In normotensive beagle dogs with hereditary glaucoma, mecarium bromide (0.125 and 0.5%) lowers intraocular pressure (IOP) and produces long-term miosis [1].

Absorption, Distribution and Excretion
DEMECARIUM IS ABSORBED THROUGH CONJUNCTIVAL SAC AS WELL AS THROUGH INTACT SKIN... /DEMECARIUM/

Interactions
...INHIBITION PRODUCED BY DEMECARIUM IS "REVERSIBLE". LOCAL EFFECTS OF DRUG CAN BE ANTAGONIZED BY ATROPINE AS WELL AS BY PRALIDOXIME (PROTOPAM). EFFECTS OF DEMECARIUM ARE NOT INHIBITED BY PRIOR INSTILLATION OF PHYSOSTIGMINE. /DEMECARIUM/

[1]. Activation and blockade of cardiac muscarinic receptors by endogenous acetylcholine and cholinesterase inhibitors. J Pharmacol Exp Ther. 1982 Oct;223(1):20-4.

[2]. 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.

Demecarium bromide is the methobromide salt of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is an inhibitor of acetylcholinesterase and pseudocholinesterase, with a long duration of action. It is used in the treatment of chronic open-angle glaucoma: in the eye, it causes constriction of the iris sphincter muscle and the ciliary muscle, facilitating the outflow of the aqueous humor and so reducing intraocular pressure. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a quaternary ammonium salt, a bromide salt and a carbamate ester. It contains a demarcarium.
Demecarium Bromide is the bromide salt form of demecarium, a quaternary ammonium compound and a long-acting cholinesterase inhibitor with parasympathomimetic activity. When used topically, demecarium inactivates both pseudocholinesterase and acetylcholinesterase, thereby preventing acetylcholine breakdown and increasing acetylcholine activity. This causes contraction of the iris sphincter muscle (producing miosis) and the ciliary muscle (affecting the accommodation reflex). In so doing, this agent increases the outflow of the aqueous humor, thereby reducing intraocular pressure.
See also: Demecarium (has active moiety).

---

Mechanism of Action
/INCR FACILITY OF AQ OUTFLOW/...ACCOMPANIED BY VASODILATATION OF CONJUNCTIVAL VESSELS & INCR PERMEABILITY OF BLOOD-AQ BARRIER. INDIRECT DECR IN ACTIVITY OF EXTRAOCULAR MUSCLES OF CONVERGENCE ALSO OCCURS. ...CHOLINESTERASE INHIBITION PRODUCED BY DEMECARIUM IS "REVERSIBLE".
DEMECARIUM BROMIDE...IS A QUATERNARY AMMONIUM ANTICHOLINESTERASE DRUG. ... RESULTING ACCUM OF ACETYLCHOLINE PRODUCES MIOSIS & STIMULATES CILIARY MUSCLE...REDUCING INTRAOCULAR PRESSURE BY INCR FACILITY OF AQ OUTFLOW.

---

Therapeutic Uses
Cholinesterase Inhibitors; Miotics
/IN TREATMENT OF ESOTROPIA/ THERAPY SHOULD BE DISCONTINUED AFTER 4 MO IF INSTILLATION AS OFTEN AS EVERY 2 DAYS IS STILL REQUIRED.
/CONGESTIVE IRITIS, IRIDOCYCLITIS, & CONJUNCTIVAL & INTRAOCULAR HYPEREMIA/ ... CAN BE MINIMIZED BY INSTILLATION OF SOLN OF LOWEST EFFECTIVE CONCN @ BEDTIME, & THEY OFTEN SUBSIDE AFTER FIRST FEW DAYS OF THERAPY. INSTILLATION OF 10% PHENYLEPHRINE HYDROCHLORIDE SOLN MAY BE HELPFUL IF CIRCUMCORNEAL INJECTION IS SEVERE.
FOLLOWING INSTILLATION OF DEMECARIUM IN EYE, MIOSIS APPEARS WITHIN 1 HR & REACHES ITS MAX IN 2 TO 4 HR. REDUCTION OF INTRAOCULAR PRESSURE OCCURS IN CA 12 HR & IS FREQUENTLY PRECEDED BY SLIGHT RISE IN PRESSURE. PUPILLARY CONSTRICTION & DECR INTRAOCULAR PRESSURE MAY PERSIST FOR WK OR MORE FOLLOWING SINGLE INSTILLATION.
For more Therapeutic Uses (Complete) data for DEMECARIUM BROMIDE (10 total), please visit the HSDB record page.

---

Drug Warnings
GONIOSCOPIC EXAM SHOULD CONFIRM THAT ANGLE OF EYE IS OPEN PRIOR TO DEMECARIUM THERAPY... IN PT WITH NARROW ANGLE (CONGESTIVE) GLAUCOMA, INTRAOCULAR PRESSURE MAY BE INCR & ACUTE ATTACKS MAY BE PPT. ...INCR IN INTRAOCULAR PRESSURE MAY OCCUR EVEN WHEN ANGLE IS OPEN...
DEMECARIUM IS CONTRAINDICATED IN PT WITH MARKED VASOMOTOR INSTABILITY, BRONCHIAL ASTHMA, SPASTIC GI CONDITIONS, PEPTIC ULCER, SEVERE BRADYCARDIA OR HYPOTENSION, RECENT MYOCARDIAL INFARCTION, EPILEPSY, OR PARKINSONISM.
.../DEMECARIUM/ SHOULD BE USED WITH GREAT CAUTION, IF AT ALL, IN PT WITH HISTORY OF RETINAL DETACHMENT & IN THOSE WITH OCULAR HYPERTENSION ACCOMPANIED BY INTRAOCULAR INFLAMMATORY PROCESSES. ...CONTRAINDICATED IN PT WITH NARROW ANGLE GLAUCOMA.
/DEMECARIUM/...SHOULD NOT BE ADMIN PRIOR TO IRIDECTOMY IN ANGLE-CLOSURE GLAUCOMA BECAUSE...MORE APT TO AGGRAVATE ANGLE CLOSURE THAN WEAKER MIOTICS.

C32H52N4O4.2BR

716.59

714.235

56-94-0

16505-84-3 (cation);56-94-0 (bromide);

5965

White to off-white solid powder

164 - 170ºC

0.77

0

6

17

42

686

0

YHKBUDZECQDYBR-UHFFFAOYSA-L

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

trimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium;dibromide

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~160 mg/mL (~223.28 mM)

Solubility in Formulation 1: ≥ 2.67 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 26.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

---

Solubility in Formulation 2: ≥ 2.67 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 26.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

---

View More

Solubility in Formulation 3: ≥ 2.67 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 26.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

---

 (Please use freshly prepared in vivo formulations for optimal results.)