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Celestone

HCID 3003
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
378-44-9
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

Overview

9-fluoro-11,17-dihydroxy-17-(2-hydroxy-1-oxoethyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one is a 21-hydroxy steroid.

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

CelestoneHormezonGF120918ABebate.beta.-Methasone.beta.-Methasone alcoholC22H29FO59-Fluoro-16.beta.-methylprednisolone9alpha-Fluoro-16 beta-methyl-prednisolonePrednisolone, 9-fluoro-16.beta.-methyl-9.alpha.-Fluoro-16.beta.-methylprednisolone9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Show more names
BetamethasonBetametasonebetamethasone standardC22H29O5FDermabet17,21-trihydrFLUBENISOLONEBetamethazoneDexamethasone EP Impurity B
Dexamethasone - USP CRSMLS000686794Corticosterone, 1-dehydro-9-fluoro-17-hydroxy-16.beta.-methyl-SCHEMBL2757815CHEBI:93851HMS3259J08HMS3267M14HMS5079A12

Database identifiers

Properties

Computed structural propertiesFilling in

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

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP1.99

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)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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 · 7 items

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

Betamethasone 21-acetateHydrochloric acid6 beta-hydroxybetamethasone 17-propionate

Related reactions

5 records
New reaction record
HRID 167680 reaction equation
HRID 167680As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 691348 reaction equation
HRID 691348As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 959610 reaction equation
HRID 959610As reactantValidation data from https://doi.org/10.1039/C8SC04228D
HRID 2140061 reaction equation
HRID 2140061As reactantTraining data from https://doi.org/10.1039/C8SC04228D (4/10)
HRID 2325899 reaction equation
HRID 2325899As reactantTraining data from https://doi.org/10.1039/C8SC04228D (10/10)

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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CAS
378-44-9
PubChem CID
3003
ChEBI
CHEBI:93851
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
Betamethasone 17,21-dipropionate
6-hydroxybetamethasone
9-fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionate
Additional notes · 1 item

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.