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378-44-9 molecular structure
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(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

ChemBase ID: 326
Molecular Formular: C22H29FO5
Molecular Mass: 392.4610632
Monoisotopic Mass: 392.19990225
SMILES and InChIs

SMILES:
F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
Canonical SMILES:
OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
InChI:
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
InChIKey:
UREBDLICKHMUKA-DVTGEIKXSA-N

Cite this record

CBID:326 http://www.chembase.cn/molecule-326.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-5-one
(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
IUPAC Traditional name
betamethasone
Brand Name
Alphatrex
Bebate
Becort
Bedifos
Beta-Methasone
Beta-Methasone Alcohol
Beta-Val
Betacorlan
Betacortril
Betaderm
Betadexamethasone
Betafluorene
Betamamallet
Betametasona [INN-Spanish]
Betametasone [DCIT]
Betamethasone Alcohol
Betamethasone Base
Betamethasone Cream
Betamethasone Dipropionate
Betamethasone Sodium Phosphate
Betamethasone Valearate
Betamethasone Valerate
Betamethasone [Usan:Ban:Inn:Jan]
Betamethasonum [INN-Latin]
Betamethasonvalerat Mikron
Betamethazone
Betapredol
Betasolon
Betatrex
Betnelan
Betsolan
Celestene
Celestone
Celestone Syrup and Tablets
Cidoten
Dermabet
Desacort-Beta
Diproderm
Diprolene
Diprolene AF
Diprosone
Flubenisolone
Hormezon
Lotrisone
Luxiq
Luxiqo
Maxivate
Methazon
Rinderon
Rinderon A
Uticort
Valisone
Valnac
Visubeta
Synonyms
Betamethasone
(11β,16β)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
Sch-4831
NCS-39470
9α-Fluoro-16 β-methyl-prednisolone
9α-Fluoro-16 β-methyl-11β,17α, 21-trihydroxy-1,4-pregnadiene-3,20-dione
1,4-Pregnadiene-3,20-dione-9α-fluoro-16 β-methyl-11β,17α,21-triol
Betamethasone
Betamethasone valerate impurity A (PhEur)
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
Celestone
Betadexamethasone
Flubenisolone
Betamethasone (Celestone)
9α-氟-11β,17α,21-三羟基-16β-甲基孕甾-1,4-二烯-3,20-二酮
9α-氟-16β-甲基-11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮
9α-氟-16β-甲基泼尼松龙
倍他米松
CAS Number
378-44-9
EC Number
206-825-4
MDL Number
MFCD00062969
PubChem SID
24278276
24860978
24892150
46505155
160963789
PubChem CID
9782
CHEBI ID
3077
ATC CODE
R03BA04
S03BA03
S02BA07
C05AA05
A07EA04
H02AB01
S01CB04
D07AC01
S01BA06
R01AD06
CHEMBL
632
Chemspider ID
9399
DrugBank ID
DB00443
KEGG ID
D00244
Unique Ingredient Identifier
9842X06Q6M
Wikipedia Title
Betamethasone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.423736  H Acceptors
H Donor LogD (pH = 5.5) 1.6815696 
LogD (pH = 7.4) 1.6815655  Log P 1.6815697 
Molar Refractivity 102.4929 cm3 Polarizability 39.61867 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.93  LOG S -3.89 
Solubility (Water) 5.05e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
DMSO expand Show data source
Insoluble expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
234-236°C expand Show data source
235-237 °C(lit.) expand Show data source
Optical Rotation
[α]20/D +105°, c = 1 in acetone expand Show data source
Hydrophobicity(logP)
1.1 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
TU4000000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
oral or topical expand Show data source
Excretion
Renal (in urine) expand Show data source
Half Life
36-54 hours expand Show data source
Metabolism
hepatic CYP3A4 expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C (US) expand Show data source
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) expand Show data source
Purity
≥95.0% (HPLC) expand Show data source
≥98% expand Show data source
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Description
free compound expand Show data source
Impurities
≤10.0% related substances expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Loss on Drying
≤5.0% loss on drying expand Show data source
Empirical Formula (Hill Notation)
C22H29FO5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02154853 external link
(9α-Fluoro-16β-methyl-prednisolone; 9α-Fluoro-16β-methyl-11β,17α, 21-trihydroxy-1,4-pregnadiene-3,20-dione; 1,4-Pregnadiene-3,20-dione-9α-fluoro-16β-methyl-11<
DrugBank - DB00443 external link
Item Information
Drug Groups approved
Description A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)
Indication Topical use (cream, lotion and ointment): for relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses
Topical use (foam): relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses of the scalp
Systemic use: for the treatment of edocrine disorders, rheumatic disorders, collagen diseases, dermatological diseases, allergic states, ophthalmic diseases, respiratory diseases, hematologic disorders, neoplastic diseases, edematous states, gastrointestinal diseases, tuberculous meningitis and trichinosis.
Pharmacology Betamethasone and its derivatives, betamethasone sodium phosphate and betamethasone acetate, are synthetic glucocorticoids. Used for its antiinflammatory or immunosuppressive properties, betamethasone is combined with a mineralocorticoid to manage adrenal insufficiency and is used in the form of betamethasone benzoate, betamethasone dipropionate, or betamethasone valerate for the treatment of inflammation due to corticosteroid-responsive dermatoses. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections.
Toxicity Symptoms of overdose include burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, and miliaria.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Minimal if applied topically.
Half Life 5.6 hours
Protein Binding 64%
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1500 external link
Research Area: Immunology
Biological Activity:
Betamethasone is a moderately potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties.Betamethasone is a corticosteroid used as a topical cream to relieve skin irritation, such as itching and flaking from eczema. Betamethasone dipropionate and salicylic acid can be used as a treatment for local psoriasis. [1]
Sigma Aldrich - B7005 external link
包装
100, 500 mg in poly bottle
Sigma Aldrich - 34166 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - B327000 external link
Betamethasone is a glucocorticoid used as an anti-inflammatory agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Betamethasone
  • • Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977)
  • • Li, A., et al.: Chem. Biol. Interact., 142, 7 (1977)
  • • Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (1977)
  • • Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (1977)
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PATENTS

PATENTS

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INTERNET

INTERNET

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