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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
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
MolcaBenzethonium Chloride + Proflavine
Triple DyeBrilliant Green + Gentian Violet + Proflavine Hemisulfate
CategoriesNot Available
CAS number92-62-6
WeightAverage: 209.2465
Monoisotopic: 209.095297367
Chemical FormulaC13H11N3
InChI KeyInChIKey=WDVSHHCDHLJJJR-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
Mass Specshow(7.48 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassQuinolines and Derivatives
SubclassBenzoquinolines
Direct parentAcridines
Alternative parentsAnilines; Primary Aromatic Amines; Pyridines and Derivatives; Polyamines
Substituentsaniline; primary aromatic amine; pyridine; benzene; polyamine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocyle which consists of two benzene rings joined by a pyridine ring.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9762
Blood Brain Barrier + 0.9388
Caco-2 permeable + 0.7041
P-glycoprotein substrate Non-substrate 0.7289
P-glycoprotein inhibitor I Non-inhibitor 0.9623
P-glycoprotein inhibitor II Non-inhibitor 0.8593
Renal organic cation transporter Non-inhibitor 0.7993
CYP450 2C9 substrate Non-substrate 0.8805
CYP450 2D6 substrate Non-substrate 0.8649
CYP450 3A4 substrate Non-substrate 0.7682
CYP450 1A2 substrate Inhibitor 0.8698
CYP450 2C9 substrate Non-inhibitor 0.758
CYP450 2D6 substrate Non-inhibitor 0.8692
CYP450 2C19 substrate Non-inhibitor 0.7273
CYP450 3A4 substrate Non-inhibitor 0.6799
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7368
Ames test AMES toxic 0.9302
Carcinogenicity Non-carcinogens 0.8204
Biodegradation Not ready biodegradable 0.994
Rat acute toxicity 2.5383 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9803
hERG inhibition (predictor II) Non-inhibitor 0.7051
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 solubility1.04e-01 g/lALOGPS
logP2.1ALOGPS
logP1.85ChemAxon
logS-3.3ALOGPS
pKa (strongest basic)8.32ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area64.93ChemAxon
rotatable bond count0ChemAxon
refractivity65.46ChemAxon
polarizability23.17ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC11181
PubChem Compound7099
PubChem Substance46505401
ChemSpider6832
BindingDB12590
ChEBI8452
ChEMBLCHEMBL55400
Therapeutic Targets DatabaseDAP000995
PharmGKBPA164748742
HETPRL
WikipediaProflavine
ATC CodesD08AA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(71.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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

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