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Identification
NamePentolinium
Accession NumberDB01090  (APRD00038)
TypeSmall Molecule
GroupsApproved
Description

A nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
PentolineumNot AvailableNot Available
PentoloniumNot AvailableNot Available
PentolonumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AnsolysenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pentolinium tartrate
52-62-0
Thumb
  • InChI Key: HSMKTIKKPMTUQH-WBPXWQEISA-L
  • Monoisotopic Mass: 538.273774818
  • Average Mass: 538.5858
DBSALT000236
Categories
CAS number144-44-5
WeightAverage: 240.428
Monoisotopic: 240.256549034
Chemical FormulaC15H32N2
InChI KeyXSBSKEQEUFOSDD-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassN-alkylpyrrolidines
Direct ParentN-alkylpyrrolidines
Alternative Parents
Substituents
  • N-alkylpyrrolidine
  • Quaternary ammonium salt
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed to produce controlled hypotension during surgical procedures and in hypertensive crises.
PharmacodynamicsPentolinium 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 actionPentolinium 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, mouse: LD50 = 512 mg/kg; Oral, rat: LD50 = 890 mg/kg.
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-0.9722
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 substrateNon-inhibitor0.9533
CYP450 2D6 substrateNon-inhibitor0.9312
CYP450 2C19 substrateNon-inhibitor0.9348
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point213 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (61.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-10

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-10 Q9GZZ6 Details

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
  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
  3. McKay DB, Burkman AM: Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. Pubmed
  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. Pubmed

2. Neuronal acetylcholine receptor subunit alpha-3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-3 P32297 Details

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. Pubmed

3. Neuronal acetylcholine receptor subunit beta-4

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit beta-4 P30926 Details

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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13