Sonidegib

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

What is the Sonidegib?

The molecule Sonidegib presents a molecular formula of C26H26F3N3O3 and its IUPAC name is N-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide.

Sonidegib (marketed as Odomzo) is a hedgehog pathway inhibitor discovered by Novartis. It is an orally available small molecule that covalently binds and inhibits Smoothened. Sonidegib was approved by the U.S. Food and Drug Administration (FDA) on July 31, 2012, for the treatment of adults with basal cell carcinoma (BCC) that is locally advanced or metastatic..

Basal cell carcinoma (BCC) is the most common type of skin cancer, accounting for approximately 80% of all non-melanoma skin cancers. BCCs are typically slow-growing tumors that arise from the basal cells in the lowermost layer of the epidermis. BCCs can occur anywhere on the body, but are most commonly found on sun-exposed areas, such as the face, ears, neck, chest, and back..

BCC is considered a locally advanced or metastatic disease when it is no longer confined to the site of the original tumor and has spread to nearby tissues or organs, or when it has metastasized (spread) to distant parts of the body. Sonidegib is indicated for the treatment of patients with BCC that is locally advanced or metastatic..

Sonidegib works by inhibiting the hedgehog signaling pathway, which participes in the development and maintenance of many tissues and organs during embryonic development. In adults, the hedgehog signaling pathway is active in certain types of cancer, including BCC. By inhibiting the hedgehog signaling pathway, Sonidegib slows the growth and spread of BCC cells..

Sonidegib exists as a 150-mg tablet for oral administration. The recommended dose is 150 mg once daily, taken with or without food. Sonidegib should be taken at approximately the same time each day..

If you miss a dose of Sonidegib, take it as soon as you remember. If it is almost time for your next dose, skip the missed dose and take your next dose at the regular time. Do not take two doses of Sonidegib at the same time..

Sonidegib can cause serious side effects, including:.

• Muscle pain.

• Joint pain.

• Numbness and tingling in the hands and feet.

• Tiredness.

• Diarrhea.

• Weight loss.

• Changes in taste.

• Hair loss.

• Skin rash.

• Kidney problems.

• Liver problems.

• Low blood cell counts.

• Infections.

• Bleeding.

• Bruising.

• Flu-like symptoms.

• Muscle spasms.

Sonidegib may also cause less serious side effects, such as:.

• Stomach pain.

• Nausea.

• Vomiting.

• Heartburn.

• Indigestion.

• Gas.

• Constipation.

• Headache.

• Dizziness.

• Muscle aches.

• Pain in the arms or legs.

• Back pain.

• Dry mouth.

• Dry eyes.

• Skin dryness, itching, or redness.

• Swelling of the hands, feet, ankles, or lower legs.

• Weight gain.

• Depression.

• Anxiety.

• Trouble sleeping.

• Changes in mood.

• Hair thinning.

• Mild skin rash.

• Mild kidney problems.

Tell your doctor if you experience any of these side effects. Most side effects are mild and will go away on their own. However, some side effects can become serious and may require medical attention..

If you experience any serious side effects, stop taking Sonidegib and call your doctor right away..

Sonidegib is a prescription medication used to treat adults with basal cell carcinoma that is locally advanced or metastatic. Sonidegib is a hedgehog pathway inhibitor that works by inhibiting the hedgehog signaling pathway, which participes in the development and maintenance of many tissues and organs during embryonic development. In adults, the hedgehog signaling pathway is active in certain types of cancer, including BCC. By inhibiting the hedgehog signaling pathway, Sonidegib slows the growth and spread of BCC cells..

Sonidegib exists as a 150-mg tablet. The recommended dose is 150 mg once daily, taken with or without food. Sonidegib should be taken at approximately the same time each day..

Common side effects of Sonidegib include muscle pain, joint pain, numbness and tingling in the hands and feet, tiredness, diarrhea, weight loss, changes in taste, hair loss, skin rash, kidney problems, and liver problems..

Sonidegib can cause serious side effects, including muscle pain, joint pain, numbness and tingling in the.

