(S)-Fenoldopam

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (S)-Fenoldopam are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (S)-Fenoldopam?

The molecule (S)-Fenoldopam presents a molecular formula of C16H16ClNO3 and its IUPAC name is (5S)-9-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol.

Fenoldopam (trade name Corlopam) is a selective dopamine D1 receptor agonist that is used in the treatment of high blood pressure. It has a rapid onset of action and a short half-life, making it useful for controlling blood pressure spikes. Fenoldopam has also been shown to be effective in treating postoperative hypertension and has potential for use in treating other conditions..

The (S)-enantiomer of fenoldopam is the more active form of the drug, and it is this enantiomer that is used clinically. Fenoldopam has a high affinity for the dopamine D1 receptor and a relatively low affinity for the dopamine D2 receptor. This selective binding to the D1 receptor is thought to be responsible for the drug's therapeutic effects..

Fenoldopam is rapidly absorbed from the gastrointestinal tract and has a bioavailability of approximately 100%. The drug is metabolized in the liver and has a half-life of around 1 hour. Fenoldopam is excreted in the urine, and its elimination is not affected by changes in renal function..

Fenoldopam has been shown to be effective in reducing blood pressure in both short-term and long-term studies. In short-term studies, fenoldopam has been shown to reduce blood pressure within 30 minutes of administration. The drug has also been shown to be effective in reducing blood pressure over 24 hours in patients with hypertension. In long-term studies, fenoldopam has been shown to reduce blood pressure and improve blood pressure control in patients with hypertension..

Fenoldopam has also been shown to be effective in treating postoperative hypertension. In a study of patients who underwent surgery, fenoldopam was shown to reduce blood pressure and the need for antihypertensive medication. Fenoldopam has also been shown to be effective in reducing blood pressure in patients with renovascular hypertension..

Fenoldopam has potential for use in other conditions. The drug has been shown to reduce the symptoms of withdrawal in patients with alcohol dependence. Fenoldopam has also been shown to improve cognitive function in patients with Alzheimer's disease..

3D structure

Cartesian coordinates

Geometry of (S)-Fenoldopam in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(S)-Fenoldopam TVURRHSHRRELCG-ZDUSSCGKSA-N chemical compound 2D structure molecule svg
(S)-Fenoldopam

 

Molecule descriptors

 
IUPAC name(5S)-9-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
InChI codeInChI=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/t13-/m0/s1
InChI KeyTVURRHSHRRELCG-ZDUSSCGKSA-N
SMILESOc1ccc([C@@H]2CNCCc3c2cc(O)c(O)c3Cl)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-SKF-82526
  • (-)-Fenoldopam
  • (1S)-6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
  • (5S)-9-chloranyl-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
  • (5S)-9-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
  • (S)-(-)-Fenoldopam
  • (S)-Fenoldopam
  • (S)-SKF-82526
  • 1H-3-Benzazepine-7,8-diol, 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-, (1S)-
  • 1H-3-Benzazepine-7,8-diol, 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-, (S)-
  • 85145-23-9
  • 97BT14C36A
  • A835664
  • BIDD:GT0702
  • Fenoldopam, (S)-
  • GTPL933
  • Lopac-F-6800
  • NCGC00015444-01
  • NCGC00015444-02
  • NCGC00025246-01
  • PDSP1_000784
  • PDSP2_000772
  • Q27088811
  • SKF-82526
  • Tocris-1659

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC22116608
  • UNII-97BT14C36A
  • CHEMBL1161520
  • SCHEMBL41214

Physico-Chemical properties

IUPAC name(5S)-9-chloro-5-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
Molecular formulaC16H16ClNO3
Molecular weight305.756
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity86.16
LogP3.1
Topological polar surface area72.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.