Distigmine Bromide | Ubretid | BC-51 | CAS#15876-67-2 | CAS#17299-00-2 | Acetylcholinesterase Inhibitor

MedKoo Cat#: 329010 | Name: Distigmine Bromide

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Description:

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

Distigmine Bromide, also known as Ubretid and BC-51, is an acetylcholinesterase inhibitor used for the treatment of underactive neurogenic bladder and myasthenia gravis.

Chemical Structure

Distigmine Bromide

CAS#15876-67-2 (bromide)

Theoretical Analysis

MedKoo Cat#: 329010

Name: Distigmine Bromide

CAS#: 15876-67-2 (bromide)

Chemical Formula: C22H32Br2N4O3

Exact Mass: 0.0000

Molecular Weight: 560.33

Elemental Analysis: C, 47.16; H, 5.76; Br, 28.52; N, 10.00; O, 8.57

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 400.00	2 Weeks
250mg	USD 750.00	2 Weeks

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Related CAS #

15876-67-2 (bromide) 17299-00-2 (cation)

Synonym

Distigmine Bromide; Ubretid; Ubritil; Bromure de distigmine; Hexamarium; BC-51; BC 51; BC51;

IUPAC/Chemical Name

3-(((6-(N,1-dimethylpyridin-1-ium-3-carboxamido)hexyl)(methyl)carbamoyl)oxy)-1-methylpyridin-1-ium bromide

InChi Key

OPJQIUFQBIQOHZ-UHFFFAOYSA-L

InChi Code

InChI=1S/C22H32N4O3.2BrH/c1-23-13-9-11-19(17-23)21(27)25(3)15-7-5-6-8-16-26(4)22(28)29-20-12-10-14-24(2)18-20;;/h9-14,17-18H,5-8,15-16H2,1-4H3;2*1H/q+2;;/p-2

SMILES Code

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

Appearance

Solid powder

Purity

>96% (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 DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Related CAS# 15876-67-2 (Distigmine Bromide) 17299-00-2 (Distigmine)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ubretid (distigmine bromide) is a potent inhibitor of plasma cholinesterase.

In vitro activity:

TBD

In vivo activity:

Distigmine (0.1 mg/kg) significantly increased the maximum intravesical pressure at micturition reflex for 12 h post-administration. The inhibitory effects of distigmine on AChE activity were sustained during the measurement period and statistically significant effects were observed for 12 h after the administration of all tested doses (Fig. 5A) in guinea pigs. Reference: Biol Pharm Bull. 2017;40(6):807-814. https://pubmed.ncbi.nlm.nih.gov/28566624/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	178.47

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 560.33 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. Obara K, Chino D, Tanaka Y. Distigmine Bromide Produces Sustained Potentiation of Guinea-Pig Urinary Bladder Motility by Inhibiting Cholinesterase Activity. Biol Pharm Bull. 2017;40(6):807-814. doi: 10.1248/bpb.b16-00901. PMID: 28566624. 2. Ito Y, Harada T, Fushimi K, Kagawa Y, Oka H, Nakazawa H, Homma R, Kato Y, Yamada S. Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats. Drug Metab Pharmacokinet. 2010;25(3):254-61. doi: 10.2133/dmpk.25.254. PMID: 20610884.

In vitro protocol:

TBD

In vivo protocol:

