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50-02-2 molecular structure
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(1R,2S,10S,11S,13R,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: 1103
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+/m1/s1
InChIKey:
UREBDLICKHMUKA-CXSFZGCWSA-N

Cite this record

CBID:1103 http://www.chembase.cn/molecule-1103.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,10S,11S,13R,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,13R,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
(1R,2S,10S,11S,13R,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
IUPAC Traditional name
dexamethasone
Brand Name
Adexone
Aeroseb-D
Aeroseb-Dex
Anaflogistico
Aphtasolon
Aphthasolone
Auxiron
Azium
Bisu Ds
Calonat
Corson
Corsone
Cortisumman
Decacort
Decacortin
Decaderm
Decadron
Decadron Tablets, Elixir
Decadron-La
Decagel
Decalix
Decasone
Decaspray
Dectancyl
Dekacort
Deltafluorene
Dergramin
Deronil
Desadrene
Desameton
Deseronil
Dex-Ide
Dexa
Dexa Mamallet
Dexa-Cortidelt
Dexa-Cortisyl
Dexa-Mamallet
Dexa-Scheroson
Dexa-Sine
Dexacen-4
Dexacidin
Dexacort
Dexacortal
Dexacortin
Dexadeltone
Dexafarma
Dexair
Dexalona
Dexaltin
Dexameth
Dexamethasone Intensol
Dexamonozon
Dexapolcort
Dexapos
Dexaprol
Dexason
Dexasone
Dexinolon
Dexinoral
Dexone
Dexone 0.5
Dexone 0.75
Dexone 1.5
Dexone 4
Dexonium
Dextelan
Dezone
Dinormon
Fluormone
Fluorocort
Fortecortin
Gammacorten
Hexadecadrol
Hexadrol
Hexadrol Elixir
Hexadrol Tablets
Hl-Dex
Isopto-Dex
Lokalison F
Loverine
Luxazone
Maxidex
Maxitrol
Mediamethasone
Mexidex
Millicorten
Mymethasone
Ocu-Trol
Oradexon
Pet Derm Iii
Pet-Derm Iii
Policort
Prednisolon F
Prednisolone F
Sk-Dexamethasone
Spoloven
Sunia Sol D
Superprednol
Turbinaire
Visumetazone
Posurdex
IontoDex
Synonyms
Desametasone [DCIT]
Desametasone
Desamethasone
Dexametasona [INN-Spanish]
Dexamethasone Acetate
Dexamethasone Sodium Phosphate
Dexamethasonum [INN-Latin]
Dexamethazone
Fluormethylprednisolone
Dexamethasone
Dexamethasonum
(1R,2S,10S,11S,13R,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
16α-Methyl-9α-fluoroprednisolone
Aeroseb-Dex
Corson
Cortisumman
Decacort
Decaderm
Decalix
Decasone
Dekacort
(11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
9α-Fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione
9α-Fluoro-16α-methylprednisolone
Prednisolone F
Dexamethasone
9α-Fluoro-16α-methylprednisolone
Decadron
地塞米松
21α-乙酰氧基-9α-氟-11β,17α-二羟基-16α-甲基孕甾-1,4-二烯-3,20-二酮
9α-氟-16α-甲基氢化泼尼松
9-氟-11,17,21-三羟基-16-甲基(11b,16a)-孕甾-1,4-二烯-3,20-二酮
德沙美松
地塞米松
CAS Number
50-02-2
EC Number
200-003-9
MDL Number
MFCD00064136
Beilstein Number
2066651
PubChem SID
24869878
160964566
24893536
24894235
46508930
24893906
24894273
24858929
PubChem CID
5743
CHEBI ID
41879
ATC CODE
R01AD03
S03BA01
C05AA09
D07AB19
A01AC02
H02AB02
S01BA01
D10AA03
S02BA06
CHEMBL
384467
Chemspider ID
5541
DrugBank ID
DB01234
KEGG ID
D00292
Unique Ingredient Identifier
7S5I7G3JQL
Wikipedia Title
Dexamethasone
Medline Plus
a682792

