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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
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 Weight 716.6 g/mol
Molecular Formula C32H52Br2N4O4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count17
Exact Mass716.23348 g/mol
Monoisotopic Mass714.23553 g/mol
Topological Polar Surface Area59.1 Ų
Heavy Atom Count42
Formal Charge0
Complexity686
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
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


REF. STANDARDS & IMPURITIES

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ABOUT THIS PAGE

Demecarium Manufacturers

A Demecarium manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Demecarium, including repackagers and relabelers. The FDA regulates Demecarium manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Demecarium API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Demecarium manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Demecarium Suppliers

A Demecarium supplier is an individual or a company that provides Demecarium active pharmaceutical ingredient (API) or Demecarium finished formulations upon request. The Demecarium suppliers may include Demecarium API manufacturers, exporters, distributors and traders.

click here to find a list of Demecarium suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Demecarium NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Demecarium as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Demecarium API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Demecarium as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Demecarium and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Demecarium NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Demecarium suppliers with NDC on PharmaCompass.

Demecarium GMP

Demecarium Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Demecarium GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Demecarium GMP manufacturer or Demecarium GMP API supplier for your needs.

Demecarium CoA

A Demecarium CoA (Certificate of Analysis) is a formal document that attests to Demecarium's compliance with Demecarium specifications and serves as a tool for batch-level quality control.

Demecarium CoA mostly includes findings from lab analyses of a specific batch. For each Demecarium CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Demecarium may be tested according to a variety of international standards, such as European Pharmacopoeia (Demecarium EP), Demecarium JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Demecarium USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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