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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.BrH.3H2O
Molecular Weight 438.311
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SCOPOLAMINE HYDROBROMIDE

SMILES

O.O.O.Br.[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2N3C)OC(=O)[C@H](CO)C4=CC=CC=C4

InChI

InChIKey=LACQPOBCQQPVIT-SEYKEWMNSA-N
InChI=1S/C17H21NO4.BrH.3H2O/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10;;;;/h2-6,11-16,19H,7-9H2,1H3;1H;3*1H2/t11-,12-,13-,14+,15-,16+;;;;/m1..../s1

HIDE SMILES / InChI

Description

The alkaloid L-(-)-scopolamine [L-(-)-hyoscine], a belladonna alkaloid, competitively inhibits muscarinic receptors for acetylcholine and acts as a nonselective muscarinic antagonist, producing both peripheral antimuscarinic properties and central sedative, antiemetic, and amnestic effects. Scopolamine acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center. Scopolamine can inhibit the secretion of saliva and sweat, decrease gastrointestinal secretions and motility, cause drowsiness, dilate the pupils, increase heart rate, and depress motor function. Scopolamine is used for premedication in anesthesia and for the prevention of nausea and vomiting (post operative and associated with motion sickness).

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.09 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
TRANSDERM SCOP
Preventing
TRANSDERM SCOP
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
5 ng/mL
0.5 mg single, intravenous
SCOPOLAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2.1 ng × h/mL
1 mg single, topical
SCOPOLAMINE plasma
Homo sapiens
369 ng × min/mL
0.5 mg single, intravenous
SCOPOLAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.5 h
1 mg single, topical
SCOPOLAMINE plasma
Homo sapiens
68.7 min
0.5 mg single, intravenous
SCOPOLAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
0.5 mg single, intravenous
SCOPOLAMINE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Transderm Scōp (scopolamine) transdermal system patch. Each Transderm Scōp patch is formulated to deliver in-vivo approximately 1 mg of scopolamine over 3 days. Initiation of Therapy Motion Sickness To prevent the nausea and vomiting associated with motion sickness, one Transderm Scōp patch (formulated to deliver approximately 1 mg of scopolamine over 3 days) should be applied to the hairless area behind one ear at least 4 hours before the antiemetic effect is required. Post Operative Nausea and Vomiting To prevent post operative nausea and vomiting, one Transderm Scōp patch should be applied the evening before scheduled surgery, except for caesarian section. For caesarian section surgery, to minimize exposure of the newborn baby to the drug, apply the patch one hour prior to caesarian section. Continuation of Therapy Should the patch become displaced, it should be discarded, and a fresh one placed on the hairless area behind the other ear. Motion Sickness If therapy is required for longer than 3 days, the first patch should be removed and a fresh one placed on the hairless area behind the other ear. Post Operative Nausea and Vomiting For perioperative use, the patch should be kept in place for 24 hours following surgery at which time it should be removed and discarded.
Route of Administration: Transdermal
In Vitro Use Guide
Rosmarinic acid treatment increases the expression of BDNF and GluR-2 proteins and prevents cell death of scopolamine-exposed (300 μM) organotypic hippocampal slice cultures.