Cortisone

HCID 222786

Basic information

CAS
53-06-5
Standard SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChIKey
MFYSYFVPBJMHGN-ZPOLXVRWSA-N
Molecular formula
C21H28O5
Average molar mass
360.4 g/mol
Monoisotopic mass
360.19367399

Names & identifiers

Preferred name
Cortisone
IUPAC
(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
English name
CORTISONE
Molecular formula
C21H28O5
Molecular weight
360.44

Names & synonyms

cortisone53-06-5Kendall's compound EReichstein's substance FAWintersteiner's compound F17-Hydroxy-11-dehydrocorticosterone11-Dehydro-17-hydroxycorticosteronePregn-4-ene-3,11,20-trione, 17,21-dihydroxy-Cortisona17,21-Dihydroxypregn-4-ene-3,11,20-trioneCortisonumKortison
Show more names
KECortisonCorlinCORTONE17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,11(2H)-dioneCortonAdreson
4-Pregnene-17alpha,21-diol-3,11,20-trione17alpha,21-Dihydroxypregn-4-ene-3,11,20-trioneDTXSID5022857Pregn-4-en-17alpha,21-diol-3,11,20-trione17alpha,21-Dihydroxy-4-pregnene-3,11,20-trioneNSC-9703V27W9254FZDTXCID102857

Database identifiers

CAS
53-06-5
PubChem CID
222786
DTXSID
DTXSID5022857
ChEMBL
CHEMBL1499
ChEBI
CHEBI:16962
UNII
V27W9254FZ
EC Number
200-162-4
Nikkaji
J4.139D

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
91.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
26

Experimental & physicochemical properties

LogP1.47
Solubility0.28 mg/mL at 25 °C
Melting Point222 °C
Physical DescriptionSolid
Collision Cross Section · 6 items

257.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5022857]

180.07 Ų [M-H2O-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)];188.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

172.48 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];186.07 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];182.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

184 Ų [M+H]+ [CCS Type: TW]

184.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

213.2 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];191.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];188.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

Physicochemical properties

Melting point
223 · 223-228 °C (dec.)(lit.)
alpha
25 · D25 +209° (c = 1.2 in 95% alcohol); 25546 +269° (c = 0.125 in benzene); 25546 +248° (c = 0.1 to 0.2 in alcohol)
Boiling point
412.46 °C · 412.46°C (rough estimate)
Density
1.28 · 1.28±0.1 g/cm3 (20 ºC 760 Torr)
refractive index
210 ° · 210 ° (C=1, EtOH)
Flash point
9 ℃ · 9℃

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H361 (98%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 5 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationCortisone: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-: Human health tier I assessment;IMAP assessments - Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (98%)

Toxicology

Effects During Pregnancy and Lactation · 1 item

◉ Summary of Use during Lactation;Cortisone is a normal component of breastmilk that passes from the mother's bloodstream into milk and might have a role in intestinal maturation, the intestinal microbiome, growth, body composition or neurodevelopment, but adequate studies are lacking. Concentrations follow a diurnal rhythm, with the highest concentrations in the morning at about 7:00 am and the lowest concentrations in the late afternoon and evening. Cortisone has not been studied in breastmilk after exogenous administration in pharmacologic amounts. Although it is unlikely that dangerous amounts of cortisone would reach the infant, a better studied alternate drug might be preferred. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;◉ Effects in Breastfed Infants;None reported with any corticosteroid.;◉ Effects on Lactation and Breastmilk;Published information on the effects of cortisone on serum prolactin or on lactation in nursing mothers was not found as of the revision date. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;A study of 46 women who delivered an infant before 34 weeks of gestation found that a course of another corticosteroid (betamethasone, 2 intramuscular injections of 11.4 mg of betamethasone 24 hours apart) given between 3 and 9 days before delivery resulted in delayed lactogenesis II and lower average milk volumes during the 10 days after delivery. Milk volume was not affected if the infant was delivered less than 3 days or more than 10 days after the mother received the corticosteroid. An equivalent dosage regimen of cortisone might have the same effect.;A study of 87 pregnant women found that betamethasone given as above during pregnancy caused a premature stimulation of lactose secretion during pregnancy. Although the increase was statistically significant, the clinical importance appears to be minimal. An equivalent dosage regimen of cortisone might have the same effect.

Regulatory information

Regulatory InformationCortisone: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
18
wgk
3
rtecs
GM9020000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
2937210000
risk_code
11-23/24/25-39/23/24/25-63

Chemistry & industry

Pharmacology

ATC Code · 4 items

H - Systemic hormonal preparations, excl. sex hormones and insulins;H02 - Corticosteroids for systemic use;H02A - Corticosteroids for systemic use, plain;H02AB - Glucocorticoids;H02AB10 - Cortisone

S - Sensory organs;S01 - Ophthalmologicals;S01B - Antiinflammatory agents;S01BA - Corticosteroids, plain;S01BA03 - Cortisone

QH - Systemic hormonal preparations, excl. sex hormones and insulin;QH02 - Corticosteroids for systemic use;QH02A - Corticosteroids for systemic use, plain;QH02AB - Glucocorticoids;QH02AB10 - Cortisone

QS - Sensory organs;QS01 - Ophthalmologicals;QS01B - Antiinflammatory agents;QS01BA - Corticosteroids, plain;QS01BA03 - Cortisone

FDA Pharmacological Classification · 5 items

V27W9254FZ

CORTISONE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Cortisone is a Corticosteroid. The mechanism of action of cortisone is as a Corticosteroid Hormone Receptor Agonist.

MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.
Tissue LocationsAdipose Tissue;Adrenal Cortex;Adrenal Gland;Epidermis;Fibroblasts;Intestine;Kidney;Neuron;Placenta;Skeletal Muscle;Testis;Thyroid Gland
Cellular LocationsEndoplasmic reticulum;Extracellular;Membrane
Metabolite Pathways · 1 item

11-beta-hydroxylase deficiency (CYP11B1);17-alpha-hydroxylase deficiency (CYP17);21-hydroxylase deficiency (CYP21);3-Beta-Hydroxysteroid Dehydrogenase Deficiency;Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency;Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency;Apparent mineralocorticoid excess syndrome;Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH;Corticosterone methyl oxidase I deficiency (CMO I);Corticosterone methyl oxidase II deficiency - CMO II;Total 11 pathways, visit the HMDB page for details

Uses & manufacturing

UsesCalculated removal (%): 45.8
Use Classification · 2 items

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Pharmaceuticals -> Steroid hormones

Applications · 5 items

UsesGlucocorticoid, anti-inflammatory agent

Usesantiinflammatory, glucocorticoid

UsesAnticoagulant

UsesCortisone is used for inflammatory processes, allergies, and adrenal insufficiency.

General DescriptionCortisone is a corticosteroid produced in the adrenal glands. Cortisone is administered for short term pain relief and to reduce swelling from inflammation. This Certified Spiking Solution is applicable in LC-MS/MS applications for endocrinology, clinical chemistry and neonatal screening.

Suppliers100 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]

Additional notes

DefinitionChEBI: A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.

Related reactions

3 records

Compound notes

Loading…