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DEMECARIUM BROMIDE

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Chemistry

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Also known as: 56-94-0, Humorsol, Demekastigmine bromide, Demecarii bromidum, Bromuro de demecario, Bromure de demecarium

Molecular Formula

C₃₂H₅₂Br₂N₄O₄

Molecular Weight

716.6 g/mol

InChI Key

YHKBUDZECQDYBR-UHFFFAOYSA-L

FDA UNII

61D5V4OKTP

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.

1 2D Structure

Demecarium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

YHKBUDZECQDYBR-UHFFFAOYSA-L

2.1.4 Canonical SMILES

CN(CCCCCCCCCCN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C)C(=O)OC2=CC=CC(=C2)[N+](C)(C)C.[Br-].[Br-]

2.2 Other Identifiers

2.2.1 UNII

61D5V4OKTP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Demecarium

2. Demecastigmine

3. Humorsol

4. Tosmilen

2.3.2 Depositor-Supplied Synonyms

1. 56-94-0

2. Humorsol

3. Demekastigmine Bromide

4. Demecarii Bromidum

5. Bromuro De Demecario

6. Bromure De Demecarium

7. Bc-48

8. N,n'-bis(3-trimethylammoniumphenoxycarbonyl)-n,n'-dimethyldecamethylenediamine Dibromide

9. 3,3'-(((decane-1,10-diylbis(methylazanediyl))bis(carbonyl))bis(oxy))bis(n,n,n-trimethylbenzenaminium) Bromide

10. 56-94-0 (bromide)

11. 61d5v4oktp

12. (m-hydroxyphenyl)trimethylammonium Bromide Decamethylenebis(methylcarbamate)

13. (m-hydroxyphenyl)trimethylammonium Bromide Decamethylenebis(methylcarbamate) (2:1)

14. Decamethylenebis(n-methylcarbamic Acid M-dimethylaminophenyl Ester) Bromomethylate

15. Chebi:4391

16. Frumtosnil

17. Visumiotic

18. Tonilen

19. Tosmicil

20. Tosmilen

21. Tosmilene

22. Visumatic

23. Demekarium Bromide

24. Benzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(n,n,n-trimethyl-, Dibromide

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

26. Demecarii Bromidum [inn-latin]

27. Bc 48

28. Bromure De Demecarium [inn-french]

29. Bromuro De Demecario [inn-spanish]

30. Humorsol (tn)

31. 3,3'-(((decane-1,10-diylbis(methylazanediyl))bis(carbonyl))bis(oxy))bis(n,n,n-trimethylbenzenaminium) Bromide.

32. Hsdb 2168

33. Einecs 200-301-9

34. Unii-61d5v4oktp

35. Demecarium Bromide (usp/inn)

36. Decamethylenebis(m-dimethylaminophenyl-n-methylcarbamate) Dimethobromide

37. Demecarium Bromide [usp:inn:ban]

38. Ammonium, (m-hydroxyphenyl)trimethyl-, Bromide, Decamethylenebis(methylcarbamate) (2:1)

39. Ammonium, (m-hydroxyphenyl)trimethyl-, Bromide, Decamethylenebis(methylcarbamate)

40. Schembl34283

41. Demecarium Bromide [mi]

42. Chembl1200514

43. Demecarium Bromide [inn]

44. Hy-b1626a

45. Demecarium Bromide [hsdb]

46. Demecarium Bromide [vandf]

47. Hms2096l14

48. Hms3713l14

49. Hms3887m05

50. Demecarium Bromide [mart.]

51. Bcp24065

52. Demecarium Bromide [usp-rs]

53. Demecarium Bromide [who-dd]

54. Ac-305

55. Decamethylenebis(m-dimethylaminophenyl-n-methylcarbamate)dimethobromide

56. Akos015896671

57. Ccg-220616

58. 3,3'-{decane-1,10-diylbis[(methylcarbamoyl)oxy]}bis(n,n,n-trimethylanilinium) Dibromide

59. Demecarium Bromide [orange Book]

60. As-11735

61. Demecarium Bromide [usp Monograph]

62. Cs-0030928

63. Ft-0698614

64. D00667

65. A924356

66. Sr-01000838877

67. Q5255128

68. Sr-01000838877-2

69. W-105496

70. 3,3'-(((decane-1,10-diylbis(methylazanediyl))bis(carbonyl))bis(oxy))bis(n,n,n-trimethylbenzenaminium)bromide

71. 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(n,n,n-trimethylbenzenaminium)dibromide

72. 3,3'-(decane-1,10-diylbis(methylazanediyl))bis(oxomethylene)bis(oxy)bis(n,n,n-trimethylbenzenaminium) Bromide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₅₂Br₂N₄O₄
Molecular Weight	716.6 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	17
Exact Mass	716.23348 g/mol
Monoisotopic Mass	714.23553 g/mol
Topological Polar Surface Area	59.1 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	686
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Therapeutic Uses

Cholinesterase Inhibitors; Miotics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

/IN TREATMENT OF ESOTROPIA/ THERAPY SHOULD BE DISCONTINUED AFTER 4 MO IF INSTILLATION AS OFTEN AS EVERY 2 DAYS IS STILL REQUIRED.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

/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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

For more Therapeutic Uses (Complete) data for DEMECARIUM BROMIDE (10 total), please visit the HSDB record page.

4.2 Drug Warning

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...

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

.../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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

/DEMECARIUM/...SHOULD NOT BE ADMIN PRIOR TO IRIDECTOMY IN ANGLE-CLOSURE GLAUCOMA BECAUSE...MORE APT TO AGGRAVATE ANGLE CLOSURE THAN WEAKER MIOTICS.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 922

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

5.2 Absorption, Distribution and Excretion

DEMECARIUM IS ABSORBED THROUGH CONJUNCTIVAL SAC AS WELL AS THROUGH INTACT SKIN... /DEMECARIUM/

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

5.3 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".

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:20

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