Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H21NO4 |
| Molecular Weight | 303.3529 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2C[C@@H](C[C@@H]1[C@H]3O[C@@H]23)OC(=O)[C@H](CO)C4=CC=CC=C4
InChI
InChIKey=STECJAGHUSJQJN-FWXGHANASA-N
InChI=1S/C17H21NO4/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/t11-,12-,13-,14+,15-,16+/m1/s1
| Molecular Formula | C17H21NO4 |
| Molecular Weight | 303.3529 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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).
Originator
Sources: A. Ladenburg, Ann. 206, 274 (1881); E. Schmidt, Arch. Pharm. 230, 207 (1892).
Curator's Comment: Scopolamine is an anticholinergic, tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq. and other Solanaceae. Constituent of impure duboisine from Duboisia myoporoides R. Br., pure duboisine is l-hyoscyamine, q.v. reference retrieved from http://www.drugfuture.com/chemdata/scopolamine.html
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27108935 |
2.09 µM [IC50] | ||
Target ID: CHEMBL2094109 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | TRANSDERM SCOP Approved UseTransderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with:
Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date1979 |
|||
| Preventing | TRANSDERM SCOP Approved UseTransderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with:
Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date1979 |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5 ng/mL |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
369 ng × min/mL |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.1 ng × h/mL |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
68.7 min |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9.5 h |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
70% |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: |
Other AEs: Dizziness, Lightheadedness... Other AEs: Dizziness (3 patients) Sources: Lightheadedness (3 patients) Nasal burning (1 patient) |
0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years |
Other AEs: Blurred vision, Dizziness... |
6 ug/kg single, intravenous Dose: 6 ug/kg Route: intravenous Route: single Dose: 6 ug/kg Sources: |
healthy, 22.8 years |
|
1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: |
Other AEs: Dizziness, Dry mouth... Other AEs: Dizziness (4 patients) Sources: Dry mouth (3 patients) Blurred vision (4 patients) |
10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years |
Other AEs: Consciousness abnormal, Hyperthermia... Other AEs: Consciousness abnormal (1 patient) Sources: Hyperthermia (1 patient) |
0.5 mg single, intravenous Dose: 0.5 mg Route: intravenous Route: single Dose: 0.5 mg Sources: |
healthy, adult |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nasal burning | 1 patient | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: |
| Dizziness | 3 patients | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: |
| Lightheadedness | 3 patients | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: |
| Blurred vision | 0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years |
|
| Dizziness | 0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years |
|
| Dry mouth | 3 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: |
| Blurred vision | 4 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: |
| Dizziness | 4 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: |
| Consciousness abnormal | 1 patient | 10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years |
| Hyperthermia | 1 patient | 10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 21.0 |
yes [IC50 119.2 uM] | |||
Page: 21.0 |
yes [IC50 217.9 uM] | |||
Page: 21.0 |
yes [IC50 540.8 uM] | |||
Page: 21.0 |
yes [IC50 6.7 uM] | |||
Page: 21.0 |
yes [IC50 699.9 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | yes (co-administration study) Comment: The AUC0–24h values of scopolamine were higher during the grapefruit juice period. They reached approximately 142% of the values associated with the control group (water period; P . 0.005) Sources: https://pubmed.ncbi.nlm.nih.gov/16175141/ |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Simultaneous modulation of retrieval by dopaminergic D(1), beta-noradrenergic, serotonergic-1A and cholinergic muscarinic receptors in cortical structures of the rat. | 2001-09-28 |
|
| Pharmacological modulation of behavioral and neuronal correlates of repetition priming. | 2001-09-01 |
|
| Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine. | 2001-09 |
|
| Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats. | 2001-09 |
|
| Substance P and its transglutaminase-synthesized spermine derivative elicit yawning behavior via nitric oxide in rats. | 2001-09 |
|
| Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications. | 2001-08-04 |
|
| Pentyl-4-yn-valproic acid enhances both spatial and avoidance learning, and attenuates age-related NCAM-mediated neuroplastic decline within the rat medial temporal lobe. | 2001-08 |
|
| Ultrasonic vocalizations as an index of social memory in female mice. | 2001-08 |
|
| Auditory sensory memory and the cholinergic system: implications for Alzheimer's disease. | 2001-08 |
|
| Cholinergic synaptic potentials in the supragranular layers of auditory cortex. | 2001-08 |
|
| Anti-ischemic and cognition-enhancing properties of NNC-711, a gamma-aminobutyric acid reuptake inhibitor. | 2001-07-13 |
|
| Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats. | 2001-07-06 |
|
| Interaction between the cholinergic system and CRH in the modulation of spatial discrimination learning in mice. | 2001-07-06 |
|
| Effects of Hypericum perforatum (St. John's wort) on passive avoidance in the rat: evaluation of potential neurochemical mechanisms underlying its antidepressant activity. | 2001-07 |
|
