Prednisolone

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

What is the Prednisolone?

The molecule Prednisolone presents a molecular formula of C21H28O5 and its IUPAC name is (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one.

Prednisolone is a molecule in the class of organic compounds known as glucocorticoids. It is a white, crystalline solid with a molecular weight of 360.5. Prednisolone is a synthetic analogue of the naturally occurring cortisol molecule. It is used as an anti-inflammatory and immunosuppressive agent. Prednisolone has a wide range of clinical uses, including the treatment of allergies, asthma, autoimmune diseases, and inflammatory conditions. It is also used as a prophylactic agent to prevent the rejection of transplanted organs. Prednisolone is a potent molecule with a wide range of biological activity. It binds to and activates the glucocorticoid receptor, which leads to the induction of a variety of biochemical and physiological changes. Prednisolone is a highly effective anti-inflammatory agent and is used in a wide variety of inflammatory conditions. It is also an immunosuppressive agent, which makes it useful in the treatment of autoimmune diseases and transplantation. Prednisolone is a relatively safe molecule, with a wide therapeutic index. The most common side effects are gastrointestinal upset and weight gain. Prednisolone is a molecule with a wide range of clinical uses. It is an effective anti-inflammatory and immunosuppressive agent. It is also a prophylactic agent to prevent the rejection of transplanted organs. Prednisolone is a safe molecule with a wide therapeutic index. The most common side effects are gastrointestinal upset and weight gain..

3D structure

Cartesian coordinates

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

2D drawing

 

Prednisolone OIGNJSKKLXVSLS-VWUMJDOOSA-N chemical compound 2D structure molecule svg
Prednisolone

 

Molecule descriptors

 
IUPAC name(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
InChI KeyOIGNJSKKLXVSLS-VWUMJDOOSA-N
SMILESC[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO

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.

