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Hexamethonium: Difference between revisions

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Revision as of 10:44, 1 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').← Previous edit Latest revision as of 04:09, 18 September 2024 edit undoCitation bot (talk | contribs)Bots5,452,015 edits Added publisher. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Quaternary ammonium compounds | #UCB_Category 117/249 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400104475 | verifiedrevid = 458440658
| IUPAC_name = ''N,N,N,N',N',N'''-hexamethylhexane-1,6-diaminium | IUPAC_name = ''N,N,N,N',N',N''-hexamethylhexane-1,6-diaminium
| image = Hexamethonium.png | image = Hexamethonium.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| pregnancy_category = | pregnancy_category = D
| legal_status = | legal_status = Rx-only
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 3963
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 60-26-4 --> | CAS_number = 60-26-4
| ATC_prefix = | ATC_prefix =
| ATC_suffix = | ATC_suffix =
| PubChem = 3604 | PubChem = 3604
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB08960
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3478 | ChemSpiderID = 3478
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3C9PSP36Z2 | UNII = 3C9PSP36Z2
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 105608 --> | ChEMBL = 105608
| chemical_formula = C<sub>12</sub>H<sub>30</sub>N<sub>2</sub>


<!--Chemical data-->
| molecular_weight = 202.38 g/mol
| C=12 | H=30 | N=2
| smiles = C(CCCC(C)(C)C)C(C)(C)C | smiles = C(CCCC(C)(C)C)C(C)(C)C
| InChI = 1/C12H30N2/c1-13(2,3)11-9-7-8-10-12-14(4,5)6/h7-12H2,1-6H3/q+2
| InChIKey = VZJFGSRCJCXDSG-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H30N2/c1-13(2,3)11-9-7-8-10-12-14(4,5)6/h7-12H2,1-6H3/q+2 | StdInChI = 1S/C12H30N2/c1-13(2,3)11-9-7-8-10-12-14(4,5)6/h7-12H2,1-6H3/q+2
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}} }}


'''Hexamethonium''' is a ],<ref name="pmid10702597">{{cite journal |author=Sonoyama K, Tajima K, Fujiwara R, Kasai T |title=Intravenous infusion of hexamethonium and atropine but not propranolol diminishes apolipoprotein A-IV gene expression in rat ileum |journal=The Journal of nutrition |volume=130 |issue=3 |pages=637–41 |year=2000 |month=March |pmid=10702597 |doi= |url=http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=10702597}}</ref> a nicotinic ] (N<sub>N</sub>) receptor ] that acts in ] by binding mostly in or on the N<sub>N</sub> receptor, and not the ] binding site itself. It does not have any effect on the muscarinic acetylcholine receptors (]) located on target organs of the ] but acts as antagonist at the nicotinic acetylcholine receptors located in sympathetic and parasympathetic ganglia (N<sub>N</sub>) <ref> Howland RD, Mycek MJ 2006. Lippincott's illustrated reviews: Pharmacology. 3:d edition, page 47.</ref>. '''Hexamethonium''' is a non-depolarising ], a neuronal nicotinic (]) ]<ref>{{cite web|title=Hexamethonium - Compound Summary| url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3604|date=2013-06-18 | work = PubChem | publisher = U.S. National Library of Medicine }}</ref> that acts in ] by binding mostly in or on the ] receptor, and not the ] binding site itself. It does not have any effect on the muscarinic acetylcholine receptors (]) located on target organs of the ], nor on the nicotinic receptors at the skeletal neuromuscular junction, but acts as antagonist at the nicotinic acetylcholine receptors located in sympathetic and parasympathetic ganglia (]).<ref>{{cite book | vauthors = Howland RD, Mycek MJ | date = 2006 | title = Lippincott's illustrated reviews: Pharmacology | edition = 3rd | page = 47 }}</ref>


== Pharmacology == == Pharmacology ==


By blocking the neuronal nicotinic receptors in autonomic ganglia, which are necessary for transmission in all autonomic ganglia, both the sympathetic and parasympathetic nervous systems are inhibited. Its action on the neuronal nicotinic receptors is primarily through the block of the ion pore, rather than through competition with the binding site for acetylcholine.<ref>{{cite journal | vauthors = Gurney AM, Rang HP | title = The channel-blocking action of methonium compounds on rat submandibular ganglion cells | journal = British Journal of Pharmacology | volume = 82 | issue = 3 | pages = 623–642 | date = July 1984 | pmid = 6146366 | doi = 10.1111/j.1476-5381.1984.tb10801.x | pmc = 1987010 }}</ref>
⚫ It can act on receptors at pre-ganglionic sites in both the sympathetic and parasympathetic nervous systems, which are both regulated by nicotinic ligand-gated ionotropic acetylcholine receptors. Postganglionic sympathetic systems are usually regulated by ] (noradrenaline) (adrenergic receptors), whereas parasympathetic systems are acetylcholine-based, and instead rely on muscarinic receptors (some post-ganglionic sympathetic neurons, such as those stimulating sweat glands, release acetylcholine).


