ID: ALA100116

Max Phase: Approved

First Approval: 1967

Molecular Formula: C19H27NO

Molecular Weight: 285.43

Molecule Type: Small molecule

Representations

Synonyms (6): Dl-pentazocine | Pentazocine | NIH-7958 | NSC-107430 | WIN 20,228 | WIN-20228
Synonyms from Alternative Forms(6):

Canonical SMILES:  CC(C)=CCN1CCC2(C)c3cc(O)ccc3CC1C2C

Standard InChI:  InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3

Standard InChI Key:  VOKSWYLNZZRQPF-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: No

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 285.43

Molecular Weight (Monoisotopic): 285.2093

AlogP: 3.88

#Rotatable Bonds: 2

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.42

CX Basic pKa: 9.57

CX LogP: 3.89

CX LogD: 1.99

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: 1.75

References

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

2. Ramaprasad GC, Kalluraya B, Sunil Kumar B, Mallya S.  (2013)  Synthesis of new oxadiazole derivatives as anti-inflammatory, analgesic, and antimicrobial agents,  22  (11): [10.1007/s00044-012-0298-1]

3. WHO Anatomical Therapeutic Chemical Classification, 

4. Bergkemper M, Kronenberg E, Thum S, Börgel F, Daniliuc C, Schepmann D, Nieto FR, Brust P, Reinoso RF, Alvarez I, Wünsch B..  (2018)  Synthesis, Receptor Affinity, and Antiallodynic Activity of Spirocyclic σ Receptor Ligands with Exocyclic Amino Moiety.,  61  (21): [PMID:30350997] [10.1021/acs.jmedchem.8b01183]

5.  (2016)  7  (12): [10.1039/C6MD00441E]

6. Zampieri D, Romano M, Menegazzi R, Mamolo MG..  (2018)  New piperidine-based derivatives as sigma receptor ligands. Synthesis and pharmacological evaluation.,  28  (19): [PMID:30143421] [10.1016/j.bmcl.2018.08.016]

7. Estrada Valencia M, Herrera-Arozamena C, de Andrés L, Pérez C, Morales-García JA, Pérez-Castillo A, Ramos E, Romero A, Viña D, Yáñez M, Laurini E, Pricl S, Rodríguez-Franco MI..  (2018)  Neurogenic and neuroprotective donepezil-flavonoid hybrids with sigma-1 affinity and inhibition of key enzymes in Alzheimer's disease.,  156  [PMID:30025348] [10.1016/j.ejmech.2018.07.026]

8. Unpublished dataset, 

9. Tangherlini G, Kalinin DV, Schepmann D, Che T, Mykicki N, Ständer S, Loser K, Wünsch B..  (2019)  Development of Novel Quinoxaline-Based κ-Opioid Receptor Agonists for the Treatment of Neuroinflammation.,  62  (2): [PMID:30543421] [10.1021/acs.jmedchem.8b01609]

10. Thum S, Schepmann D, Ayet E, Pujol M, Nieto FR, Ametamey SM, Wünsch B..  (2019)  Tetrahydro-3-benzazepines with fluorinated side chains as NMDA and σ₁ receptor antagonists: Synthesis, receptor affinity, selectivity and antiallodynic activity.,  177  [PMID:31129453] [10.1016/j.ejmech.2019.05.034]

11. Abatematteo FS, Majellaro M, Montsch B, Prieto-Díaz R, Niso M, Contino M, Stefanachi A, Riganti C, Mangiatordi GF, Delre P, Heffeter P, Sotelo E, Abate C..  (2023)  Development of Fluorescent 4-[4-(3H-Spiro[isobenzofuran-1,4'-piperidin]-1'-yl)butyl]indolyl Derivatives as High-Affinity Probes to Enable the Study of σ Receptors via Fluorescence-Based Techniques.,  66  (6): [PMID:36919956] [10.1021/acs.jmedchem.2c01227]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification