METHYLATROPINE BROMIDE

US Previously Marketed

First marketed in 1911

Details

Stereochemistry	EPIMERIC
Molecular Formula	C18H26NO3.Br
Molecular Weight	384.308
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].C[N+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3

InChI

InChIKey=XMLNCADGRIEXPK-KUMOIWDRSA-M

InChI=1S/C18H26NO3.BrH/c1-19(2)14-8-9-15(19)11-16(10-14)22-18(21)17(12-20)13-6-4-3-5-7-13;/h3-7,14-17,20H,8-12H2,1-2H3;1H/q+1;/p-1/t14-,15+,16+,17?;

HIDE SMILES / InChI

Molecular Formula	C18H25NO3
Molecular Weight	303.396
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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://www.ncbi.nlm.nih.gov/pubmed/21032188http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1987730/pdf/archdisch01465-0039.pdf

Methylatropine (methylatroponium) is a belladonna derivative. In 1902 the Bayer Company introduced atropine methonitrate, a quaternary ammonium salt of atropine (Eumydrin), as a mydriatic for dilation of the pupil during ophthalmic examination. Due to its highly polar nature it penetrates less readily into the central nervous system than atropine and was therefore introduced for relieving pyloric spasms in infants. Atropine methyl nitrate is a muscarinic acetylcholine receptor antagonist that does not cross the blood-brain barrier. Atropine methyl nitrate has been used for its peripheral muscarinic effects (targeting the bladder, respiratory tract, and to block parasympathetic signaling to the heart, among others) and to separate central from peripheral nervous system effects, or to protect against peripheral side effects when using muscarinics that do cross the blood brain barrier.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: DOI: 10.1021/jm980320h, Gyermek L., 'Pharmacology of Antimuscarinic Agents' (1997), p. 162, Retrieved from https://books.google.es/books?id=_VyDxfdunv4C&pg	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Pyloric stenosis 3 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1987730/pdf/archdisch01465-0039.pdf	Curative	Preclinical	Unknown Approved Use Unknown
Eye diseases 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18799813	Diagnostic	Approved 8429	Eumydrin Approved Use Unknown Launch Date 1901
Pyloric stenosis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21032188	Palliative	Approved 8429	Eumydrin Approved Use Unknown

Doses

Dose	Population	Adverse events
0.8 mg multiple, oral (total) Dose: 0.8 mg Route: oral Route: multiple Dose: 0.8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 1 week n = 1 Health Status: unhealthy Age Group: 1 week Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	Other AEs: Paralytic ileus, Hypotonic urinary bladder... Other AEs: Paralytic ileus (1 patient) Hypotonic urinary bladder (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
0.4 mg 6 times / day multiple, oral Dose: 0.4 mg, 6 times / day Route: oral Route: multiple Dose: 0.4 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5909489	unhealthy, 2 month n = 1 Health Status: unhealthy Age Group: 2 month Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5909489	Other AEs: Dilated pupils, Fever... Other AEs: Dilated pupils Fever Sources: https://pubmed.ncbi.nlm.nih.gov/5909489
2.5 mL 1 times / day multiple, oral Dose: 2.5 mL, 1 times / day Route: oral Route: multiple Dose: 2.5 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	unhealthy, 37 days n = 1 Health Status: unhealthy Age Group: 37 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	Other AEs: Paralytic ileus... Other AEs: Paralytic ileus (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/21032188
16 mg multiple, oral (total) Highest studied dose Dose: 16 mg Route: oral Route: multiple Dose: 16 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 7 weeks n = 1 Health Status: unhealthy Age Group: 7 weeks Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	Other AEs: Irritable, Hypertonia... Other AEs: Irritable (1 patient) Hypertonia (1 patient) Dilated pupils (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
0.1 mg 1 times / day multiple, oral (starting) Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	unhealthy, babies n = 15 Health Status: unhealthy Age Group: babies Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	Disc. AE: Abdominal distension... AEs leading to discontinuation/dose reduction: Abdominal distension Sources: https://pubmed.ncbi.nlm.nih.gov/21032188

