HEXAMETHONIUM BROMIDE

First approved in 1951

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H30N2.2Br
Molecular Weight	362.188
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].[Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C

InChI

InChIKey=FAPSXSAPXXJTOU-UHFFFAOYSA-L

InChI=1S/C12H30N2.2BrH/c1-13(2,3)11-9-7-8-10-12-14(4,5)6;;/h7-12H2,1-6H3;2*1H/q+2;;/p-2

HIDE SMILES / InChI

Molecular Formula	C12H30N2
Molecular Weight	202.38
Charge	2
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://profiles.nlm.nih.gov/ps/access/XFBBJR.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11834748 |

Hexamethonium is a nicotinic cholinergic antagonist. It was used to treat hypertension, but has never been approved and was discontinued because of the non-specified treatment. When this drug tried to use in medical study via inhalation, one of the volunteer died, the death has been described as “particularly disturbing ”because it was a healthy volunteer who had no thing to gain by taking part in the study. This volunteer participated in a study designed to provoke a mild asthma attack in order to help doctors discover the reﬂex that protects the lungs of healthy people against asthma attacks. Hexamethonium is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. Now it is widely used a research tool.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptors 17 Target ID: Nicotinic acetylcholine receptors Sources: https://www.ncbi.nlm.nih.gov/mesh/68018738	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14928537	Primary		Withdrawn	Unknown Approved Use Unknown
Hypertensive crisis 10 Sources: https://www.vidal.by/poisk_preparatov/benzohexony-zdorovye.html	Primary		Approved 8429	Unknown Approved Use hypertensive crisis; acute ventricular failure in arterial hypertension; controlled hypotension.

Doses

Dose	Population	Adverse events
500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/	unhealthy, adult n = 18 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/	Other AEs: Hypotension, Constipation... Other AEs: Hypotension (18 patients) Constipation (18 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/

AEs

AE	Significance	Dose	Population
Constipation	18 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/	unhealthy, adult n = 18 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/
Hypotension	18 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/	unhealthy, adult n = 18 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/13126825/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1/3 12

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1/3 12	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0928098710001284 Page: 4.0	yes [Inhibition 20 uM]

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RD7
ABI Chem	AC1L1GAW
AK Scientific	6061AF
AK Scientific	6062AF
AK Scientific	6063AF
AK Scientific	6064AF
AK Scientific	M555
AbovChem LLC	HY-B0569
Acros Organics	20470
Alfa Chemistry	ACM2079789
Alfa Chemistry	ACM556810
Alfa Chemistry	ACM55970
Alfa Chemistry	ACM60253
Alfa Chemistry	ACM60264
Ambinter	Amb23552375	http://www.ambinter.com/reference/23552375
Aurora Fine Chemicals LLC	K16.684.434	http://online.aurorafinechemicals.com/info?ID=K16.684.434
BLD Pharm	BD133258
BOC Sciences	55-97-0
BOC Sciences	870-62-2
Capot Chemical	25636
Chem Scene	CS-2677
ChemShuttle	151864
Chemspace	CSC025760597
Combi-Blocks	QC-3857
Compound Cloud	3604
Compound Cloud	5938
Enamine	BBV-91331839
Hairui	HR144684
Hangzhou Yuhao Chemical Technology	LX1019
KeyOrganics	AS-57514
Lab Network	56
Lab Network	LN00193832
Lab Network	LN01347834
MedChem Express	HY-B0569
MolPort	MolPort-001-785-872
MolPort	MolPort-003-935-868
MolPort	MolPort-003-941-624
MolPort	MolPort-023-221-482
MolPort	MolPort-035-784-050
Molnova	M15035
NCI Plated 2007	163965
NCI Plated 2007	21643
NCI Plated 2007	24530
NovoSeek	3604
Princeton BioMolecular Research	OSSL_839864
Ryan Scientific	Olsalazine_disodium
Selleck Chemicals	S4069
Sigma Aldrich	52590
Sigma Aldrich	52590\|SIAL
Sigma Aldrich	52605\|ALDRICH
Sigma Aldrich	H0879\|SIGMA
Sigma Aldrich	H2138\|SIGMA
TargetMol	T0287
Tetrahedron	TS74349
Tocris	4111
Toronto Research Chemicals	H296703
W&J PharmaChem	50A184301
Wonderchem	WD06CKW
ZINC	ZINC000001530808	http://zinc15.docking.org/substances/ZINC000001530808
eMolecules	260194751
eMolecules	42607164
eMolecules	517315
eMolecules	539026
eMolecules	979657
eNovation Chemicals	D753398
mcule	MCULE-2066640980
mcule	MCULE-6298691663

PubMed

Title	Date	PubMed
The interaction of hexamethonium with muscarinic receptor subtypes in vitro.	1989 Oct	2819331

Patents

Sample Use Guides

In Vivo Use Guide

intravenous: 5 to 50 mg; ora: 0.5 mg subcutaneous: 10-100 mg

Route of Administration: Other

In Vitro Use Guide

The action of hexamethonium has been studied at a range of muscarinic receptors in vitro by use of both functional and radioligand binding studies. In functional studies, hexamethonium exhibited little or no significant (P less than 0.05) antagonism of contractile responses to carbachol at muscarinic receptors in the guinea-pig ileum, oesophageal muscularis mucosae, urinary bladder and trachea. However, antagonism was observed at muscarinic receptors in the guinea-pig left atria mediating negative inotropic responses and the calculated pKB value was 3.80. Hexamethonium also antagonized contractile responses to carbachol in the canine saphenous vein. The pKB value at these receptors was 3.75. 3. In the presence of 3.2 mM hexamethonium, the pA2 value for methoctramine at atrial muscarinic receptors was reduced by approximately 10 fold (control pA2 value was 7.81 +/- 0.05; pA2 value in hexamethonium was 6.73 +/- 0.04).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:19 UTC 2023` Edited by `admin` on `Fri Dec 15 15:13:19 UTC 2023`
Record UNII	8J77X3S603
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HEXAMETHONIUM BROMIDE

Official Name

English

HEXAMETHONIUM BROMIDE [MART.]

Common Name

English

NSC-163965

Code

English

hexamethonium bromide [INN]

Common Name

English

Hexamethonium bromide [WHO-DD]

Common Name

English

HEXAMETHONE BROMIDE

Common Name

English

HEXAMETHONIUM BROMIDE [JAN]

Common Name

English

HEXAMETHONIUM BROMIDE [MI]

Common Name

English

HEXAMETHYLENEBIS(TRIMETHYLAMMONIUM BROMIDE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66886