Identification

Generic Name
Neamine
DrugBank Accession Number
DB04808
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 322.358
Monoisotopic: 322.185234584
Chemical Formula
C12H26N4O6
Synonyms
  • 2-desoxy-4-O-(2,6-diamino-2,6-didesoxy-α-D-glucopyranosyl)-D-streptamin
  • 4-O-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine
  • Dekamycin V
  • Nebramycin X
  • Negamicin
  • Neomycin A

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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
AbacavirNeamine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Neamine is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Neamine is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Neamine is combined with Acenocoumarol.
AcetaminophenNeamine may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetylcholineThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Neamine.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Neamine is combined with Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Neamine.
AclidiniumNeamine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineNeamine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / 1,2-aminoalcohols / Oxacyclic compounds / Acetals
show 3 more
Substituents
1,2-aminoalcohol / 2-deoxystreptamine aminoglycoside / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino cyclitol glycoside / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
aminoglycoside, 2,6-dideoxy-alpha-D-glucoside (CHEBI:7489)
Affected organisms
Not Available

Chemical Identifiers

UNII
5981U00LY0
CAS number
3947-65-7
InChI Key
SYJXFKPQNSDJLI-HKEUSBCWSA-N
InChI
InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1
IUPAC Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}oxane-3,4-diol
SMILES
NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

References

Synthesis Reference

Eiichi Akita, Tsutomu Tsuchiya, Shinichi Kondo, Shuntaro Yasuda, Sumio Umezawa, Hamao Umezawa, "1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin and the production thereof." U.S. Patent US4008218, issued February, 1974.

US4008218
General References
Not Available
KEGG Compound
C01441
PubChem Compound
72392
PubChem Substance
46507306
ChemSpider
65325
BindingDB
8580
ChEBI
7489
ChEMBL
CHEMBL427409
ZINC
ZINC000004095654
Therapeutic Targets Database
DNC001004
PDBe Ligand
XXX
Wikipedia
Neamine
PDB Entries
2et8 / 2f4s / 2fcx / 5z8k / 6e0d / 6s0v / 7cl6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility101.0 mg/mLALOGPS
logP-2.9ALOGPS
logP-5.3ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)12.66ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area203.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.72 m3·mol-1ChemAxon
Polarizability32.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8567
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7666
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.7518
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8516
CYP450 2C9 substrateNon-substrate0.8033
CYP450 2D6 substrateNon-substrate0.8275
CYP450 3A4 substrateNon-substrate0.6391
CYP450 1A2 substrateNon-inhibitor0.9186
CYP450 2C9 inhibitorNon-inhibitor0.9257
CYP450 2D6 inhibitorNon-inhibitor0.9224
CYP450 2C19 inhibitorNon-inhibitor0.9062
CYP450 3A4 inhibitorNon-inhibitor0.9569
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.914
Ames testNon AMES toxic0.6928
CarcinogenicityNon-carcinogens0.952
BiodegradationNot ready biodegradable0.7421
Rat acute toxicity1.6749 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9779
hERG inhibition (predictor II)Non-inhibitor0.8599
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

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52