FENOLDOPAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H16ClNO3
Molecular Weight	305.756
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2CNCCC3=C(Cl)C(O)=C(O)C=C23

InChI

InChIKey=TVURRHSHRRELCG-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H16ClNO3
Molecular Weight	305.756
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf | https://www.drugbank.ca/drugs/DB00800

Fenoldopam (marketed under the brand name Corlopam) is a drug and synthetic benzazepine derivative which acts as a selective D1 receptor partial agonist. 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. Fenoldopam Mesylate Injection, USP is indicated 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 98 Target ID: CHEMBL2056 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9784114 \| https://www.ncbi.nlm.nih.gov/pubmed/7525564	Agonist 2637		40.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 546 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf	Primary		Approved 8307	CORLOPAM Approved Use Adult Patients: Fenoldopam is indicated 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. Transition to oral therapy with another agent can begin at any time after blood pressure is stable during fenoldopam infusion. Pediatric Patients: Fenoldopam is indicated for the in-hospital, short-term (up to 4 hours) reduction in blood pressure. Launch Date 8.7497277E11

C_max

Value	Dose	Co-administered	Analyte	Population
10.9 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FED
26.5 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
26.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FED
44.7 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FED
2.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1673097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOLDOPAM plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
1.5 ug/kg/min single, intravenous Highest studied dose Dose: 1.5 ug/kg/min Route: intravenous Route: single Dose: 1.5 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/1967592 Page: 1-61	unhealthy, 46±3 n = 9 Health Status: unhealthy Condition: Hypertension Age Group: 46±3 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/1967592 Page: 1-61	Sources: https://pubmed.ncbi.nlm.nih.gov/1967592 Page: 1-61
0.8 ug/kg/min single, intravenous Recommended Dose: 0.8 ug/kg/min Route: intravenous Route: single Dose: 0.8 ug/kg/min Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1	Disc. AE: Tachycardia, Hypokalemia... AEs leading to discontinuation/dose reduction: Tachycardia Hypokalemia Anaphylactic reaction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Anaphylactic reaction	Disc. AE	0.8 ug/kg/min single, intravenous Recommended Dose: 0.8 ug/kg/min Route: intravenous Route: single Dose: 0.8 ug/kg/min Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1
Hypokalemia	Disc. AE	0.8 ug/kg/min single, intravenous Recommended Dose: 0.8 ug/kg/min Route: intravenous Route: single Dose: 0.8 ug/kg/min Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1
Tachycardia	Disc. AE	0.8 ug/kg/min single, intravenous Recommended Dose: 0.8 ug/kg/min Route: intravenous Route: single Dose: 0.8 ug/kg/min Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019922s016lbl.pdf Page: p.1

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5002	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5002
ChemicalBook	CB6729842	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6729842
MolPort	MolPort-006-167-637	https://www.molport.com/shop/molecule-link/MolPort-006-167-637
Selleck Chemicals	fenoldopam-corlopam	http://www.selleckchem.com/products/fenoldopam-corlopam.html
eMolecules	36518021	https://www.emolecules.com/cgi-bin/more?vid=36518021

