Scopolamine butylbromide

• CAS: 149-64-4
• Catalog Number: ACM149644-3
• Category: Main Products
• Molecular Weight: 440.37
• Molecular Formula: C21H30BrNO4
• Synonyms: (1S,2R,4S,5S)-9-butyl-7-[(3-hydroxy-2-phenylpropanoyl)oxy]-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.0~2,4~]nonane bromide
• IUPAC Name: [(1S,2S,4R,5R)-9-butyl-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate;bromide
• Canonical SMILES: CCCC[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)C4=CC=CC=C4)C.[Br-]
• 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?;/m1./s1
• InChI Key: HOZOZZFCZRXYEK-HNHWXVNLSA-M
• Melting Point: 142-144 °C
• Appearance: Powder
• EC Number: 205-744-1
• Exact Mass: 439.13600
• Hazard Statements: Xn
• Packing Group: III
• Stability: Stable at normal temperatures and pressures.
• Supplemental Hazard Statements: H302
• Symbol: GHS07
• WGK Germany: 3

Case Study

Preventive Effect of Scopolamine Butylbromide on Irinotecan-Related Cholinergic Syndrome

Iihara, Hirotoshi, et al. Cancer Chemotherapy and Pharmacology, 2019, 83, 393-398.

This was a preventive analysis of scopolamine butylbromide for irinotecan-related cholinergic syndrome. The result was that scopolamine butylbromide can protect against this syndrome in patients who receive ≥ 150 mg/m2 of irinotecan who are more likely to experience cholinergic symptoms.
Assessment methods and results
· For prophylactic use, scopolamine butylbromide was prepared by mixing 20 mg of the injection with normal saline or a 5% glucose solution to dissolve irinotecan, followed by an intravenous infusion within 90 minutes.
· Between 59 patients who received irinotecan and those who received scopolamine butylbromide, 50.8% developed cholinergic syndrome, a proportion that significantly decreased to 3.4% with the intervention of scopolamine butylbromide (P < 0.01).
· Other symptoms related to irinotecan-associated cholinergic syndrome were also effectively or almost completely eliminated by scopolamine butylbromide: hyperhidrosis (30.5% vs 3.4%, P < 0.01), abdominal pain (16.9% vs 0%, P < 0.01), rhinitis (11.9% vs 0%, P < 0.01), and diarrhoea (3.4% vs 0%, P = 0.05).

Scopolamine Butylbromide for the Prevention of Metabolic Dysfunction in Male Rats

Malta, Ananda, et al. Scientific reports, 2016, 6(1), 30745.

This work tested whether cholinergic antagonist treatment (scopolamine butylbromide) can reduce insulin levels in the early postnatal period and alleviate metabolic dysfunction caused by early overfeeding in adult male rats. The results are the first to report that short-term use of scopolamine butylbromide treatment in the early lactation period can prevent metabolic dysfunction caused by early overfeeding.
Experimental design and results
Wistar rats raised in small litters (SLs, 3 pups/dam) and normal litters (NLs, 9 pups/dam) were utilized for models of early overfeeding and normal feeding, respectively. Throughout the first 12 days of lactation, pups in the SL and NL groups were administered scopolamine butylbromide (B), while the control group received saline (S) injections.
This drug treatment resulted in reduced insulin levels in pups from both groups, and as adults, these animals exhibited enhanced glucose tolerance, improved insulin sensitivity, increased vagus nerve activity, and reduced fat tissue accretion, insulinemia, leptinemia, body weight gain, and food intake. Both groups displayed low glucose and cholinergic insulinotropic effects in pancreatic islets. The protein expression of the muscarinic M3 acetylcholine receptor subtype (M3mAChR) was low, while expression of the M2mAChR subtype was elevated in SL-B islets. Furthermore, beta-cell density was diminished in rats treated with the drug.