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
89 mg/L expand Show data source
Acetone expand Show data source
Dioxane expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
240-242°C (dec.) expand Show data source
253 - 255°C expand Show data source
262-264 ; 268-271 °C expand Show data source
262-264 °C(lit.) expand Show data source
Optical Rotation
[α]20/D +76±4°, c = 1% in dioxane expand Show data source
[α]25/D +77.5° in dioxane expand Show data source
Hydrophobicity(logP)
1.1 expand Show data source
1.785 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
TU3980000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) 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
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38-42/43 expand Show data source
Safety Statements
22-26-36/37-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H317-H319-H334-H335 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338-P342 + P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
IL receptor expand Show data source
Admin Routes
Oral, IV, IM, SC and IO expand Show data source
Bioavailability
80-90% expand Show data source
Excretion
renal expand Show data source
Half Life
36-54 hours expand Show data source
Metabolism
hepatic expand Show data source
Protein Bound
70% 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), Ptgs2(19225), Tnf(21926)rat ... Ar(24208), Nr3c1(24413), Tnf(24835) expand Show data source
human ... NR3C1(2908) expand Show data source
Purity
≥80% (HPLC) expand Show data source
≥97% expand Show data source
≥97.0% (HPLC) expand Show data source
95% expand Show data source
98% expand Show data source
Grade
Ph Eur expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Potency
4-500 ng/mL expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
suitable for cell culture expand Show data source
Sterility
γ-irradiated expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia 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 - 02190040 external link
Crystalline
MP Biomedicals - 02194561 external link
Cell Culture Reagent
Crystalline
MP Biomedicals - 02194560 external link
Cell Culture Reagent
γ-Irradiated
Crystalline
DrugBank - DB01234 external link
Item Information
Drug Groups approved; investigational
Description An anti-inflammatory 9-fluoro-glucocorticoid. [PubChem]
Indication Injection: for the treatment of endocrine disorders, rheumatic D=disorders, collagen diseases, dermatologic diseases, allergic statesc, ophthalmic diseases, gastrointestinal diseases, respiratory diseases, hematologic disorders, neoplastic diseases, edematous states, cerebral edema.

Ophthalmic ointment and solution: for the treatment of steroid responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe.

Ophthalmic solution only: for the treatment of steroid responsive inflammatory conditions of the external auditory meatus

Topic cream: for relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses

Oral aerosol: for the treatment of bronchial asthma and related corticosteroid responsive bronchospastic states intractable to adequate trial of conventional therapy

Intranasal aerosol: for the treatment of allergic ot inflammatory nasal conditions, and nasal polyps
Pharmacology Dexamethasone and its derivatives, dexamethasone sodium phosphate and dexamethasone acetate, are synthetic glucocorticoids. Used for its antiinflammatory or immunosuppressive properties and ability to penetrate the CNS, dexamethasone is used alone to manage cerebral edema and with tobramycin to treat corticosteroid-responsive inflammatory ocular conditions.
Toxicity Oral, rat LD50: >3 gm/kg. Signs of overdose include retinal toxicity, glaucoma, subcapsular cataract, gastrointestinal bleeding, pancreatitis, aseptic bone necrosis, osteoporosis, myopathies, obesity, edemas, hypertension, proteinuria, diabetes, sleep disturbances, psychiatric syndromes, delayed wound healing, atrophy and fragility of the skin, ecchymosis, and pseudotumor cerebri.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption 80-90%
Half Life 36-54 hours
Protein Binding 70%
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1322 external link
Research Area: Inflammation
Biological Activity:
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of the naturally occurring hormone hydrocortisone and 4-5 times of prednisone. [1]
Sigma Aldrich - D8893 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
一种抗炎糖皮质素,对细胞存活、细胞信号传导和基因表达具有一系列的影响。用于研究细胞凋亡、细胞信号传导通路和基因表达。
Reconstitution
要制备 20μg/ml 储备液:加入 1ml 无水乙醇,缓缓搅拌溶解,加入 49ml 无菌培养基。
Physical form
2-8°C 下为粉末状,分成小份冻存以避免使用时反复冷冻/解冻。
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。
Sigma Aldrich - D157 external link
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。
Sigma Aldrich - D9184 external link
Application
一种抗炎糖皮质素,对细胞存活、细胞信号传导和基因表达具有一系列的影响。用于研究细胞凋亡、细胞信号传导通路和基因表达。
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。
Sigma Aldrich - D4902 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
An anti-inflammatory glucocorticoid with a range of effects on cell survival, cell signaling and gene expression. Use to study apoptosis, cell signaling pathways and gene expression.
Reconstitution
To prepare 20 μg/ml stock solution, add 1ml absolute ethanol per mg product; gently swirl to dissolve. Add 49 ml sterile medium per ml of ethanol added, while mixing, to acheive final concentration of 20 μg/ml.
Physical form
powder 2-8 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。
Sigma Aldrich - 861871 external link
Packaging
100 mg in glass bottle
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.
Sigma Aldrich - 46165 external link
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 31375 external link
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.
Sigma Aldrich - 31381 external link
Other Notes
Useful for the induction of liver metallothionein1
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.
Toronto Research Chemicals - D298800 external link
Dexamethasone is a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.rxlist.com/decadron-drug.htm
  • • Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995)
  • • Riccardi, C., et al.: Cell Death Diff., 6, 1182 (1995)
  • • Llanos, S.L. and Roldan, A.: Bio Cell, 23, 29 (1999)
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PATENTS

PATENTS

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INTERNET

INTERNET

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