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
Exanthem	N.A.	Approved	[1]
Granuloma annulare	N.A.	Approved	[1]
Inflammation	1A00-CA43.1	Approved	[2]
Primary cutaneous T-cell lymphoma	N.A.	Approved	[1]
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Therapeutic Class

Antiinflammatory Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

502.6

Logarithm of the Partition Coefficient (xlogp)

3.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Metabolism: The drug is metabolized via skin []

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

Repurposed Drugs (RPD)

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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	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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
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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

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References

1	Amcinonide FDA Label
2	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).
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
4	Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35.