Avanafil

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

What is the Avanafil?

The molecule Avanafil presents a molecular formula of C23H26ClN7O3 and its IUPAC name is 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide.

Avanafil is a small molecule drug that is used to treat erectile dysfunction (ED), a condition that affects the ability to achieve and maintain an erection sufficient for sexual activity. ED is a common condition that can be caused by a variety of factors, including age, physical illness, and psychological conditions..

Avanafil works by inhibiting the enzyme phosphodiesterase type 5 (PDE5), which is responsible for the breakdown of cyclic guanosine monophosphate (cGMP). cGMP is a signaling molecule that is involved in the relaxation of smooth muscle cells and the dilation of blood vessels in the penis. By inhibiting the breakdown of cGMP, avanafil helps to improve blood flow to the penis and facilitate the achievement and maintenance of an erection..

Avanafil is available in oral tablet form and is taken as needed, typically about 30 minutes before sexual activity. It is generally well tolerated, with the most common side effects being headache, flushing, and nasal congestion. More serious side effects, such as low blood pressure and vision changes, have also been reported..

Avanafil is generally considered to be a safe and effective treatment for ED, but it is not suitable for use in all patients. It should not be used in patients who are taking nitrates or alpha-blockers, as this can lead to serious and potentially life-threatening side effects. In addition, avanafil should be used with caution in patients with certain medical conditions, such as heart disease, liver or kidney disease, or bleeding disorders..

Summary

From all the above, this molecule is a small molecule drug that is used to treat erectile dysfunction (ED). It works by inhibiting the enzyme PDE5 and improving blood flow to the penis, which helps to facilitate the achievement and maintenance of an erection. Avanafil is available in oral tablet form and is generally well tolerated, with the most common side effects being headache, flushing, and nasal congestion. However, it should not be used in all patients and should be used with caution in certain medical conditions..

3D structure

Cartesian coordinates

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

2D drawing

 

Avanafil WEAJZXNPAWBCOA-INIZCTEOSA-N chemical compound 2D structure molecule svg
Avanafil

 

Molecule descriptors

 
IUPAC name4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
InChI codeInChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
InChI KeyWEAJZXNPAWBCOA-INIZCTEOSA-N
SMILESCOc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2/C(O)=N/Cc2ncccn2)cc1Cl

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.

  • (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine
  • (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidylmethyl)carbamoyl]-pyrimidine
  • (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
  • (S)-4-(3-Chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-N-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide
  • (S)-4-[(3-Chlor-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1- pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamid
  • (S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide
  • 330784-47-9
  • 4-((3-Chloro-4-methoxybenzyl)amino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
  • 4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide
  • 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimid
  • 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimid ine-5-carboxamide
  • 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
  • 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
  • 5-Pyrimidinecarboxamide, 4-(((3-chloro-4-methoxyphenyl)methyl)amino)-2-((2S)-2-(hydroxymethyl)-1-pyrrolidinyl)-N-(2-pyrimidinylmethyl)-
  • AB01565827_02
  • AMY1794
  • AS-20106
  • Avanafil
  • Avanafil (USAN/INN)
  • Avanafil; (S)-4-chloro-6-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
  • BDBM50036629
  • CCG-229896
  • CS1566
  • D03217
  • DB06237
  • DR5S136IVO
  • E6L
  • GTPL7448
  • HY-18252
  • J-019006
  • MFCD11977961
  • NCGC00386241-01
  • Q2873270
  • STENDRA
  • SW219217-1
  • Spedra
  • TA 1790
  • TA-1790
  • TA1790
  • VI-0162
  • Zepeed
  • ine-5-carboxamide
  • s4019

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC11677857
  • UNII-DR5S136IVO
  • AKOS024462448
  • BRD-K65781196-001-01-4
  • DTXSID50186727
  • CHEMBL1963681
  • CHEBI:66876
  • SCHEMBL118799

Physico-Chemical properties

IUPAC name4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
Molecular formulaC23H26ClN7O3
Molecular weight483.951
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity133.04
LogP3.1
Topological polar surface area128.9

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.