Synonym
Guanethidine Sulfate; Guanethidine monosulfate; Ismelin sulfate; Guanethidine (sulfate); Octadine; Oktadin; Sulfate, Guanethidine;
IUPAC/Chemical Name
2-[2-(azocan-1-yl)ethyl]guanidine;sulfuric acid
InChi Key
YUFWAVFNITUSHI-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H22N4.H2O4S/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14;1-5(2,3)4/h1-9H2,(H4,11,12,13);(H2,1,2,3,4)
SMILES Code
C1CCCN(CCC1)CCN=C(N)N.OS(=O)(=O)O
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
Biological target:
Guanethidine sulfate (Guanethidine monosulfate) ia an antihypertensive agents. Guanethidine is also an adrenergic neurone blocking drug, enters noradrenergic nerve terminals by the neuronal amine carrier.
In vitro activity:
Guanethidine (0.1 and 1 microM) also decreased S-I efflux but increased resting efflux, both effects being concentration dependent.
Reference: Pharmacol Res. 1996 Mar;33(3):171-80. https://pubmed.ncbi.nlm.nih.gov/8880888/
In vivo activity:
In GUA (guanethidine)-treated animals, a significant decrease in the number of small-sized SP+ bladder-projecting neurons (Figure 5a–d-short arrows; 60.9 ± 4.4%) was observed, while simultaneously the number of medium-sized FB+/SP+ neurons (39.1 ± 4.4%) distinctly increased.
Reference: Int J Mol Sci. 2021 Dec 13;22(24):13399. https://pubmed.ncbi.nlm.nih.gov/34948196/
|
Solvent |
mg/mL |
mM |
| Solubility |
| PBS (pH 7.2) |
10.0 |
33.74 |
| Water |
79.5 |
268.23 |
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
296.39
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. Fabiani ME, Story DF. Inhibition of sympathetic noradrenergic transmission by guanabenz and guanethidine in rat isolated mesenteric artery: involvement of neuronal potassium channels. Pharmacol Res. 1996 Mar;33(3):171-80. doi: 10.1006/phrs.1996.0024. PMID: 8880888.
2. Janikiewicz P, Wasilewska B, Mazur U, Franke-Radowiecka A, Majewski M, Bossowska A. The Influence of an Adrenergic Antagonist Guanethidine (GUA) on the Distribution Pattern and Chemical Coding of Dorsal Root Ganglia (DRG) Neurons Supplying the Porcine Urinary Bladder. Int J Mol Sci. 2021 Dec 13;22(24):13399. doi: 10.3390/ijms222413399. PMID: 34948196; PMCID: PMC8708101.
3. Bossowska A, Lepiarczyk E, Janikiewicz P, Wasilewska B, Mazur U, Markiewicz W, Majewski M. The Influence of an Adrenergic Antagonist Guanethidine on the Distribution Pattern and Chemical Coding of Caudal Mesenteric Ganglion Perikarya and Their Axons Supplying the Porcine Bladder. Int J Mol Sci. 2021 May 5;22(9):4896. doi: 10.3390/ijms22094896. PMID: 34063103; PMCID: PMC8124201.
In vitro protocol:
1. Fabiani ME, Story DF. Inhibition of sympathetic noradrenergic transmission by guanabenz and guanethidine in rat isolated mesenteric artery: involvement of neuronal potassium channels. Pharmacol Res. 1996 Mar;33(3):171-80. doi: 10.1006/phrs.1996.0024. PMID: 8880888.
In vivo protocol:
1. Janikiewicz P, Wasilewska B, Mazur U, Franke-Radowiecka A, Majewski M, Bossowska A. The Influence of an Adrenergic Antagonist Guanethidine (GUA) on the Distribution Pattern and Chemical Coding of Dorsal Root Ganglia (DRG) Neurons Supplying the Porcine Urinary Bladder. Int J Mol Sci. 2021 Dec 13;22(24):13399. doi: 10.3390/ijms222413399. PMID: 34948196; PMCID: PMC8708101.
2. Bossowska A, Lepiarczyk E, Janikiewicz P, Wasilewska B, Mazur U, Markiewicz W, Majewski M. The Influence of an Adrenergic Antagonist Guanethidine on the Distribution Pattern and Chemical Coding of Caudal Mesenteric Ganglion Perikarya and Their Axons Supplying the Porcine Bladder. Int J Mol Sci. 2021 May 5;22(9):4896. doi: 10.3390/ijms22094896. PMID: 34063103; PMCID: PMC8124201.
