General Information of the Compound
Compound ID
CP0048724
Compound Name
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-bis(oxidanyl)-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
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Synonyms
(-)-Naltrexone
16590-41-3
5S6W795CQM
BRN 3596648
CCRIS 3506
CHEBI:7465
Celupan
Depotrex
EINECS 240-649-9
EN-1639A [AS HYDROCHLORIDE]
HSDB 6750
IBS therapy, Pain Therapeutics
Irritable bowel syndrome therapy, Pain Therapeutics
N-Cyclopropylmethyl-14-hydroxydihydromorphinone
N-Cyclopropylmethylnoroxymorphone
Naltrel
Naltrexona [INN-Spanish]
Naltrexone
Naltrexone (low-dose), Pain Therapeutics
Naltrexone (once-monthly controlled-release, Medisorb), Alkermes
Naltrexone (polymer microcapsule depot, opioid addiction/alcohol dependency), Biotek
Naltrexone (sustained release), DAS
Naltrexone (sustained release), elbion
Naltrexone (transdermal, alcohol/opioid dependence), Syntropharma
Naltrexone Depot
Naltrexone [USAN:INN:BAN]
Naltrexone depot (injectable suspension), DrugAbuse Sciences
Naltrexone depot (injectable suspension), elbion
Naltrexone hydrochloride
Naltrexonum [INN-Latin]
Nemexin
Opioid antagonists (irritable bowel syndrome), Pain Therapeutics
PTI-901
ReVia
UM-792
UNII-5S6W795CQM
Vivitrex
Vivitrol
XR-NTX
naltrexone
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Structure
Formula
C20H23NO4
Molecular Weight
341.407
Canonical SMILES
Oc1ccc2C[C@H]3N(CC4CC4)CC[C@@]45[C@@H](Oc1c24)C(=O)CC[C@@]35O
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InChI
InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
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InChIKey
DQCKKXVULJGBQN-XFWGSAIBSA-N
CAS
16590-41-3
Physicochemical Property
logP
1.5254
Rotatable Bonds
2
Heavy Atom Count
25
Polar Areas
70
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Complexity
25

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 5360515
SID: 14875729
ChEMBL ID
CHEMBL19019
DrugBank ID
DB00704
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00817, Cytochrome P450 2D6
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000023 BTI-Tn-5B1-4 Trichoplusia ni (Cabbage looper)  1
1
IC50 = 1000 nM
   TI
   LI
   LO
   TS
Protein ID: PT01200, Delta-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  16
1
EC50 = 4.4 nM
   TI
   LI
   LO
   TS
2
EC50 = 5.44 nM
   TI
   LI
   LO
   TS
3
EC50 = 21 nM
   TI
   LI
   LO
   TS
4
IC50 = 5.44 nM
   TI
   LI
   LO
   TS
5
IC50 = 130 nM
   TI
   LI
   LO
   TS
6
Ki = 10.8 nM
   TI
   LI
   LO
   TS
7
Ki = 11 nM
   TI
   LI
   LO
   TS
8
Ki = 11.06 nM
   TI
   LI
   LO
   TS
9
Ki = 14 nM
   TI
   LI
   LO
   TS
10
Ki = 16.31 nM
   TI
   LI
   LO
   TS
11
Ki = 25.12 nM
   TI
   LI
   LO
   TS
12
Ki = 38 nM
   TI
   LI
   LO
   TS
13
Ki = 60 nM
   TI
   LI
   LO
   TS
14
Ki = 95.5 nM
   TI
   LI
   LO
   TS
15
Ki = 117 nM
   TI
   LI
   LO
   TS
16
Ki = 117.06 nM
   TI
   LI
   LO
   TS
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  1
1
Ki = 6.31 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  2
1
Ki = 16.31 nM
   TI
   LI
   LO
   TS
2
Ki = 66.8 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 10 nM
2 Ki = 10.8 nM
3 Ki = 11 nM
4 Ki = 95.46 nM
Protein ID: PT01791, Delta-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  2
1
EC50 = 4.4 nM
   TI
   LI
   LO
   TS
2
Ki = 143.5 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  2
1
Ki = 44.7 nM
   TI
   LI
   LO
   TS
2
Ki = 55.7 nM
   TI
   LI
   LO
   TS
Protein ID: PT00983, Kappa-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  15
1
EC50 = 0.81 nM
   TI
   LI
   LO
   TS
2
EC50 = 3.3 nM
   TI
   LI
   LO
   TS
3
IC50 = 1.86 nM
   TI
   LI
   LO
   TS
