbiol. 2003 Nov;69(11):6412-7. [PubMed:14602594]
  5. Hu H, Ochi K: Novel approach for improving the productivity of antibiotic-producing strains by inducing combined resistant mutations. Appl Environ Microbiol. 2001 Apr;67(4):1885-92. [PubMed:11282646]
  6. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [PubMed:10619838]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Adduct
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Doi Y, de Oliveira Garcia D, Adams J, Paterson DL: Coproduction of novel 16S rRNA methylase RmtD and metallo-beta-lactamase SPM-1 in a panresistant Pseudomonas aeruginosa isolate from Brazil. Antimicrob Agents Chemother. 2007 Mar;51(3):852-6. Epub 2006 Dec 11. [PubMed:17158944]
  4. Bogaerts P, Galimand M, Bauraing C, Deplano A, Vanhoof R, De Mendonca R, Rodriguez-Villalobos H, Struelens M, Glupczynski Y: Emergence of ArmA and RmtB aminoglycoside resistance 16S rRNA methylases in Belgium. J Antimicrob Chemother. 2007 Mar;59(3):459-64. Epub 2007 Jan 15. [PubMed:17224412]
  5. Aslangul E, Massias L, Meulemans A, Chau F, Andremont A, Courvalin P, Fantin B, Ruimy R: Acquired gentamicin resistance by permeability impairment in Enterococcus faecalis. Antimicrob Agents Chemother. 2006 Nov;50(11):3615-21. [PubMed:17065620]
  6. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [PubMed:10619838]

Drug created on September 11, 2007 11:49 / Updated on August 02, 2018 05:25