⚫ Postganglionic sympathetic systems are usually regulated by ] (noradrenaline) (adrenergic receptors), whereas parasympathetic systems are acetylcholine-based, and instead rely on muscarinic receptors (some post-ganglionic sympathetic neurons, such as those stimulating sweat glands, release acetylcholine).
⚫ The organ system and adverse effects of ] are due to the parasympathetic and sympathetic stimuli blockage at preganglionic sites. Side-effects include combined ] (e.g., ] and ]) and ] (e.g., constipation, ], ], blurry vision, decreased lacrymal secretion, dry mouth (])) effects.

⚫ The organ system and adverse effects of ] are due to the parasympathetic and sympathetic stimuli blockage at preganglionic sites. Side-effects include combined ] (e.g., ] and ]) and ] (e.g., constipation, ], ], blurry vision, decreased lacrimal gland secretion, dry mouth (])) effects.


== Uses == == Uses ==
⚫ It was formerly used to treat disorders, such as chronic ], of the ], which is innervated only by the ]. The non-specificity of this treatment led to discontinuing its use.<ref>{{cite book | vauthors = Hardman JB, Limbird LE, Gilman AG | title = Goodman and Gilman's The Pharmacological Basis of Therapeutics | edition = 10th | date = 2001 | pages = 210–211 | publisher = McGraw-Hill | isbn = 978-0071354691 }}</ref>


⚫ The use of inhaled hexamethonium, an unapproved drug, in a normal volunteer during a medical study is believed to have caused or contributed to her death<ref name="urlJohns Hopkins’ Tragedy: Could Librarians Have Prevented a Death?">{{cite web | vauthors = Perkins E |url=http://newsbreaks.infotoday.com/nbreader.asp?ArticleID=17534 |title=Johns Hopkins' Tragedy: Could Librarians Have Prevented a Death? |date = August 7, 2001 | work = Information Today, Inc. |access-date=2008-10-06}}</ref><ref name="pmid11834748">{{cite journal | vauthors = Savulescu J, Spriggs M | title = The hexamethonium asthma study and the death of a normal volunteer in research | journal = Journal of Medical Ethics | volume = 28 | issue = 1 | pages = 3–4 | date = February 2002 | pmid = 11834748 | pmc = 1733509 | doi = 10.1136/jme.28.1.3 }}</ref> in light of the presence of abnormal "ground glass opacities" on her chest X-ray.{{Context inline|date=August 2018}}
⚫ It was formerly used to treat disorders, such as chronic ], of the ], which is innervated only by the ]. The non-specificity of this treatment led to discontinuing its use.<ref>Hardman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 10th edition, 2001, pp 210-211.</ref>

⚫ The use of inhaled hexamethonium, an unapproved drug, in a normal volunteer during a medical study is believed to have caused or contributed to her death<ref name="urlJohns Hopkins’ Tragedy: Could Librarians Have Prevented a Death?">{{cite web |url=http://newsbreaks.infotoday.com/nbreader.asp?ArticleID=17534 |title=Johns Hopkins’ Tragedy: Could Librarians Have Prevented a Death? |format= |work= |accessdate=2008-10-06}}</ref><ref name="pmid11834748">{{cite journal |author=Savulescu J, Spriggs M |title=The hexamethonium asthma study and the death of a normal volunteer in research |journal=Journal of medical ethics |volume=28 |issue=1 |pages=3–4 |year=2002 |month=February |pmid=11834748 |pmc=1733509 |doi= 10.1136/jme.28.1.3|url=http://jme.bmj.com/cgi/pmidlookup?view=long&pmid=11834748}}</ref> in light of the presence of abnormal "ground glass opacities" on her chest X-ray.


== See also == == See also ==
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== References == == References ==
{{Reflist|2}} {{Reflist|2}}



{{Antihypertensives}} {{Antihypertensives}}
{{Nicotinic acetylcholine receptor modulators}}
{{Cholinergics}}


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