PubMed

Title	Date	PubMed
Cardiovascular function during induced hypotension by fenoldopam or sodium nitroprusside in anesthetized dogs.	1992 Jan	1346487
Effect of fenoldopam on the acute and subacute nephrotoxicity produced by amphotericin B in the dog.	1992 Jan	1346161
Design and rationale of CONTRAST--a prospective, randomized, placebo-controlled trial of fenoldopam mesylate for the prevention of radiocontrast nephropathy.	2001	12439366
Clinical experience with the use of fenoldopam for prevention of radiocontrast nephropathy in high-risk patients.	2001	12439365
Managing the high-risk patient: experience with fenoldopam, a selective dopamine receptor agonist, in prevention of radiocontrast nephropathy during percutaneous coronary intervention.	2001	12439364
Radiocontrast-induced acute renal failure: allocations and outcomes.	2001	12439362
Pathophysiology of radiocontrast nephropathy and use of fenoldopam for its prevention.	2001	12439361
Use of fenoldopam for prevention of radiocontrast nephropathy in the cardiac catheterization laboratory: a case series.	2001 Apr	12053301
Controlled hypotension in children: a critical review of available agents.	2002	12083972
Clinical review: splanchnic ischaemia.	2002 Aug	12225604
Higher basal serine phosphorylation of D1A receptors in proximal tubules of old Fischer 344 rats.	2002 Aug	12110520
Management of patients with hypertensive urgencies and emergencies: a systematic review of the literature.	2002 Dec	12472930
Prevention of postoperative acute renal failure.	2002 Jan-Mar	12082335
Immunohistochemical study on inducible type of nitric oxide (iNOS), basic fibroblast growth factor (bFGF) and tumor growth factor-beta1 (TGF-beta1) in arteritis induced in rats by fenoldopam and theophylline, vasodilators.	2002 Jul	12180796
Effects of fenoldopam, a dopamine D-1 agonist, and clevidipine, a calcium channel antagonist, in acute renal failure in anesthetized rats.	2002 May	12069360
The therapeutic potential of dopamine modulators on the cardiovascular and renal systems.	2002 May	11996645
In vivo effects of fenoldopam on autonomic nervous system after inhibition or activation of ganglionic transmission.	2002 May 31	12063080
The third strike.	2002 Nov	12410498
Prospective randomized study of N-acetylcysteine, fenoldopam, and saline for prevention of radiocontrast-induced nephropathy.	2002 Nov	12410497
Contrast-associated nephropathy.	2002 Nov-Dec	12441014
Using a dopamine type 1A receptor agonist in high-risk patients to ameliorate contrast-associated nephropathy.	2002 Sep	12185025
Desensitization of human renal D1 dopamine receptors by G protein-coupled receptor kinase 4.	2002 Sep	12164861
Hypertensive emergencies. Etiology and management.	2003	14727943
The role of the DA1 receptor agonist fenoldopam in the management of critically ill, transplant, and hypertensive patients.	2003	12556736
Contemporary strategies to preserve renal function during cardiac and vascular surgery.	2003	12556734
A review of contemporary prevention strategies for radiocontrast nephropathy: a focus on fenoldopam and N-acetylcysteine.	2003	12556733
Pharmacological profile of the vascular responses to dopamine in the canine external carotid circulation.	2003 Apr	12753419
Fenoldopam and N-acetylcysteine for the prevention of radiographic contrast material-induced nephropathy: a review.	2003 Dec	14695041
Monitoring renal oxygen supply in critically-ill patients using urinary oxygen tension.	2003 Dec	14633556
Malignant hypertension presenting as hemolysis, thrombocytopenia, and renal failure.	2003 Fall	14674379
The vasodilatory effects of hydralazine, nicardipine, nitroglycerin, and fenoldopam in the human umbilical artery.	2003 Feb	12538209
Dopamine-1 receptor stimulation impairs intestinal oxygen utilization during critical hypoperfusion.	2003 Feb	12399258
Compatibility of fenoldopam mesylate with other drugs during simulated Y-site administration.	2003 Jan 1	12533982
Fenoldopam--but not dopamine--selectively increases gastric mucosal oxygenation in dogs.	2003 Jul	12847395
Acetylcysteine and fenoldopam. Promising new approaches for preventing effects of contrast nephrotoxicity.	2003 Jun	12830779
Receptor mechanisms of prenodal lymphatic constriction by dopamine.	2003 Jun 15	12763634
Radiocontrast-induced nephropathy.	2003 Mar-Apr	12629594
Fenoldopam treatment improves peripheral insulin sensitivity and renal function in STZ-induced type 2 diabetic rats.	2003 May	12797596
Radiocontrast-induced nephropathy and percutaneous coronary intervention: a review of preventive measures.	2003 May	12739990
The effects of intraoperative fenoldopam on renal blood flow and tubular function following suprarenal aortic cross-clamping.	2003 Nov	14569432
Clinical review: the management of hypertensive crises.	2003 Oct	12974970
Perturbation of D1 dopamine and AT1 receptor interaction in spontaneously hypertensive rats.	2003 Oct	12900438
Effects of fenoldopam on renal blood flow and its function in a canine model of rhabdomyolysis.	2003 Sep	12974592
In vitro effects of antihypertensive drugs on thromboxane agonist (U46619)-induced vasoconstriction in human internal mammary artery.	2004 Aug	15169740
American society of nephrology-36th annual meeting and renal week 2003.	2004 Jan	14968812
Dopamine under alpha1-blockade, but not dopamine alone or fenoldopam, increases depressed gastric mucosal oxygenation.	2004 Jan	14707574
Prevention of radiocontrast-induced nephropathy.	2004 Jul	15211433
Aberrant D1 and D3 dopamine receptor transregulation in hypertension.	2004 Mar	14732731
Fenoldopam versus nitroprusside for the treatment of hypertensive emergency.	2004 May	15039472
Effects of short-term fenoldopam infusion on gastric mucosal blood flow in septic shock.	2004 Sep	15329581

Patents

Sample Use Guides

In Vivo Use Guide

Adults: Initiate dosing at 0.01 to 0.3 mcg/kg/min by continuous infusion. Dosing can be increased in increments of 0.05 to 0.1 mcg/kg/minute every 15 minutes or longer until target blood pressure is reached. Dilute prior to administration Pediatrics: Initiate dosing at 0.2 mcg/kg/minute by continuous infusion and titrate dose by 0.3 to 0.5 mcg/kg/min every 20-30 minutes to a maximum dose of 0.8 mcg/kg/minute

Route of Administration: Intravenous

In Vitro Use Guide

Incubation of freshly isolated mouse kidney slices with the selective D(1)-like receptor agonists fenoldopam (10 uM) and SKF-38393 (10 uM) for 1 h induced NaPi-IIa internalization and reduced expression of NaPi-IIa in the brush border membrane (BBM).

Substance Class	Chemical Created by `admin` on `Fri Dec 16 17:17:24 UTC 2022` Edited by `admin` on `Fri Dec 16 17:17:24 UTC 2022`
Record UNII	INU8H2KAWG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOLDOPAM

Official Name

English

FENOLDOPAM [MI]

Common Name

English

Fenoldopam [WHO-DD]

Common Name

English

CARLACOR

Brand Name

English

fenoldopam [INN]

Common Name

English

FENOLDOPAM [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884