NAV

Almitrine

Identification

Generic Name
Almitrine
DrugBank Accession Number
DB01430
Background

Almitrine is a respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. It is used in the treatment of chronic obstructive pulmonary disease. It is also reported to have a potentially beneficial effect in treating the noctural oxygen desaturation without impairing the quality of sleep.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 477.5522
Monoisotopic: 477.245250373
Chemical Formula
C26H29F2N7
Synonyms
  • 2,4-Bis(allylamino)-6-(4-(bis(p-fluorophenyl)methyl)-1-piperazinyl)-s-triazine
  • Almitrina
  • Almitrine
  • Almitrinum
External IDs
  • SE 5023
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Pharmacology

Indication

For the treatment of chronic obstructive pulmonary disease.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAge-related cognitive declineCombination Product in combination with: Raubasine (DB15949)•••••••••••••••••••••••••• ••••••
Used in combination to manageDizzinessCombination Product in combination with: Raubasine (DB15949)•••••••••••••••••••••••••• ••••••
Used in combination to manageDizzinessCombination Product in combination with: Raubasine (DB15949)•••••••••••••••••••••••••• ••••••
Used in combination to manageNeurological disordersCombination Product in combination with: Raubasine (DB15949)•••••••••••••••••••••••••• ••••••
Used in combination to manageNeurological disordersCombination Product in combination with: Raubasine (DB15949)•••••••••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Almitrine is a respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies.

Mechanism of action

Almitrine is an agonist at the peripheral chemoreceptors expressed on carotid bodies. It enhances respiration in patients with chronic obstructive pulmonary disease by increasing the arterial oxygen tension while decreasing the arterial carbon dioxide tension.

TargetActionsOrganism
ASodium/potassium-transporting ATPase subunit alpha-1
binder
Humans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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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Product Ingredients
IngredientUNIICASInChI Key
Almitrine mesylate6RY6V6XM8T29608-49-9MRDBGMJEPGXQHJ-UHFFFAOYSA-N
International/Other Brands
Duxil (Servier) / Vectarion

Categories

ATC Codes
R07AB07 — Almitrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
N-arylpiperazines / Dialkylarylamines / Secondary alkylarylamines / N-alkylpiperazines / N-aliphatic s-triazines / Fluorobenzenes / Aralkylamines / Aryl fluorides / 1,3,5-triazines / Heteroaromatic compounds
show 5 more
Substituents
1,3,5-triazine / 1,4-diazinane / Amine / Amino-1,3,5-triazine / Aminotriazine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
triamino-1,3,5-triazine, piperazines (CHEBI:53778)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9A1222NBG4
CAS number
27469-53-0
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0015499
KEGG Drug
D07126
PubChem Compound
33887
PubChem Substance
46505517
ChemSpider
31235
RxNav
528
ChEBI
53778
ChEMBL
CHEMBL1183717
ZINC
ZINC000004214772
Therapeutic Targets Database
DAP000468
PharmGKB
PA164750492
Wikipedia
Almitrine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Hypoxemic Respiratory Failure1
Not AvailableRecruitingNot AvailableAcute Respiratory Distress Syndrome (ARDS) / Coronavirus Disease 2019 (COVID‑19) / Hypoxemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Centocor Ortho Biotech Inc.
Dosage Forms
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0144 mg/mLALOGPS
logP4.9ALOGPS
logP6.05Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.27Chemaxon
pKa (Strongest Basic)8.47Chemaxon
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 FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f89-0096200000-41257a678ccba5a72f46
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-4be45f8a9fc9b249ea2f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-0000900000-f1a11d12d15c08de84f8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-f7311e66e90e435628fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udj-4179300000-e149c5a8b0e26f4f8bae
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ba-0002900000-c1752ab8fb06984ae35e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-5139600000-9dd24f3452be473f3604
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]-235.3375562
predicted
DarkChem Lite v0.1.0
[M-H]-211.00317
predicted
DeepCCS 1.0 (2019)
[M+H]+236.7047562
predicted
DarkChem Lite v0.1.0
[M+H]+213.39873
predicted
DeepCCS 1.0 (2019)
[M+Na]+237.1299562
predicted
DarkChem Lite v0.1.0
[M+Na]+219.64688
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Details1. Sodium/potassium-transporting ATPase subunit alpha-1
Kind
Protein
Organism
Humans
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 th...
Gene Name
ATP1A1
Uniprot ID
P05023
Uniprot Name
Sodium/potassium-transporting ATPase subunit alpha-1
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at July 24, 2007 15:02 / Updated at December 02, 2023 06:59