Fenoldopam Mesylate
Basic information
- CAS
67227-57-0- Standard SMILES
CS(=O)(=O)O.Oc1ccc(C2CNCCc3c2cc(O)c(O)c3Cl)cc1- InChIKey
CVKUMNRCIJMVAR-UHFFFAOYSA-N- Molecular formula
- C17H20ClNO6S
- Average molar mass
- 401.9 g/mol
- Monoisotopic mass
- 401.0699862
Overview
Fenoldopam mesylate is a benzazepine.
Names & identifiers
- Preferred name
- Fenoldopam Mesylate
- IUPAC
- 9-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;methanesulfonic acid
- English name
- Fenoldopam mesylate
- Molecular formula
- C17H20ClNO6S
- Molecular weight
- 401.86
Names & synonyms
FENOLDOPAM MESYLATE67227-57-0CorlopamFenoldopam mesilateFenoldopam methanesulfonateSK&F 82526-JFendolopam mesylateNSC-759860HA3R0MY016SK&F-82526-JDTXSID00904650SK-82526-J
Show more names
SKF R-825269CL-CORLOPAM(R)-SKF-82526(S)-SKF-82526CORLOPAM MESYLATESKF-82526 mesylateFenodopam mesylateFENOLDIPAM MESYLATE
RefChem:56466DTXCID801333767266-612-76-Chloro-2,3,4,5-tetrahydro-1-(p-hydroxyphenyl)-1H-3-benzazepine-7,8-diol methanesulfonate(salt)Fenoldopam (mesylate)MFCD041129869-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;methanesulfonic acidCHEBI:5003
Database identifiers
- CAS
67227-57-0- PubChem CID
- 49659
- DTXSID
DTXSID00904650- ChEMBL
CHEMBL1026- ChEBI
CHEBI:5003- UNII
- HA3R0MY016
- EC Number
Properties
Computed structural properties
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 441
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Dopamine Agents; Dopamine Agonists; Vasodilator Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 274 ° · 274° (dec)
- storage temp.
- room temp
- solubility
- 15 mg/mL · DMSO: ≥15mg/mL at ~60°C
- form
- powder
- color
- white to tan
- InChI
- InChI=1S/C17H18ClNO5S/c1-25(22,23)24-17-15(21)8-13-12(16(17)18)6-7-19-9-14(13)10-2-4-11(20)5-3-10/h2-5,8,14,19-21H,6-7,9H2,1H3
- InChIKey
- WOFIIEUMIDZJEJ-UHFFFAOYSA-N
- SMILES
- C12C(=C(Cl)C(OS(C)(=O)=O)=C(O)C=1)CCNCC2C1=CC=C(O)C=C1
- CAS DataBase Reference
- 67227 · 67227-57-0(CAS DataBase Reference)
- FDA UNII
- 3 R0MY016 · HA3R0MY016
- UNSPSC Code
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Fenoldopam mesylate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- hs_code
- 2933995300
- risk_code
- 22-36-42/43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-26-36/37/39
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs used to cause dilation of the blood vessels.
Drugs that bind to and activate dopamine receptors.
Uses & manufacturing
UsesUse (kg) in USA (2002): 2
Applications
DescriptionFenoldopam, first approved in the Netherlands in 1992, ended by reaching its first market, the US, for the short-term management of severe hypertension, including malignant hypertension, in the hospital setting. Fenoldopam can be prepared in 3 steps from the corresponding phenethylamine and aryloxiran, the pivotal step being the cyclisation in benzazepine in acidic medium. Fenoldopam is a potent dopamine D1 receptor agonist acting peripherally to produce systemic vasodilation.As it does not cross the bloodbrain barrier, it does not exert significant central dopaminergic activity. Fenoldopam also interacts significantly with 5HT1c and 5HT2 receptors. In comparative trials with the most common drug used for this condition in Europe, Fenoldopam was found to be appreciably more potent than nifedipine. Furthermore, Fenoldopam is fast acting and maintains a long-lasting antihypertensive effect.
DescriptionFenoldopam is an agonist of dopamine D1A (D1R) and D1B (D5R) receptors (Kds = 17 and 11 nM, respectively). Fenoldopam is used to study the roles of these receptors, in cells and in vivo, and to alter hemodynamic properties, including hypertension, in animals.
UsesDopamine D1-receptor agonist. Antihypertensive.
Usesantihypertensive, dopamine agonist
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