Bethanidine Sulfate | CAS# 114-85-2 | Antihypertensive Agent

MedKoo Cat#: 317321 | Name: Bethanidine Sulfate

Description:

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

Bethanidine sulfate is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission.

Chemical Structure

Bethanidine Sulfate

CAS#114-85-2 (sulfate)

Theoretical Analysis

MedKoo Cat#: 317321

Name: Bethanidine Sulfate

CAS#: 114-85-2 (sulfate)

Chemical Formula: C10H17N3O4S

Exact Mass:

Molecular Weight: 275.32

Elemental Analysis: C, 43.62; H, 6.22; N, 15.26; O, 23.24; S, 11.65

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Related CAS #

55-73-2 (free base) 114-85-2 (sulfate)

Synonym

Bethanidine Sulfate; Bentanidol; Benzanidin; Benzanidine; Bendogen; Benzaidin; Benzoxine; Betaling; Eusmanid; Hypersin; Tenathan; Esbatal; Regulin; Batel; Bethanidine; hemisulfate, UNII-J4THI5N7O2, Bethanidine sulfate [USAN], 55-73-2 (Parent), EINECS 204-056-9, CID8248

IUPAC/Chemical Name

1-benzyl-2,3-dimethylguanidine;sulfuric acid

InChi Key

WDLCALUKNKNIDF-UHFFFAOYSA-N

InChi Code

InChI=1S/C10H15N3.H2O4S/c1-11-10(12-2)13-8-9-6-4-3-5-7-9;1-5(2,3)4/h3-7H,8H2,1-2H3,(H2,11,12,13);(H2,1,2,3,4)

SMILES Code

CNC(=NC)NCC1=CC=CC=C1.OS(=O)(=O)O

Appearance

Solid powder

Purity

>98% (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, not in water

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bethanidine sulfate is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission.

In vitro activity:

The effects of bethanidine sulphate were studied on action potentials (APs) and K+, Na+, and Ca2+ currents of single cultured embryonic chick heart cells using the whole-cell current clamp and voltage clamp technique. Extracellular application of bethanidine (3 X 10(-4) M) increased the overshoot and the duration of the APs and greatly decreased the outward K+ current (IK) and potentiated the inward fast Na+ currents (INa) and the inward slow calcium current (ICa). However, intracellular introduction of bethanidine (10(-4) M) blocked Ina. These findings suggest that when applied extracellularly, bethanidine exerts a potentiating effect on the myocardial fast Na+ current and slow Ca2+ current and an inhibitory effect of IK. The positive inotropic effect of bethanidine could be due, at least in part, to an increase of Ca2+ influx via the slow Ca2+ channel and the Na-Ca exchange. It is suggested that the decrease of IK by bethanidine may account for its antifibrillatory action. Reference: Can J Physiol Pharmacol. 1988 Mar;66(3):190-6. https://cdnsciencepub.com/doi/10.1139/y88-033?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 275.32 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. Dangman KH, Miura DS. Electrophysiological effects of bethanidine sulfate on canine cardiac Purkinje fibers and ventricular muscle cells. J Cardiovasc Pharmacol. 1985 Jan-Feb;7(1):50-8. doi: 10.1097/00005344-198501000-00009. PMID: 2580150. 2. Bkaily G, Payet MD, Benabderrazik M, Renaud JF, Sauvé R, Bacaner MB, Sperelakis N. Bethanidine increased Na+ and Ca2+ currents and caused a positive inotropic effect in heart cells. Can J Physiol Pharmacol. 1988 Mar;66(3):190-6. doi: 10.1139/y88-033. PMID: 3383015.

In vitro protocol:

In vivo protocol:

