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

• ChemBase ID: 679
• Molecular Formular: C16H16ClNO3
• Molecular Mass: 305.75614
• Monoisotopic Mass: 305.08187106
• SMILES: Clc1c2c(C(CNCC2)c2ccc(O)cc2)cc(O)c1O
• Canonical SMILES: Oc1ccc(cc1)C1CNCCc2c1cc(O)c(c2Cl)O
• InChI: InChI=1S/C16H16ClNO3/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
• InChIKey: TVURRHSHRRELCG-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
• IUPAC Traditional name: fenoldopam
• Brand Name: Corlopam
• Synonyms: 6-Chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol; (±)-Fenoldopam; (±)-SKF 82526; SKF 82526; Fenodopam mesylate; Fenoldopam mesylate; Fenoldopamum [Latin]; Fenoldopam; 6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol

Database IDs

• CAS Number: 67227-57-0; 67227-56-9
• MDL Number: MFCD00865806
• PubChem SID: 160964142; 46504963
• PubChem CID: 3341
• CHEBI ID: 5002
• ATC CODE: C01CA19
• CHEMBL: 588
• Chemspider ID: 3224
• DrugBank ID: DB00800
• IUPHAR ligand ID: 939
• KEGG ID: D07946
• Unique Ingredient Identifier: HA3R0MY016
• Wikipedia Title: Fenoldopam

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 2.39
• LOG S: -3.05
• Solubility (Water): 2.72e-01 g/l

PROPERTIES

Physical Property

• Solubility: 4000 mg/L
• Hydrophobicity(logP): 2; 2.4

Pharmacology Properties

• Admin Routes: IV
• Excretion: Renal (90%) and fecal (10%)
• Half Life: 5 minutes
• Metabolism: Hepatic (CYP not involved)
• Legal Status: Rx-only (US)
• Pregnancy Category: B (US)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00800

• Drug Groups: approved
• Description: A dopamine D1 receptor agonist that is used as an antihypertensive agent. It lowers blood pressure through arteriolar vasodilation. [PubChem]
• Indication: For the in-hospital, short-term (up to 48 hours) management of severe hypertension when rapid, but quickly reversible, emergency reduction of blood pressure is clinically indicated, including malignant hypertension with deteriorating end-organ function.
• Pharmacology: Fenoldopam is an agonist at D₁-like dopamine receptors, binds to α₂-adrenoceptors, increasing renal blood flow.
• Toxicity: The most likely reaction of overdose would be excessive hypotension which should be treated with drug discontinuation and appropriate supportive measures.
• Affected Organisms: Humans and other mammals
• Biotransformation: Elimination is largely by conjugation, without participation of cytochrome P-450 enzymes. Methylation, glucuronidation, and sulfation are the main routes of conjugation.
• Half Life: The elimination half-life is about 5 minutes in mild to moderate hypertensives, with little difference between the R (active) and S isomers.
• Elimination: Radiolabeled studies show that about 90% of infused fenoldopam is eliminated in urine, 10% in feces.; Elimination is largely by conjugation, without participation of cytochrome P-450 enzymes. Only 4% of the administered dose is excreted unchanged.
• External Links: Wikipedia; RxList

Toronto Research Chemicals - F248785

Dopamine D1-receptor agonist. Antihypertensive.

REFERENCES

• Stote, R.M., et al.: Clin. Pharmacol. Ther., 34, 309 (1983)
• Carey, M., et al.: J. Clin. Invest., 74, 2198 (1983)
• Caruana, M.P., et al.: Br. J. Clin. Pharmacol., 24, 721 (1983)