Naloxone

Details

• Internal ID: 4316c49f-7c71-4bd3-bd99-a3fec175a0ee
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• SMILES (Canonical): C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
• SMILES (Isomeric): C=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
• InChI: InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
• InChI Key: UZHSEJADLWPNLE-GRGSLBFTSA-N
• Popularity: 35,724 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 465-65-6
• l-Naloxone
• n-Allylnoroxymorphone
• (-)-Naloxone
• Naloxona
• EN 1530 base
• Naloxonum
• Nalossone
• N-Allyl-noroxymorphone
• DBL Naloxone
• 1-N-Allyl-14-hydroxynordihydromorphinone
• Naloxone Nasal Spray
• 1-N-Allyl-7,8-dihydro-14-hydroxynormorphinone
• l-N-Allyl-14-hydroxynordihydromorphinone
• NSC-70413
• 17-Allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one
• 17-Allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-one
• l-N-Allyl-7,8-dihydro-14-hydroxynormorphinone
• 36B82AMQ7N
• CHEBI:7459
• DTXSID8023349
• N-Allyl-4,5alpha-epoxy-3,14-dihydroxy-6-morphinanon
• 12-Allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4aH-8,9c-iminoethanophenanthro(4,5-bcd)furanone
• Morphinan-6-one, 17-allyl-4,5alpha-epoxy-3,14-dihydroxy-
• Morphinan-6-one, 4,5alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)-
• Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5alpha)-
• 17-allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one
• Normorphinone, N-allyl-7,8-dihydro-14-hydroxy-, (-)-
• DTXCID703349
• (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• Morphinan-6-one, 4,5-alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)-
• (1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
• Abello, Naloxone
• Curamed, Naloxon
• Naloxon ratiopharm
• (1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-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,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-one
• naloxoni hydrochloridum
• Hydrobromide, Naloxone
• RefChem:6051
• MRZ 2593Br
• MRZ 2593 Br
• MRZ 2593-Br
• A06AH04
• Dihydride, Naloxone Hydrochloride
• Hydrochloride Dihydride, Naloxone
• MRZ2593
• V03AB15
• MRZ 2593
• (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-one
• 207-365-7
• Narcan
• Nalossone [DCIT]
• Naloxonum [INN-Latin]
• Naloxona [INN-Spanish]
• HSDB 3279
• Naloxone (INN)
• NIOSH/QD2135000
• RAM-301
• Nalone
• Narcon
• NALOXONE [INN]
• 7,8-Dihydro-N-allyl-14-hydroxynormorphinone
• Naloxone [INN:BAN]
• NSC 70413
• QD21350000
• Normorphinone, 7,8-dihydro-N-allyl-14-hydroxy-
• 17-Allyl-3,14-dihydroxy-4,5-alpha-epoxymorphinan-6-one
• Morphinan-6-one, 17-allyl-3,14-dihydroxy-4,5-alpha-epoxy-
• MLS000069540
• (5alpha)-3,14-dihydroxy-17-prop-2-en-1-yl-4,5-epoxymorphinan-6-one
• [3H]naloxone
• CAS-465-65-6
• MLS000736771
• SMR000058766
• EINECS 207-365-7
• BRN 1089071
• UNII-36B82AMQ7N
• Nyxoid
• [N-allyl-2,3-3H]naloxone
• NCGC00162267-02
• Normorphinone, N-allyl-dihydro-14-hydroxy-
• NALOXONE [HSDB]
• NALOXONE [MI]
• CHEMBL80
• NALOXONE [VANDF]
• NLX
• Prestwick0_000111
• Prestwick1_000111
• Prestwick2_000111
• Prestwick3_000111
• NALOXONE [USP-RS]
• NALOXONE [WHO-DD]
• NALOXONE [EMA EPAR]
• SCHEMBL34284
• BSPBio_000122
• (-)-N-allyl-14-hydroxynordihydroxymorphinan-6-one
• BIDD:GT0110
• SPBio_002061
• NALOXONE [ORANGE BOOK]
• BPBio1_000136
• GTPL1638
• GTPL1676
• SCHEMBL29427581
• BDBM54795
• cid_5464092
• Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5.alpha.)-
• BDBM579486
• HMS2090F20
• US11484525, Compound Naloxone
• Tox21_112006
• (5alpha)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one
• 3,14-dihydroxy-17-(prop-2-en-1-yl)-4,5alpha-epoxymorphinan-6-one
• BDBM50000788
• HY-17417A
• PDSP2_001520
• AKOS016009988
• Tox21_112006_1
• DB01183
• FN61467
• SMP1_000205
• NCGC00024674-02
• NCGC00024674-03
• NCGC00024674-14
• NCGC00274058-01
• 12-Allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4aH-8,9c-iminoethanophenanthro[4,5-bcd]furan-5(6H)-one
• DA-65917
• 4683B
• CS-0012343
• Kloxxado (naloxone hydrochloride nasal spray)
• NS00002914
• C07252
• D08249
• 465N656
• EN300-19748912
• Morphinan-6-one,5.alpha.-epoxy-3,14-dihydroxy-
• Q282902
• (-)-N-ALLYL-14-HYDROXYNORDIHYDROMORPHINONE
• BRD-K67511046-001-02-3
• BRD-K67511046-003-03-7
• BRD-K67511046-003-14-4
• BRD-K67511046-003-15-1
• BRD-K67511046-003-16-9
• 17-ALLYL-4,5A-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE
• (5?)-3,14-Dihydroxy-17-prop-2-en-1-yl-4,5-epoxymorphinan-6-one
• Morphinan-6-one, 17-allyl-4,5alpha-epoxy-3,14-dihydroxy- (8CI)
• Morphinan-6-one,5.alpha.-epoxy-3,14-dihydroxy-17-(2-propenyl)-
