Synonym
Demecarium bromide; Demekastigmine bromide; Humorsol; Tosmilen; Tosmilene; Demekarium bromide; Frumtosnil; Tonilen; Tosmicil; Visumatic; Visumiotic;
IUPAC/Chemical Name
3,3'-(((decane-1,10-diylbis(methylazanediyl))bis(carbonyl))bis(oxy))bis(N,N,N-trimethylbenzenaminium) bromide.
InChi Key
YHKBUDZECQDYBR-UHFFFAOYSA-L
InChi Code
InChI=1S/C32H52N4O4.2BrH/c1-33(31(37)39-29-21-17-19-27(25-29)35(3,4)5)23-15-13-11-9-10-12-14-16-24-34(2)32(38)40-30-22-18-20-28(26-30)36(6,7)8;;/h17-22,25-26H,9-16,23-24H2,1-8H3;2*1H/q+2;;/p-2
SMILES Code
CN(C(OC1=CC([N+](C)(C)C)=CC=C1)=O)CCCCCCCCCCN(C(OC2=CC([N+](C)(C)C)=CC=C2)=O)C.[Br-].[Br-]
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in water
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Demecarium Bromide (BC-48) is a potent cholinesterase inhibitor and glaucoma agent, with an apparent affinity (Kiapp) of 0.15 μM.
In vivo activity:
The objective of this study was to assess the effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase (AChE) levels in normal dogs. Fifty micro L of 0.25% demecarium bromide were applied to one eye of each dog every 8 h for 6 days. Acetylcholinesterase levels declined over the first 24 h following commencement of demecarium administration in most dogs. This decline was highly variable and was statistically significant by 24 h. In some individuals AChE levels were suppressed to levels approaching clinical toxicity. By day 3 AChE levels had risen to levels above baseline in most dogs.
Reference: Vet Ophthalmol. 2003 Mar;6(1):23-5. https://pubmed.ncbi.nlm.nih.gov/12641839/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
160.0 |
223.28 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
716.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Krohne SG. Effect of topically applied 2% pilocarpine and 0.25% demecarium bromide on blood-aqueous barrier permeability in dogs. Am J Vet Res. 1994 Dec;55(12):1729-33. PMID: 7887518. 2. Ward DA, Abney K, Oliver JW. The effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase levels in normal dogs. Vet Ophthalmol. 2003 Mar;6(1):23-5. doi: 10.1046/j.1463-5224.2003.00257.x. PMID: 12641839
In vivo protocol:
1. Krohne SG. Effect of topically applied 2% pilocarpine and 0.25% demecarium bromide on blood-aqueous barrier permeability in dogs. Am J Vet Res. 1994 Dec;55(12):1729-33. PMID: 7887518. 2. Ward DA, Abney K, Oliver JW. The effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase levels in normal dogs. Vet Ophthalmol. 2003 Mar;6(1):23-5. doi: 10.1046/j.1463-5224.2003.00257.x. PMID: 12641839
1: BECKER B, GAGE T. Demecarium bromide and echothiophate iodide in chronic glaucoma. Arch Ophthalmol. 1960 Jan;63:102-7. doi: 10.1001/archopht.1960.00950020104015. PMID: 13798061.
2: PANT MC, PARMAR SS, BHARGAVA KP. ROLE OF THE POLYMETHYLENE CHAIN IN DERIVATIVES OF DEMECARIUM BROMIDE ON THE INHIBITION OF MONOAMINE OXIDASE. J Pharm Pharmacol. 1964 Jul;16:503-4. doi: 10.1111/j.2042-7158.1964.tb07504.x. PMID: 14207098.
3: Ward DA, Abney K, Oliver JW. The effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase levels in normal dogs. Vet Ophthalmol. 2003 Mar;6(1):23-5. doi: 10.1046/j.1463-5224.2003.00257.x. PMID: 12641839.
4: Cohn LJ, Greely VJ, Tibbetts DL. Determination of demecarium bromide and related compounds by high-performance liquid chromatography. J Chromatogr. 1985 Mar 15;321(2):401-5. doi: 10.1016/s0021-9673(01)90458-3. PMID: 4039333.
5: DEUTSCH AR, ROWLETT WM. Demecarium bromide: analysis of its action in selected group of glaucomas. J Tn State Med Assoc. 1963 Jan;56:5-9. PMID: 14027379.
6: Caccamise WC, Townes PL. Bilateral congenital mydriasis. Am J Ophthalmol. 1976 Apr;81(4):515-7. doi: 10.1016/0002-9394(76)90312-3. PMID: 944537.
