HEXOCYCLIUM METHYLSULFATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H33N2O.CH3O4S
Molecular Weight	428.586
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COS([O-])(=O)=O.C[N+]1(C)CCN(CC(O)(C2CCCCC2)C3=CC=CC=C3)CC1

InChI

InChIKey=NSILVESQCSUIAJ-UHFFFAOYSA-M

InChI=1S/C20H33N2O.CH4O4S/c1-22(2)15-13-21(14-16-22)17-20(23,18-9-5-3-6-10-18)19-11-7-4-8-12-19;1-5-6(2,3)4/h3,5-6,9-10,19,23H,4,7-8,11-17H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C20H33N2O
Molecular Weight	317.4888
Charge	1
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	CH3O4S
Molecular Weight	111.097
Charge	-1
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13520691 | https://www.ncbi.nlm.nih.gov/pubmed/13487546

Hexocyclium is an old anticholinergic drug. Hexocyclium is an antimuscarinic. Hexocyclium in therapeutic doses produces a prolonged reduction of gastric acidity. It was used for the treatment of peptic ulcer. Hexocyclium is effective for the control of cramps and diarrhea in cases of irritable bowel syndrome.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704370 \| https://www.ncbi.nlm.nih.gov/pubmed/9183081 \| https://www.ncbi.nlm.nih.gov/pubmed/8075869	Antagonist 2778	13.0 nM [IC50]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704370 \| https://www.ncbi.nlm.nih.gov/pubmed/9183081	Antagonist 2778	40.0 nM [IC50]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704370 \| https://www.ncbi.nlm.nih.gov/pubmed/9183081 \| https://www.ncbi.nlm.nih.gov/pubmed/8075869	Antagonist 2778	9.0 nM [IC50]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704370 \| https://www.ncbi.nlm.nih.gov/pubmed/9183081 \| https://www.ncbi.nlm.nih.gov/pubmed/8075869	Antagonist 2778	39.0 nM [IC50]
Muscarinic acetylcholine receptor M5 62 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704370	Antagonist 2778	14.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13520691 https://www.ncbi.nlm.nih.gov/pubmed/13487546	Primary		Approved 8429	Tral Approved Use Tral is used in the treatment of peptic ulcers. Launch Date -3.43007986E11

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13487546 Page: p.18	unhealthy n = 33 Health Status: unhealthy Condition: Duodenal ulcer Population Size: 33 Sources: https://pubmed.ncbi.nlm.nih.gov/13487546 Page: p.18	Sources: https://pubmed.ncbi.nlm.nih.gov/13487546 Page: p.18

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2NA2
Alfa Chemistry	189328
Alfa Chemistry	ACM6004984
BOC Sciences	115-63-9
BOC Sciences	6004-98-4
Compound Cloud	101587
Compound Cloud	24199
Frontier Scientific Services	500055010
Frontier Scientific Services	502049006
Frontier Scientific Services	502053275
MuseChem	M069018
NCI Plated 2007	30256
Nanjing Pope Bio-tech	NSTH-C029470
Norris Pharm	NSTH-C029470
NovoSeek	24199
Toronto Research Chemicals	C987483
ZINC	ZINC000000000363	http://zinc15.docking.org/substances/ZINC000000000363
ZINC	ZINC000000897263	http://zinc15.docking.org/substances/ZINC000000897263
eMolecules	261640856
eMolecules	36761515

PubMed

Title	Date	PubMed
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.	1989 Apr	2704370

Patents

Sample Use Guides

In Vivo Use Guide

Single oral doses of 25 mg and 50 mg

Route of Administration: Oral

In Vitro Use Guide

Acetylcholine-induced concentration-dependent tonic contraction of isolated rat fundus was concentration-dependently antagonized by hexocyclium (KB = 2.82 x 10(-10)M).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:13:49 UTC 2023` Edited by `admin` on `Sat Dec 16 16:13:49 UTC 2023`
Record UNII	84OPZ2Q0VB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HEXOCYCLIUM METHYLSULFATE

Common Name

English

Hexocyclium metilsulfate [WHO-DD]

Common Name

English

4-(.BETA.-CYCLOHEXYL-.BETA.-HYDROXYPHENETHYL)-1,1-DIMETHYLPIPERAZINUM METHYLSULFATE

Common Name

English

4-(.BETA.-CYCLOHEXYL-.BETA.-HYDROXYPHENETHYL)-1,1-DIMETHYLPIPERAZINUM METHYLSULPHATE

Common Name

English

HEXOCYCLIUM METHYLSULFATE [ORANGE BOOK]

Common Name

English

HEXOCYCLIUM METHYLSULFATE [VANDF]

Common Name

English

HEXOCYCLIUM METHYLSULPHATE

Common Name

English

hexocyclium metilsulfate [INN]

Common Name

English

HEXOCYCLIUM METILSULFATE [MART.]

Common Name

English

HEXOCYCLIUM METHYL SULFATE [MI]

Common Name

English

HEXOCYCLIUM METILSULFATE

Official Name

English

HEXOCYCLIUM METILSULPHATE

Common Name

English

TRAL

Brand Name

English

NSC-30256

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29704