4
IC50 = 130 nM
   TI
   LI
   LO
   TS
5
IC50 = 200 nM
   TI
   LI
   LO
   TS
6
Ki = 0.19 nM
   TI
   LI
   LO
   TS
7
Ki = 0.25 nM
   TI
   LI
   LO
   TS
8
Ki = 0.4 nM
   TI
   LI
   LO
   TS
9
Ki = 0.81 nM
   TI
   LI
   LO
   TS
10
Ki = 0.9 nM
   TI
   LI
   LO
   TS
11
Ki = 2.99 nM
   TI
   LI
   LO
   TS
12
Ki = 4.4 nM
   TI
   LI
   LO
   TS
13
Ki = 5.15 nM
   TI
   LI
   LO
   TS
14
Ki = 5.28 nM
   TI
   LI
   LO
   TS
15
Ki = 10 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  2
1
Ki = 0.042 nM
   TI
   LI
   LO
   TS
2
Ki = 0.81 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 0.4 nM
2 Ki = 0.9 nM
Protein ID: PT02264, Kappa-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  2
1
EC50 = 0.81 nM
   TI
   LI
   LO
   TS
2
Ki = 1.44 nM
   TI
   LI
   LO
   TS
Protein ID: PT01188, Kappa-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  1
1
Ki = 0.5012 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 0.5 nM
2 Ki = 0.31 nM
3 Ki = 0.373 nM
4 Ki = 0.702 nM
5 Ki = 3.9 nM
6 Ki = 4.71 nM
7 Ki = 6 nM
Protein ID: PT01460, Kappa-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  3
1
Ki = 1.8 nM
   TI
   LI
   LO
   TS
2
Ki = 4.2 nM
   TI
   LI
   LO
   TS
3
Ki = 12.7 nM
   TI
   LI
   LO
   TS
Protein ID: PT02699, Mu-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  6
1
EC50 = 0.16 nM
   TI
   LI
   LO
   TS
2
IC50 = 6.62 nM
   TI
   LI
   LO
   TS
3
Ki = 0.33 nM
   TI
   LI
   LO
   TS
4
Ki = 0.39 nM
   TI
   LI
   LO
   TS
5
Ki = 0.4 nM
   TI
   LI
   LO
   TS
6
Ki = 0.7 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 0.6457 nM
   TI
   LI
   LO
   TS
Protein ID: PT01515, Mu-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  22
1
EC50 = 0.38 nM
   TI
   LI
   LO
   TS
2
EC50 = 16 nM
   TI
   LI
   LO
   TS
3
IC50 = 0.59 nM
   TI
   LI
   LO
   TS
4
IC50 = 2.87 nM
   TI
   LI
   LO
   TS
5
IC50 = 4.1 nM
   TI
   LI
   LO
   TS
6
IC50 = 4.8 nM
   TI
   LI
   LO
   TS
7
IC50 = 8.9 nM
   TI
   LI
   LO
   TS
8
IC50 = 15.5 nM
   TI
   LI
   LO
   TS
9
IC50 = 17 nM
   TI
   LI
   LO
   TS
10
Ki = 0.07 nM
   TI
   LI
   LO
   TS
11
Ki = 0.11 nM
   TI
   LI
   LO
   TS
12
Ki = 0.2 nM
   TI
   LI
   LO
   TS
13
Ki = 0.23 nM
   TI
   LI
   LO
   TS
14
Ki = 0.26 nM
   TI
   LI
   LO
   TS
15
Ki = 0.3 nM
   TI
   LI
   LO
   TS
16
Ki = 0.59 nM
   TI
   LI
   LO
   TS
17
Ki = 0.7 nM
   TI
   LI
   LO
   TS
18
Ki = 0.87 nM
   TI
   LI
   LO
   TS
19
Ki = 1 nM
   TI
   LI
   LO
   TS
20
Ki = 1.15 nM
   TI
   LI
   LO
   TS
21
Ki = 1.995 nM
   TI
   LI
   LO
   TS
22
Ki = 2.71 nM
   TI
   LI
   LO
   TS
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  1
1
Ki = 0.1585 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  5
1
Ki = 0.1995 nM
   TI
   LI
   LO
   TS
2
Ki = 0.2754 nM
   TI
   LI
   LO
   TS
3
Ki = 0.3 nM
   TI
   LI
   LO
   TS
4
Ki = 0.45 nM
   TI
   LI
   LO
   TS
5
Ki = 3.6 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 0.2 nM
2 Ki = 0.34 nM
3 Ki = 0.56 nM
Protein ID: PT01549, Mu-type opioid receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  3
1
Ki = 1.6 nM
   TI
   LI
   LO
   TS
2
Ki = 2 nM
   TI
   LI
   LO
   TS
3
Ki = 2.5 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 0.56 nM
2 Ki = 1.39 nM
Protein ID: PT01360, Nociceptin receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki > 10000 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Naltrexone )
Drug Name Naltrexone
Company Tni biotech; DrugAbuse Sciences; Alkermes Inc
Indication
Alcohol dependence
Approved
Human immunodeficiency virus infection
Phase 4
Drug 2 ( Naltrexone )
Drug Name Naltrexone
Indication
Chronic alcoholism
Approved
Coronavirus Disease 2019 (COVID-19)
Phase 2