7: Brooks DE. Glaucoma in the dog and cat. Vet Clin North Am Small Anim Pract. 1990 May;20(3):775-97. doi: 10.1016/s0195-5616(90)50062-5. PMID: 2194358.
8: KRISHNA N, LEOPOLD IH. Use of BC-48 (demecarium bromide) in treatment of glaucoma. Am J Ophthalmol. 1960 Mar;49:554-60. doi: 10.1016/0002-9394(60)91657-3. PMID: 14412037.
9: Binder DR, Herring IP, Gerhard T. Outcomes of nonsurgical management and efficacy of demecarium bromide treatment for primary lens instability in dogs: 34 cases (1990-2004). J Am Vet Med Assoc. 2007 Jul 1;231(1):89-93. doi: 10.2460/javma.231.1.89. PMID: 17605669.
10: DRANCE SM. Effect of demecarium bromide (BC 48) on intraocular pressure in man. Arch Ophthalmol. 1959 Oct;62:673-8. doi: 10.1001/archopht.1959.04220040135019. PMID: 13817989.
11: Krohne SG. Effect of topically applied 2% pilocarpine and 0.25% demecarium bromide on blood-aqueous barrier permeability in dogs. Am J Vet Res. 1994 Dec;55(12):1729-33. PMID: 7887518.
12: Gum GG, Gelatt KN, Gelatt JK, Jones R. Effect of topically applied demecarium bromide and echothiophate iodide on intraocular pressure and pupil size in beagles with normotensive eyes and beagles with inherited glaucoma. Am J Vet Res. 1993 Feb;54(2):287-93. PMID: 8430939.
13: DRANCE SM. Phospholine iodine (217MI) and demecarium bromide (BC48) in the management of glaucoma. Am J Ophthalmol. 1960 Aug;50:270-6. PMID: 13817991.
14: KRISHNA N, LEOPOLD IH. The effect of BC-48 (demecarium bromide) on normal rabbit and human eyes. Am J Ophthalmol. 1960 Feb;49:270-7. PMID: 14412036.
15: GBURKOWA A, POJDA SM. KILKA W ASNYCH SPOSTRZEZE'N KLINICZNYCH NAD STOSOWANIEM BROMKU DEMEKARIUM W JASKRZE NIEKT'ORE W A'SCIWO'SCI FARMAKOLOGICZNE DEMEKARIUM I FIZOSTYGMINY W DO'SWIADCZENIU [CLINICAL OBSERVATIONS ON THE USE OF DEMECARIUM BROMIDE IN GLAUCOMA. PHARMACOLOGIC PROPERTIES OF DEMECARIUM AND PHYSOSTIGMINE IN EXPERIMENTS]. Klin Oczna. 1965;35:207-12. Polish. PMID: 14306815.
16: TERNER IS, LINN JG Jr, GOLDSTROHM R. Clinical experiences with demecarium bromide (BC-48) in the treatment of glaucoma. Am J Ophthalmol. 1961 Oct;52:553-60. doi: 10.1016/0002-9394(61)90016-2. PMID: 13920329.
17: Fiore PM. Drug-induced ocular cicatrization. Int Ophthalmol Clin. 1989 Fall;29(3):147-50. doi: 10.1097/00004397-198902930-00003. PMID: 2666329.
18: Miller PE, Schmidt GM, Vainisi SJ, Swanson JF, Herrmann MK. The efficacy of topical prophylactic antiglaucoma therapy in primary closed angle glaucoma in dogs: a multicenter clinical trial. J Am Anim Hosp Assoc. 2000 Sep- Oct;36(5):431-8. doi: 10.5326/15473317-36-5-431. PMID: 10997520.
19: Dees DD, Fritz KJ, Maclaren NE, Esson DW, Sheehan Gaerig AM, Atkins RM, Knollinger AM. Efficacy of prophylactic antiglaucoma and anti-inflammatory medications in canine primary angle-closure glaucoma: a multicenter retrospective study (2004-2012). Vet Ophthalmol. 2014 May;17(3):195-200. doi: 10.1111/vop.12069. Epub 2013 Jul 5. PMID: 23826812.
20: Attwood D, Natarajan R. Micellar properties and surface activity of some bolaform drugs in aqueous solution. J Pharm Pharmacol. 1980 Jul;32(7):460-2. doi: 10.1111/j.2042-7158.1980.tb12969.x. PMID: 6105180.
