NAV

Diminazene

Identification

Generic Name
Diminazene
DrugBank Accession Number
DB03608
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 281.3158
Monoisotopic: 281.138893515
Chemical Formula
C14H15N7
Synonyms
  • 4,4'-(1-triazene-1,3-diyl)bis-benzenecarboximidamide
  • 4,4'-(diazoamino)benzamidine
  • Diminazene
  • Diminazène
  • Diminazeno
  • Diminazenum
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus aureus
UTrypsin-1Not AvailableHumans
UAmiloride-sensitive amine oxidase [copper-containing]Not AvailableHumans
UPeroxiredoxin-5, mitochondrialNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Azidin / Berenil / Ganasag / Pirocide

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amidine / Aromatic homomonocyclic compound / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative / Organic 1,3-dipolar compound / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylhydrazine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxamidine, triazene derivative (CHEBI:81724)
Affected organisms
Not Available

Chemical Identifiers

UNII
Y5G36EEA5Z
CAS number
536-71-0
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

References

General References
Not Available
KEGG Compound
C18388
PubChem Compound
2354
PubChem Substance
46504758
ChemSpider
2264
BindingDB
50000999
ChEBI
81724
ChEMBL
CHEMBL35241
ZINC
ZINC000003830706
PDBe Ligand
BRN
Wikipedia
Diminazene
PDB Entries
1d63 / 268d / 2dbe / 2gby / 2gvr / 3gy2 / 3gy5 / 3gy6 / 3gy8 / 3hig …
show 1 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)19.91Chemaxon
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-MSsplash10-00ll-4890000000-6c6ad84e2572cc7692f1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-86d8c9928c35208e636e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-2e52175cd93c97ea87b6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-be8acd29d78e5b623ea8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-dc4605b44a1655fe76f0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-4900000000-3d7dd497c4e525af69bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-0960000000-28a551506bed7f1ec657
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-168.42043
predicted
DeepCCS 1.0 (2019)
[M+H]+170.77841
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.72502
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. HTH-type transcriptional regulator QacR
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. [Article]
Details2. Trypsin-1
Kind
Protein
Organism
Humans
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. [Article]
Details3. Amiloride-sensitive amine oxidase [copper-containing]
Kind
Protein
Organism
Humans
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. [Article]
Details4. Peroxiredoxin-5, mitochondrial
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51