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targets (4)
for drugs
Identification
Name Proflavine
Accession Number DB01123 (APRD00535)
Type small molecule
Groups approved
Description

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

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Isoflav Base
Pro-Gen
Proflavin
Profoliol-B
Proformiphen
Profura
Progarmed
Progesic
Brand mixtures
Brand Name Ingredients
Triple Dye Brilliant Green + Gentian Violet + Proflavine Hemisulfate
Categories
  • Anti-Infective Agents, Local
  • Anti-Infectives, local
CAS number 92-62-6
Weight Average: 209.2465
Monoisotopic: 209.095297367
Chemical Formula C13H11N3
InChI Key InChIKey=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
Plain Text
IUPAC Name
acridine-3,6-diamine
SMILES
NC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C1
Plain Text
Mass Spec show (7.48 KB)
Taxonomy
Kingdom Organic
Classes
  • Acridines
Substructures
  • Acridines
  • Pyridines and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Aminoquinolines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • (Iso)quinolines and Derivatives
  • Anilines
Pharmacology
Indication Topical antiseptic used mainly in wound dressings.
Pharmacodynamics Proflavine 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 action Proflavine 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.
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
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 285 °C PhysProp
water solubility 5E+005 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 1.83 HANSCH,C ET AL. (1995)
pKa 8.06 (at 20 °C) PERRIN,DD (1972)
Predicted Properties
Property Value Source
water solubility 1.04e-01 g/l ALOGPS
logP 2.1 ALOGPS
logP 1.85 ChemAxon
logS -3.3 ALOGPS
pKa (strongest basic) 8.32 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 64.93 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 65.46 ChemAxon
polarizability 23.17 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C11181 Link_out
PubChem Compound 7099 Link_out
PubChem Substance 46505401 Link_out
ChemSpider 6832 Link_out
BindingDB 12590 Link_out
ChEBI 8452 Link_out
ChEMBL 8452 Link_out
Therapeutic Targets Database DAP000995 Link_out
PharmGKB PA164748742 Link_out
HET PRL Link_out
Wikipedia http://en.wikipedia.org/wiki/Proflavine Link_out
ATC Codes
  • D08AA02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (71.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. DNA

Pharmacological action: yes
Actions: intercalation

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

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

Pharmacological action: no
Actions: other/unknown

Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C

Organism class: human
UniProt ID: P00734 Link_out
Gene: F2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown

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 its IR1 site by binding to one of many structurally dissimilar cationic lipophilic compounds, which are also substrates of qacA

Organism class: bacterial
UniProt ID: P0A0N4 Link_out
Gene: qacR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Organism class: bacterial
UniProt ID: Q58L87 Link_out
Gene: lfrR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19