Diminazene

Identification

Name
Diminazene
Accession Number
DB03608  (EXPT00754)
Type
Small Molecule
Groups
Experimental
Description

Diminazene, also known as Diminazine, 4,4'-(Diazoamino)benzamidine, 4,4'-(1-Triazene-1,3-diyl)bis-benzenecarboximidamide, Diminazine aceturate, or Diminazene aceturate, is a trypanocidal agent. Major brands of Diminazene are Berenil, Pirocide, Ganasag, and Azidin. This substance is a solid. This compound belongs to the phenylhydrazines. These are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group. Known drug targets of diminazene include HTH-type transcriptional regulator QacR, trypsin-1, amiloride-sensitive amine oxidase [copper-containing], and mitochondrial peroxiredoxin-5.

Structure
Thumb
Synonyms
  • 1,3-TRIS-(4'AMIDINOPHENYL)TRIAZINE
  • 4,4'-(1-Triazene-1,3-diyl)bis-benzenecarboximidamide
  • 4,4'-(Diazoamino)benzamidine
  • Diminazene
  • Diminazene aceturate
  • diminazeno
  • Diminazine
  • Diminazine aceturate
International/Other Brands
Azidin / Berenil / Ganasag / Pirocide
Categories
UNII
Y5G36EEA5Z
CAS number
536-71-0
Weight
Average: 281.3158
Monoisotopic: 281.138893515
Chemical Formula
C14H15N7
InChI Key
XNYZHCFCZNMTFY-UHFFFAOYSA-N
InChI
InChI=1S/C14H15N7/c15-13(16)9-1-5-11(6-2-9)19-21-20-12-7-3-10(4-8-12)14(17)18/h1-8H,(H3,15,16)(H3,17,18)(H,19,20)
IUPAC Name
4-[(2E)-3-(4-carbamimidoylphenyl)triaz-2-en-1-yl]benzene-1-carboximidamide
SMILES
NC(=N)C1=CC=C(N\N=N\C2=CC=C(C=C2)C(N)=N)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPeroxiredoxin-5, mitochondrialNot AvailableHuman
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus aureus
UTrypsin-1Not AvailableHuman
UAmiloride-sensitive amine oxidase [copper-containing]Not AvailableHuman
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C18388
PubChem Compound
2354
PubChem Substance
46504758
BindingDB
50000999
ChEBI
81724
ChEMBL
CHEMBL35241
HET
BRN
Wikipedia
Diminazene
PDB Entries
1d63 / 268d / 2dbe / 2gby / 2gvr / 3gy2 / 3gy5 / 3gy6 / 3gy8 / 3hig
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.102 mg/mLALOGPS
logP1.09ALOGPS
logP1.76ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)12.07ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.49 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.73 m3·mol-1ChemAxon
Polarizability30.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8986
Blood Brain Barrier+0.9385
Caco-2 permeable+0.5696
P-glycoprotein substrateNon-substrate0.7439
P-glycoprotein inhibitor INon-inhibitor0.9482
P-glycoprotein inhibitor IINon-inhibitor0.9581
Renal organic cation transporterNon-inhibitor0.7378
CYP450 2C9 substrateNon-substrate0.7641
CYP450 2D6 substrateNon-substrate0.8448
CYP450 3A4 substrateNon-substrate0.7666
CYP450 1A2 substrateInhibitor0.5762
CYP450 2C9 inhibitorNon-inhibitor0.5568
CYP450 2D6 inhibitorNon-inhibitor0.8011
CYP450 2C19 inhibitorNon-inhibitor0.773
CYP450 3A4 inhibitorNon-inhibitor0.7833
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5599
Ames testAMES toxic0.9244
CarcinogenicityCarcinogens 0.5924
BiodegradationNot ready biodegradable0.994
Rat acute toxicity2.7762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9378
hERG inhibition (predictor II)Non-inhibitor0.9192
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylhydrazines. These are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylhydrazines
Direct Parent
Phenylhydrazines
Alternative Parents
Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenylhydrazine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Carboxylic acid amidine / Amidine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxamidine, triazene derivative (CHEBI:81724)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rna polymerase iii regulatory region dna binding
Specific Function
Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling.
Gene Name
PRDX5
Uniprot ID
P30044
Uniprot Name
Peroxiredoxin-5, mitochondrial
Molecular Weight
22086.245 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]
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
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 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
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tum...
Gene Name
AOC1
Uniprot ID
P19801
Uniprot Name
Amiloride-sensitive amine oxidase [copper-containing]
Molecular Weight
85377.1 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 December 14, 2018 12:40