Basic information
- Standard SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO- InChIKey
UREBDLICKHMUKA-UHFFFAOYSA-N- Molecular formula
- C22H29FO5
- Average molar mass
- 392.5 g/mol
- Monoisotopic mass
- 392.19990218
Names & identifiers
- Preferred name
- Celestone
- IUPAC
- 9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- English name
- Betamethasone
- Molecular formula
- C22H29FO5
- Molecular weight
- 392.47
Names & synonyms
Show more names
Database identifiers
- CAS
378-44-9- PubChem CID
- 3003
- ChEBI
CHEBI:93851
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 805
Physicochemical properties
- Melting point
- 235 · 235-237°C
- alpha
- 108 ° · D +108° (acetone)
- Boiling point
- 568.2 · 568.2±50.0 °C(Predicted)
- Density
- 1.1283 · 1.1283 (estimate)
- refractive index
- 118 ° · 118 ° (C=1, Dioxane)
- storage temp.
- 0 · 0-6°C
- solubility
- Practically insoluble in water, sparingly soluble in anhydrous ethanol, very slightly soluble in methylene chloride.
- pka
- 12.13 · 12.13±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic (organic)
- Water Solubility
- 58 mg/L · 58mg/L(25 ºC)
- Merck
- 14 · 14,1180
- InChIKey
- UREBDLICKHMUKA-DVTGEIKXSA-N
- SMILES
- [H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
- LogP
- 2.01 at · 2.01 at 25℃
- CAS DataBase Reference
- 378 · 378-44-9(CAS DataBase Reference)
- FDA UNII
- 9842 X06Q6M · 9842X06Q6M
- NCI Drug Dictionary
- betamethasone
- ATC code
- 7 EA04,C05AA05,D07AC01,D07XC01,H02AB01,R01AD06,R03BA04,S01BA06,S01CB04,S02BA07,S03BA03 · A07EA04,C05AA05,D07AC01,D07XC01,H02AB01,R01AD06,R03BA04,S01BA06,S01CB04,S02BA07,S03BA03
- NIST Chemistry Reference
- -1 · Pregna-1,4-diene-3,20-dione, 9alpha-fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-(378-44-9)
- EPA Substance Registry System
- -1 · Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)- (378-44-9)
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
- Protein binding
- 65 % · 65%
- Excreted unchanged in urine
- 5 % · 5%
- Volume of distribution
- 1.4 · 1.4(L/kg)
- Biological half-life
- 5.5 · 5.5 / -
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 360 FD-H373 · H360FD-H373
- Precautionary statements
- 202 · P202-P260-P280-P308+P313-P405-P501
- target organs
- Liver,Kidney,Endocrine system
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,Xn,T
- Risk Statements
- 40 · 40-48/20/21-61
- Safety Statements
- 22 · 22-36-45-53
- WGK Germany
- 2 · 2
- RTECS
- 4000000 · TU4000000
- HS Code
- 29379000 · 29379000
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 BSTOT · Repr. 1BSTOT RE 2
- Hazardous Substances Data
- 378 · 378-44-9(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in mouse: > 4500mg/kg
- REACH Registrations
- Active
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- TU4000000
- hs_code
- 29379000
- Toxicity
- LD50 oral in mouse: > 4500mg/kg
- risk_code
- 40-48/20/21-61
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xi,Xn,T
- safety_code
- 22-36-45-53
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Liver,Kidney,Endocrine system
- Hazard statements
- H360FD-H373
- REACH Registrations
- Active
- Hazard Classifications
- Repr. 1BSTOT RE 2
- Precautionary statements
- P202-P260-P280-P308+P313-P405-P501
- Hazardous Substances Data
- 378-44-9(Hazardous Substances Data)
Chemistry & industry
Applications
UsesHormone drugs.It is mainly used for anti-inflammatory and anti-allergic. It is suitable for rheumatoid arthritis and various skin diseases. Betamethasone role is similiar to dexamethasone, its anti-inflammatory effect is stronger than dexamethasone, triamcinolone, hydrocortisone and it has few side effects.
DescriptionShortly after the introduction of dexamethasone, betamethasone, which differs from dexamethasone only in configuration of the 16-methyl group, was made available for the treatment of rheumatic diseases and dermatologic disorders. This analogue, which contains a 16β-methyl group, has received sufficient clinical trial examination to indicate that it is as effective as dexamethasone or, perhaps, even slightly more active. Although this drug has been reported to be less toxic than other steroids, some clinical investigators suggest that it is best used for short-term therapy.
DescriptionBetamethasone is a synthetic corticosteroid. Like other corticosteroids, betamethasone has anti-inflammatory actions. Betamethasone also accelerates fetal lung maturation and has been used to decrease neonatal mortality and morbidity in infants born before 34 weeks of gestation.
Usesglucocorticoid, antiinflammatory
Usesanti-inflammatory, immunosuppressive
UsesBetamethasone is a glucocorticoid used as an anti-inflammatory agent.
General DescriptionBetamethasone, 9-fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione,is available as a variety of ester derivatives.Betamethasone valerate, USP (17-valerate)Betamethasone acetate, USP (21-acetate)Betamethasone sodium phosphate, USP (21-sodiumphosphate)Betamethasone dipropionate, USP (17-propionate,21-propionate).
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Betamethasone is a glucocorticoid, a 20-oxo steroid, a 21-hydroxy steroid, a 17alpha-hydroxy steroid, a fluorinated steroid, an 11beta-hydroxy steroid, a 3-oxo-Delta(1),Delta(4)-steroid, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It has a role as an anti-inflammatory drug, an anti-asthmatic agent and an immunosuppressive agent. It derives from a hydride of a pregnane.
Related reactions
Linked notes
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