Pyrvinium

ID: ALA1201303

Chembl Id: CHEMBL1201303

Cas Number: 7187-62-4

PubChem CID: 5281035

Max Phase: Approved

First Approval: 1982

Molecular Formula: C26H28N3+

Molecular Weight: 382.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pyrvinium (cation) | Pyrvinium cation | Pyrvinium hydroxide | Pyrvinium ion | Pyrvinum (base) | PYRVINIUM|7187-62-4|Pyrvinum|pyrvinium (cation)|Pyrvinium ion|Pyrvinium cation|Pyrvinum (base)|CHEBI:8687|HSDB 3178|6B9991FLU3|2-[(E)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine|Quinolinium, 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl)-1-methyl-|pyrvinium-pamoate|PYRVINIUM [HSDB]|6-(Dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yShow More⌵

Synonyms from Alternative Forms(10): Pyrvinium pamoate | Pyrvinium embonate | Pyrvinium (as embonate) | Viprynium embonate | NSC-223622 | Poquil | Povan | Vanquil | Vanquin | Pyrvinium chloride

Canonical SMILES:  Cc1cc(/C=C/c2ccc3cc(N(C)C)ccc3[n+]2C)c(C)n1-c1ccccc1

Standard InChI:  InChI=1S/C26H28N3/c1-19-17-21(20(2)29(19)24-9-7-6-8-10-24)11-13-23-14-12-22-18-25(27(3)4)15-16-26(22)28(23)5/h6-18H,1-5H3/q+1

Standard InChI Key:  QMHSXPLYMTVAMK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1201303

   PYRVINIUM

2. Alternative Forms:

   

   ALA1201303

   3-carboxy-1-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-olate;2-[(E)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
3. 

   ALA1201303

   Pyrvinium Pamoate
4. 

   ALA1201303

   PYRVINIUM CHLORIDE
5. 

   ALA1201303

   CID 73707346
6. 

   ALA1201303

   6-(Dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-YL)vinyl]-1-methylquinolinium iodide
7. 

   ALA1201303

   Pirvinio pamoato

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.53

Molecular Weight (Monoisotopic): 382.2278

AlogP: 5.31

#Rotatable Bonds: 4

Polar Surface Area: 12.05

Molecular Species: NEUTRAL

HBA: 2

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 1.48

CX LogP: 1.41

CX LogD: 1.41

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.03

References

1. Downey AS, Chong CR, Graczyk TK, Sullivan DJ..  (2008)  Efficacy of pyrvinium pamoate against Cryptosporidium parvum infection in vitro and in a neonatal mouse model.,  52  (9): [PMID:18591280] [10.1128/aac.00207-08]

2. Lanier M, Schade D, Willems E, Tsuda M, Spiering S, Kalisiak J, Mercola M, Cashman JR..  (2012)  Wnt inhibition correlates with human embryonic stem cell cardiomyogenesis: a structure-activity relationship study based on inhibitors for the Wnt response.,  55  (2): [PMID:22191557] [10.1021/jm2010223]

3. Unpublished dataset, 

4. WHO Anatomical Therapeutic Chemical Classification, 

5. Obianom ON, Ai Y, Li Y, Yang W, Guo D, Yang H, Sakamuru S, Xia M, Xue F, Shu Y..  (2019)  Triazole-Based Inhibitors of the Wnt/β-Catenin Signaling Pathway Improve Glucose and Lipid Metabolisms in Diet-Induced Obese Mice.,  62  (2): [PMID:30605343] [10.1021/acs.jmedchem.8b01408]

6. Yang W, Li Y, Ai Y, Obianom ON, Guo D, Yang H, Sakamuru S, Xia M, Shu Y, Xue F..  (2019)  Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation.,  62  (24): [PMID:31769984] [10.1021/acs.jmedchem.9b01252]

7.  (2016)  Compositions and methods relating to inhibiting serine hyrdoxymethyltransferase 2 activity, 

8.  (2017)  Synaptojanin-2 inhibitors for use in the treatment of cancer, 

9.  (2015)  Synaptojanin-2 inhibitors and uses thereof, 

10.  (2017)  Methods of preventing tumor metastasis, treating and prognosing cancer and identifying agents which are putative metastasis inhibitors, 

11. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

12. 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]

13. Wen J, Hadden MK..  (2021)  Medulloblastoma drugs in development: Current leads, trials and drawbacks.,  215  [PMID:33636537] [10.1016/j.ejmech.2021.113268]

14. Xiang W, Wang S..  (2022)  Therapeutic Strategies to Target the Androgen Receptor.,  65  (13.0): [PMID:35786895] [10.1021/acs.jmedchem.2c00716]

15. Phull MS, Jadav SS, Gundla R, Mainkar PS..  (2021)  A perspective on medicinal chemistry approaches towards adenomatous polyposis coli and Wnt signal based colorectal cancer inhibitors.,  212  [PMID:33445154] [10.1016/j.ejmech.2020.113149]

16. Liu Z, Wang P, Wold EA, Song Q, Zhao C, Wang C, Zhou J..  (2021)  Small-Molecule Inhibitors Targeting the Canonical WNT Signaling Pathway for the Treatment of Cancer.,  64  (8.0): [PMID:33822624] [10.1021/acs.jmedchem.0c01799]

17. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(6):

• Scientific Literature
• Gene Expression Atlas Compounds
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6