  • (+)-PREDNISOLONE
  • (11alpha)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione
  • (11beta)-11,17,21-Trihydroxypregna-1,4-diene-3,20-dione
  • (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadeca-3,6-dien-5-one
  • (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
  • (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  • (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
  • (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-8,10,13-trimethyl-3-oxo-6,7,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid;Prednisolone
  • .DELTA.(sup 1)-Cortisol
  • .DELTA.(sup 1)-Dehydrocortisol
  • .DELTA.(sup 1)-Dehydrohydrocortisone
  • .DELTA.(sup 1)-Hydrocortisone
  • .DELTA.1-Cortisol
  • .DELTA.1-Dehydrocortisol
  • .DELTA.1-Dehydrohydrocortisone
  • .DELTA.1-Hydrocortisone
  • .delta.-Cortef
  • .delta.-Stab
  • 003P649
  • 1,2-Dehydrohydrocortisone
  • 1,4-Pregnadien-11-.beta.,17-.alpha.,21-triol-3,20-dione
  • 1,4-Pregnadien-11-beta,17-alpha,21-triol-3,20-dione
  • 1,4-Pregnadiene-11-.beta.,17-.alpha.,21-triol-3,20-dione
  • 1,4-Pregnadiene-11-beta,17-alpha,21-triol-3,20-dione
  • 1,4-Pregnadiene-11beta,17alpha,21-triol-3,20-dione
  • 1,4-Pregnadiene-3,20-dione-11-.beta.,17-.alpha.,21-triol
  • 1,4-Pregnadiene-3,20-dione-11-beta,17-alpha,21-triol
  • 1,4-Pregnadiene-3,20-dione-11beta,17alpha,21-triol
  • 1-Dehydrohydrocortisone
  • 11,17,21-Trihydroxypregna-1,4-diene-3,20-dione, (11.beta.)-
  • 11-.beta.,17,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11-.beta.,17-.alpha.,21-Trihydroxy-1,4-pregnadiene-3,20-dione
  • 11-.beta.,17-.alpha.,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11-beta,17,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11.BETA.,17,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE
  • 11.BETA.,17,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE.
  • 11.beta.,17.alpha.,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11b,17,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11beta,17,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 11beta,17,21-trihydroxy-1,4-pregnadiene-3,20-dione
  • 11beta,17alpha,21-Trihydroxypregna-1,4-diene-3,20-dione
  • 3,20-Dioxo-11beta,17alpha,21-trihydroxy-1,4-pregnadiene
  • 50-24-8
  • 8056-11-9
  • 9PHQ9Y1OLM
  • A929791
  • AC-1773
  • APREDNISLON
  • AS-13665
  • BCP09053
  • BDBM19190
  • BPBio1_000164
  • BRN 1354103
  • BSPBio_000148
  • Bubbli-Pred
  • C07369
  • CCG-220274
  • CCRIS 980
  • CO-Hydeltra
  • Codelcortone
  • Cordrol
  • Cortalone
  • Cotogesic
  • Cotolone
  • CHLOROPTIC-P S.O.P. COMPONENT PREDNISOLONE
  • D00472
  • D91990
  • DB00860
  • DELTA.1-Cortisol
  • DSSTox_CID_1184
  • DSSTox_GSID_21184
  • DSSTox_RID_75996
  • Decaprednil
  • Decortin H
  • Delcortol
  • Delta F
  • Delta(1)-dehydrohydrocortisone
  • Delta-Cortef
  • Delta-Ef-Cortelan
  • Delta-stab
  • Deltacortenol
  • Deltacortril
  • Deltahydrocortisone
  • Deltasolone
  • Deltisilone
  • Derpo PD
  • Dexa-Cortidelt hostacortin H
  • Di-adreson F
  • Dicortol
  • Donisolone
  • Dydeltrone
  • EC 200-021-7
  • EN300-53017
  • EQUISOLON
  • Eazolin D
  • Erbacort
  • Erbasona
  • Estilsona
  • Fernisolone
  • Fernisolone P
  • Fernisolone-P
  • GTPL2866
  • HMS1568H10
  • HMS2090J05
  • HMS2095H10
  • HMS2230P10
  • HMS3259E09
  • HMS3712H10
  • HSDB 3385
  • HY-17463
  • Hostacortin H
  • Hydeltra
  • Hydeltrone
  • Hydrodeltalone
  • Hydrodeltisone
  • Hydroretrocortin
  • Hydroretrocortine
  • K 1557
  • Klismacort
  • LMST02030179
  • Lentosone
  • MFCD00003649
  • MLS001304083
  • MLS002154250
  • MLS002207037
  • MLS002548883
  • MLS002638110
  • Metacortandralone
  • Meti-Derm
  • Meticortelone
  • NC00473
  • NCGC00094764-01
  • NCGC00179649-01
  • NCGC00179649-02
  • NCGC00179649-03
  • NCGC00179649-04
  • NCGC00179649-06
  • NCGC00256577-01
  • NCGC00259222-01
  • NSC 9120
  • NSC-9120
  • NSC-9900
  • NSC9120
  • NSC9900
  • Neo-Delta-Cortef
  • P0637
  • PRDL
  • PREDNISOLONE (EMA EPAR: VETERINARY)
  • PREDNISOLONE ANHYDROUS
  • PREDNISOLONE COMPONENT OF CHLOROPTIC-P S.O.P.
  • PREGNA-1,4-DIENE-3,20-DIONE, 11,17,21-TRIHYDROXY-, (11.BETA)-
  • Panafcortelone
  • Paracortol
  • Paracotol
  • Poly-Pred
  • Precortancyl
  • Precortilon
  • Precortisyl
  • Predisolone Sodium Phosphate
  • Predne-Dome
  • Prednelan
  • Prednicen
  • Predniliderm
  • Predniretard
  • Prednis
  • Prednisolona
  • Prednisolone
  • Prednisolone (JP17/USP/INN)
  • Prednisolone Powder
  • Prednisolonum
  • Predonin
  • Predonine
  • Preflam
  • Pregna-1,20-dione, 11,17,21-trihydroxy-, (11.beta.)-
  • Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-
  • Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-
  • Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11b)-
  • Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11beta)-
  • Pregna-1,4-diene-3,20-dione, 11.beta.,17,21-trihydroxy-
  • Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-
  • Prelone
  • Prenolone
  • Prestwick0_000274
  • Prestwick1_000274
  • Prestwick2_000274
  • Prestwick3_000274
  • Prestwick_404
  • Q-201616
  • Q11426176
  • Rolisone
  • SMR000718761
  • SR-01000837502
  • SR-01000837502-2
  • Scherisolon
  • Solone
  • Steran
  • Sterane
  • Sterolone
  • Supercortisol
  • TUA
  • Ulacort
  • Ultracorten H
  • Ultracortene-H
  • Ultracortene-hydrogen
  • VETSOLONE
  • Z1245633279
  • component of Ataraxoid
  • component of K-Predne-Dome
  • delta(1)-Cortisol
  • delta(1)-Dehydrocortisol
  • delta(1)-Hydrocortisone
  • delta(sup 1)-Cortisol
  • delta(sup 1)-Dehydrocortisol
  • delta(sup 1)-Dehydrohydrocortisone
  • delta(sup 1)-Hydrocortisone
  • delta-dehydrocortisol
  • delta-dehydrohydrocortisone
  • delta-hydrocortisone
  • prednisolon
  • prednisolone
  • s1737

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3833821
  • CAS-50-24-8
  • UNII-9PHQ9Y1OLM
  • AKOS015894935
  • BRD-K98039984-001-03-0
  • BRD-K98039984-001-06-3
  • DTXSID9021184
  • CHEMBL131
  • CHEBI:8378
  • Tox21_111327
  • Tox21_201673
  • Tox21_302987
  • Tox21_111327_1
  • EINECS 200-021-7
  • SPBio_002367
  • SCHEMBL3233

Physico-Chemical properties

IUPAC name(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
Molecular formulaC21H28O5
Molecular weight360.444
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.06
LogP1.6
Topological polar surface area94.8

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.