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B7005

Sigma-Aldrich

Betamethasone

≥98%

Synonym(s):

9α-Fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione, 9α-Fluoro-16β-methylprednisolone

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About This Item

Empirical Formula (Hill Notation):
C22H29FO5
CAS Number:
378-44-9
Molecular Weight:
392.46
EC Number:
206-825-4
MDL number:
MFCD00062969
UNSPSC Code:
51111800
PubChem Substance ID:
57653954
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

sterility

non-sterile

assay

≥98%

form

powder

mp

235-237 °C (lit.)

solubility

water: 0.063 g/L at 37 °C

shipped in

ambient

storage temp.

room temp

SMILES string

[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

InChI

1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

InChI key

UREBDLICKHMUKA-DVTGEIKXSA-N

Gene Information

human ... ABCB1(5243) , CYP3A4(1576) , IL4(3565) , IL5(3567) , NR3C1(2908)
mouse ... Abcb1a(18671) , Abcb1b(18669) , Ifng(15978) , Nos2(18126) , Tnf(21926)
rat ... Ar(24208) , Nr3c1(24413) , Tnf(24835)

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Application

Betamethasone has been used as a corticosteroid (CORT) standard.

Biochem/physiol Actions

Betamethasone, an isomer of dexamethasone is also termed as 9α-fluoro-16β-methyl-11 β,17,21-trihydroxypregna-1,4-dien-3,20-dione or 9α-fluoro-16β-methylprednisolone (27.1.52). It can be used as an anti-itch agent and treating dermatitis and eczema.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Repr. 1B - STOT RE 2

target_organs

Liver,Kidney,Endocrine system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ceá C Tillis et al.
American journal of physiology. Lung cellular and molecular physiology, 300(6), L940-L950 (2011-03-15)
Adequate expression of surfactant protein-B (SP-B) is critical in the function of pulmonary surfactant to reduce alveolar surface tension. Expression of SP-B mRNA is restricted to specific lung-airway epithelial cells, and human SP-B mRNA stability is increased in the presence
Jennifer J P Collins et al.
American journal of physiology. Lung cellular and molecular physiology, 304(6), L438-L444 (2013-01-22)
Inflammation and antenatal glucocorticoids, the latter given to mothers at risk for preterm birth, affect lung development and may contribute to the development of bronchopulmonary dysplasia (BPD). The effects of the combined exposures on inflammation and antenatal glucocorticoids on transforming
Elizabeth V Asztalos et al.
JAMA pediatrics, 167(12), 1102-1110 (2013-10-16)
A single course of antenatal corticosteroid therapy is recommended for pregnant women at risk of preterm birth between 24 and 33 weeks' gestational age. However, 50% of women remain pregnant 7 to 14 days later, leading to the question of
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