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Identification
NameDiminazene
Accession NumberDB03608  (EXPT00754)
TypeSmall Molecule
GroupsExperimental
DescriptionDiminazene, 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 aceturate
Diminazine
Diminazine aceturate
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AzidinNot Available
BerenilNot Available
GanasagNot Available
PirocideNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIY5G36EEA5Z
CAS number536-71-0
WeightAverage: 281.3158
Monoisotopic: 281.138893515
Chemical FormulaC14H15N7
InChI KeyXNYZHCFCZNMTFY-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Peroxiredoxin-5, mitochondrialProteinunknownNot AvailableHumanP30044 details
HTH-type transcriptional regulator QacRProteinunknownNot AvailableStaphylococcus aureusP0A0N4 details
Trypsin-1ProteinunknownNot AvailableHumanP07477 details
Amiloride-sensitive amine oxidase [copper-containing]ProteinunknownNot AvailableHumanP19801 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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylhydrazines
Direct ParentPhenylhydrazines
Alternative Parents
Substituents
  • Phenylhydrazine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

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
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:
Transcription factor activity, sequence-specific dna binding
Specific 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.
Gene Name:
qacR
Uniprot ID:
P0A0N4
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 against all of these substrates.
Gene Name:
PRSS1
Uniprot ID:
P07477
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, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
AOC1
Uniprot ID:
P19801
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23