Showing Compound Dexamethasone (FDB001355)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:56 UTC

Update date

2018-05-28 23:05:47 UTC

Primary ID

FDB001355

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dexamethasone

Description

Glucocorticoid with potent antiinflammatory props. Not FDA approved for use in food-producing animals, but may be used illegally Dexamethasone and its derivatives, dexamethasone sodium phosphate and dexamethasone acetate, are synthetic glucocorticoids. It is 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.; Dexamethasone can be used in the context of congenital adrenal hyperplasia, to prevent virilisation of a female fetus. If one or both parents are carriers of mutations to the CYP21 (CYP21A2) gene, the mother may start dexamethasone treatment within 7 weeks of conception. At the 12th week, a chorionic villus sample will determine whether the fetus is male (in which case the dexamethasone is stopped) or female. Subsequent DNA analysis can then reveal whether the female fetus is a carrier of the mutation, in which case dexamethasone treatment must continue until birth. The side-effects for the mother can be severe and the long-term impact on the child is not clear.; Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of hydrocortisone and 4-5 times of prednisone.

CAS Number

50-02-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
1-dehydro-16a-Methyl-9a-fluorohydrocortisone	Generator
1-dehydro-16alpha -Methyl-9alpha -fluorohydrocortisone	HMDB
1-Dehydro-16alpha-methyl-9alpha-fluorohydrocortisone	biospider
1-Dehydro-16α-methyl-9α-fluorohydrocortisone	biospider
1-dehydro-16α-methyl-9α-fluorohydrocortisone	Generator
16-alpha-Methyl-9-alpha-fluoro-1-dehydrocortisol	biospider
16-alpha-Methyl-9-alpha-fluoro-delta(sup 1)-hydrocortisone	biospider
16-alpha-Methyl-9-alpha-fluoro-delta1-hydrocortisone	biospider
16-alpha-Methyl-9-alpha-fluoroprednisolone	biospider
16a-Methyl-9a-fluoro-1-dehydrocortisol	Generator

Showing 1 to 10 of 167 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.68	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.49 m³·mol⁻¹	ChemAxon
Polarizability	41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C22H29FO5

IUPAC name

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

InChI Identifier

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

InChI Key

UREBDLICKHMUKA-UHFFFAOYSA-N

Isomeric SMILES

CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO

Average Molecular Weight

392.4611

Monoisotopic Molecular Weight

392.199902243

Classification

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
9-halo-steroid
Halo-steroid
Oxosteroid
Delta-1,4-steroid
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Ketone
Fluorohydrin
Halohydrin
Secondary alcohol
Cyclic ketone
Organooxygen compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Organohalogen compound
Organofluoride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a steroid (CPD-10549 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	1.83	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Experimental Water Solubility	0.089 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Isoelectric point	Not Available
Mass Composition	C 67.33%; H 7.45%; F 4.84%; O 20.38%	DFC
Melting Point	Mp 262-264°	DFC
Optical Rotation	[a]25D +77.5 (dioxan)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dexamethasone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02ai-3954000000-23089bc94ed617ffe0c0	Spectrum
Predicted GC-MS	Dexamethasone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dexamethasone, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-05g0-0985000000-d5d465b5ab57ee590338	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0498000000-233b2490f89112ad539e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-0970000000-36eebd63d78f040ae67f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000j-0791000000-c83a21019f43596e6804	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0009000000-431895662c53cadb563c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0940000000-730013951a30cf080ad4	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0596-0009000000-41b3ee4ad8cb73926aee	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-0139000000-f023386adf0b6870cd28	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-1950000000-ad56d3956b789869d082	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-f7184f0127b744d5e23f	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-0009000000-a6c2a4b020bb58da6a2d	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-3119000000-cf22b594d4110329ede9	2021-10-12	View Spectrum