Details of the Drug

General Information of Drug (ID: DMM1JL9)

Drug Name
Amcinonide
Synonyms
Amcinonida; Amcinonido; Amcinonidum; Cyclocort; Cyclort; Triamcinolonacetatcyclopentanonid; Visderm; CL 34699; Amcinonido [INN-Spanish]; Amcinonidum [INN-Latin]; CL 34,699; CL-34699; Cyclocort (TN); Amcinonide (JAN/USP/INN); Amcinonide [USAN:INN:BAN:JAN]; Triamcinolone 16,17-cyclopentylidenedioxy-21-acetate; 1,4-Pregnadiene-2,20-dione-16,17-cyclopentylidenedioxy-9-fluoro-11,21-dihydroxy-21-acetate; 16alpha,17alpha-(cyclopentane-1,1-diyldioxy)-9-fluoro-11beta-hydroxy-3,20-dioxopregna-1,4-dien-21-yl acetate; 19alpha-Fluor-11beta,21-dihydroxy-16alpha,17alpha-(tetramethylen)methylendioxy-1,4-pregnadien-3,20-dion 21-acetat; 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclopentanone, 21-acetate
Indication
Disease Entry ICD 11 Status REF
Inflammation 1A00-CA43.1 Approved [1], [2]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 502.6
Topological Polar Surface Area (xlogp) 3.6
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Metabolism
The drug is metabolized via skin [3]
Chemical Identifiers
Formula
C28H35FO7
IUPAC Name
[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate
Canonical SMILES
CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3CCC5=CC(=O)C=C[C@@]54C)F)O)C)OC6(O2)CCCC6
InChI
InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
InChIKey
ILKJAFIWWBXGDU-MOGDOJJUSA-N
Cross-matching ID
PubChem CID
443958
ChEBI ID
CHEBI:31199
CAS Number
51022-69-6
DrugBank ID
DB00288
TTD ID
D06XHC
INTEDE ID
DR0082
ACDINA ID
D00830

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Steroid hormone receptor ERR (ESRR) TTP3UTW ERR1_HUMAN; ERR2_HUMAN; ERR3_HUMAN Modulator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Benzyl alcohol E00010 244 Antimicrobial preservative; Solvent
Kyselina citronova E00014 311 Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Lactic acid E00020 612 Acidulant
Propyl gallate E00075 4947 Antimicrobial preservative; Antioxidant
Isopropyl palmitate E00193 8907 Emollient; Oleaginous vehicle; Penetration agent; Solvent
Butylhydroxyanisole E00308 24667 Antimicrobial preservative; Antioxidant
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Water E00035 962 Solvent
Sorbitan tristearate E00516 17800859 Dispersing agent; Emulsifying agent; Solubilizing agent; Surfactant; Suspending agent; Vaccine adjuvant
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Amcinonide 0.1% ointment 0.10% Ointment Topical
Amcinonide 0.1% lotion 0.10% Lotion Topical
Amcinonide 0.1% cream 0.10% Cream Topical
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7060).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076065.
3 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5 Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35.
6 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
7 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
8 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
9 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
10 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
11 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
12 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
13 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
14 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.