Hexamethonium

Identification

Generic Name
Hexamethonium
DrugBank Accession Number
DB08960
Background

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been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 202.38
Monoisotopic: 202.24089897
Chemical Formula
C12H30N2
Synonyms
  • N,N,N,N',N',N'-hexamethylhexane-1,6-diaminium

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Hexamethonium is combined with 1,2-Benzodiazepine.
AcebutololAcebutolol may increase the hypotensive activities of Hexamethonium.
AceclofenacThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Hexamethonium.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Hexamethonium.
Acetyl sulfisoxazoleThe risk or severity of adverse effects can be increased when Acetyl sulfisoxazole is combined with Hexamethonium.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Hexamethonium.
AclidiniumHexamethonium may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Hexamethonium.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hexamethonium Bromide8J77X3S60355-97-0FAPSXSAPXXJTOU-UHFFFAOYSA-L
International/Other Brands
Bistrium (Bristol-Myers Squibb)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Hexamethonium / Hydrocarbon derivative / Organic cation / Organic salt / Organopnictogen compound / Tetraalkylammonium salt
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium salt (CHEBI:5700)
Affected organisms
Not Available

Chemical Identifiers

UNII
3C9PSP36Z2
CAS number
60-26-4
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

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. [Article]
KEGG Compound
C07510
PubChem Compound
3604
PubChem Substance
310264925
ChemSpider
3478
BindingDB
50038416
ChEBI
5700
ChEMBL
CHEMBL100622
ZINC
ZINC000001530808
Wikipedia
Hexamethonium

Clinical Trials

Clinical Trials
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)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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created on May 28, 2014 22:19 / Updated on May 06, 2021 01:45