Pegaptanib

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

What is the Pegaptanib?

The molecule Pegaptanib presents a molecular formula of C22H44N3O10P and its IUPAC name is 7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid.

Pegaptanib (brand name Macugen) is a small molecule that inhibits the growth of new blood vessels. It was the first anti-angiogenic therapy approved by the FDA for the treatment of age-related macular degeneration, a leading cause of blindness in the United States..

Pegaptanib works by binding to and inhibiting the activity of vascular endothelial growth factor (VEGF), a protein that is critical for the growth and proliferation of new blood vessels. Inhibition of VEGF activity by pegaptanib leads to a reduction in the growth of new blood vessels and subsequently slows the progression of age-related macular degeneration..

Pegaptanib was initially developed by Eyetech Pharmaceuticals and is now marketed by Pfizer. It exists in the United States as an intravitreal injection, which is administered by a healthcare professional in a doctor’s office or outpatient setting..

Pegaptanib is generally well-tolerated, with the most common side effects being mild to moderate injection-related reactions such as pain, redness, and swelling at the injection site. More serious side effects are rare, but can include increased intraocular pressure and endophthalmitis (inflammation of the eye)..

Pegaptanib represents a major advance in the treatment of age-related macular degeneration and has revolutionized the way this disease is managed. Pegaptanib is the first therapy to specifically target the underlying cause of the disease, which is the abnormal growth of new blood vessels in the retina..

By inhibiting the growth of new blood vessels, pegaptanib slows the progression of the disease and helps preserve vision. In clinical trials, pegaptanib has been shown to be effective in slowing the progression of the disease and preventing vision loss..

Pegaptanib is an important new option for the treatment of age-related macular degeneration and offers hope to patients with this debilitating disease..

3D structure

Cartesian coordinates

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

2D drawing

 

Pegaptanib WLCZTRVUXYALDD-IBGZPJMESA-N chemical compound 2D structure molecule svg
Pegaptanib

 

Molecule descriptors

 
IUPAC name7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid
InChI codeInChI=1S/C22H44N3O10P/c1-31-15-17-33-21(27)24-13-9-7-11-19(25-22(28)34-18-16-32-2)20(26)23-12-8-5-4-6-10-14-35-36(3,29)30/h19H,4-18H2,1-3H3,(H,23,26)(H,24,27)(H,25,28)(H,29,30)/t19-/m0/s1
InChI KeyWLCZTRVUXYALDD-IBGZPJMESA-N
SMILESCOCCOC(=O)NCCCC[C@H](NC(=O)OCCOC)C(=O)NCCCCCCCO[P@](C)(=O)O

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.

  • 7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid
  • EYEOO1
  • GTPL6836
  • Macugen
  • NX183
  • Pegaptanib
  • Pegaptanib sodium
  • Q27088289

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC name7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid
Molecular formulaC22H44N3O10P
Molecular weight541.573
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity132.90
LogP3.3
Topological polar surface area180.6

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.