TBD

1: Bauman JL, Gallastegui J, Prechel D, Anderson JL. Bethanidine sulfate in paroxysmal ventricular tachycardia: toxicity and antifibrillatory actions. Pharmacotherapy. 1986 Jul-Aug;6(4):184-92. doi: 10.1002/j.1875-9114.1986.tb03474.x. PMID: 3774563. 2: Bethanidine. Br Med J. 1967 Feb 4;1(5535):285-6. PMID: 6017482; PMCID: PMC1840649. 3: Taghvaei S, Minuchehr Z, Sabouni F. Computational drug repurposing of bethanidine for SENP1 inhibition in cardiovascular diseases treatment. Life Sci. 2022 Mar 1;292:120122. doi: 10.1016/j.lfs.2021.120122. Epub 2021 Nov 6. PMID: 34748762. 4: Dangman KH, Miura DS. Electrophysiological effects of bethanidine sulfate on canine cardiac Purkinje fibers and ventricular muscle cells. J Cardiovasc Pharmacol. 1985 Jan-Feb;7(1):50-8. doi: 10.1097/00005344-198501000-00009. PMID: 2580150. 5: Benditt DG, Benson DW Jr, Dunnigan A, Kriett JM, Pritzker MR, Bacaner MB. Antiarrhythmic and electrophysiologic actions of bethanidine sulfate in primary ventricular fibrillation or life-threatening ventricular tachycardia. Am J Cardiol. 1984 May 1;53(9):1268-74. doi: 10.1016/0002-9149(84)90077-8. PMID: 6711426. 6: Teichman SL, Waspe LE, Matos JA, Kim SG, Fisher JD. Bethanidine sulfate: efficacy in prevention of ventricular tachyarrhythmias during programmed stimulation. Report of a multicenter study of 56 patients. J Am Coll Cardiol. 1985 Sep;6(3):510-7. doi: 10.1016/s0735-1097(85)80106-6. PMID: 3897340. 7: Kabell G. Ischemia-induced conduction delay and ventricular arrhythmias: comparative electropharmacology of bethanidine sulfate and bretylium tosylate. J Cardiovasc Pharmacol. 1989 Mar;13(3):471-82. doi: 10.1097/00005344-198903000-00017. PMID: 2471895. 8: Somberg JC, Butler B, Torres V, Flowers D, Tepper D, Wynn J, Keren G, Miura DS. Antiarrhythmic action of bethanidine. Am J Cardiol. 1984 Aug 1;54(3):343-6. doi: 10.1016/0002-9149(84)90194-2. PMID: 6465015. 9: GIFFORD RW Jr. BETHANIDINE SULFATE--A NEW ANTIHYPERTENSIVE AGENT. JAMA. 1965 Sep 13;193:901-5. doi: 10.1001/jama.1965.03090110039011. PMID: 14341134. 10: Villafane J, Xu H, McCormack J, Gelband H, Stolfi A, Pickoff AS. The non- catecholamine-mediated electrophysiological effects of intravenous bethanidine sulfate on the immature mammalian heart. J Cardiovasc Pharmacol. 1988 Oct;12(4):486-91. doi: 10.1097/00005344-198810000-00016. PMID: 2465451. 11: DiMarco JP, Sellers TD, Shipe JR, Savory J, Spyker DH. Acute electrophysiologic effects of bethanidine sulfate in patients with ventricular tachycardia or fibrillation. Am Heart J. 1984 Nov;108(5):1244-9. doi: 10.1016/0002-8703(84)90748-8. PMID: 6496282. 12: BEWLEY TH. TO-DAY'S DRUGS. BETHANIDINE SULPHATE. Br Med J. 1964 Oct 3;2(5413):865. PMID: 14185642; PMCID: PMC1816291. 13: Bacaner MB, Hoey MF, Macres MG. Suppression of ventricular fibrillation and positive inotropic action of bethanidine sulfate, a chemical analog of bretylium tosylate that is well absorbed orally. Am J Cardiol. 1982 Jan;49(1):45-55. doi: 10.1016/0002-9149(82)90276-4. PMID: 7053610. 14: Ramirez EA, Elson L, Gear AS, Oster JR, Talmers FN, Thomas JR. Multiclinic controlled trial of bethanidine and guanethidine in severe hypertension. Circulation. 1977 Mar;55(3):519-25. doi: 10.1161/01.cir.55.3.519. PMID: 319922. 15: Myers MG. New drugs in hypertension. Can Med Assoc J. 1977 Jan 22;116(2):173-6. PMID: 343894; PMCID: PMC1879000. 16: Corder CN, Klaniecki TS, McDonald RH Jr, Berlin C. Fluorometric assay of bethanidine in plasma. J Pharm Sci. 1975 May;64(5):785-92. doi: 10.1002/jps.2600640511. PMID: 239198. 17: Zimmerman JM, Patterson E, Pitt B, Lucchesi B. Antidysrhythmic actions of meobentine sulfate. Am Heart J. 1984 Jun;107(6):1117-24. doi: 10.1016/0002-8703(84)90266-7. PMID: 6720538. 18: Bacaner MB, Benditt DG. Antiarrhythmic, antifibrillatory, and hemodynamic actions of bethanidine sulfate: an orally effective analog of bretylium for suppression of ventricular tachyarrhythmias. Am J Cardiol. 1982 Oct;50(4):728-34. doi: 10.1016/0002-9149(82)91226-7. PMID: 6812406. 19: Green AF. The discovery of bretylium and bethanidine. Br J Clin Pharmacol. 1982 Jan;13(1):25-34. doi: 10.1111/j.1365-2125.1982.tb01333.x. PMID: 7066153; PMCID: PMC1401770. 20: Corder CN. Bethanidine dose, plasma levels, and antihypertensive effects. J Clin Pharmacol. 1978 May-Jun;18(5-6):249-58. doi: 10.1002/j.1552-4604.1978.tb02443.x. PMID: 641213.