Identification

Name
Hexamethonium
Accession Number
DB08960
Type
Small Molecule
Groups
Experimental
Description

A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.

Structure
Thumb
Synonyms
  • N,N,N,N',N',N'-hexamethylhexane-1,6-diaminium
Product Ingredients
IngredientUNIICASInChI Key
Hexamethonium Bromide8J77X3S60355-97-0FAPSXSAPXXJTOU-UHFFFAOYSA-L
International/Other Brands
Bistrium (Bristol-Myers Squibb)
Categories
UNII
3C9PSP36Z2
CAS number
60-26-4
Weight
Average: 202.38
Monoisotopic: 202.24089897
Chemical Formula
C12H30N2
InChI Key
VZJFGSRCJCXDSG-UHFFFAOYSA-N
InChI
InChI=1S/C12H30N2/c1-13(2,3)11-9-7-8-10-12-14(4,5)6/h7-12H2,1-6H3/q+2
IUPAC Name
trimethyl[6-(trimethylazaniumyl)hexyl]azanium
SMILES
C[N+](C)(C)CCCCCC[N+](C)(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
antagonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Hexamethonium.
AcebutololAcebutolol may increase the hypotensive activities of Hexamethonium.
AcemetacinThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Acetylsalicylic acid.
AgmatineThe risk or severity of adverse effects can be increased when Agmatine is combined with Hexamethonium.
AlfuzosinAlfuzosin may increase the hypotensive activities of Hexamethonium.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Hexamethonium.
AliskirenHexamethonium may increase the hypotensive activities of Aliskiren.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Hexamethonium.
AlprenololAlprenolol may increase the hypotensive activities of Hexamethonium.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,641,610.

General References
  1. Adams DJ, Bevan S, Terrar DA: Modes of hexamethonium action on acetylcholine receptor channels in frog skeletal muscle. Br J Pharmacol. 1991 Jan;102(1):135-45. [PubMed:1710523]
External Links
KEGG Compound
C07510
PubChem Compound
3604
PubChem Substance
310264925
ChemSpider
3478
BindingDB
50038416
ChEBI
5700
ChEMBL
CHEMBL100622
Wikipedia
Hexamethonium

Clinical Trials

Clinical Trials
Not Available

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)290-291U.S. Patent 2,641,610.
Predicted Properties
PropertyValueSource
Water Solubility2.24e-05 mg/mLALOGPS
logP-3.6ALOGPS
logP-6.6ChemAxon
logS-7.1ALOGPS
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.55 m3·mol-1ChemAxon
Polarizability27.43 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hexamethonium compounds. These are organic compounds containing a N,N,N,N',N',N'-hexamethylhexane-1,6-diaminium moiety.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Hexamethonium compounds
Alternative Parents
Tetraalkylammonium salts / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Hexamethonium / Tetraalkylammonium salt / Organopnictogen compound / Hydrocarbon derivative / Organic salt / Amine / Organic cation / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium salt (CHEBI:5700)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Drug binding
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
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Zhou X, Ren J, Brown E, Schneider D, Caraballo-Lopez Y, Galligan JJ: Pharmacological properties of nicotinic acetylcholine receptors expressed by guinea pig small intestinal myenteric neurons. J Pharmacol Exp Ther. 2002 Sep;302(3):889-97. doi: 10.1124/jpet.102.033548. [PubMed:12183644]
  2. Loiacono R, Stephenson J, Stevenson J, Mitchelson F: Multiple binding sites for nicotine receptor antagonists in inhibiting [3H](-)-nicotine binding in rat cortex. Neuropharmacology. 1993 Sep;32(9):847-53. [PubMed:8232788]

Drug created on May 28, 2014 16:19 / Updated on August 02, 2018 07:48