| Differential effects of trihexyphenidyl on place preference conditioning and locomotor stimulant activity of cocaine and methamphetamine. | 2001-07 |
|
| Occurrence of cadaverine in hairy roots of Brugmansia candida. | 2001-07 |
|
| The role of muscarinic cholinoceptors in the retrieval of an operant food-related conditioned reflex in cats. | 2001-06-30 |
|
| The role of the cholinergic system of the sensorimotor cortex of the rat brain in controlling different types of movement. | 2001-06-05 |
|
| Drug-induced variations in the probability of occurrence of multiple corrective saccades. | 2001-06 |
|
| The alpha 2 adrenoceptor antagonists RX 821002 and yohimbine delay-dependently impair choice accuracy in a delayed non-matching-to-position task in rats. | 2001-06 |
|
| Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum. | 2001-06 |
|
| N-tert-butyl-alpha-phenylnitrone, a free radical scavenger with anticholinesterase activity does not improve the cognitive performance of scopolamine-challenged rats. | 2001-06 |
|
| Dose- and time-dependent scopolamine-induced recovery of an inhibitory avoidance response after its extinction in rats. | 2001-06 |
|
| The acetylcholine release enhancer linopirdine induces Fos in neocortex of aged rats. | 2001-05-30 |
|
| Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin. | 2001-05-01 |
|
| Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee. | 2001-05 |
|
| Subchronic administration of various pretreatments of nerve agent poisoning. II. Compared efficacy against soman toxicity. | 2001-05 |
|
| Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity. | 2001-05 |
|
| Intrahippocampal scopolamine impairs both acquisition and consolidation of contextual fear conditioning. | 2001-05 |
|
| Scopolamine nasal spray in motion sickness: a randomised, controlled, and crossover study for the comparison of two scopolamine nasal sprays with oral dimenhydrinate and placebo. | 2001-05 |
|
| Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001-04-27 |
|
| Antimuscarinic treatment for lung diseases from research to clinical practice. | 2001-04-27 |
|
| M5 muscarinic receptors are needed for slow activation of dopamine neurons and for rewarding brain stimulation. | 2001-04-27 |
|
| The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse. | 2001-04-13 |
|
| Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats. | 2001-04 |
|
| Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. | 2001-04 |
|
| Male-female differences in rat hypothalamic-pituitary-adrenal axis responses to nicotine stimulation. | 2001-04 |
|
| Infralimbic muscarinic M1 receptors modulate anxiety-like behaviour and spontaneous working memory in mice. | 2001-04 |
|
| Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots. | 2001-04 |
|
| Compensatory mechanisms enhance hippocampal acetylcholine release in transgenic mice expressing human acetylcholinesterase. | 2001-04 |
|
| Tiotropium bromide. | 2001-04 |
|
| Could the 5-HT1B receptor inverse agonism affect learning consolidation? | 2001-03 |
|
| Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm. | 2001-02 |
|
| Differences in parasympathetic vasodilator and salivary responses in the cat submandibular gland between lingual and chorda-lingual nerve stimulation. | 2001-02 |
|
| Neural mechanisms of motion sickness. | 2001-02 |
|
| Inhaled anticholinergic therapy: applied pharmacology and interesting developments. | 2001-01 |
|
| Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats. | 2001 |
|
| Nucleus accumbens muscarinic receptors in the control of behavioral depression: antidepressant-like effects of local M1 antagonist in the Porsolt swim test. | 2001 |
|
| Interactions between cholinergic and GABAergic neurotransmitters in and around the locus coeruleus for the induction and maintenance of rapid eye movement sleep in rats. | 2001 |
|
| Dopaminergic lateralisation in the forebrain: relations to behavioural asymmetries and anxiety in male Wistar rats. | 2001 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27163641
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.
| Substance Class |
Chemical
Created
by
admin
on
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| Record UNII |
DL48G20X8X
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ATC |
A04AD51
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A04AD01
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WHO-ATC |
N05CM05
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CFR |
21 CFR 310.533
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WHO-VATC |
QA04AD51
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NDF-RT |
N0000175574
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N0000175370
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S01FA02
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S01BB01
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LIVERTOX |
875
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QS01FA02
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WHO-VATC |
QN05CM05
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NCI_THESAURUS |
C29704
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QA04AD01
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NCI_THESAURUS |
C29706
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Scopolamine
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DB00747
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m9813
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9601
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51-34-3
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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| Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
URINE
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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