Naltrexone hydrochloride

ID: ALA1201149

Chembl Id: CHEMBL1201149

Cas Number: 16676-29-2

PubChem CID: 5485201

Product Number: N129461B

Max Phase: Approved

First Approval: 1984

Molecular Formula: C20H24ClNO4

Molecular Weight: 341.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Naltrexone hcl | Naltrexone hydrochloride | Trexan | EN-1639A | EN-1639A (AS HYDROCHLORIDE) | Naltrexone hydrochloride|Naltrexone Hcl|16676-29-2|Depade|Trexan|Antaxone|ReVia|Naltrexone (Hydrochloride)|naltrexone.HCl|NIH 8503|CCRIS 1168|EN-1639A|EINECS 240-723-0|UNII-Z6375YW9SF|Z6375YW9SF|N-Cyclopropylmethyl-noroxymorphone hydrochloride|naltrexone monohydrochloride|EN-1639A (AS HYDROCHLORIDE)|17-(Cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-one hydrochloride|MLS000069607|CYTO-205Show More⌵

Trade Names(6): Adepend | Depade | Nalorex | Naltrexone hydrochloride | Opizone | Revia

Canonical SMILES:  Cl.O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C20H23NO4.ClH/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;1H/t15-,18+,19+,20-;/m1./s1

Standard InChI Key:  RHBRMCOKKKZVRY-ITLPAZOVSA-N

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 341.41

Molecular Weight (Monoisotopic): 341.1627

AlogP: 1.53

#Rotatable Bonds: 2

Polar Surface Area: 70.00

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 8.88

CX LogP: 1.36

CX LogD: 0.13

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: 1.72

References

1. Portoghese PS, Garzon-Aburbeh A, Nagase H, Lin CE, Takemori AE..  (1991)  Role of the spacer in conferring kappa opioid receptor selectivity to bivalent ligands related to norbinaltorphimine.,  34  (4): [PMID:1849995] [10.1021/jm00108a008]

2. Ko RP, Gupte SM, Nelson WL..  (1984)  Opioid agonists and antagonists. 6,6-Hydrazi and 6-oximino derivatives of 14-hydroxydihydromorphinones.,  27  (12): [PMID:6389867] [10.1021/jm00378a034]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

5. PubChem BioAssay data set, 

6. Unpublished dataset, 

7. PubChem BioAssay data set, 

8. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

9. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

10. Jiang JB, Hanson RN, Portoghese PS, Takemori AE..  (1977)  Stereochemical studies on medicinal agents. 23. Synthesis and biological evaluation of 6-amino derivatives of naloxone and naltrexone.,  20  (8): [PMID:894682] [10.1021/jm00218a023]

11. British National Formulary (72nd edition), 

12. Unpublished dataset, 

13. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

14. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

15. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

16. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

17. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

18.  (2022)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomis Library 2 (Incucyte),  [10.6019/CHEMBL5058564]

19. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

20. EUbOPEN.  (2023)  GPCR results for EUbOPEN Chemogenomics Library 3,  [10.6019/CHEMBL5209801]

Source

Source(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• CO-ADD antimicrobial screening data
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• Fraunhofer HDAC6