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Scopolamine butylbromide

CAS# 149-64-4

Scopolamine butylbromide

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Quality Control of Scopolamine butylbromide

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Chemical structure

Scopolamine butylbromide

3D structure

Chemical Properties of Scopolamine butylbromide

Cas No. 149-64-4 SDF Download SDF
PubChem ID 9003 Appearance Powder
Formula C21H30BrNO4 M.Wt 440.37
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Hyoscine butylbromide; (-)-Scopolamine butylbromide; Butylscopolammonium bromide; Butylscopolamine bromide
Solubility DMSO : ≥ 90 mg/mL (204.37 mM)
*"≥" means soluble, but saturation unknown.
SMILES CCCC[N+]1(C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4)C.[Br-]
Standard InChIKey HOZOZZFCZRXYEK-GXLSIKBRSA-M
Standard InChI InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15?,16?,17-,18-,19-,20+,22?;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Scopolamine butylbromide

The herbs of Atropa belladonna L.

Biological Activity of Scopolamine butylbromide

DescriptionScopolamine butylbromide is a competitive antagonist of muscarinic acetylcholine receptor (mAChR) with an IC50 of 55.3 ± 4.3 nM, it possesses anticholinergic, and anti-tumor effects, it used as an abdominal-specific antispasmodic agent. Scopolamine butylbromide is effective in preventing succinylcholine-induced bradycardia in infants and children.
TargetsAChR
In vivo

Effect of Scopolamine Butylbromide on Clozapine-induced Hypersalivation in Schizophrenic Patients: A Case Series.[Pubmed: 25912544]

Clin Psychopharmacol Neurosci. 2015 Apr 30;13(1):109-12.

This study investigated the efficacy of the anticholinergic agent Scopolamine butylbromide against clozapine-induced hypersalivation.
METHODS AND RESULTS:
Five schizophrenia patients were coadministered Scopolamine butylbromide (30-60 mg/ day) for 4 weeks. At the baseline and after 4 weeks' treatment, we subjectively evaluated hypersalivation using a visual analog scale and objectively assessed it using the Drooling Severity Scale and Drooling Frequency Scale. As a result, improvements in the patients' Drooling Severity Scale and Drooling Frequency Scale scores, but no improvements in their visual analog scale scores, were observed after Scopolamine butylbromide treatment. These results indicate that at least some schizophrenic patients with clozapine-induced hypersalivation would benefit from Scopolamine butylbromide treatment.
CONCLUSIONS:
We conclude that clozapine-induced hypersalivation is one factor of stress to patients. Subjective hypersalivation was not improved, but objective hypersalivation was, by Scopolamine butylbromide treatment. However, Scopolamine butylbromide and clozapine possess anticholinergic effects so clinicians should closely monitor patients who take Scopolamine butylbromide.

Randomized clinical trial comparing octreotide and scopolamine butylbromide in symptom control of patients with inoperable bowel obstruction due to advanced ovarian cancer.[Pubmed: 25889313]

World J Surg Oncol. 2015 Feb 15;13:50.

The aim of this randomized controlled study was to determine whether octreotide (OCT) or Scopolamine butylbromide (SB) was the more effective antisecretive drug controlling gastrointestinal (GI) symptoms due to malignant bowel obstruction (MBO) caused by advanced ovarian cancer.
METHODS AND RESULTS:
Ninety-seven advanced ovarian cancer patients with inoperable MBO were randomized to OCT 0.3 mg/day (OCT group, n = 48) or Scopolamine butylbromide 60 mg/day (Scopolamine butylbromide group, n = 49) for 3 days through a continuous subcutaneous infusion. One patient in the Scopolamine butylbromide group is not included in any assessments since she withdrew consent prior to receiving any treatment because of rapidly progressing cancer. OCT significantly reduced the amount of GI secretions at T1, T2, and T3 (P < 0.05) compared with Scopolamine butylbromide. NGT secretions significantly reduced at T1, T2, and T3 compared with T0 (P < 0.05) in the OCT group, while in the Scopolamine butylbromide group, only at T3, NGT secretions significantly reduced compared with T0. OCT treatment induced a significantly rapid reduction in the number of daily episodes of vomiting and intensity of nausea compared with Scopolamine butylbromide treatment. No significant changes were observed in dry mouth, drowsiness, and colicky pain after either drug. Continuous pain values were significantly lower in the OCT group than in the Scopolamine butylbromide group at T2 and T3 (P < 0.05).
CONCLUSIONS:
At the doses used in this study, OCT was more effective than Scopolamine butylbromide in controlling gastrointestinal symptoms of bowel obstruction. Further studies are necessary to understand the role of hydration more clearly in such a clinical situation.

