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Methylscopolamine bromide: Difference between revisions

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{{Short description|Pharmaceutical drug}}
{{Unreferenced stub|auto=yes|date=December 2009}}
{{Merge|Methylscopolamine|date=October 2009}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 442016426
| Verifiedfields = changed
⚫ | IUPAC_name = (1''R'',2''S'',4''R'',5''S'',7''R''<nowiki>)-{oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclononane
⚫ | verifiedrevid = 402390676
⚫ | image = Methscopolamine.png
⚫ | IUPAC_name = (1''R'',2''S'',4''R'',5''S'',7''R'')-{oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclononane
<!--Clinical data-->| tradename = Pamine, Extendryl, AlleRx, Rescon
⚫ | image = Methscopolamine.png
| Drugs.com = {{drugs.com|monograph|methscopolamine-bromide}}
| CASNo_Ref = {{cascite|correct|CAS}}
| MedlinePlus = a606008
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | ChemSpiderID = 21106347
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | pregnancy_category =
⚫ | ChEMBL = 376897
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| UNII_Ref = {{fdacite|correct|FDA}}
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| UNII = RTN51LK7WL
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | InChI = 1/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| InChIKey = LZCOQTDXKCNBEE-IKIFYQGPBD
⚫ | legal_status =
⚫ | smiles = OC(c1ccccc1)C(=O)O2C3(C)(C)(C2)4O34
⚫ | routes_of_administration = <!--Pharmacokinetic data-->
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | bioavailability =
| StdInChI = 1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1
| protein_bound =
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| metabolism =
⚫ | StdInChIKey = LZCOQTDXKCNBEE-IKIFYQGPSA-N
⚫ | elimination_half-life = 3–4 hrs
| CAS_number = 155-41-9
| ATC_prefix = none | excretion = <!--Identifiers-->
| ATC_suffix = | CAS_number = 155-41-9
| PubChem = 441342 | ATC_prefix = A03
| DrugBank = APRD00314 | ATC_suffix = BB03
| ATC_supplemental = {{ATC|S01|FA03}}
⚫ | C = 18 | H = 24 | N = 1 | O = 4
| PubChem = 441342
⚫ | molecular_weight = 318.388 g/mol
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | bioavailability =
| protein_bound = | DrugBank = DB00462
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | metabolism =
⚫ | ChemSpiderID = 21106347
⚫ | elimination_half-life = 3 - 4hr
| excretion = | UNII_Ref = {{fdacite|correct|FDA}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | UNII = RTN51LK7WL
| pregnancy_US = <!-- A / B / C / D / X --> | KEGG = D00715
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | pregnancy_category=
| PDB_ligand = 3C0
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | ChEMBL = 376897
⚫ | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> <!--Chemical data-->| C = 18
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | H = 24
| legal_status = | N = 1
⚫ | O = 4
⚫ | routes_of_administration =
⚫ | molecular_weight = 318.388 g/mol (398.297 g/mol with bromide)
⚫ | smiles = OC(c1ccccc1)C(=O)O2C3(C)(C)(C2)4O34
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = LZCOQTDXKCNBEE-IKIFYQGPSA-N
}} }}


'''Methscopolamine''', usually provided as a bromide salt (Pamine), is an oral ] used along with other medications to treat ]s by reducing ] ] secretion. With the advent of proton pump inhibitors and antihistamine medications it is rarely used for this anymore. It can also be used for stomach or intestinal spasms, to reduce ], and to treat ]. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold,irritable bowel syndrome and allergy medications (Extendryl, AlleRx, Rescon). '''Methylscopolamine''' or '''methscopolamine''', usually provided as the ] or ] salt, is an oral ] used along with other medications to treat ]s by reducing ] ] secretion.<ref>Drugs.com: </ref> Proton pump inhibitors and antihistamine medications have made this use obsolete. It can also be used for stomach or intestinal spasms, to reduce ], and to treat ]. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications<ref>{{cite book | vauthors = Gennaro AR | publisher = Remington | title = The Science and Practice of Pharmacy | pages = 402–403, 1025 | isbn = 0912734043 }}</ref>


Methscopolamine, a ]ated derivative of ], is a ] structurally similar to the neurotransmitter ]. Its ] involves blocking the ]s. Methscopolamine, a ]ated derivative of ], is a ] structurally similar to the neurotransmitter ]. Its ] involves blocking the ]s.

<!-- Society and culture -->
It was patented in 1902 and approved for medical use in 1947.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=446 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA446 |language=en}}</ref> Methscopolamine is an FDA-approved analog to ].

==Brand names==
Brand names include Extendryl, AlleRx, Rescon, Pamine.

==References==
{{reflist}}

{{Drugs for functional gastrointestinal disorders}}
{{Muscarinic acetylcholine receptor modulators}}


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{{Pharma-stub}} {{gastrointestinal-drug-stub}}

Latest revision as of 02:57, 26 October 2024

Pharmaceutical drug Pharmaceutical compound
Methylscopolamine bromide
Clinical data
Trade namesPamine, Extendryl, AlleRx, Rescon
AHFS/Drugs.comMonograph
MedlinePlusa606008
ATC code
Pharmacokinetic data
Elimination half-life3–4 hrs
Identifiers
IUPAC name
  • (1R,2S,4R,5S,7R)-{oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclononane
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.005.314 Edit this at Wikidata
Chemical and physical data
FormulaC18H24NO4
Molar mass318.388 g/mol (398.297 g/mol with bromide) g·mol
3D model (JSmol)
SMILES
  • OC(c1ccccc1)C(=O)O2C3(C)(C)(C2)4O34
InChI
  • InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1
  • Key:LZCOQTDXKCNBEE-IKIFYQGPSA-N
  (verify)

Methylscopolamine or methscopolamine, usually provided as the bromide or nitrate salt, is an oral medication used along with other medications to treat peptic ulcers by reducing stomach acid secretion. Proton pump inhibitors and antihistamine medications have made this use obsolete. It can also be used for stomach or intestinal spasms, to reduce salivation, and to treat motion sickness. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications

Methscopolamine, a methylated derivative of scopolamine, is a muscarinic antagonist structurally similar to the neurotransmitter acetylcholine. Its mechanism of action involves blocking the muscarinic acetylcholine receptors.

It was patented in 1902 and approved for medical use in 1947. Methscopolamine is an FDA-approved analog to hyoscine butylbromide.

Brand names

Brand names include Extendryl, AlleRx, Rescon, Pamine.

References

  1. Drugs.com: Methscopolamine
  2. Gennaro AR. The Science and Practice of Pharmacy. Remington. pp. 402–403, 1025. ISBN 0912734043.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.
Drugs for functional gastrointestinal disorders (A03)
Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium
compounds
Phosphodiesterase
inhibitors
Acting on
serotonin receptors
Other
Belladonna
and derivatives
(antimuscarinics)
Propulsives
Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators


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