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2D Structure
Also known as: 7187-62-4, Pyrvinum, Pyrvinium (cation), Pyrvinium ion, Pyrvinium cation, Pyrvinum (base)
Molecular Formula
C26H28N3+
Molecular Weight
382.5  g/mol
InChI Key
QMHSXPLYMTVAMK-UHFFFAOYSA-N
FDA UNII
6B9991FLU3

Pyrvinium is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinum's anti-cancer properties are currently under investigation.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(E)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
2.1.2 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
2.1.3 InChI Key
QMHSXPLYMTVAMK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=C(N1C2=CC=CC=C2)C)C=CC3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C
2.1.5 Isomeric SMILES
CC1=CC(=C(N1C2=CC=CC=C2)C)/C=C/C3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C
2.2 Other Identifiers
2.2.1 UNII
6B9991FLU3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Molevac

2. Pamoxan

3. Povanyl

4. Pyrcon

5. Pyrvinium Iodide

6. Pyrvinium Monohydroxide

7. Pyrvinium Pamoate

8. Pyrvinium Pamoate (2:1)

9. Vankin

10. Vanquin

2.3.2 Depositor-Supplied Synonyms

1. 7187-62-4

2. Pyrvinum

3. Pyrvinium (cation)

4. Pyrvinium Ion

5. Pyrvinium Cation

6. Pyrvinum (base)

7. Hsdb 3178

8. Chebi:8687

9. 6b9991flu3

10. 2-[(e)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-n,n,1-trimethylquinolin-1-ium-6-amine

11. Quinolinium, 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1h-pyrrol-3-yl)ethenyl)-1-methyl-

12. Pyrvinium-pamoate

13. Pyrvinium [hsdb]

14. 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1h-pyrrol-3-yl)ethenyl)-1-methylquinolinium

15. Unii-6b9991flu3

16. Chembl1201303

17. Dtxsid2043795

18. Zinc3831401

19. Db06816

20. Quinolinium, 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl)-1-methyl-

21. C07412

22. Ab00053809_02

23. Q264039

24. 2-[(e)-2-(2,5-dimethyl-1-phenyl-pyrrol-3-yl)vinyl]-n,n,1-trimethyl-quinolin-1-ium-6-amine

25. 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1h-pyrrol-3-yl)vinyl)-1-methylquinolinium

26. 6-(dimethylamino)-2-[(e)-2-(2,5-dimethyl-1-phenyl-1h-pyrrol-3-yl)ethenyl]-1-methylquinolinium

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 382.5 g/mol
Molecular Formula C26H28N3+
XLogP35.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Exact Mass382.228322906 g/mol
Monoisotopic Mass382.228322906 g/mol
Topological Polar Surface Area12 Ų
Heavy Atom Count29
Formal Charge1
Complexity552
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anthelmintics; Fluorescent Dyes

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


FOR CONTROL OF PINWORM INFESTATION IN CHILDREN & ADULTS PYRVINIUM PAMOATE IS GIVEN ORALLY IN SINGLE DOSE ... SECOND DOSE SHOULD BE ADMIN 2 WK LATER, TO ELIM WORMS THAT HAVE DEVELOPED FROM OVA INGESTED AFTER FIRST DOSE. /PAMOATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1030


...OCCUPANTS OF ENTIRE HOUSEHOLD MAY BE TREATED RATHER THAN INVESTIGATING EACH MEMBER BY ANAL SWABS. INVESTIGATIONS ON EFFECT OF THIS DRUG ON STRONGYLOIDIASIS HAVE SHOWN PROMISING RESULTS. ... BECAUSE OF STAINING QUALITY OF DRUG, TABLETS SHOULD BE SWALLOWED IMMEDIATELY WITHOUT CHEWING.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1030


PARENTS & PT SHOULD BE INFORMED THAT DRUG WILL COLOR STOOLS BRIGHT RED, & THAT SUSPENSION, IF SPILLED, WILL STAIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1030


For more Therapeutic Uses (Complete) data for PYRVINIUM (7 total), please visit the HSDB record page.


4.2 Drug Warning

VET: ALTHOUGH EQUALLY EFFECTIVE, CHLORIDE FORM IS 4 TIMES AS TOXIC AS PAMOATE FORM. /CHLORIDE; PAMOATE/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 501


A CASE OF ACCIDENTAL PARENTERAL INJECTION OF POVAN IS DESCRIBED.

SILVERMAN ET AL; A CASE OF ACCIDENTAL PARENTERAL INJECTION OF POVAN; TOXICOL APPL PHARMACOL 16 (3): 740 (1970)


4.3 Drug Indication

Pyrvinium was once used in the treatment of pinworm infestations.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pyrvinium is an anthelmintic agent which acts to kill pinworms.


5.2 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)


5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02C - Antinematodal agents

P02CX - Other antinematodals

P02CX01 - Pyrvinium


5.4 Absorption, Distribution and Excretion

Absorption

Pyrvinium is not significantly absorbed from the gastrointestinal tract.


WHEN GIVEN BY ORAL ROUTE, PYRVINIUM PAMOATE IS NOT ABSORBED FROM GI TRACT TO ANY APPRECIABLE EXTENT. /PAMOATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1030


5.5 Mechanism of Action

Pyrvinium is believed to interfere with glucose uptake by pinworms. Pyrvinium is also thought to inhibit mitochondrial respiration complex 1 and suppress the unfolded protein response. It is also believed to supress the Wnt pathway by activating casein kinase 1. These properties have led to the investigation of pyrvinium's activity against cancers like intestinal polyposis.


INHIBITION OF OXYGEN UPTAKE OF ADULT LITOMOSOIDES IS EFFECTED BY...COMPD CONTAINING AMIDINIUM ION SYSTEM, IN WHICH A QUATERNARY NITROGEN IS SEPARATED FROM A TERTIARY NITROGEN BY RESONATING CARBON CHAIN OF ALTERNATING DOUBLE & SINGLE BONDS. THIS RESP INHIBITION IS ASSOC WITH COMPENSATORY INCR IN AEROBIC GLYCOLYSIS. /PAMOATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1029


...ANTHELMINTIC ACTIVITY...IS ASSOC WITH INHIBITION OF RESP IN AEROBES, & INTERFERENCE WITH ABSORPTION OF EXOGENOUS GLUCOSE IN INTESTINAL HELMINTHS. SUCH INTERFERENCE MAY ACCOUNT FOR ANTHELMINTIC EFFECTS OF CYANINES IN TRICHURIASIS & IN OTHER INTESTINAL HELMINTHIASES. /PAMOATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1030