NAV

Pentolinium

Identification

Generic Name
Pentolinium
DrugBank Accession Number
DB01090
Background

Pentolinium is a nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 240.428
Monoisotopic: 240.256549034
Chemical Formula
C15H32N2
Synonyms
  • Pentolineum
  • Pentolonium
  • Pentolonum
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Pharmacology

Indication

Used to produce controlled hypotension during surgical procedures and in hypertensive crises.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Pentolinium acts as a ganglionic blocking agent. Pentolinium inhibits release of adrenaline and noradrenaline from adrenergic nerves. It is used as an antihypertensive, and can be administered orally, intramuscularly, and subcutaneously.

Mechanism of action

Pentolinium binds to the nicotinic (ganglion) acetylcholine receptor. This receptor/channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. Blockage of the receptor leads to smooth muscle relaxation and vasodilaton.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-3
antagonist
Humans
ANeuronal acetylcholine receptor subunit beta-4
antagonist
Humans
ANeuronal acetylcholine receptor subunit alpha-10
antagonist
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

Oral, mouse: LD50 = 512 mg/kg; Oral, rat: LD50 = 890 mg/kg.

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.
DrugInteraction
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interactions in your software
AbaloparatideAbaloparatide may increase the hypotensive activities of Pentolinium.
AcebutololPentolinium may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Pentolinium.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pentolinium tartrate953357GACY52-62-0HSMKTIKKPMTUQH-WBPXWQEISA-L
International/Other Brands
Ansolysen

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-alkylpyrrolidines. These are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
N-alkylpyrrolidines
Direct Parent
N-alkylpyrrolidines
Alternative Parents
Tetraalkylammonium salts / Azacyclic compounds / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Aliphatic heteromonocyclic compound / Amine / Azacycle / Hydrocarbon derivative / N-alkylpyrrolidine / Organic cation / Organic nitrogen compound / Organic salt / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
organic cation (CHEBI:347401)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
ULL76WPU5X
CAS number
144-44-5
InChI Key
XSBSKEQEUFOSDD-UHFFFAOYSA-N
InChI
InChI=1S/C15H32N2/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17/h3-15H2,1-2H3/q+2
IUPAC Name
1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium
SMILES
C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1

References

General References
Not Available
Human Metabolome Database
HMDB0015222
PubChem Compound
5850
PubChem Substance
46507977
ChemSpider
5641
BindingDB
50084945
ChEBI
347401
ChEMBL
CHEMBL1271
ZINC
ZINC000002041380
Therapeutic Targets Database
DAP001144
PharmGKB
PA164777033
Wikipedia
Pentolinium
MSDS
Download (61.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)213 °C (tartrate salt)Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.16e-05 mg/mLALOGPS
logP-2.3ALOGPS
logP-6.3Chemaxon
logS-7.4ALOGPS
Physiological Charge2Chemaxon
Hydrogen Acceptor Count0Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area0 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity99.03 m3·mol-1Chemaxon
Polarizability31.36 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9722
Blood Brain Barrier+0.9922
Caco-2 permeable+0.6627
P-glycoprotein substrateSubstrate0.5993
P-glycoprotein inhibitor INon-inhibitor0.9697
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.6294
CYP450 2C9 substrateNon-substrate0.8782
CYP450 2D6 substrateNon-substrate0.607
CYP450 3A4 substrateNon-substrate0.5941
CYP450 1A2 substrateNon-inhibitor0.9834
CYP450 2C9 inhibitorNon-inhibitor0.9533
CYP450 2D6 inhibitorNon-inhibitor0.9312
CYP450 2C19 inhibitorNon-inhibitor0.9348
CYP450 3A4 inhibitorNon-inhibitor0.9943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9857
Ames testNon AMES toxic0.758
CarcinogenicityNon-carcinogens0.8783
BiodegradationReady biodegradable0.7183
Rat acute toxicity2.7632 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7283
hERG inhibition (predictor II)Non-inhibitor0.7476
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.38612
predicted
DeepCCS 1.0 (2019)
[M+H]+159.74413
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.87976
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neuronal acetylcholine receptor subunit alpha-3
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Cachelin AB, Rust G: Beta-subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflugers Arch. 1995 Jan;429(3):449-51. [Article]
Details2. Neuronal acetylcholine receptor subunit beta-4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Cachelin AB, Rust G: Beta-subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflugers Arch. 1995 Jan;429(3):449-51. [Article]
Details3. Neuronal acetylcholine receptor subunit alpha-10
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor binding
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an i...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
Molecular Weight
49704.295 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]
  3. McKay DB, Burkman AM: Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [Article]
  4. Cachelin AB, Rust G: Beta-subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflugers Arch. 1995 Jan;429(3):449-51. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:50