Fenoldopam mesylate Chemical Properties

Melting point:

274° (dec)

storage temp. 

room temp

solubility 

DMSO: ≥15mg/mL at ~60°C

form 

powder

color 

white to tan

InChIKey

WOFIIEUMIDZJEJ-UHFFFAOYSA-N

CAS DataBase Reference

67227-57-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-42/43

Safety Statements 

22-26-36/37/39

WGK Germany 

3

HS Code 

2933995300

Fenoldopam mesylate Usage And Synthesis

Description

Fenoldopam, first approved in the Netherlands in 1992, ended by reaching its first market, the US, for the short-term management of severe hypertension, including malignant hypertension, in the hospital setting. Fenoldopam can be prepared in 3 steps from the corresponding phenethylamine and aryloxiran, the pivotal step being the cyclisation in benzazepine in acidic medium. Fenoldopam is a potent dopamine D1 receptor agonist acting peripherally to produce systemic vasodilation.As it does not cross the bloodbrain barrier, it does not exert significant central dopaminergic activity. Fenoldopam also interacts significantly with 5HT1c and 5HT2 receptors. In comparative trials with the most common drug used for this condition in Europe, Fenoldopam was found to be appreciably more potent than nifedipine. Furthermore, Fenoldopam is fast acting and maintains a long-lasting antihypertensive effect.

Description

Fenoldopam is an agonist of dopamine D_1A (D1R) and D_1B (D5R) receptors (K_ds = 17 and 11 nM, respectively). Fenoldopam is used to study the roles of these receptors, in cells and in vivo, and to alter hemodynamic properties, including hypertension, in animals.

Chemical Properties

White to Off-White Solid

Originator

SmithKline Beecham (US)

Uses

Dopamine D1-receptor agonist. Antihypertensive.

Uses

antihypertensive, dopamine agonist

Uses

Fenoldopam mesylate may be used to study dopamine D₁-mediated cell signaling.

Definition

ChEBI: Fenoldopam mesylate is a benzazepine.

Manufacturing Process

2-Chloro-3,4-dimethoxyphenethylamine (1.0 g) was reacted with 0.70 g of pmethoxystyrene oxide to give the hydroxyphenethylamine; m.p. 118.5-121°C. This compound (2.16 g) was stirred at room temperature in 15 ml of trifluoroacetic acid with 4 drops of conc. sulfuric acid. After purification over a silica gel column with chloroform, 10% methanol/chloroform as eluates, was obtained 6-chloro-7,8-dimethoxy-1-p-methoxyphenyl-2,3,4,5-tetrahydro-1H- 3-benzazepine (0.78 g), m.p. 143-145°C.
The trimethoxy product (0.87 g, 2.50 mmoles) in 25 ml of dry methylene chloride was cooled in an ice-methanol bath and 12.5 ml (25.0 mmoles) of boron tribromide in methylene chloride was added dropwise. After stirring for 4 hours, the mixture was cooled in an ice bath while methanol was carefully added to give 0.37 g of 6-chloro-7,8-dihydroxy-1-p-hydroxyphenyl-2,3,4,5- tetrahydro-1H-3-benzazepine hydrobromide, m.p. 215°C.
The base was regenerated from the hydrobromide salt using sodium carbonate solution in 85% yield. Treating the base with various acids gave the following salts: dl-tartrate, fumarate, hydrochloride, sulfate, and the most water soluble one, the methanesulfonate, m.p. 272°C.

brand name

Corlopam (Hospira).

Therapeutic Function

Antihypertensive

Biochem/physiol Actions

Fenoldopam mesylate (FM) is considered as an effective therapeutic agent to prevent the onset of postoperative AKI (PO-AKI). In healthy cats, FM can stimulate diuresis and be well-tolerated. This benzazepine-derivative is regional specific and does not cause cerebral vasodilation.

Fenoldopam mesylate(67227-57-0)Related Product Information

• Methanesulfonic acid
• Phentolamine mesilate
• Fenoldopam