ChemFOnt: Showing chemical card for Hydrocortisone (CFc000009212)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:16 UTC

Chemfont ID

CFc000009212

Molecule Identification

Common Name

Hydrocortisone

Definition

Hydrocortisone is only found in individuals that have used or taken this drug. It is the main glucocorticoid secreted by the adrenal cortex. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. [PubChem]Hydrocortisone binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11beta)-11,17,21-Trihydroxypregn-4-ene-3,20-dione	ChEBI
11beta,17alpha,21-Trihydroxy-4-pregnene-3,20-dione	ChEBI
11beta-Hydrocortisone	ChEBI
17-Hydroxycorticosterone	ChEBI
4-Pregnen-11beta,17alpha,21-triol-3,20-dione	ChEBI
Hidrocortisona	ChEBI
Hydrocortisone	ChEBI
Hydrocortisonum	ChEBI
Kendall's compound F	ChEBI
Reichstein's substance m	ChEBI
HC	Kegg
Acticort	Kegg
Anusol HC	Kegg
Colocort	Kegg
Cortef	Kegg
Hytone	Kegg
Plenadren	Kegg
(11b)-11,17,21-Trihydroxypregn-4-ene-3,20-dione	Generator
(11Β)-11,17,21-trihydroxypregn-4-ene-3,20-dione	Generator
11b,17a,21-Trihydroxy-4-pregnene-3,20-dione	Generator
11Β,17α,21-trihydroxy-4-pregnene-3,20-dione	Generator
11b-Hydrocortisone	Generator
11Β-hydrocortisone	Generator
4-Pregnen-11b,17a,21-triol-3,20-dione	Generator
4-Pregnen-11β,17α,21-triol-3,20-dione	Generator
11beta-Hydroxycortisone	HMDB
17alpha-Hydroxycorticosterone	HMDB
Anti-inflammatory hormone	HMDB
Dihydrocostisone	HMDB
Hydrocorticosterone	HMDB
Hydrocortisone acetate	HMDB
Hydrocortisone alcohol	HMDB
Hydrocortisone base	HMDB
Hydrocortisone butyrate	HMDB
Hydrocortisone free alcohol	HMDB
Hydrocortisone sodium phosphate	HMDB
Hydrocortisone valerate	HMDB
Hydroxycortisone	HMDB
Idrocortisone	HMDB
Balneol-HC	ChEMBL, HMDB
CORTRIL	ChEMBL, HMDB, MeSH
Cetacort	ChEMBL, HMDB
Cort-dome	ChEMBL, HMDB
Flexicort	ChEMBL, HMDB
Hi-cor	ChEMBL, HMDB
Hydrocortisone in absorbase	ChEMBL, HMDB
Nogenic HC	ChEMBL, HMDB
Aeroseb-HC	ChEMBL, HMDB
Ala-cort	ChEMBL, HMDB
Ala-scalp	ChEMBL, HMDB
Penecort	ChEMBL, HMDB
Texacort	ChEMBL, HMDB
H-Cort	ChEMBL, HMDB
HYDROCORTONE	ChEMBL, HMDB
Ophthocort	ChEMBL, HMDB
Terra-cortril	ChEMBL, HMDB
Cor-oticin	ChEMBL, HMDB
Nutracort	ChEMBL, HMDB
Cortifoam	ChEMBL, HMDB
Glycort	ChEMBL, HMDB
HC #1	ChEMBL, HMDB
HC #4	ChEMBL, HMDB
Proctocort	ChEMBL, HMDB
Anucort-HC	ChEMBL, HMDB
Cortenema	ChEMBL, HMDB
Dermacort	ChEMBL, HMDB
Micort-HC	ChEMBL, HMDB
Synacort	ChEMBL, HMDB
U-cort	ChEMBL, HMDB
Eldecort	ChEMBL, HMDB
Epicort	ChEMBL, HMDB
neo-Cortef	ChEMBL, HMDB
Stie-cort	ChEMBL, HMDB
Anusol-HC	ChEMBL, HMDB
Beta-HC	ChEMBL, HMDB
hydro-RX	ChEMBL, HMDB
Locoid	ChEMBL, HMDB
b-HC	Generator, HMDB
β-HC	Generator, HMDB
11-beta-Hydrocortisone	HMDB
11-beta-Hydroxycortisone	HMDB
11-Hydrocortisone	HMDB
11a-Hydroxycorticosterone	HMDB
11alpha-Hydroxycorticosterone	HMDB
11b,17,21-Trihydroxyprogesterone	HMDB
11b-Hydroxycortisone	HMDB
11beta,17,21-Trihydroxyprogesterone	HMDB
17a-Hydroxycorticosterone	HMDB
4-Pregnene-11alpha,21-triol 3,20-dione	HMDB
4-Pregnene-11b,17a,21-triol-3,20-dione	HMDB
Aeroseb HC	HMDB
Alacort	HMDB
Algicirtis	HMDB
Alphaderm	HMDB
Amberin	HMDB
Anflam	HMDB
Aquacort	HMDB
Aquanil HC	HMDB
Barseb HC	HMDB
Basan-corti	HMDB
CaldeCORT spray	HMDB
Chronocort	HMDB
Clear aid	HMDB
Cleiton	HMDB
Cobadex	HMDB
Compound F	HMDB
Cor-tar-quin	HMDB
Cort-quin	HMDB
Cortanal	HMDB
Cortesal	HMDB
Corticreme	HMDB
Cortifan	HMDB
Cortiment	HMDB
Cortisol alcohol	HMDB
Cortisolonum	HMDB
Cortisporin	HMDB
Cortisporin otico	HMDB
Cortispray	HMDB
Cortizol	HMDB
Cortolotion	HMDB
Cortonema	HMDB
Cortoxide	HMDB
Cremesone	HMDB
Cremicort-H	HMDB
Cutisol	HMDB
Delacort	HMDB
Derm-aid	HMDB
Dermil	HMDB
Dermolate	HMDB
Dioderm	HMDB
Dome-cort	HMDB
Domolene-HC	HMDB
Drotic	HMDB
Ef corlin	HMDB
Efcorbin	HMDB
Efcortelan	HMDB
Efcortelin	HMDB
Eldercort	HMDB
Epiderm H	HMDB
Esiderm H	HMDB
Evacort	HMDB
Ficortril	HMDB
Fiocortril	HMDB
Foille insetti	HMDB
Genacort	HMDB
gyno-Cortisone	HMDB
Heb cort	HMDB
Heb-cort	HMDB
Hidalone	HMDB
hidro-Colisona	HMDB
Hycort	HMDB
Hycortol	HMDB
Hycortole	HMDB
Hydracort	HMDB
Hydrasson	HMDB
hydro-Adreson	HMDB
hydro-Colisona	HMDB
Hydrocort	HMDB
Hydrocortal	HMDB
Hydrocortistab	HMDB
Hydrocortisyl	HMDB
Hydroskin	HMDB
Hysone	HMDB
Hytisone	HMDB
Hytone lotion	HMDB
Incortin-H	HMDB
Incortin-hydrogen	HMDB
Komed HC	HMDB
Kyypakkaus	HMDB
Lacticare HC	HMDB
Lacticare-HC	HMDB
Lactisona	HMDB
Lubricort	HMDB
Maintasone	HMDB
Medicort	HMDB
Meusicort	HMDB
Mildison	HMDB
Milliderm	HMDB
neo-Cort-dome	HMDB
Neosporin-H ear	HMDB
Nystaform-HC	HMDB
Optef	HMDB
Otalgine	HMDB
Otic-neo-cort-dome	HMDB
Otobiotic	HMDB
Otocort	HMDB
Otosone-F	HMDB
Pediotic suspension	HMDB
Permicort	HMDB
Polcort H	HMDB
Preparation H hydrocortisone cream	HMDB
Prepcort	HMDB
Prestwick_265	HMDB
Prevex HC	HMDB
Proctofoam	HMDB
Protocort	HMDB
Racet	HMDB
Rectoid	HMDB
Remederm HC	HMDB
Sanatison	HMDB
Scalpicin capilar	HMDB
Schericur	HMDB
Scheroson F	HMDB
Sigmacort	HMDB
Signef	HMDB
Stiefcorcil	HMDB
Systral hydrocort	HMDB
Tarcortin	HMDB
Timocort	HMDB
Topicort	HMDB
Transderma H	HMDB
Traumaide	HMDB
Uniderm	HMDB
Vioform-hydrocortisone	HMDB
VoSol HC	HMDB
Vytone	HMDB
Zenoxone	HMDB
11-Epicortisol	MeSH, HMDB
Hydrocortisone, (11 alpha)-isomer	MeSH, HMDB
Hydrocortisone, (9 beta,10 alpha,11 alpha)-isomer	MeSH, HMDB
11 Epicortisol	MeSH, HMDB
Cortifair	MeSH, HMDB
Epicortisol	MeSH, HMDB