Scopolamine butylbromide (0.2 mg.kg-1) prevents succinylcholine-induced bradycardia in infants and children.[Pubmed: 1578626]

Masui. 1992 Apr;41(4):670-2.


METHODS AND RESULTS:
We evaluated the effectiveness of Scopolamine butylbromide in preventing succinylcholine-induced bradycardia in infants and children. Forty-two infants and children were randomly assigned into two groups. In group I, 0.2 mg.kg-1 and in group II, 0.4 mg.kg-1 of Scopolamine butylbromide in mixture with succinylcholine (2 mg.kg-1) was administered after halothane induction. HR decreased significantly after halothane induction. Following the injection of the mixture, HR increased above the preinduction value within 20 seconds without any decrease in HR. HR changes were identical in the two groups.
CONCLUSIONS:
In conclusion, Scopolamine butylbromide (0.2 mg.kg-1) was effective in preventing succinylcholine-induced bradycardia in infants and children.

Protocol of Scopolamine butylbromide

Animal Research

Comparison of gastric peristalsis inhibition by scopolamine butylbromide and glucagon: evaluation by electrogastrography and analysis of heart rate variability.[Pubmed: 12898354]

Muscarinic receptor subtype-3 gene ablation and scopolamine butylbromide treatment attenuate small intestinal neoplasia in Apcmin/+ mice.[Pubmed: 21705482]

Carcinogenesis. 2011 Sep;32(9):1396-402.

M3 subtype muscarinic receptors (CHRM3) are over-expressed in colon cancer.
METHODS AND RESULTS:
In this study, we used Apc(min/+) mice to identify the role of Chrm3 expression in a genetic model of intestinal neoplasia, explored the role of Chrm3 in intestinal mucosal development and determined the translational potential of inhibiting muscarinic receptor activation. We generated Chrm3-deficient Apc(min/+) mice and compared intestinal morphology and tumor number in 12-week-old Apc(min/+)Chrm3(-/-) and Apc(min/+)Chrm3(+/+) control mice. Compared with Apc(min/+)Chrm3(+/+) mice, Apc(min/+)Chrm3(-/-) mice showed a 70 and 81% reduction in tumor number and volume, respectively (P < 0.01). In adenomas, β-catenin nuclear staining was reduced in Apc(min/+)Chrm3(-/-) compared with Apc(min/+)Chrm3(+/+) mice (P < 0.02). Whereas Apc gene mutation increased the number of crypt and Paneth cells and decreased villus goblet cells, these changes were absent in Apc(min/+)Chrm3(-/-) mice. To determine whether pharmacological inhibition of muscarinic receptor activation attenuates intestinal neoplasia, we treated 6-week-old Apc(min/+) mice with Scopolamine butylbromide, a non-subtype-selective muscarinic receptor antagonist. After 8 weeks of continuous treatment, Scopolamine butylbromide-treated mice showed a 22% reduction in tumor number (P = 0.027) and a 36% reduction in tumor volume (P = 0.004) as compared with control mice. Compared with Chrm3 gene ablation, the muscarinic antagonist was less efficacious, most probably due to shorter duration of treatment and incomplete blockade of muscarinic receptors.
CONCLUSIONS:
Overall, these findings indicate that interplay of Chrm3 and β-catenin signaling is important for intestinal mucosal differentiation and neoplasia and provide a proof-of-concept that pharmacological inhibition of muscarinic receptor activation can attenuate intestinal neoplasia in vivo.

