Demecarium bromide | CAS#56-94-0 | parasympathomimetic

Demecarium bromide
featured

WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 300162

CAS#: 56-94-0 (bromide)

Description: Demecarium is a parasympathomimetic that acts as an acetylcholinesterase inhibitor. It is one of several topical (applied directly to the affected area) medications used to reduce elevated intraocular pressure (IOP) associated with primary glaucoma in cats, dogs, and other animals. a cholinesterase inhibitor with sustained activity. It acts mainly on true (erythrocyte) cholinesterase. Application of HUMORSOL (demecarium) to the eye produces intense miosis and ciliary muscle contraction due to inhibition of cholinesterase, allowing acetylcholine to accumulate at sites of cholinergic transmission. These effects are accompanied by increased capillary permeability of the ciliary body and iris, increased permeability of the blood-aqueous barrier, and vasodilation. Myopia may be induced or, if present, may be augmented by the increased refractive power of the lens that results from the accommodative effect of the drug. HUMORSOL (demecarium) indirectly produces some of the muscarinic and nicotinic effects of acetylcholine as quantities of the latter accumulate.

Chemical Structure

Demecarium bromide

CAS# 56-94-0 (bromide)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 300162
Name: Demecarium bromide
CAS#: 56-94-0 (bromide)
Chemical Formula: C32H52Br2N4O4
Exact Mass: 0.00
Molecular Weight: 716.590
Elemental Analysis: C, 53.64; H, 7.31; Br, 22.30; N, 7.82; O, 8.93

Price and Availability

Size	Price	Availability
10mg	USD 250	2 Weeks
25mg	USD 400	2 Weeks
100mg	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 16505-84-3 (cation) 56-94-0 (bromide)

Synonym: Demecarium bromide; Band name: Humorsol; Frumtosnil; Tonilen; Tosmicil; Tosmilen; Tosmilene; 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-]

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Demecarium Bromide (BC-48) is a potent cholinesterase inhibitor and glaucoma agent, with an apparent affinity (Kiapp) of 0.15 μM.
In vitro activity:	TBD
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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	160.0	223.28

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 vitro protocol:	TBD
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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

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.

Your view history

Demecarium bromide featured