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Identification
NameProflavine
Accession NumberDB01123  (APRD00535)
TypeSmall Molecule
GroupsApproved
Description

3,6-Diaminoacridine. Topical antiseptic used mainly in wound dressings. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2,8-DiaminoacridineNot AvailableNot Available
3,6-acridinediamineNot AvailableNot Available
3,6-diaminoacridineNot AvailableNot Available
DiaminoacridineNot AvailableNot Available
ProflavinNot AvailableNot Available
ProflavinaNot AvailableNot Available
ProflavineNot AvailableNot Available
ProflavinumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
Brand NameIngredients
MolcaBenzethonium Chloride + Proflavine
Triple DyeBrilliant Green + Gentian Violet + Proflavine Hemisulfate
SaltsNot Available
Categories
CAS number92-62-6
WeightAverage: 209.2465
Monoisotopic: 209.095297367
Chemical FormulaC13H11N3
InChI KeyWDVSHHCDHLJJJR-UHFFFAOYSA-N
InChI
InChI=1S/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2
IUPAC Name
acridine-3,6-diamine
SMILES
NC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • Benzenoid
  • Pyridine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationTopical antiseptic used mainly in wound dressings.
PharmacodynamicsProflavine is an acriflavine derivative which is a disinfectant bacteriostatic against many gram-positive bacteria. Proflavine is toxic and carcinogenic in mammals and so it is used only as a surface disinfectant or for treating superficial wounds.
Mechanism of actionProflavine acts by interchelating DNA (intercalation), thereby disrupting DNA synthesis and leading to high levels of mutation in the copied DNA strands. This prevents bacterial reproduction.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9762
Blood Brain Barrier+0.9388
Caco-2 permeable+0.7041
P-glycoprotein substrateNon-substrate0.7289
P-glycoprotein inhibitor INon-inhibitor0.9623
P-glycoprotein inhibitor IINon-inhibitor0.8593
Renal organic cation transporterNon-inhibitor0.7993
CYP450 2C9 substrateNon-substrate0.8805
CYP450 2D6 substrateNon-substrate0.8649
CYP450 3A4 substrateNon-substrate0.7682
CYP450 1A2 substrateInhibitor0.8698
CYP450 2C9 substrateNon-inhibitor0.758
CYP450 2D6 substrateNon-inhibitor0.8692
CYP450 2C19 substrateNon-inhibitor0.7273
CYP450 3A4 substrateNon-inhibitor0.6799
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7368
Ames testAMES toxic0.9302
CarcinogenicityNon-carcinogens0.8204
BiodegradationNot ready biodegradable0.994
Rat acute toxicity2.5383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9803
hERG inhibition (predictor II)Non-inhibitor0.7051
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point285 °CPhysProp
water solubility5E+005 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.83HANSCH,C ET AL. (1995)
pKa8.06 (at 20 °C)PERRIN,DD (1972)
Predicted Properties
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP2.1ALOGPS
logP1.85ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.93 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.46 m3·mol-1ChemAxon
Polarizability23.17 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.48 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (71.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: yes

Actions: intercalation

Components

Name UniProt ID Details

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
  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
  3. Sinha R, Hossain M, Kumar GS: Interaction of small molecules with double-stranded RNA: spectroscopic, viscometric, and calorimetric study of hoechst and proflavine binding to PolyCG structures. DNA Cell Biol. 2009 Apr;28(4):209-19. Pubmed
  4. Berezniak EG, gladkovskaia NA, Khrebtova AS, Dukhopel’nikov EV, Zinchenko AV: [Features of binding of proflavine to DNA at different DNA-ligand concentration ratios] Biofizika. 2009 Sep-Oct;54(5):805-12. Pubmed

2. Prothrombin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Prothrombin P00734 Details

References:

  1. Sie P, Bezeaud A, Dupouy D, Archipoff G, Freyssinet JM, Dugoujon JM, Serre G, Guillin MC, Boneu B: An acquired antithrombin autoantibody directed toward the catalytic center of the enzyme. J Clin Invest. 1991 Jul;88(1):290-6. Pubmed
  2. Koehler KA, Magnusson S: The binding of proflavin to thrombin. Arch Biochem Biophys. 1974 Jan;160(1):175-84. Pubmed
  3. Sonder SA, Fenton JW 2nd: Proflavin binding within the fibrinopeptide groove adjacent to the catalytic site of human alpha-thrombin. Biochemistry. 1984 Apr 10;23(8):1818-23. Pubmed
  4. Valeri AM, Wilson SM, Feinman RD: Reaction of antithrombin with proteases. Evidence for a specific reaction with papain. Biochim Biophys Acta. 1980 Aug 7;614(2):526-33. Pubmed
  5. De Cristofaro R, De Candia E, Picozzi M, Landolfi R: Conformational transitions linked to active site ligation in human thrombin: effect on the interaction with fibrinogen and the cleavable platelet receptor. J Mol Biol. 1995 Jan 27;245(4):447-58. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. HTH-type transcriptional regulator QacR

Kind: protein

Organism: Staphylococcus aureus

Pharmacological action: unknown

Components

Name UniProt ID Details
HTH-type transcriptional regulator QacR P0A0N4 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. TetR family transcriptional repressor LfrR

Kind: protein

Organism: Mycobacterium smegmatis

Pharmacological action: unknown

Components

Name UniProt ID Details
TetR family transcriptional repressor LfrR Q58L87 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13