J Gastroenterol. 2003;38(7):629-35.

Activation of glucagon receptors of the smooth muscle membrane suppresses gastric peristalsis. We evaluated autonomic nervous activity by two methods, electrogastrography (EGG) and analysis of heart rate variability, to compare the inhibiting effects of glucagon and Scopolamine butylbromide on gastric peristalsis.
METHODS AND RESULTS:
Heart rate variability, EGG, and blood catecholamine levels were measured before and after administration of glucagon (G group), Scopolamine butylbromide (SB group), or physiological saline (C group). Autonomic nervous function was evaluated using spectral analysis of heart rate variability, and low frequency (LF) and high frequency (HF) power; the LF/HF ratios were also determined. After administration of Scopolamine butylbromide, HF power, an index of parasympathetic nervous activity, decreased; and the LF/HF ratio, an index of sympathetic nervous activity, increased. In contrast, no significant change was observed in autonomic nervous activity after administration of glucagon. The peak power amplitudes of the EGG decreased significantly in the G and SB groups after intramuscular injection, but the difference between the groups was not significant. Furthermore, the dominant frequency increased significantly in the G and SB groups after injection. Serum catecholamine levels showed no significant changes after administration of Scopolamine butylbromide or glucagon.
CONCLUSIONS:
Inhibition of gastric peristalsis by glucagon via glucagon receptors on smooth muscles did not influence autonomic nervous activity, unlike the results obtained after administration of Scopolamine butylbromide. Therefore, glucagon may be safe for use with elderly patients and those with cardiopulmonary complications.

Scopolamine butylbromide Dilution Calculator

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Preparing Stock Solutions of Scopolamine butylbromide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2708 mL 11.3541 mL 22.7082 mL 45.4164 mL 56.7704 mL
5 mM 0.4542 mL 2.2708 mL 4.5416 mL 9.0833 mL 11.3541 mL
10 mM 0.2271 mL 1.1354 mL 2.2708 mL 4.5416 mL 5.677 mL
50 mM 0.0454 mL 0.2271 mL 0.4542 mL 0.9083 mL 1.1354 mL
100 mM 0.0227 mL 0.1135 mL 0.2271 mL 0.4542 mL 0.5677 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Scopolamine butylbromide

Scopolamine butylbromide is a competitive antagonist of muscarinic acetylcholine receptor (mAChR) with an IC50 of 55.3 ± 4.3 nM. Target: mAChR Scopolamine (USAN), also known as levo-duboisine and hyoscine, sold as Scopoderm, is a tropane alkaloid drug with muscarinic antagonist effects. It is among the secondary metabolites of plants from Solanaceae (nightshade) family of plants, such as henbane, jimson weed (Datura), angel's trumpets (Brugmansia), and corkwood (Duboisia). Scopolamine exerts its effects by acting as a competitive antagonist at muscarinic acetylcholine receptors, specifically M1 receptors it is thus classified as an anticholinergic, antimuscarinic drug. Its use in medicine is relatively limited, with its chief uses being in the treatment of motion sickness and postoperative nausea and vomiting. Scopolamine is named after the plant genus Scopolia. The name hyoscine is from the scientific name for henbane, Hyoscyamus niger.

References:
[1]. Putcha L, et al. Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun 6(6):481-5.

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References on Scopolamine butylbromide

[Scopolamine butylbromide (0.2 mg.kg-1) prevents succinylcholine-induced bradycardia in infants and children].[Pubmed:1578626]

Masui. 1992 Apr;41(4):670-2.

We evaluated the effectiveness of Scopolamine butylbromide in preventing succinylcholine-induced bradycardia in infants and children. Forty-two infants and children were randomly assigned into two groups. In group I, 0.2 mg.kg-1 and in group II, 0.4 mg.kg-1 of Scopolamine butylbromide in mixture with succinylcholine (2 mg.kg-1) was administered after halothane induction. HR decreased significantly after halothane induction. Following the injection of the mixture, HR increased above the preinduction value within 20 seconds without any decrease in HR. HR changes were identical in the two groups. In conclusion, Scopolamine butylbromide (0.2 mg.kg-1) was effective in preventing succinylcholine-induced bradycardia in infants and children.

