Guanethidine

Base Information

• Chemical Name: Guanethidine
• CAS No.: 55-65-2
• Molecular Formula: C10H22 N4
• Molecular Weight: 198.311
• European Community (EC) Number: 200-241-3
• UNII: ZTI6C33Q2Q
• DSSTox Substance ID: DTXSID5023116
• Nikkaji Number: J4.562D
• Wikipedia: Guanethidine
• Wikidata: Q420673
• NCI Thesaurus Code: C65830
• Pharos Ligand ID: XSVDCUPXXRUS
• Metabolomics Workbench ID: 43388
• ChEMBL ID: CHEMBL765
• Mol file: 55-65-2.mol

Synonyms:((2-Hexahydro-1(2H)-azocinyl)ethyl)guanidine;Guanethidine;Guanethidine Monosulfate;Guanethidine Sulfate;Guanethidine Sulfate (1:1);Guanethidine Sulfate (1:2);Guanethidine Sulfate (2:1);Guanethidine Sulfate (2:1), 14C-Labeled;Ismelin;Isobarin;Monosulfate, Guanethidine;Octadine;Oktadin;Sulfate, Guanethidine

Chemical Property of Guanethidine

Chemical Property:

• Vapor Pressure: 6.09E-05mmHg at 25°C
• Refractive Index: 1.4910 (estimate)
• Boiling Point: 345.6°Cat760mmHg
• PKA: pKa 11.4 (Uncertain)
• Flash Point: 162.8°C
• PSA: 65.14000
• Density: 1.13g/cm³
• LogP: 1.86440
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 198.18444672
• Heavy Atom Count: 14
• Complexity: 167

Purity/Quality:

97% ^*data from raw suppliers

GUANETHIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCN(CCC1)CCN=C(N)N
• Recent EU Clinical Trials: En proof of concept (POC) studie g?llande guanethidines sm?rtlindrande effekt vid regional i.v administrering f?r behandling av komplext regional sm?rtsyndrom (CRP)
• Description: Guanethidine is used for severe hypertension when the use of the more generally accepted drugs turns out to be unsuccessful. It is a powerful, long-lasting antihypertensive drug; however, it affects a patient’s blood pressure only in the orthostatic position, and not when lying down. Guanethidine is a very powerful and long-lasting drug, and its action often lasts 2–3 days after its use has been stopped.
• Uses: Antihypertensive.
• Therapeutic Function: Antihypertensive
• Biological Functions: Guanethidine (Ismelin) is a powerful antihypertensive agent that is quite effective in the treatment of moderate to severe hypertension. It is most frequently used in the treatment of severe hypertension that is resistant to other agents. Guanethidine exerts its effects at peripheral sympathetic nerve endings following its active transport into the nerve varicosities by the neuronal amine transport system. This is the same uptake system that transports norepinephrine into the varicosity).The accumulation of guanethidine in adrenergic neurons, through an as yet unexplained mechanism, disrupts the process by which action potentials trigger the release of stored norepinephrine and other cotransmitters from nerve terminals. It is this action of guanethidine that is primarily responsible for its antihypertensive properties. Parasympathetic function is not altered, a fact that distinguishes guanethidine from the ganglionic blocking agent. Guanethidine is suitable for oral use, and this is its usual route of administration. However, absorption from the gastrointestinal tract is variable. The half-life of guanethidine is 5 days, with about one-seventh of the total administered dose eliminated per day. The slow elimination contributes to the cumulative and prolonged effects of the drug. Guanethidine reduces blood pressure by its ability to diminish vascular tone; both the arterial and venous sides of the circulatory system are involved. The resulting venous pooling contributes to orthostatic hypotension, a prominent feature of guanethidine treatment. The reduction in blood pressure is more prominent when the patient is standing than recumbent.

Technology Process of Guanethidine

There total 2 articles about Guanethidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-ethylamin (1126-67-6) + aminoiminomethanesulfonic acid (1184-90-3) → guanethidine (55-65-2)

Guidance literature:

Reference yield:

→ guanethidine (55-65-2)

Guidance literature:

1-(2-Amino-ethyl)-octahydroazocin, Guanidin-hydrochlorid (135-150grad, 4h);

Reference yield:

guanethidine (55-65-2) + C42H55NO9 → 4-(((((6aR,6bS,8aS,11R,12S,14bR)-8a-((N-(2-(azocan-1-yl)ethyl)carbamimidoyl)carbamoyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy)carbonyl)oxy)benzoic acid

Guidance literature:

In methanol; at 20 ℃; for 24h;

upstream raw materials:

2-ethylamin

aminoiminomethanesulfonic acid

Refernces

Some new prazosin analogues

10.1002/ardp.19893220607

Prazosin, a selective a1-adrenergic antagonist used in antihypertensive therapy, has limitations due to its short half-life and side effects. To address these issues, the researchers synthesized new analogues by modifying the C-2 side-chain of prazosin, incorporating fragments from tienilic acid, guanethidine, and lidoflazine. The compounds were synthesized using various chemical procedures and their structures were confirmed through analytical data. The pharmacological properties were evaluated in terms of acute toxicity and hypotensive effects in mice and genetically hypertensive rats, respectively. The results showed that compound 5, featuring a tienilic residue in place of the furan ring, exhibited the highest hypotensive effect and a more long-lasting activity compared to prazosin. The study concludes that the new compounds, particularly compound 5, have potential for improved pharmacokinetic properties and hypotensive activity, warranting further investigation for their therapeutic applications.

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