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Identification
Name Fenoldopam
Accession Number DB00800 (APRD00969)
Type small molecule
Groups approved
Description

A dopamine D1 receptor agonist that is used as an antihypertensive agent. It lowers blood pressure through arteriolar vasodilation. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Fenodopam mesylate
Fenoldopam mesylate
Fenoldopamum [Latin]
Salts Not Available
Brand names
Name Company
Corlopam
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Vasodilator Agents
  • Dopamine Agonists
CAS number 67227-57-0
Weight Average: 305.756
Monoisotopic: 305.08187109
Chemical Formula C16H16ClNO3
InChI Key InChIKey=TVURRHSHRRELCG-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
SMILES
OC1=CC=C(C=C1)C1CNCCC2=C(Cl)C(O)=C(O)C=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Benzazepines
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Catechols
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Benzazepines
  • Phenyl Esters
  • Catecholamines and Derivatives
Pharmacology
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.
Pharmacodynamics Fenoldopam is an agonist at D1-like dopamine receptors, binds to α2-adrenoceptors, increasing renal blood flow.
Mechanism of action Fenoldopam is a rapid-acting vasodilator. It is an agonist for D1-like dopamine receptors and binds with moderate affinity to α2-adrenoceptors. It has no significant affinity for D2-like receptors, α1 and β-adrenoceptors, 5HT1 and 5HT2 receptors, or muscarinic receptors. Fenoldopam is a racemic mixture with the R-isomer responsible for the biological activity. The R-isomer has approximately 250-fold higher affinity for D1-like receptors than does the S-isomer. In non-clinical studies, fenoldopam had no agonist effect on presynaptic D2-like dopamine receptors, or α or β -adrenoceptors, nor did it affect angiotensin-converting enzyme activity. Fenoldopam may increase norepinephrine plasma concentration.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Elimination is largely by conjugation, without participation of cytochrome P-450 enzymes. Methylation, glucuronidation, and sulfation are the main routes of conjugation.
Route of 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.
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.
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Bedford laboratories
  • Pharmaforce inc
  • Sandoz canada inc
  • Teva parenteral medicines inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intravenous drip
Prices
Unit description Cost Unit
Fenoldopam 10 mg/ml ampule 213.75 USD ml
Corlopam 10 mg/ml ampul 81.9 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility 4000 mg/L Not Available
logP 2 Not Available
Predicted Properties
Property Value Source
water solubility 2.72e-01 g/l ALOGPS
logP 2.39 ALOGPS
logP 1.92 ChemAxon
logS -3 ALOGPS
pKa (strongest acidic) 8.12 ChemAxon
pKa (strongest basic) 10.4 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 72.72 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 82.68 ChemAxon
polarizability 30.71 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00613 Link_out
PubChem Compound 3341 Link_out
PubChem Substance 46504963 Link_out
ChemSpider 3224 Link_out
ChEBI 5002 Link_out
ChEMBL 5002 Link_out
Therapeutic Targets Database DAP000254 Link_out
PharmGKB PA164784034 Link_out
IUPHAR 939 Link_out
Guide to Pharmacology 939 Link_out
RxList http://www.rxlist.com/cgi/generic3/fenoldopam.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Fenoldopam Link_out
ATC Codes
  • C01CA19
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (239 KB)
MSDS Not Available
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. D(1B) dopamine receptor

Pharmacological action: yes
Actions: agonist

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

Organism class: human
UniProt ID: P21918 Link_out
Gene: DRD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Zeng C, Han Y, Huang H, Yu C, Ren H, Shi W, He D, Huang L, Yang C, Wang X, Zhou L, Jose PA: D1-like receptors inhibit insulin-induced vascular smooth muscle cell proliferation via down-regulation of insulin receptor expression. J Hypertens. 2009 May;27(5):1033-41. Pubmed
  4. Dhasmana KM, Villalon CM, Zhu YN, Parmar SS: The role of dopamine (D2), alpha and beta-adrenoceptor receptors in the decrease in gastrointestinal transit induced by dopamine and dopamine-related drugs in the rat. Pharmacol Res. 1993 May-Jun;27(4):335-47. Pubmed

2. D(1A) dopamine receptor

Pharmacological action: yes
Actions: agonist

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

Organism class: human
UniProt ID: P21728 Link_out
Gene: DRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Zeng C, Han Y, Huang H, Yu C, Ren H, Shi W, He D, Huang L, Yang C, Wang X, Zhou L, Jose PA: D1-like receptors inhibit insulin-induced vascular smooth muscle cell proliferation via down-regulation of insulin receptor expression. J Hypertens. 2009 May;27(5):1033-41. Pubmed
  3. Dhasmana KM, Villalon CM, Zhu YN, Parmar SS: The role of dopamine (D2), alpha and beta-adrenoceptor receptors in the decrease in gastrointestinal transit induced by dopamine and dopamine-related drugs in the rat. Pharmacol Res. 1993 May-Jun;27(4):335-47. Pubmed

3. Alpha-2B adrenergic receptor

Pharmacological action: unknown
Actions: antagonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol

Organism class: human
UniProt ID: P18089 Link_out
Gene: ADRA2B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Martin SW, Broadley KJ: Renal vasodilatation by dopexamine and fenoldopam due to alpha 1-adrenoceptor blockade. Br J Pharmacol. 1995 May;115(2):349-55. Pubmed

4. Alpha-2C adrenergic receptor

Pharmacological action: unknown
Actions: antagonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins

Organism class: human
UniProt ID: P18825 Link_out
Gene: ADRA2C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Martin SW, Broadley KJ: Renal vasodilatation by dopexamine and fenoldopam due to alpha 1-adrenoceptor blockade. Br J Pharmacol. 1995 May;115(2):349-55. Pubmed

5. Alpha-2A adrenergic receptor

Pharmacological action: unknown
Actions: antagonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Martin SW, Broadley KJ: Renal vasodilatation by dopexamine and fenoldopam due to alpha 1-adrenoceptor blockade. Br J Pharmacol. 1995 May;115(2):349-55. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19