AEs

AE	Significance	Dose	Population
Hypotonic urinary bladder	1 patient	0.8 mg multiple, oral (total) Dose: 0.8 mg Route: oral Route: multiple Dose: 0.8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 1 week n = 1 Health Status: unhealthy Age Group: 1 week Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
Paralytic ileus	1 patient	0.8 mg multiple, oral (total) Dose: 0.8 mg Route: oral Route: multiple Dose: 0.8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 1 week n = 1 Health Status: unhealthy Age Group: 1 week Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
Dilated pupils		0.4 mg 6 times / day multiple, oral Dose: 0.4 mg, 6 times / day Route: oral Route: multiple Dose: 0.4 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5909489	unhealthy, 2 month n = 1 Health Status: unhealthy Age Group: 2 month Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5909489
Fever		0.4 mg 6 times / day multiple, oral Dose: 0.4 mg, 6 times / day Route: oral Route: multiple Dose: 0.4 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5909489	unhealthy, 2 month n = 1 Health Status: unhealthy Age Group: 2 month Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5909489
Paralytic ileus	grade 5	2.5 mL 1 times / day multiple, oral Dose: 2.5 mL, 1 times / day Route: oral Route: multiple Dose: 2.5 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	unhealthy, 37 days n = 1 Health Status: unhealthy Age Group: 37 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/21032188
Dilated pupils	1 patient	16 mg multiple, oral (total) Highest studied dose Dose: 16 mg Route: oral Route: multiple Dose: 16 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 7 weeks n = 1 Health Status: unhealthy Age Group: 7 weeks Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
Hypertonia	1 patient	16 mg multiple, oral (total) Highest studied dose Dose: 16 mg Route: oral Route: multiple Dose: 16 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 7 weeks n = 1 Health Status: unhealthy Age Group: 7 weeks Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
Irritable	1 patient	16 mg multiple, oral (total) Highest studied dose Dose: 16 mg Route: oral Route: multiple Dose: 16 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6807409	unhealthy, 7 weeks n = 1 Health Status: unhealthy Age Group: 7 weeks Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6807409
Abdominal distension	Disc. AE	0.1 mg 1 times / day multiple, oral (starting) Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21032188	unhealthy, babies n = 15 Health Status: unhealthy Age Group: babies Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/21032188

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	6458AF
AK Scientific	6459AF
BOC Sciences	2870-71-5
BOC Sciences	52-88-0
Chem Scene	CS-0043286
ChemDiv	6264-0458
Chemieliva Pharmaceutical Co., Ltd	PBCM1271376
Compound Cloud	23724526
Compound Cloud	656597
Compound Cloud	656598
Compound Cloud	656864
Compound Cloud	657381
Enamine	EN300-312881
Hairui	HR142467
Hairui	HR144203
IBScreen	STOCK1N-27068
IBScreen	STOCK1N-93371
Lab Network	395
Lab Network	LN01753260
Lab Network	LN01755054
MedChem Express	HY-112076
MolPort	MolPort-000-703-558
MolPort	MolPort-000-711-438
MolPort	MolPort-009-758-008
MolPort	MolPort-039-140-487
MolPort	MolPort-044-179-469
MuseChem	M010675
MuseChem	R034282
NCI Plated 2007	61810
Pharmeks	PHAR009239
Pharmeks	PHAR018930
Princeton BioMolecular Research	OSSK_579999
Scientific Exchange	F-035069
TimTec	ST51039050
Vitas-M Laboratory	STK108600
ZINC	ZINC000001620937	http://zinc15.docking.org/substances/ZINC000001620937
ZINC	ZINC000012466871	http://zinc15.docking.org/substances/ZINC000012466871
ZINC	ZINC000012466998	http://zinc15.docking.org/substances/ZINC000012466998
ZINC	ZINC000100371013	http://zinc15.docking.org/substances/ZINC000100371013
ZINC	ZINC000100371018	http://zinc15.docking.org/substances/ZINC000100371018
eMolecules	104671449
eMolecules	35780000
eMolecules	36091971
eMolecules	50420744
eMolecules	7349288
mcule	MCULE-1521238572
mcule	MCULE-7662254879

