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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
Salts
Name/CAS Structure Properties
Pentolinium tartrate
52-62-0
Thumb
  • InChI Key: HSMKTIKKPMTUQH-WBPXWQEISA-L
  • Monoisotopic Mass: 538.273774818
  • Average Mass: 538.5858
DBSALT000236
Brand names
NameCompany
AnsolysenNot Available
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyrrolidines
SubclassNot Available
Direct parentPyrrolidines
Alternative parentsPolyamines
Substituentspolyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the pyrrolidines. These are compounds containing a pyrrolidine ring, which is a five-member saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
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
Property Value Probability
Human Intestinal Absorption - 0.9722
Blood Brain Barrier + 0.9922
Caco-2 permeable + 0.6627
P-glycoprotein substrate Substrate 0.5993
P-glycoprotein inhibitor I Non-inhibitor 0.9697
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Inhibitor 0.6294
CYP450 2C9 substrate Non-substrate 0.8782
CYP450 2D6 substrate Non-substrate 0.607
CYP450 3A4 substrate Non-substrate 0.5941
CYP450 1A2 substrate Non-inhibitor 0.9834
CYP450 2C9 substrate Non-inhibitor 0.9533
CYP450 2D6 substrate Non-inhibitor 0.9312
CYP450 2C19 substrate Non-inhibitor 0.9348
CYP450 3A4 substrate Non-inhibitor 0.9943
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9857
Ames test Non AMES toxic 0.758
Carcinogenicity Non-carcinogens 0.8783
Biodegradation Ready biodegradable 0.7183
Rat acute toxicity 2.7632 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7283
hERG inhibition (predictor II) Non-inhibitor 0.7476
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
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 g/lALOGPS
logP-2.3ALOGPS
logP-6.3ChemAxon
logS-7.4ALOGPS
physiological charge2ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area0ChemAxon
rotatable bond count6ChemAxon
refractivity99.03ChemAxon
polarizability31.36ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound5850
PubChem Substance46507977
ChemSpider5641
BindingDB50084945
Therapeutic Targets DatabaseDAP001144
PharmGKBPA164777033
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(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