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HomeProduct name listNylidrin

Nylidrin

  • CAS NO.:447-41-6
  • Empirical Formula: C19H25NO2
  • Molecular Weight: 299.4073
  • MDL number: MFCD00599550
  • EINECS: 207-182-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-21 10:59:17
Nylidrin Structural

What is Nylidrin?

Absorption

Readily absorbed from the gastrointestinal tract .

Toxicity

Adverse effects of oral sympathomimetics, such as Nylidrin, are common. The most frequent effects are hypertension, palpitations, nausea, anxiety, mydriasis, and restlessness/agitation .
Large overdoses and severe toxicity may lead to seizures, hallucinations, agitated delirium, and tachydysrhythmias including supraventricular tachycardia and ventricular tachycardia. Vasospasm can lead to myocardial ischemia focal cerebrovascular deficits. Severe hypertension may also result in intracranial hemorrhage or renal insufficiency. Reflex bradycardia because of significant hypertension is possible. Prolonged agitation can lead to rhabdomyolysis and hyperthermia .

Originator

Arlidin,U.S.V. ,US,1955

The Uses of Nylidrin

Buphenin (Nylidrin), is shown to be an effective inhibitor of IgE-mediated release of histamine from human basophils, and thus can be used as antiallergic agent. It is also one of the FDA approved drug as Inhibitors of the Human Sodium Taurocholate Cotransporting Polypeptide (NTCP).

Indications

Nylidrin is mainly indicated in conditions like arteriosclerosis, cerebrovascular disease, peripheral vascular disease, Raynaud's disease, thrombo-angitis obliterans, and thrombophlebitis . It may sometimes be used in the treatment of peripheral vascular disorders in addition premature labor (however, the drug is not approved for premature labor).

Background

Nylidrin, also known as buphenine belongs to the category of drugs called vasodilators, which relax blood vessels and increase blood flow. Nylidrin is a peripheral vasodilator. Some studies show the evidence of improving cognitive impairment in selected individuals, such as geriatric patients with mild to moderate symptoms of cognitive, emotional and physical impairment .
Nylidrin is utilized to treat several disorders that may benefit from increased blood flow (for example, certain mental disorders, blood vessel disease due to diabetes, frostbite, night leg cramps, and certain types of ulcers). This medication works by dilating (widening) blood vessels to help increase blood flow (improving circulation) throughout the body, including the extremities and central nervous system. This effect may help to improve memory/judgment, improve walking ability, and support the healing of frostbite/ulcers .
FDA has considered nylidrin as "lacking substantial evidence of effectiveness" in cerebral ischemia, cerebral arteriosclerosis, and other cerebral circulatory insufficiencies. Therefore, the FDA has withdrawn nylidrin from the U.S. market .

Definition

ChEBI: 4-[1-hydroxy-2-(4-phenylbutan-2-ylamino)propyl]phenol is an alkylbenzene.

Manufacturing Process

8 grams of the hydrobromide of 1-(p-benzoxyphenyl)-2-(α-methyl-γ-phenylpropylamino)-propanone-(1) were obtained by heating equivalent quantities of p-benzoxy-α-bromopropiophenone and 1-phenyl-3-amino-butane for an hour on the water bath in the absence of solvents. The product was purified by twice boiling with five times the quantity of acetic acid and filtration at 80°C, then shaken in contact with hydrogen with 0.8 gram of Raney nickel in 70 cc of pure methanol containing 0.96 gram (corresponding to 1 mol) of KOH. After 4 hours 2 mols of hydrogen had been taken up and the solution was filtered from the catalyst, evaporated in vacuo, and the residue triturated first with water to remove potassium bromide and then with methanol to remove potassium bromide. 3.7 grams (72% of the theoretical yield) of the compound specified, melting at 110° to 112°C, were obtained, as described in US Patent 2,661,373.

Therapeutic Function

Vasodilator

Pharmacokinetics

Nylidrin hydrochloride acts mainly by beta-receptor stimulation , . Beta stimulation with nylidrin has been studied and confirmed in a variety of isolated tissues from rabbits, guinea pigs, as well as dogs. This drug has been shown to dilate arterioles in skeletal muscle and to increase cardiac output in the anesthetized dog and cat as well as the unanesthetized man. An increase in cerebral blood flow and a decrease in vascular resistance has also been reported. The result of this combination of mechanisms is an improved blood supply to ischemic tissues, with minimal change in blood pressure (generally) .
Nylidrin causes peripheral vasodilation, a positive inotropic effect, and an increased volume of gastric acid. , . According to one study, there are two primary effects of this agent following the intra‐arterial route of administration: one, to decrease total peripheral resistance; and two, a direct effect on the heart tissue to increase cardiac output . It also acts directly on the arteries and arterioles of the skeletal muscles. Additionally, it suppresses uterine contractility thereby preventing or halting premature labor .

Metabolism

Not Available

Properties of Nylidrin

Melting point: 111-112°
Boiling point: 476.0±40.0 °C(Predicted)
Density  1.101±0.06 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml
form  A crystalline solid
pka 9.96±0.26(Predicted)

Safety information for Nylidrin

Computed Descriptors for Nylidrin

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