Chemical Formula

C₂₁H₃₀O₅

Average Molecular Weight

362.4599

Monoisotopic Molecular Weight

362.20932407

IUPAC Name

(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}]heptadec-6-en-5-one

Traditional Name

(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}]heptadec-6-en-5-one

CAS Registry Number

50-23-7

SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O5/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/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1

InChI Key

JYGXADMDTFJGBT-VWUMJDOOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Cyclic ketone
Primary alcohol
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:17650 )
11beta-hydroxy steroid (CHEBI:17650 )
17alpha-hydroxy steroid (CHEBI:17650 )
glucocorticoid (CHEBI:17650 )
20-oxo steroid (CHEBI:17650 )
21-hydroxy steroid (CHEBI:17650 )
C21-steroid (CHEBI:17650 )
Pregnane and derivatives [Fig] (C00735 )
Glucocorticoids (C00735 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C00735 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030001 )

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014879)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis (HMDB: HMDB0014879)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.28	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	39.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014879

DrugBank ID

DB00741

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00735

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydrocortisone

METLIN ID

Not Available

PubChem Compound

5754

PDB ID

Not Available

ChEBI ID

17650

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Hydrocortisone (CFc000009212)

MOL for CFc000009212 (Hydrocortisone)

3D MOL for CFc000009212 (Hydrocortisone)

3D SDF for CFc000009212 (Hydrocortisone)

3D-SDF for CFc000009212 (Hydrocortisone)

PDB for CFc000009212 (Hydrocortisone)

3D PDB for CFc000009212 (Hydrocortisone)

SMILES for CFc000009212 (Hydrocortisone)

INCHI for CFc000009212 (Hydrocortisone)

Structure for CFc000009212 (Hydrocortisone)

3D Structure for CFc000009212 (Hydrocortisone)