• (5alpha)-4,5-Epoxy-3,14-dihydroxy-17-(2-propen-1-yl)morphinan-6-one
• [17-(2,3-3H-2-propenyl)]-4, 5a -epoxy-3,14-dihydroxymorphinan-6-one
• MORPHINAN-6-ONE, 4,5-EPOXY-3,14-DIHYDROXY-17-(2-PROPENYL)-
• Morphinan-6-one,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5.alpha.)-
• 4aH-8,5-bcd]furan-5(6H)-one, N-allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-
• Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5alpha)- (9CI)
• (4R,4aS,7aR,12bS)-3-allyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
• (4R,4aS,7aR,12bS)-4a,9-bis(oxidanyl)-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
• (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
• (naloxone) 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
• (naloxone)4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
• (naloxone)4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
• 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
• 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one (naloxone)
• 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one( Naloxone)
• 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(Naxolone)
• 4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
• 4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(naloxone)C2H2O4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.5706	57.06%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.9857	98.57%
Subcellular localzation	Mitochondria	0.5800	58.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9398	93.98%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9099	90.99%
BSEP inhibitior	-	0.9231	92.31%
P-glycoprotein inhibitior	-	0.9215	92.15%
P-glycoprotein substrate	-	0.8666	86.66%
CYP3A4 substrate	+	0.5846	58.46%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	+	0.5350	53.50%
CYP3A4 inhibition	-	0.9153	91.53%
CYP2C9 inhibition	-	0.9303	93.03%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.7886	78.86%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8770	87.70%
CYP inhibitory promiscuity	-	0.9523	95.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5181	51.81%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9683	96.83%
Skin irritation	-	0.7669	76.69%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5888	58.88%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	1.0000	100.00%
skin sensitisation	-	0.6975	69.75%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8242	82.42%
Acute Oral Toxicity (c)	III	0.6217	62.17%
Estrogen receptor binding	-	0.8681	86.81%
Androgen receptor binding	+	0.5299	52.99%
Thyroid receptor binding	-	0.5341	53.41%
Glucocorticoid receptor binding	+	0.6619	66.19%
Aromatase binding	+	0.5635	56.35%
PPAR gamma	+	0.6057	60.57%
Honey bee toxicity	-	0.7932	79.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.6627	66.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	1.6 nM	IC50	PMID: 16250647
CHEMBL289	P10635	Cytochrome P450 2D6	2000 nM	IC50	via CMAUP
CHEMBL236	P41143	Delta opioid receptor	21.38 nM; 138 nM; 138 nM; 138 nM; 138 nM; 151 nM	Ki; IC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 18039010; PMID: 17451272; PMID: 17388627; PMID: 16989522; PMID: 11585443
CHEMBL237	P41145	Kappa opioid receptor	500 nM; 1.5 nM; 0.25 nM; 75 nM; 49.8 nM	IC50; IC50; Ki; IC50; IC50	via Super-PRED; PMID: 11585443; via Super-PRED; via CMAUP; PMID: 12747782
CHEMBL233	P35372	Mu opioid receptor	0.2188 nM; 1.87 nM; 7.3 nM; 7.3 nM; 7.3 nM; 7.3 nM; 2 nM	Kd; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 24171469; PMID: 18313920; PMID: 17149859; PMID: 17149858; PMID: 14643346; PMID: 11585443
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	10 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.85%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.68%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.19%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.69%	93.99%
CHEMBL217	P14416	Dopamine D2 receptor	93.66%	95.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	91.06%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.73%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.33%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.09%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.04%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.01%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.50%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.00%	100.00%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5284596
• NPASS: NPC201055
• ChEMBL: CHEMBL80
• LOTUS: LTS0111215
• wikiData: Q282902