Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1751)
Drug Name
Triamcinolone diacetate
Synonyms
Aristocort diacetate; Polcortolon; Tedarol; Aristocort Forte; Triamcinolone 16,21-diacetate; Orion; Aristocort Parenterals; Kenacort Diacetate Syrup; Aristocort diacetate forte; Aristocort Forte Parenteral; TRIAMCINOLONE DIACETATE; UNII-A73MM2Q32P; Kenacourt; Aristocort syrup; CHEBI:9669; 357RP; EINECS 200-669-0; Triamcinolone 16-alpha,21-di(acetate); A73MM2Q32P; 16alpha-Hydroxy-9alpha-fluoroprednisolone diacetate; 9-alpha-Fluoro-16-alpha-hydroxyprednisolone diacetate; NCGC00159320-03; delta1,9alpha-Fluoro-16alpha-hydroxyhydrocortisone diacetate; delta11,16alpha-Hydroxy-9alpha-fluorohydrocortisone diacetate; 16alpha,21-Diacetoxy-9alpha-fluoro-11beta,17alpha-dihydroxy-1,4-pregnadiene-3,20-dione; 9-Fluoro-11-beta,16-alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 16,21-diacetate; 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 16,21-diacetate; DSSTox_CID_28639; DSSTox_RID_82909; DSSTox_GSID_48713; Pregna-1,4-diene-3,20-dione, 16,21-bis(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11beta,16alpha)-; Polcartolone; CAS-67-78-7; Triamcinolone diacetate [JAN]; Triamcinolone diacetate [USP:JAN]; SCHEMBL12549; 67-78-7
Indication Allergy [ICD11: 4A80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 478.5 Topological Polar Surface Area 127
Heavy Atom Count 34 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
6216
ChEBI ID
CHEBI:9669
CAS Number
67-78-7
Formula
C25H31FO8
Canonical SMILES
CC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)OC(=O)C)O
InChI
1S/C25H31FO8/c1-13(27)33-12-20(31)25(32)21(34-14(2)28)10-18-17-6-5-15-9-16(29)7-8-22(15,3)24(17,26)19(30)11-23(18,25)4/h7-9,17-19,21,30,32H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22-,23-,24-,25+/m0/s1
InChIKey
XGMPVBXKDAHORN-RBWIMXSLSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6-beta-hydroxy-triamcinolone DM002380
46781919
Oxidation - 6-Beta-Hydroxylation 1 [4] , [5] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002449 Triamcinolone diacetate 6-beta-hydroxy-triamcinolone Oxidation - 6-Beta-Hydroxylation CYP3A4 ... [4], [5], [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Triamcinolone Diacetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Triamcinolone acetonide induced secondary adrenal insufficiency related to impaired CYP3A4 metabolism by coadministration of nefazodone. Pain Med. 2010 Jul;11(7):1132-5.
3 Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes. Drug Metab Dispos. 2013 Feb;41(2):379-89.
4 A mass balance study to evaluate the biotransformation and excretion of [14C]-triamcinolone acetonide following oral administration J Clin Pharmacol. 2000 Jul;40(7):770-80. doi: 10.1177/00912700022009413.
5 Metabolic fate of a synthetic corticosteroid (triamcinolone) in the dog J Biol Chem. 1961 Apr;236:1038-42.

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