CAS 124-94-7|Azmacort|triamcinolone|Triaderm|Tri-Nasal|Kenacort|Triamcinolone|(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}....

General Information

Structure

Molecular Formula

C₂₁H₂₇FO₆

Molecular Mass

394.4338832

Exact Mass

394.1791668

Charge

InChI

InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1

InChIKey

GFNANZIMVAIWHM-OBYCQNJPSA-N

Canonic Smiles

OCC(=O)[C@@]1(O)[C@H](O)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F

Isomeric Smiles

F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@H](O)C3)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C

Calculated Properties

JChem

Acid pKa

11.751343

H Acceptors

H Donor

LogD (pH = 5.5)

0.241693

LogD (pH = 7.4)

0.24167393

Log P

0.24169324

Molar Refractivity

99.3828

Polarizability

38.45974

Polar Surface Area

115.06

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.84

LOG S

-2.67

Solubility (Water)

8.47e-01 g/l

Data Source

Names and Identifiers

Synonyms

AzmacortTriadermTri-NasalKenacortTriamcinolone(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one9α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneTriamcinoloneFluoxyprednisolone9α-Fluoro-11β,16α,17,21-tetrahydroxy-1,4-pregnadiene-3,20-dioneTricortaleAdcortylVolonAristocortTriamcinlonCL 19823(11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione9α-Fluoro-16α-HydroxyprednisoloneTriamcinolonLederspanFluoxiprednisoloneTriamcinolona [INN-Spanish]Triamcinolone hexacetonideTriamcinolonum [INN]Tiamcinolonum [INN-Latin]TriamcinaloneTriamcinolone acetonideTriamcinolone diacetate

IUPAC Traditional name

triamcinolone (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

IUPAC name

(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Brand Name

KenalogKenalog-40Cinolone-TTridermTrymexDelphicortCinoloneAristocortRodinoloneTriacortKenacort-AKenalog-HNasacort AqKenalog-10Nasacort HfaOmicilonAristogelTriacetTriamcinlonTriatexVolonOrionTriloneAdcortylPolcortolonLedercortKenacort-AgOmcilonVetalogTriamcetOraloneOracortNasacortAristocort TabletsKenalog in OrabaseCelesteVolon ATristojectAzmacortTri-NasalTricortaleSk-TriamcinoloneFlutexKenacortTriam-TablinenAristocort AAristospanTriamcinolonFougera

Names and Identifiers

Registration numbers

Chemspider ID

CHEMBL

IUPHAR ligand ID

Wikipedia Title

ATC CODE

A01AC01R03BA06R01AD11D07AB09

Registration numbers

Properties

Physical Property

Product Information

Salt Data

Free Base

Empirical Formula (Hill Notation)

C21H27FO6

Certificate of Analysis

Download link

Application(s)

Immunosuppressive

Antiinflammatory agent

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00620

Drug Groups

approved

Description

A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739)

Indication

For the treatment of perennial and seasonal allergic rhinitis.

Pharmacology

Triamcinolone and its derivatives are synthetic glucocorticoids that are used for their antiinflammatory or immunosuppressive properties.

Toxicity

LD₅₀=>500mg/kg (in rats)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

Rapid absorption following oral administration

Half Life

88 minutes

Protein Binding

68%

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1933

Research Area: Inflammation
Biological Activity:
Triamcinolone(Aristocort) is a glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. [1]

Wikipedia

Triamcinolone

Sigma Aldrich

T6376

Biochem/physiol Actions
Triamcinolone is a synthetic glucocorticoid agonist; induces gene expression and apoptosis; inhibits prostaglandin synthesis; impairs tumor necrosis factor (TNF)-α-induced degradation of κB-α; potentiates the differentiation-inducing effects of bone morphogenetic proteins (BMP-2, -4, -6).
包装
1, 5 g in glass bottle
50, 250 mg in glass bottle

287334

Biochem/physiol Actions
Triamcinolone is a synthetic glucocorticoid agonist; induces gene expression and apoptosis; inhibits prostaglandin synthesis; impairs tumor necrosis factor (TNF)-α-induced degradation of κB-α; potentiates the differentiation-inducing effects of bone morphogenetic proteins (BMP-2, -4, -6).
Packaging
1 g in glass bottle
250 mg in glass bottle

TRC

T767160

Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB00620

• Bernstein, I.L., et al.: Chest, 81, 20 (1972)

• Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972)

• Bernstein, S. et al., J.A.C.S., 1956, 78, 5693, (synth)

• Florey, K., Anal. Profiles Drug Subst., 1972, 1, 367; 397; 423, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 586B, (nmr)

• Fried, J. et al., J.A.C.S., 1958, 80, 2338, (synth, pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AQX250; AQY375; AQX500; AQX750

• Zbinovsky, V. et al., Anal. Profiles Drug Subst., 1977, 6, 579, (rev)

• Toft, P. et al., Can. J. Pharm. Sci., 1972, 7, 53, (ms)

• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (rev)

• Sieh, D.H., Anal. Profiles Drug Subst., 1982, 11, 593; 615; 651, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6222; 7100; 7152

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 739

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

triamcinolone (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

IUPAC name

Brand Name

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB00620

• Bernstein, I.L., et al.: Chest, 81, 20 (1972)

• Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972)

• Bernstein, S. et al., J.A.C.S., 1956, 78, 5693, (synth)

• Florey, K., Anal. Profiles Drug Subst., 1972, 1, 367; 397; 423, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 586B, (nmr)

• Fried, J. et al., J.A.C.S., 1958, 80, 2338, (synth, pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AQX250; AQY375; AQX500; AQX750

• Zbinovsky, V. et al., Anal. Profiles Drug Subst., 1977, 6, 579, (rev)

• Toft, P. et al., Can. J. Pharm. Sci., 1972, 7, 53, (ms)

• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (rev)

• Sieh, D.H., Anal. Profiles Drug Subst., 1982, 11, 593; 615; 651, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6222; 7100; 7152

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 739

Bioactivity

PubChem BioAssay

Registration numbers

Chemspider ID

CHEMBL

IUPHAR ligand ID

Wikipedia Title

ATC CODE

A01AC01R03BA06R01AD11D07AB09

Properties

Physical Property

Product Information

Salt Data

Free Base

Empirical Formula (Hill Notation)

C21H27FO6

Certificate of Analysis

Download link

Application(s)

Immunosuppressive

Antiinflammatory agent

Molecule Details

DrugBank

DB00620

Drug Groups

approved

Description

Indication

For the treatment of perennial and seasonal allergic rhinitis.

Pharmacology

Triamcinolone and its derivatives are synthetic glucocorticoids that are used for their antiinflammatory or immunosuppressive properties.

Toxicity

LD₅₀=>500mg/kg (in rats)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

Rapid absorption following oral administration

Half Life

88 minutes

Protein Binding

68%

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

S1933

T6376

287334

Biochem/physiol Actions
Triamcinolone is a synthetic glucocorticoid agonist; induces gene expression and apoptosis; inhibits prostaglandin synthesis; impairs tumor necrosis factor (TNF)-α-induced degradation of κB-α; potentiates the differentiation-inducing effects of bone morphogenetic proteins (BMP-2, -4, -6).
Packaging
1 g in glass bottle
250 mg in glass bottle

TRC

T767160

Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

Molecule

ID:502