Oxycodone

Details

• Internal ID: 0845043e-8b8b-4041-8f87-313a8aa4cbd8
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• InChI: InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
• InChI Key: BRUQQQPBMZOVGD-XFKAJCMBSA-N
• Popularity: 13,006 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.40 g/mol
• Exact Mass: 315.14705815 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.05
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Dihydrone
• Dihydrohydroxycodeinone
• Dihydroxycodeinone
• Diphydrone
• 76-42-6
• Oxicodona
• Endone
• Oxanest
• Dihydro-14-hydroxycodeinone
• (-)-14-Hydroxydihydrocodeinone
• Oxycodonum
• Xtampza
• Remoxy
• OxyIR
• Endine (Australia)
• 14-Hydroxydihydrocodeinone
• Xtampza ER
• Eubine [France]
• Supendol [Canada]
• Codeinone, dihydrohydroxy-
• Pavinal
• PTI-821
• Oxycodone cii
• Codeinone, dihydro-14-hydroxy-
• oxymorphone 3-methyl ether
• (-)-Oxycodone
• 4,5alpha-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
• Pancodone retard (United Kingdom)
• 4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
• Pti 821
• NSC-19043
• PF-00345439
• Codeinone, 7,8-dihydro-14-hydroxy-
• CD35PMG570
• CHEBI:7852
• IDS-NO-002
• N02AA05
• DTXSID5023407
• Eubine (France)
• Morphinan-6-one, 4,5alpha-epoxy-14-hydroxy-3-methoxy-17-methyl-
• Morphinan-6-one, 4,5-epoxy-14-hydroxy-3-methoxy-17-methyl-, (5alpha)-
• NSC19043
• Supendol (Canada)
• Oxycodeinon
• Oxycone
• (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• oxicodone
• Proladone
• Oxycodone SR
• (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10-trien-14-one
• (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
• (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-one
• (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-one
• (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
• RefChem:6478
• DTXCID903407
• thecodinum (for the hydrochloride)
• (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.05,17.07,18)octadeca-7(18),8,10-trien-14-one
• 200-960-2
• Oxycodeinone
• Oxicon
• Eucodalum
• Oxycodon
• Percobarb
• Oxycontin
• Eucodal
• Oxycodonum [INN-Latin]
• Oxicodona [INN-Spanish]
• Oxicone
• DEA No. 9143
• Oxyfast
• Supendol
• Tekodin (free base)
• Ossicodone [DCIT]
• Ossicodone
• Pancodine
• NSC 19043
• Oxycodone [USAN:INN:BAN]
• Dihydrohydroxycondeinone
• Avridi
• Oxyneo
• 14-hydroxy-3-methoxy-17-methyl-5beta-4,5-epoxymorphinan-6-one
• Pancodone Retard
• Apo-oxycodone CR
• CHEMBL656
• HSDB 3142
• Oxycodone (USAN/INN)
• EINECS 200-960-2
• BRN 0043446
• UNII-CD35PMG570
• 4,5.alpha.-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
• Morphinan-6-one, 4,5-epoxy-14-hydroxy-3-methoxy-17-methyl-, (5.alpha.)-
• OOX
• OXYCODONE [INN]
• OXYCODONE [MI]
• OXYCODONE [HSDB]
• OXYCODONE [USAN]
• OXYCODONE [VANDF]
• OXYCODONE [MART.]
• OXYCODONE [WHO-DD]
• SCHEMBL2737
• 14-cis-Hydroxydihydrocodeinone
• GTPL7093
• PF06
• OXYCODONE [ORANGE BOOK]
• OXYCODONE CII [USP-RS]
• SCHEMBL29391732
• Codeinone,8-dihydro-14-hydroxy-
• Oxycodone 0.1 mg/ml in Methanol
• Oxycodone 1.0 mg/ml in Methanol
• 14-hydroxy-3-methoxy-17-methyl-4,5alpha-epoxymorphinan-6-one
• BDBM50370595
• Morphinan-6-one, 4,5-alpha-epoxy-14-hydroxy-3-methoxy-17-methyl-
• (5alpha)-14-hydroxy-17-methyl-3-(methyloxy)-4,5-epoxymorphinan-6-one
• DB00497
• AC-16043
• DB-243425
• C08018
• D05312
• Q407535
• Morphinan-6-one,5.alpha.-epoxy-14-hydroxy-3-methoxy-17-methyl-
• HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY D [EP IMPURITY]
• Morphinan-6-one,5-epoxy-14-hydroxy-3-methoxy-17-methyl-, (5.alpha.)-
• WLN: T B6566 B6/CO 4ABBC R BX FV HO PN GHT&&TTJ CQ JO1 P1
• (5.ALPHA.)-4,5-EPOXY-14-HYDROXY-3-METHOXY-17-METHYLMORPHINAN-6-ONE
• 4aH-8,5-bcd]furan-5(6H)-one, 7,7a,8,9-tetrahydro-7a-hydroxy-3-methoxy-12-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.8403	84.03%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Lysosomes	0.5740	57.40%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.9417	94.17%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6599	65.99%
BSEP inhibitior	-	0.7469	74.69%
P-glycoprotein inhibitior	-	0.9313	93.13%
P-glycoprotein substrate	-	0.8677	86.77%
CYP3A4 substrate	+	0.5660	56.60%
CYP2C9 substrate	-	0.8055	80.55%
CYP2D6 substrate	+	0.6300	63.00%
CYP3A4 inhibition	-	0.8714	87.14%
CYP2C9 inhibition	-	0.9431	94.31%
CYP2C19 inhibition	-	0.8820	88.20%
CYP2D6 inhibition	-	0.5131	51.31%
CYP1A2 inhibition	-	0.9327	93.27%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9691	96.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6523	65.23%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9781	97.81%
Skin irritation	-	0.8113	81.13%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4506	45.06%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.8287	82.87%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8535	85.35%
Acute Oral Toxicity (c)	II	0.4762	47.62%
Estrogen receptor binding	-	0.7016	70.16%
Androgen receptor binding	-	0.5481	54.81%
Thyroid receptor binding	-	0.5694	56.94%
Glucocorticoid receptor binding	+	0.5496	54.96%
Aromatase binding	-	0.5886	58.86%
PPAR gamma	+	0.6215	62.15%
Honey bee toxicity	-	0.8169	81.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5426	54.26%
Fish aquatic toxicity	-	0.3808	38.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	4000 nM	EC50	PMID: 23880538
CHEMBL237	P41145	Kappa opioid receptor	16000 nM	EC50	PMID: 23880538
CHEMBL233	P35372	Mu opioid receptor	12 nM; 500 nM	Ki; EC50	via Super-PRED; PMID: 23880538

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.08%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	94.59%	83.82%
CHEMBL217	P14416	Dopamine D2 receptor	93.48%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.91%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.86%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.80%	93.99%
CHEMBL236	P41143	Delta opioid receptor	90.64%	99.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.28%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.64%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.46%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.57%	98.95%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	83.25%	98.00%
CHEMBL4208	P20618	Proteasome component C5	82.13%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.57%	89.00%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5284603
• NPASS: NPC66909
• ChEMBL: CHEMBL656
• LOTUS: LTS0249406
• wikiData: Q407535