1: Obara K, Tanaka Y. Sustainable Effects of Distigmine Bromide on Urinary Bladder Contractile Function. Pharmacology. 2020;105(3-4):135-144. doi: 10.1159/000503453. Epub 2019 Oct 15. PMID: 31614352. 2: Obara K, Chino D, Tanaka Y. Distigmine Bromide Produces Sustained Potentiation of Guinea-Pig Urinary Bladder Motility by Inhibiting Cholinesterase Activity. Biol Pharm Bull. 2017;40(6):807-814. doi: 10.1248/bpb.b16-00901. PMID: 28566624. 3: Kotake K, Tone A, Watanabe S, Senoo M, Kaneto M, Imai Y, Teshigawara S, Kawakami Y, Nakatou T. Cholinergic Crisis Owing to Distigmine Bromide Complicated by Hyperosmolar Hyperglycemic State. Intern Med. 2021 Jul 15;60(14):2251-2254. doi: 10.2169/internalmedicine.6261-20. Epub 2021 Feb 15. PMID: 33583891; PMCID: PMC8355397. 4: Obara K, Tanaka Y. Effects of Distigmine on the Mechanical Activity of Urinary Bladder Smooth Muscle. Biol Pharm Bull. 2019;42(7):1064-1068. doi: 10.1248/bpb.b19-00201. PMID: 31257280. 5: Shah PJ, Abrams PH, Choa RG, Ashken MH, Gaches CG, Green NA, Wiles A. Distigmine bromide and post-prostatectomy voiding. Br J Urol. 1983 Apr;55(2):229-32. doi: 10.1111/j.1464-410x.1983.tb06563.x. PMID: 6132645. 6: Sera T, Kusunoki S, Shime N. Unexpected cholinergic crisis caused by distigmine bromide: A case report. Medicine (Baltimore). 2022 Nov 25;101(47):e31677. doi: 10.1097/MD.0000000000031677. PMID: 36451415; PMCID: PMC9704958. 7: Tada M, Fujita N, Umeda M, Koike H, Nagai H. [A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder]. No To Shinkei. 2004 May;56(5):415-9. Japanese. PMID: 15279199. 8: Obara K, Tanaka Y. [Mechanism of the Long-lasting Potentiating Effect of Distigmine on Urinary Bladder Motility]. Yakugaku Zasshi. 2021;141(2):245-254. Japanese. doi: 10.1248/yakushi.20-00212. PMID: 33518645. 9: Ito Y, Harada T, Fushimi K, Kagawa Y, Oka H, Nakazawa H, Homma R, Kato Y, Yamada S. Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats. Drug Metab Pharmacokinet. 2010;25(3):254-61. doi: 10.2133/dmpk.25.254. PMID: 20610884. 10: Distigmine (ubretid). Drug Ther Bull. 1968 Jul 19;6(15):60. PMID: 4875862. 11: Himmerich H, Szegedi A, Klawe C, Anghelescu I, Müller MJ. Distigmine bromide induced acute psychotic disorder in a patient with multiple sclerosis. Eur Psychiatry. 2003 Oct;18(6):318-9. doi: 10.1016/j.eurpsy.2002.11.001. PMID: 14611928. 12: Obara K, Kobayashi Y, Chino D, Tanaka Y. Effects of Distigmine on Electrical Field Stimulation-Induced Contraction of Mouse Urinary Bladder Smooth Muscles. Pharmacology. 2017;99(3-4):106-113. doi: 10.1159/000452222. Epub 2016 Nov 1. PMID: 27798943. 13: Obara K, Kobayashi Y, Chino D, Tanaka Y. Effect of distigmine on the contractile response of guinea pig urinary bladder to electrical field stimulation. Eur J Pharmacol. 2017 Aug 15;809:209-214. doi: 10.1016/j.ejphar.2017.05.031. Epub 2017 May 13. PMID: 28511871. 14: Bougas DA, Mitsogiannis IC, Mitropoulos DN, Kollaitis GC, Serafetinides EN, Giannopoulos AM. Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor. Int Urol Nephrol. 2004;36(4):507-12. doi: 10.1007/s11255-004-0847-8. PMID: 15787326. 15: Mitsuboshi S, Otaki S, Kaneko C, Tsuruma N. [Association between Distigmine- induced Adverse Events and Serum Butyrylcholinesterase Level: A Multicenter Retrospective Study]. Yakugaku Zasshi. 2022;142(9):993-998. Japanese. doi: 10.1248/yakushi.22-00078. PMID: 36047226. 16: Obara K, Chino D, Tanaka Y. Long-Lasting Inhibitory Effects of Distigmine on Recombinant Human Acetylcholinesterase Activity. Biol Pharm Bull. 2017;40(10):1739-1746. doi: 10.1248/bpb.b17-00351. PMID: 28966245. 17: Tsutsumi Y, Tanaka J, Miura T, Yamato H, Kanamori H, Kawamura T, Obara S, Asaka M, Imamura M, Masauzi N. Rhabdomyolysis caused by distigmine bromide. Intern Med. 2003 Nov;42(11):1156. doi: 10.2169/internalmedicine.42.1156. PMID: 14686764. 18: Tanaka Y, Masumori N, Itoh N, Furuya S, Nishizawa O, Tsukamoto T. Symptomatic and urodynamic improvement by oral distigmine bromide in poor voiders after transurethral resection of the prostate. Urology. 2001 Feb;57(2):270-4. doi: 10.1016/s0090-4295(00)00924-9. PMID: 11182335. 19: Yeo J, Southwell P, Rutowski S, Marchant-Williams H. A further report on the effect of distigmine bromide (Ubretid) on the neurogenic bladder. Med J Aust. 1974 Aug 10;2(6):201-3. doi: 10.5694/j.1326-5377.1974.tb70704.x. PMID: 4424051. 20: Hampf G, Bowsher D, Nurmikko T. Distigmine and amitriptyline in the treatment of chronic pain. Anesth Prog. 1989 Mar-Apr;36(2):58-62. PMID: 2574958; PMCID: PMC2148641.