Triamcinolone Acetonide

HCID 6436

Basic information

CAS
76-25-5
Standard SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
InChIKey
YNDXUCZADRHECN-JNQJZLCISA-N
Molecular formula
C24H31FO6
Average molar mass
434.5 g/mol
Monoisotopic mass
434.21046693

Overview

Triamcinolone acetonide is a synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections. It has a role as an anti-inflammatory drug and an anti-allergic agent. It is a primary alpha-hydroxy ketone, a glucocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a fluorinated steroid and a cyclic ketal. It is functionally related to a triamcinolone. It derives from a hydride of a pregnane.

Names & identifiers

Preferred name
Triamcinolone Acetonide
IUPAC
(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
English name
Triamcinolone acetonide
Molecular formula
C24H31FO6
Molecular weight
434.5

Names & synonyms

TRIAMCINOLONE ACETONIDE76-25-5AzmacortNasacortVetalogSolodelfTricinolonKenacort-AVolon AAristogelTramacinZilretta
Show more names
TRIAMCINOLONE ACETONIDE ACETATERefrigeratorTriamKENALOGTriamsinolone acetonideTriamcinolone acetonide CRSFluocinolone Acetonide EP Impurity HTrymexERIC-1
OraloneRinetonTriacetTridermNasacort AQTriacortTriatexTriesence

Database identifiers

CAS
76-25-5
PubChem CID
6436
DTXSID
DTXSID6021371
ChEMBL
CHEMBL1504
ChEBI
CHEBI:71418
UNII
F446C597KA
EC Number
200-948-7
Nikkaji
J55.714E

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
93.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
2
Heavy atoms
31

Experimental & physicochemical properties

DrugsPharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
LogP2.53
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal Drugs · 2 items

Active Ingredients (Triamcinolone Acetonide) -> FDA Greenbook

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 items

290.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6021371]

197.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
274 · 274-278°C (dec.)
alpha
23 · D23 +109° (c = 0.75 in chloroform)
Boiling point
576.9 · 576.9±50.0 °C(Predicted)
Density
1.1517 · 1.1517 (estimate)
refractive index
1.598 · 1.5980 (estimate)
storage temp.
Refrigerator

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.8% (1 of 55) of reports.

Danger

H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 55 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationTriamcinolone acetonide: Non hazardous
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (12.7%)

Safety data

wgk
3
tsca
TSCA listed
rtecs
TU3920000
hs_code
29372290
Toxicity
LD50 oral in mouse: 5gm/kg
risk_code
61

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 6 items

F446C597KA

TRIAMCINOLONE ACETONIDE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Triamcinolone acetonide is a Corticosteroid. The mechanism of action of triamcinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.

ALLERGY NASAL

MeSH Pharmacological Classification · 3 items

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Use Classification · 2 items

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing InformationPregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-: INACTIVE
Applications · 4 items

UsesTriamcinolone acetonide is a topical and systemic corticosteroid belonging to the group B (triamcinolone acetonide) type of steroids. Triamcinolone acetonide is an adrenal cortex hormone drug. As an antiasthmatic (inhalant) and antiallergic (nasal), it could used for treating diseases such as neurodermatitis, eczema, psoriasis, joint pain, and asthma.

DescriptionTriamcinolone acetonide is a synthetic corticosteroid. It decreases cytokine levels, the firing rate of sensory neurons, and mechanical hypersensitivity in a rat spinal nerve ligation model when used at a dose of 1.5 mg/kg prior to and following surgery for three days. Triamcinolone acetonide also decreases outflow facility in a mouse model of steroid-induced glaucoma when 20 μl of a 40 mg/ml suspension is administered subconjunctivally. Formulations containing triamcinolone acetonide are used in the treatment of diabetic macular edema.

General DescriptionThe three main metabolitesof triamcinolone acetonide (Azmacort, Nasacort) are 6β-hydroxytriamcinolone acetonide, 21-carboxytriamcinoloneacetonide, and 6β-hydroxy-21-carboxytriamcinolone acetonide.All are much less active than the parent compound.The 6β-hydroxyl group and the 21-carboxy group are bothstructural features that greatly reduce GC action. The increasedwater solubility of these metabolites also facilitatesmore rapid excretion.

General DescriptionTriamcinolone acetonide is approximately 8 times morepotent than prednisone in animal inflammation models.Topically applied triamcinolone acetonide is a potent antiinflammatoryagent, about 10 times more sothan triamcinolone. The plasma half-life is approximately 90minutes, although the plasma half-life and biological halflivesfor GCs do not correlate well. The hexacetonide isslowly converted to the acetonide in vivo and is given onlyby intra-articular injection. Only triamcinolone and the diacetateare given orally. The acetonide and diacetate may begiven by intra-articular or intrasynovial injection. In addition,the acetonide may be given by intrabursal or, sometimes,IM or subcutaneous injection. A single IM dose of thediacetate or acetonide may last up to 3 or 4 weeks. Plasmalevels with IM doses of the acetonide are significantly higherthan with triamcinolone itself. The acetonide is also used totreat asthma and allergic rhinitis.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东雨禾医药科技有限公司15263077727

Additional notes

DefinitionChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.

Related reactions

11 records

Compound notes

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