PubMed

Title	Date	PubMed
Effects of atropine sulfate, methylatropine nitrate (metropine) and homatropine hydrobromide on adult human eyes.	1946 Sep	20999237
Clinical pertussis treated with methyl atropine nitrate (eumydrin).	1950 Oct 7	14778526
Ganglionic blocking action of atropine and methylatropine.	1953 Dec	13109700
Analysis of cardiac chronotropic responses to diazepam and bromazepam in conscious trained dogs.	1976 Feb	2483
Effect of thyrotropin-releasing hormone (TRH) on local cerebral glucose utilization, by the autoradiographic 2-deoxy[14C]glucose method, in conscious and pentobarbitalized rats.	1980 Oct	6778968
Cardiovascular responses to intracisternal administration of nicotine in rats.	1981 Jun	7296375
Drugs for Parkinson's disease reduce tremor induced by physostigmine.	1983 Jul	6621715
Excess tachycardia: heart rate after antimuscarinic agents in conscious dogs.	1984 Feb	6696128
Pharmacological, hemodynamic and autonomic nervous system mechanisms responsible for the blood pressure and heart rate lowering effects of pergolide in rats.	1984 Mar	6707926
[Effects of oxybutynin on the cardiovascular system in dogs].	1984 Oct	6510843
Central interactions between dihydropyridines and cholinergic systems in the control of blood pressure in rat.	1987 Dec 1	2448012
Cardiovascular effects of hypocretin-1 in nucleus of the solitary tract.	2003 Apr	12531738
Central muscarinic receptors signal pilocarpine-induced salivation.	2003 Dec	14630901
Cardioacceleratory responses to hypocretin-1 injections into rostral ventromedial medulla.	2003 Nov 21	14575880
Pharmacologic evidence for a parasympathetic role in seizure-induced neurocardiac regulatory abnormalities.	2004 Feb	14751203
Cardiovascular responses produced by central injection of hydrogen peroxide in conscious rats.	2006 Dec 11	17113926
Medical countermeasure against respiratory toxicity and acute lung injury following inhalation exposure to chemical warfare nerve agent VX.	2007 Mar	17188727
Medullary pathways mediating the parasubthalamic nucleus depressor response.	2008 Apr	18287224
Acute induction of epileptiform discharges by pilocarpine in the in vitro isolated guinea-pig brain requires enhancement of blood-brain barrier permeability.	2008 Jan 2	18082973
Ghrelin infused into the portal vein inhibits glucose-stimulated insulin secretion in Wistar rats.	2008 Jul	18436343
Xenin-25 potentiates glucose-dependent insulinotropic polypeptide action via a novel cholinergic relay mechanism.	2010 Jun 25	20421298

Patents

Sample Use Guides

In Vivo Use Guide

Pyloric stenosis: The first dose was usually 0.5-1 ml (0.05-0.1 mgm. per dose), increasing by 0.5 ml at each feed till a dose of 2-3 ml, six times daily, was reached, i.e. 1.2-1.8 mgm. in twenty-four hours.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:06:12 GMT 2023` Edited by `admin` on `Fri Dec 15 17:06:12 GMT 2023`
Record UNII	63IFT0IX9N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYLATROPINE BROMIDE

Common Name

English

ATROPINE METHYL BROMIDE

Common Name

English

ATROPINE METHYLBROMIDE [MI]

Common Name

English

NSC-61810

Code

English

ATROPINE METHYLBROMIDE [JAN]

Common Name

English

ATROPINE METHOBROMIDE [MART.]

Common Name

English

ATROPINE METHOBROMIDE

Common Name

English

Atropine methylbromide [WHO-DD]

Common Name

English

3.ALPHA.-HYDROXY-8-METHYL-1AH,5AH-TROPANIUM BROMIDE

Common Name

English

ATROPINE METHYLBROMIDE

Common Name

English

TROPIN

Brand Name

English

METHYLATROPINE BROMIDE [EP IMPURITY]

Common Name

English

Code System Code Type Description

CAS

2870-71-5