1: Herskovits MS, Singh IJ. Histologic evaluation of the sympathectomy induced by guanethidine sulfate in neonatal rats. J Exp Zool. 1982 Sep 20;223(1):97-101. PubMed PMID: 7130940.
2: Ourgaud AG, Chagnon A. [Guanethidine sulfate (ismeline) and adrenaline in the treatment of postoperative secondary and residual glaucoma]. Bull Soc Ophtalmol Fr. 1976 May-Jun;76(5-6):517-21. French. PubMed PMID: 1052150.
3: Lenzi F, Gerola A. [The effects of electric stimulation of the hypothalamus on pulmonary circulation in the cat. II. Blocking action of guanethidine sulfate]. Boll Soc Ital Biol Sper. 1969 Aug 31;45(16):1091-5. Italian. PubMed PMID: 5374946.
4: Mitchell JR, Arias L, Oates JA. Antagonism of the antihypertensive action of guanethidine sulfate by desipramine hydrochloride. JAMA. 1967 Dec 4;202(10):973-6. PubMed PMID: 5630743.
5: CHANDRASEKAR RG, COPPO JO, DUANE GW, PIERRE G, THURMANN M, UTLEY JH, JANNEY JG Jr. Clinical evaluation of guanethidine sulfate, a new antihypertensive agent. Am Heart J. 1962 Mar;63:309-19. PubMed PMID: 13878057.
6: GILLIS CN, NASH CW. The initial pressor actions of bretylium tosylate and guanethidine sulfate and their relation to release of catecholamines. J Pharmacol Exp Ther. 1961 Oct;134:1-7. PubMed PMID: 13898659.
7: LECKERT JT. The antihypertensive effect of guanethidine sulfate. Discussion. J La State Med Soc. 1961 Aug;113:345-6. PubMed PMID: 13760083.
8: ZIEGLER RW, SIGNORELLI JJ, DUPUY HJ. The antihypertensive effect of guanethidine sulfate. J La State Med Soc. 1961 Jun;113:221-3. PubMed PMID: 13788429.
9: Haddad HM. Management of surgical overcorrection of ptosis with topical guanethidine sulfate: a case report. Metab Pediatr Syst Ophthalmol. 1982;6(3-4):285-6. PubMed PMID: 7185020.
10: Brown BT, Carrion HM, Politano VA. Guanethidine sulfate in the prevention of autonomic hyperreflexia. J Urol. 1979 Jul;122(1):55-7. PubMed PMID: 458989.
11: Beetz D. [Decline of spermiogram modifications after termination of guanethidine sulfate application]. Andrologie. 1972;4(3):239-44. German. PubMed PMID: 4676474.
12: Storch J. [Action of 5 per cent guanethidine sulfate (ismeline) eye drops on lid retraction during Basedow's disease]. Ann Ocul (Paris). 1971 Jun;204(6):627-44. French. PubMed PMID: 5109312.
13: Pianciola AC. [Guanethidine sulfate collyrium]. Arch Oftalmol B Aires. 1971 May-Jun;46(5):46-7. Spanish. PubMed PMID: 5128656.
14: Tománková H. [Determination of (2-(octahydro-1'-azocinyl)ethyl) guanidine sulfate (guanethidine sulfate) in non-aqueous mdium. Thin layer chromatography of guanethidine sulfate]. Cesk Farm. 1970 Apr;19(3):96-8. Czech. PubMed PMID: 5423295.
15: Bonomi L, DiComite P. Outflow facility after guanethidine sulfate administration. Arch Ophthalmol. 1967 Sep;78(3):337-40. PubMed PMID: 6040011.
16: SHAPIRO AP, KRIFCHER E. PRESSOR RESPONSES TO NOXIOUS STIMULI IN HYPERTENSIVE PATIENTS: EFFECTS OF GUANETHIDINE SULFATE AND ALPHA METHYLDOPA. Circulation. 1964 Nov;30:671-8. PubMed PMID: 14230935.
17: GREENSTEIN S. Severe essential hypertension treated by guanethidine sulfate with hydrochlorthiazide. J Albert Einstein Med Cent (Phila). 1961 Jul;9:198-205. PubMed PMID: 13708357.
