6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol hydrobromide

• ChemBase ID: 134109
• Molecular Formular: C16H17BrClNO3
• Molecular Mass: 386.66808
• Monoisotopic Mass: 385.00803309
• SMILES: c1cc(ccc1C1CNCCc2c1cc(c(c2Cl)O)O)O.Br
• Canonical SMILES: Oc1ccc(cc1)C1CNCCc2c1cc(O)c(c2Cl)O.Br
• InChI: InChI=1S/C16H16ClNO3.BrH/c17-15-11-5-6-18-8-13(9-1-3-10(19)4-2-9)12(11)7-14(20)16(15)21;/h1-4,7,13,18-21H,5-6,8H2;1H
• InChIKey: DSGOSRLTVBPLCU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol hydrobromide
• IUPAC Traditional name: fenoldopam hydrobromide
• Synonyms: SKF-82526; Fenoldopam monohydrobromide; 6-Chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol monohydrobromide; 6-Chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol Hydrobromide; (±)-Fenoldopam Hydrobromide; (±)-SKF 82526 Hydrobromide; SKF 82526 Hydrobromide; Fenoldopam Hydrobromide

Database IDs

• CAS Number: 67287-54-1
• EC Number: 266-634-7
• PubChem SID: 162228386; 24278441
• PubChem CID: 11957552

CALCULATED PROPERTIES

• Acid pKa: 8.117505
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.040907793
• LogD (pH = 7.4): 1.2619835
• Log P: 1.9205202
• Molar Refractivity: 82.6847 cm^3
• Polarizability: 31.639305 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >12 mg/mL; H2O: soluble4.75 mg/mL
• Apperance: off-white

Safety Information

• Storage Condition: protect from light; under inert gas
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36-42/43
• Safety Statements: 22-26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H319-H334
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), DRD1(1812)

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - F6800

Biochem/physiol Actions
Fenoldopam is a selective dopamine agonist that is being considered for the parenteral treatment of systemic hypertension. In both an oral and parenteral form, fenoldopam causes peripheral vasodilation by stimulating dopamine-1 adrenergic receptors. Intravenous fenoldopam may provide advantages over sodium nitroprusside because it can induce both a diuresis and natriuresis, is not light sensitive, and is not associated with cyanide toxicity. There is no evidence for rebound hypertension after discontinuation of fenoldopam infusion.

Toronto Research Chemicals - F248790

Dopamine D1-receptor agonist. Antihypertensive.

REFERENCES

• Ballo, A. et al.: J. Neurosci., 30, 8425 (2010)
• Stote, R.M., et al.: Clin. Pharmacol. Ther., 34, 309 (2010)
• Carey, M., et al.: J. Clin. Invest., 74, 2198 (2010)
• Caruana, M.P., et al.: Br. J. Clin. Pharmacol., 24, 721 (2010)