3D structure

Cartesian coordinates

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

2D drawing

 

Sonidegib VZZJRYRQSPEMTK-CALCHBBNSA-N chemical compound 2D structure molecule svg
Sonidegib

 

Molecule descriptors

 
IUPAC nameN-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide
InChI codeInChI=1S/C26H26F3N3O3/c1-16-14-32(15-17(2)34-16)24-12-9-20(13-30-24)31-25(33)23-6-4-5-22(18(23)3)19-7-10-21(11-8-19)35-26(27,28)29/h4-13,16-17H,14-15H2,1-3H3,(H,31,33)/t16-,17+
InChI KeyVZZJRYRQSPEMTK-CALCHBBNSA-N
SMILESCc1c(C(=O)Nc2ccc(N3C[C@H](C)O[C@H](C)C3)nc2)cccc1-c1ccc(OC(F)(F)F)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.

  • (1,1'-BIPHENYL)-3-CARBOXAMIDE, N-(6-((2R,6S)-2,6-DIMETHYL-4-MORPHOLINYL)-3-PYRIDINYL)-2-METHYL-4'-(TRIFLUOROMETHOXY)-, REL-
  • (1,1'-Biphenyl)-3-carboxamide, N-(6-((2R,6S)-2,6-dimethyl-4-morpholinyl)-3-pyridinyl)-2- methyl-4'-(trifluoromethoxy)-, rel-
  • 0RLU3VTK5M
  • 1218778-76-7
  • 1218778-77-8
  • 956697-53-3
  • 956697-53-3 (free base)
  • AC-32799
  • BCP02275
  • BCP9001014
  • BDBM50394562
  • CCG-264935
  • CS-0904
  • D10119
  • DB09143
  • EE-0005
  • EX-A409
  • Erismodegib
  • GTPL8199
  • HY-10296
  • HY-16582A
  • LDE 225
  • LDE-225
  • LDE225
  • LDE225 (NVP-LDE225, Erismodegib)
  • LDE225 (NVP-LDE225,Erismodegib)
  • LDE225 (NVP-LDE225; Erismodegib)
  • LDE225 - NVP-LDE225
  • LDE225(NVP-LDE225)
  • MFCD16038928
  • MLS006011198
  • N-(6-((2R,6S)-2,6-Dimethylmorpholin-4-yl)pyridin-3-yl)-2-methyl-4'- (trifluoromethoxy)biphenyl-3-carboxamide
  • N-(6-((2R,6S)-2,6-Dimethylmorpholin-4-yl)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)biphenyl-3-carboxamide
  • N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide
  • N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)biphenyl-3-carboxamide
  • N-(6-((cis-2,6-Dimethylmorpholin-4-yl)-3-pyridyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl)benzamide
  • N-(6-(cis-2,6-Dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide
  • N-[6-(cis-2,6-dimethylmorpholin-4-yl)pyridin-3-yl]-2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxamide
  • N-[6-[(2R,6S)-2,6-Dimethyl-4-morphlinyl]-3-pyridinyl]-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide
  • N-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide
  • NCGC00250382-01
  • NCGC00250382-05
  • NCGC00250382-07
  • NSC-761385
  • NSC-761386
  • NSC761385
  • NSC761386
  • NVP-LDE 225
  • NVP-LDE-225
  • NVP-LDE225
  • NVP-LDE225(Erismodegib)
  • Odomozo
  • Odomzo
  • Q22075856
  • SMR004702967
  • SW218115-2
  • Sonidegib
  • Sonidegib (LDE-225)
  • Sonidegib (NVP-LDE225)
  • Sonidegib (USAN/INN)
  • Sonidegib phospate
  • [1,1'-Biphenyl]-3-carboxamide, N-[6-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-3-pyridinyl]-2-methyl-4'-(t
  • [1,1'-Biphenyl]-3-carboxamide, N-[6-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-3-pyridinyl]-2-methyl-4'-(trifluoromethoxy)-, rel-
  • erismodegib (deleted INN)
  • n-(6-((2r,6s)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)biphenyl-3-carboxamide
  • rel-N-[6-[(2R,6S)-2,6-Dimethyl-4-morpholinyl]-3-pyridinyl]-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide
  • rel-N-{6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl}-2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxamide
  • s2151

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC68202099
  • UNII-0RLU3VTK5M
  • AKOS015994541
  • BRD-K19796430-001-01-5
  • DTXSID501009335
  • CHEMBL2105737
  • CHEBI:90863
  • SCHEMBL554455

Physico-Chemical properties

IUPAC nameN-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide
Molecular formulaC26H26F3N3O3
Molecular weight485.498
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity130.88
LogP6.0
Topological polar surface area63.7

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.