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Identification
NameAlmitrine
Accession NumberDB01430
TypeSmall Molecule
GroupsApproved
Description

A respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. The drug increases arterial oxygen tension while decreasing arterial carbon dioxide tension in patients with chronic obstructive pulmonary disease. It may also prove useful in the treatment of nocturnal oxygen desaturation without impairing the quality of sleep. [PubChem]

Structure
Thumb
Synonyms
2,4-Bis(allylamino)-6-(4-(bis(P-fluorophenyl)methyl)-1-piperazinyl)-S-triazine
Almitrina
Almitrinum
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
DuxilServier
VectarionNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Almitrine mesylate
ThumbNot applicableDBSALT000916
Categories
UNII9A1222NBG4
CAS number27469-53-0
WeightAverage: 477.5522
Monoisotopic: 477.245250373
Chemical FormulaC26H29F2N7
InChI KeyInChIKey=OBDOVFRMEYHSQB-UHFFFAOYSA-N
InChI
InChI=1S/C26H29F2N7/c1-3-13-29-24-31-25(30-14-4-2)33-26(32-24)35-17-15-34(16-18-35)23(19-5-9-21(27)10-6-19)20-7-11-22(28)12-8-20/h3-12,23H,1-2,13-18H2,(H2,29,30,31,32,33)
IUPAC Name
6-{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl}-N2,N4-bis(prop-2-en-1-yl)-1,3,5-triazine-2,4-diamine
SMILES
FC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • N-arylpiperazine
  • Dialkylarylamine
  • N-aliphatic s-triazine
  • Aralkylamine
  • N-alkylpiperazine
  • Secondary aliphatic/aromatic amine
  • Halobenzene
  • Fluorobenzene
  • Amino-1,3,5-triazine
  • 1,3,5-triazine
  • Triazine
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of chronic obstructive pulmonary disease.
PharmacodynamicsAlmitrine is a respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. The drug increases arterial oxygen tension while decreasing arterial carbon dioxide tension in patients with chronic obstructive pulmonary disease. It may also prove useful in the treatment of nocturnal oxygen desaturation without impairing the quality of sleep.
Mechanism of actionAlmitrine enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. The drug increases arterial oxygen tension while decreasing arterial carbon dioxide tension in patients with chronic obstructive pulmonary disease.
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
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9844
Blood Brain Barrier+0.8158
Caco-2 permeable-0.5851
P-glycoprotein substrateSubstrate0.7054
P-glycoprotein inhibitor IInhibitor0.8951
P-glycoprotein inhibitor IIInhibitor0.7886
Renal organic cation transporterInhibitor0.6628
CYP450 2C9 substrateNon-substrate0.8937
CYP450 2D6 substrateNon-substrate0.7478
CYP450 3A4 substrateNon-substrate0.6653
CYP450 1A2 substrateInhibitor0.8218
CYP450 2C9 inhibitorNon-inhibitor0.6926
CYP450 2D6 inhibitorInhibitor0.6928
CYP450 2C19 inhibitorInhibitor0.5949
CYP450 3A4 inhibitorNon-inhibitor0.6962
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7983
Ames testNon AMES toxic0.7426
CarcinogenicityNon-carcinogens0.8823
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6869 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7124
hERG inhibition (predictor II)Inhibitor0.8337
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Doxil 2 mg/ml vial115.78USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0144 mg/mLALOGPS
logP4.9ALOGPS
logP6.05ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.21 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.88 m3·mol-1ChemAxon
Polarizability51.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR07AB07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
binder
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Rigoulet M: Control processes in oxidative phosphorylation: kinetic constraints and stoichiometry. Biochim Biophys Acta. 1990 Jul 25;1018(2-3):185-9. [PubMed:2144185 ]
  2. Rigoulet M, Fraisse L, Ouhabi R, Guerin B, Fontaine E, Leverve X: Flux-dependent increase in the stoichiometry of charge translocation by mitochondrial ATPase/ATP synthase induced by almitrine. Biochim Biophys Acta. 1990 Jul 17;1018(1):91-7. [PubMed:2165421 ]
  3. Rigoulet M, Ouhabi R, Leverve X, Putod-Paramelle F, Guerin B: Almitrine, a new kind of energy-transduction inhibitor acting on mitochondrial ATP synthase. Biochim Biophys Acta. 1989 Aug 3;975(3):325-9. [PubMed:2527061 ]
  4. Benzi G, Gorini A, Ghigini B, Arnaboldi R, Villa RF: Synaptosomal non-mitochondrial ATPase activities and drug treatment. Neurochem Res. 1993 Jun;18(6):719-26. [PubMed:8099718 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on July 24, 2007 09:02 / Updated on September 16, 2013 17:14