Comparison of gastric peristalsis inhibition by scopolamine butylbromide and glucagon: evaluation by electrogastrography and analysis of heart rate variability.[Pubmed:12898354]

J Gastroenterol. 2003;38(7):629-35.

BACKGROUND: Activation of glucagon receptors of the smooth muscle membrane suppresses gastric peristalsis. We evaluated autonomic nervous activity by two methods, electrogastrography (EGG) and analysis of heart rate variability, to compare the inhibiting effects of glucagon and Scopolamine butylbromide on gastric peristalsis. METHODS: Heart rate variability, EGG, and blood catecholamine levels were measured before and after administration of glucagon (G group), Scopolamine butylbromide (SB group), or physiological saline (C group). Autonomic nervous function was evaluated using spectral analysis of heart rate variability, and low frequency (LF) and high frequency (HF) power; the LF/HF ratios were also determined. RESULTS: After administration of Scopolamine butylbromide, HF power, an index of parasympathetic nervous activity, decreased; and the LF/HF ratio, an index of sympathetic nervous activity, increased. In contrast, no significant change was observed in autonomic nervous activity after administration of glucagon. The peak power amplitudes of the EGG decreased significantly in the G and SB groups after intramuscular injection, but the difference between the groups was not significant. Furthermore, the dominant frequency increased significantly in the G and SB groups after injection. Serum catecholamine levels showed no significant changes after administration of Scopolamine butylbromide or glucagon. CONCLUSIONS: Inhibition of gastric peristalsis by glucagon via glucagon receptors on smooth muscles did not influence autonomic nervous activity, unlike the results obtained after administration of Scopolamine butylbromide. Therefore, glucagon may be safe for use with elderly patients and those with cardiopulmonary complications.

Randomized clinical trial comparing octreotide and scopolamine butylbromide in symptom control of patients with inoperable bowel obstruction due to advanced ovarian cancer.[Pubmed:25889313]

World J Surg Oncol. 2015 Feb 15;13:50.

BACKGROUND: The aim of this randomized controlled study was to determine whether octreotide (OCT) or Scopolamine butylbromide (SB) was the more effective antisecretive drug controlling gastrointestinal (GI) symptoms due to malignant bowel obstruction (MBO) caused by advanced ovarian cancer. METHODS: Ninety-seven advanced ovarian cancer patients with inoperable MBO were randomized to OCT 0.3 mg/day (OCT group, n = 48) or SB 60 mg/day (SB group, n = 49) for 3 days through a continuous subcutaneous infusion. The following parameters were measured: episodes of vomiting, nausea, dry mouth, drowsiness, and continuous and colicky pain, using a Likert scale corresponding to a numerical value (none 0, slight 1, moderate 2, severe 3) recorded before starting the treatment (T0) and 24 h (T1), 48 h (T2), and 72 h after (T3) and the daily quantity of GI secretions through the Nasogastric tube (NGT) during the period of study. One patient in the SB group is not included in any assessments since she withdrew consent prior to receiving any treatment because of rapidly progressing cancer. RESULTS: OCT significantly reduced the amount of GI secretions at T1, T2, and T3 (P < 0.05) compared with SB. NGT secretions significantly reduced at T1, T2, and T3 compared with T0 (P < 0.05) in the OCT group, while in the SB group, only at T3, NGT secretions significantly reduced compared with T0. OCT treatment induced a significantly rapid reduction in the number of daily episodes of vomiting and intensity of nausea compared with SB treatment. No significant changes were observed in dry mouth, drowsiness, and colicky pain after either drug. Continuous pain values were significantly lower in the OCT group than in the SB group at T2 and T3 (P < 0.05). CONCLUSIONS: At the doses used in this study, OCT was more effective than SB in controlling gastrointestinal symptoms of bowel obstruction. Further studies are necessary to understand the role of hydration more clearly in such a clinical situation.

