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
Show more names
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
- Formal charge
- 0
- Complexity
- 724
Experimental & physicochemical properties
Collision Cross Section
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℃
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Ethanol (Slightly, Heated)
- form
- Solid
- pka
- 12.37 · 12.37±0.60(Predicted)
- color
- White to Pale Beige
- Water Solubility
- 229.9 mg/L · 229.9mg/L(25 ºC)
- Merck
- 2539 · 2539
- Exposure limits
- 1 mg/m3 · PC-TWA: 1 mg/m3
- Major Application
- clinical testingclinical testing
- InChIKey
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N
- SMILES
- O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)C(=O)C2)CC1)C)C(=O)CO
- LogP
- 1.47 · 1.470
- CAS DataBase Reference
- 53 · 53-06-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- cortisone
- FDA UNII
- 27 W9254FZ · V27W9254FZ
- ATC code
- 2 AB10,S01BA03 · H02AB10,S01BA03
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H301+H311+H331-H370
- Precautionary statements
- 210 · P210-P260-P280-P301+P310-P311
- target organs
- Eyes,Central nervous system
- Hazard Codes
- F,T,Xn
- Risk Statements
- 11 · 11-23/24/25-39/23/24/25-63
- Safety Statements
- 22 · 22-24/25-45-36/37-16-7
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 3 · 3
- RTECS
- 9020000 · GM9020000
- F
- 18 · 18
- HS Code
- 2937210000 · 2937210000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Effects During Pregnancy and Lactation
◉ 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
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
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- F,T,Xn
- safety_code
- 22-24/25-45-36/37-16-7
- Storage Class
- 3 - Flammable liquids
- target organs
- Eyes,Central nervous system
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P210-P260-P280-P301+P310-P311
Chemistry & industry
Pharmacology
ATC Code
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
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.
Metabolite Pathways
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
Use Classification
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> Steroid hormones
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
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
Compound notes
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