Identification
NameProflavine
Accession NumberDB01123  (APRD00535)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
2,8-Diaminoacridine
3,6-acridinediamine
3,6-diaminoacridine
Diaminoacridine
Proflavin
Proflavina
Proflavine
Proflavinum
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Proflavine hemisulfate27V8M747VB 1811-28-5YADYXCVYLIKQJX-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Kerr 100 Triple Dye Dispos-ASwabTopicalVista Pharm, Inc.2004-05-01Not applicableUs
Perineze Triple DyeSolutionTopicalPeace Medical Inc.2011-09-28Not applicableUs
Triple DyeLiquidTopicalFrank W. Kerr Chemical Company1983-12-312004-10-27Canada
Categories
UNIICY3RNB3K4T
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
Pharmacology
Indication

Topical antiseptic used mainly in wound dressings.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
intercalation
Humannot applicabledetails
ProthrombinProteinno
other/unknown
HumanP00734 details
HTH-type transcriptional regulator QacRProteinunknownNot AvailableStaphylococcus aureusP0A0N4 details
TetR family transcriptional repressor LfrRProteinunknownNot AvailableMycobacterium smegmatisQ58L87 details
Related Articles
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (71.9 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedScreeningEsophagus, Barrett1
0CompletedScreeningEsophagus, Barrett / Intraepithelial Neoplasia1
0CompletedScreeningSquamous Cell Cancer1
0RecruitingPreventionMalignant Neoplasms of Female Genital Organs1
0TerminatedScreeningAnal Intraepithelial Neoplasia (AIN) / Colon Polyps / Colonic Dysplasia1
0TerminatedScreeningEsophagus, Barrett / GERD1
2RecruitingOtherEsophagus, Barrett1
2RecruitingOtherPrior History of Squamous Cell Dysplasia and /or Neoplasia / Suspected or Known Squamous Cell Neoplasia1
2WithdrawnTreatmentUterine Cancers1
Not AvailableActive Not RecruitingPreventionCervical Cancers1
Not AvailableRecruitingDiagnosticCervical Cancers1
Not AvailableRecruitingDiagnosticCervix Carcinoma1
Not AvailableRecruitingTreatmentHead and Neck Carcinoma1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
SwabTopical
SolutionTopical
LiquidTopical
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)285 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.758
CYP450 2D6 inhibitorNon-inhibitor0.8692
CYP450 2C19 inhibitorNon-inhibitor0.7273
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (7.48 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct ParentAcridines
Alternative ParentsAminoquinolines and derivatives / Pyridines and derivatives / Primary aromatic amines / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsAcridine / Aminoquinoline / Benzenoid / Pyridine / Primary aromatic amine / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsaminoacridines (CHEBI:8452 )

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 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. [PubMed:17139284 ]
  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:17016423 ]
  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. doi: 10.1089/dna.2008.0838. [PubMed:19364280 ]
  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:19894617 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Thrombospondin receptor activity
Specific Function:
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. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Uniprot Name:
Prothrombin
Molecular Weight:
70036.295 Da
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:1711542 ]
  2. Koehler KA, Magnusson S: The binding of proflavin to thrombin. Arch Biochem Biophys. 1974 Jan;160(1):175-84. [PubMed:4857231 ]
  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:6722124 ]
  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:7407200 ]
  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:7837275 ]
  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:10592235 ]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
unknown
General 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 its IR1 site by binding to one of many structurally dissimilar cationic lipophilic compounds, which are also substrates of QacA.
Specific Function:
Dna binding
Gene Name:
qacR
Uniprot ID:
P0A0N4
Uniprot Name:
HTH-type transcriptional regulator QacR
Molecular Weight:
22174.175 Da
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:10592235 ]
Kind
Protein
Organism
Mycobacterium smegmatis
Pharmacological action
unknown
General Function:
Dna binding
Specific Function:
Not Available
Gene Name:
lfrR
Uniprot ID:
Q58L87
Uniprot Name:
TetR family transcriptional regulator
Molecular Weight:
20618.16 Da
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:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:30