Effect of Scopolamine Butylbromide on Clozapine-induced Hypersalivation in Schizophrenic Patients: A Case Series.[Pubmed:25912544]

Clin Psychopharmacol Neurosci. 2015 Apr 30;13(1):109-12.

Clozapine has been demonstrated to be useful for treating refractory schizophrenia. However, hypersalivation occurs in 31.0- 97.4% of the patients treated with clozapine. Accordingly, some patients who are disturbed by their hypersalivation refuse to continue with clozapine treatment. This study investigated the efficacy of the anticholinergic agent Scopolamine butylbromide against clozapine-induced hypersalivation. Five schizophrenia patients were coadministered Scopolamine butylbromide (30-60 mg/ day) for 4 weeks. At the baseline and after 4 weeks' treatment, we subjectively evaluated hypersalivation using a visual analog scale and objectively assessed it using the Drooling Severity Scale and Drooling Frequency Scale. As a result, improvements in the patients' Drooling Severity Scale and Drooling Frequency Scale scores, but no improvements in their visual analog scale scores, were observed after Scopolamine butylbromide treatment. These results indicate that at least some schizophrenic patients with clozapine-induced hypersalivation would benefit from Scopolamine butylbromide treatment. We conclude that clozapine-induced hypersalivation is one factor of stress to patients. Subjective hypersalivation was not improved, but objective hypersalivation was, by Scopolamine butylbromide treatment. However, Scopolamine butylbromide and clozapine possess anticholinergic effects so clinicians should closely monitor patients who take Scopolamine butylbromide.

Muscarinic receptor subtype-3 gene ablation and scopolamine butylbromide treatment attenuate small intestinal neoplasia in Apcmin/+ mice.[Pubmed:21705482]

Carcinogenesis. 2011 Sep;32(9):1396-402.

M3 subtype muscarinic receptors (CHRM3) are over-expressed in colon cancer. In this study, we used Apc(min/+) mice to identify the role of Chrm3 expression in a genetic model of intestinal neoplasia, explored the role of Chrm3 in intestinal mucosal development and determined the translational potential of inhibiting muscarinic receptor activation. We generated Chrm3-deficient Apc(min/+) mice and compared intestinal morphology and tumor number in 12-week-old Apc(min/+)Chrm3(-/-) and Apc(min/+)Chrm3(+/+) control mice. Compared with Apc(min/+)Chrm3(+/+) mice, Apc(min/+)Chrm3(-/-) mice showed a 70 and 81% reduction in tumor number and volume, respectively (P < 0.01). In adenomas, beta-catenin nuclear staining was reduced in Apc(min/+)Chrm3(-/-) compared with Apc(min/+)Chrm3(+/+) mice (P < 0.02). Whereas Apc gene mutation increased the number of crypt and Paneth cells and decreased villus goblet cells, these changes were absent in Apc(min/+)Chrm3(-/-) mice. To determine whether pharmacological inhibition of muscarinic receptor activation attenuates intestinal neoplasia, we treated 6-week-old Apc(min/+) mice with Scopolamine butylbromide, a non-subtype-selective muscarinic receptor antagonist. After 8 weeks of continuous treatment, Scopolamine butylbromide-treated mice showed a 22% reduction in tumor number (P = 0.027) and a 36% reduction in tumor volume (P = 0.004) as compared with control mice. Compared with Chrm3 gene ablation, the muscarinic antagonist was less efficacious, most probably due to shorter duration of treatment and incomplete blockade of muscarinic receptors. Overall, these findings indicate that interplay of Chrm3 and beta-catenin signaling is important for intestinal mucosal differentiation and neoplasia and provide a proof-of-concept that pharmacological inhibition of muscarinic receptor activation can attenuate intestinal neoplasia in vivo.

Description

Scopolamine butylbromide is a competitive antagonist of muscarinic acetylcholine receptor (mAChR) with an IC50 of 55.3 ± 4.3 nM.

Keywords:

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