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67227-57-0 molecular structure
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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 and InChIs

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

Cite this record

CBID:679 http://www.chembase.cn/molecule-679.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
67227-57-0
67227-56-9
MDL Number
MFCD00865806
PubChem SID
46504963
160964142
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.117505  H Acceptors
H Donor LogD (pH = 5.5) -0.040907793 
LogD (pH = 7.4) 1.2619835  Log P 1.9205202 
Molar Refractivity 82.6847 cm3 Polarizability 31.639305 Å3
Polar Surface Area 72.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.39  LOG S -3.05 
Solubility (Water) 2.72e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
4000 mg/L expand Show data source
Hydrophobicity(logP)
2 expand Show data source
2.4 expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
IV expand Show data source
Excretion
Renal (90%) and fecal (10%) expand Show data source
Half Life
5 minutes expand Show data source
Metabolism
Hepatic (CYP not involved) expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
B (US) expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00800 external link
Item Information
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 external link
Dopamine D1-receptor agonist. Antihypertensive.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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