NAV

Rhodamine 6G

Identification

Generic Name
Rhodamine 6G
DrugBank Accession Number
DB03825
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 479.02
Monoisotopic: 478.2023206
Chemical Formula
C28H31ClN2O3
Synonyms
  • Basic red 1
  • Calcozine rhodamine 6GX
  • CI basic red 1
  • R6G
External IDs
  • CI 45160
  • NSC-36345
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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
TargetActionsOrganism
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus haemolyticus
UAcriflavine resistance protein BNot AvailableEscherichia coli (strain K12)
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Rhodamine 6G is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Rhodamine 6G is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Rhodamine 6G is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Rhodamine 6G is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Rhodamine 6G is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Xanthenes
Alternative Parents
Benzoic acid esters / Benzoyl derivatives / Secondary alkylarylamines / Heteroaromatic compounds / Carboxylic acid esters / Amino acids and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic chloride salt, rhodamine 6G(1+), xanthene dye (CHEBI:52672)
Affected organisms
Not Available

Chemical Identifiers

UNII
037VRW83CF
CAS number
989-38-8
InChI Key
XFKVYXCRNATCOO-UHFFFAOYSA-M
InChI
InChI=1S/C28H31N2O3.ClH/c1-6-29-23-15-25-21(13-17(23)4)27(19-11-9-10-12-20(19)28(31)32-8-3)22-14-18(5)24(30-7-2)16-26(22)33-25;/h9-16,29-30H,6-8H2,1-5H3;1H/q+1;/p-1
IUPAC Name
9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-10λ⁴-xanthen-10-ylium chloride
SMILES
[Cl-].CCNC1=CC2=[O+]C3=C(C=C(C)C(NCC)=C3)C(C3=CC=CC=C3C(=O)OCC)=C2C=C1C

References

General References
Not Available
KEGG Compound
C11177
PubChem Compound
13806
PubChem Substance
46505461
ChemSpider
16740341
ChEBI
52672
PDBe Ligand
RHQ
Wikipedia
Rhodamine_6G

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
0SuspendedDiagnosticCoronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility2E+004 mg/LGREEN,FJ (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.000496 mg/mLALOGPS
logP6.36ALOGPS
logP6.71Chemaxon
logS-6ALOGPS
pKa (Strongest Acidic)18.72Chemaxon
pKa (Strongest Basic)2.34Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.5 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity138.49 m3·mol-1Chemaxon
Polarizability52.04 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7376
Blood Brain Barrier+0.6795
Caco-2 permeable-0.5964
P-glycoprotein substrateSubstrate0.5805
P-glycoprotein inhibitor IInhibitor0.732
P-glycoprotein inhibitor IIInhibitor0.9654
Renal organic cation transporterNon-inhibitor0.7894
CYP450 2C9 substrateNon-substrate0.7886
CYP450 2D6 substrateNon-substrate0.763
CYP450 3A4 substrateNon-substrate0.5354
CYP450 1A2 substrateInhibitor0.7318
CYP450 2C9 inhibitorInhibitor0.5489
CYP450 2D6 inhibitorNon-inhibitor0.6169
CYP450 2C19 inhibitorInhibitor0.6843
CYP450 3A4 inhibitorNon-inhibitor0.5394
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8769
Ames testNon AMES toxic0.8768
CarcinogenicityCarcinogens 0.7764
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity2.4983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9642
hERG inhibition (predictor II)Inhibitor0.6637
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-8500900000-e8691e7ca80488454a5e
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-230.8803321
predicted
DarkChem Lite v0.1.0
[M-H]-234.5501321
predicted
DarkChem Lite v0.1.0
[M-H]-201.83737
predicted
DeepCCS 1.0 (2019)
[M+H]+231.0121321
predicted
DarkChem Lite v0.1.0
[M+H]+234.8178321
predicted
DarkChem Lite v0.1.0
[M+H]+204.23293
predicted
DeepCCS 1.0 (2019)
[M+Na]+230.6766321
predicted
DarkChem Lite v0.1.0
[M+Na]+235.2458321
predicted
DarkChem Lite v0.1.0
[M+Na]+210.14546
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. HTH-type transcriptional regulator QacR
Kind
Protein
Organism
Staphylococcus haemolyticus
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from...
Gene Name
qacR
Uniprot ID
P0A0N5
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 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. [Article]
  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. [Article]
Details2. Acriflavine resistance protein B
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), a...
Gene Name
acrB
Uniprot ID
P31224
Uniprot Name
Multidrug efflux pump subunit AcrB
Molecular Weight
113572.75 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. [Article]
  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. [Article]

Transporters

Details1. Multidrug resistance-associated protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Saengkhae C, Loetchutinat C, Garnier-Suillerot A: Kinetic analysis of rhodamines efflux mediated by the multidrug resistance protein (MRP1). Biophys J. 2003 Sep;85(3):2006-14. [Article]
Details2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Saengkhae C, Loetchutinat C, Garnier-Suillerot A: Kinetic analysis of rhodamines efflux mediated by the multidrug resistance protein (MRP1). Biophys J. 2003 Sep;85(3):2006-14. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52