Amcinonide

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

What is the Amcinonide?

The molecule Amcinonide presents a molecular formula of C28H35FO7 and its IUPAC name is [2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate.

Amcinonide is a synthetic corticosteroid used as an anti-inflammatory and anti-pruritic medication. It is structurally related to triamcinolone and is a more potent analog. It is used topically as a cream, ointment, or lotion for the treatment of eczema, psoriasis, and other inflammatory skin disorders. It is also used intranasally for the treatment of allergic rhinitis. Amcinonide is not approved for use in children..

Amcinonide was first synthesized in 1966. It is a white to off-white crystalline powder with a melting point of 208-210°C. It is insoluble in water and has a molecular weight of 434.52..

The mechanism of action of amcinonide is not fully understood, but it is thought to work by inhibiting inflammation at the cellular level. It is a highly potent corticosteroid and is thought to be more potent than prednisone..

Amcinonide is absorbed through the skin and into the bloodstream. It is then metabolized by the liver and excreted by the kidneys..

Amcinonide is generally well-tolerated, but side effects can include burning, stinging, itching, redness, and irritation at the site of application. It can also cause headaches, dizziness, and nausea. If used intranasally, it can cause nosebleeds, sore throat, and headaches..

Amcinonide should not be used by people with a history of hypersensitivity to corticosteroids. It should also be used with caution in people with diabetes, glaucoma, or cataracts..

Amcinonide is a potent corticosteroid and should be used only as directed by a healthcare provider. It is important to follow all instructions on the prescription label. Do not use more or less of this medication than prescribed..

If you are using amcinonide topical on your skin, avoid contact with your eyes, nose, or mouth. If this medication gets in your eyes, rinse them with cool water and seek medical attention..

Amcinonide topical is for use only on the skin. Do not use it on open wounds or on sunburned, windburned, dry, chapped, or irritated skin..

To use amcinonide topical, apply a small amount to the affected area and rub it in gently. Do not bandage or wrap the affected area unless directed by your healthcare provider..

Amcinonide topical is usually applied 2-4 times daily. Follow your healthcare provider's instructions..

Do not use amcinonide topical for longer than prescribed. Your condition will not improve any faster, and your risk of side effects will increase..

If you are using amcinonide intranasal, blow your nose gently before using the medication..

To use the spray, insert the tip of the bottle into one nostril and point the bottle towards the back of your head. Press down on the pump to deliver the prescribed number of sprays. Repeat in the other nostril..

After using the spray, wipe the tip of the bottle with a clean tissue and replace the cap..

Amcinonide intranasal is usually used 2-4 times daily. Follow your healthcare provider's instructions..

Do not use amcinonide intranasal for longer than prescribed. Your condition will not improve any faster, and your risk of side effects will increase..

Call your healthcare provider if your symptoms do not improve or if they get worse..

Do not stop using amcinonide suddenly. This can cause serious side effects. If you need to stop using this medication, your healthcare provider will gradually decrease your dose..

Amcinonide is a prescription medication. It exists as a cream, ointment, or lotion for topical use and as a nasal spray for intranasal use..

Amcinonide topical is used to treat eczema, psoriasis, and other inflammatory skin disorders. It is also used intranasally for the treatment of allergic rhinitis..

Amcinonide is a potent corticosteroid and should be used only as directed by a healthcare provider. Side effects can include burning, stinging, itching, redness, and irritation at the site of application. It can also cause headaches, dizziness, and nausea. If used intranasally, it can cause nosebleeds, sore throat, and headaches..

3D structure

Cartesian coordinates

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

2D drawing

 

Amcinonide ILKJAFIWWBXGDU-MOGDOJJUSA-N chemical compound 2D structure molecule svg
Amcinonide

 

Molecule descriptors

 
IUPAC name[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate
InChI codeInChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
InChI KeyILKJAFIWWBXGDU-MOGDOJJUSA-N
SMILESCC(=O)OCC(=O)[C@@]12OC3(CCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]12C

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.

  • 1,4-Pregnadiene-2,20-dione-16,17-cyclopentylidenedioxy-9-fluoro-11,21-dihydroxy-21-acetate
  • 16alpha,17alpha-(cyclopentane-1,1-diyldioxy)-9-fluoro-11beta-hydroxy-3,20-dioxopregna-1,4-dien-21-yl acetate
  • 19alpha-Fluor-11beta,21-dihydroxy-16alpha,17alpha-(tetramethylen)methylendioxy-1,4-pregnadien-3,20-dion 21-acetat
  • 423W026MA9
  • 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]-1H-indolehydrochloride
  • 51022-69-6
  • 9-Fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclopentanone, 21-acetate
  • 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclopentanone, 21-acetate
  • AC-13190
  • AMY38534
  • Amcinonide
  • Amcinonide (JAN/USP/INN)
  • Amcinonido
  • Amcinonidum
  • CCG-221135
  • CL 34699
  • CL-34699
  • CS-4805
  • Cyclocort
  • D01387
  • DB00288
  • DSSTox_CID_25905
  • DSSTox_GSID_45905
  • DSSTox_RID_81217
  • GTPL7060
  • HMS2235K23
  • HMS3715D11
  • HY-B1197
  • MLS000028656
  • MLS001146959
  • MLS001333715
  • MLS002695893
  • NCGC00021193-03
  • NCGC00095071-01
  • NSC 758620
  • NSC-758620
  • Opera_ID_1472
  • PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-16,17-(CYCLOPENTYLIDENEBIS(OXY))-9-FLUORO-11-HYDROXY-, (11.BETA.,16.ALPHA.)-
  • Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-16,17-(cyclopentylidenebis(oxy))-9-fluoro-11-hydroxy-, (11beta,16alpha)-
  • Q4742041
  • SMR000058920
  • SR-01000003161
  • SR-01000003161-2
  • Triamcinolonacetatcyclopentanonid
  • Visderm
  • [2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate
  • [2-[(4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate
  • amcinonida
  • amcinonide
  • s5671

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3977777
  • CAS-51022-69-6
  • UNII-423W026MA9
  • AKOS015961167
  • BRD-K13960744-001-09-7
  • DTXSID6045905
  • CHEMBL1200732
  • CHEBI:31199
  • Tox21_111411
  • EINECS 256-915-2
  • SCHEMBL4720

Physico-Chemical properties

IUPAC name[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate
Molecular formulaC28H35FO7
Molecular weight502.572
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity127.74
LogP3.5
Topological polar surface area99.1

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.