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Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O6.C11H14N2S
Molecular Weight 594.677
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PYRANTEL PAMOATE

SMILES

CN1CCCN=C1\C=C\C2=CC=CS2.OC(=O)C3=CC4=C(C=CC=C4)C(CC5=C6C=CC=CC6=CC(C(O)=O)=C5O)=C3O

InChI

InChIKey=AQXXZDYPVDOQEE-MXDQRGINSA-N
InChI=1S/C23H16O6.C11H14N2S/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2,4-6,9H,3,7-8H2,1H3/b;6-5+

HIDE SMILES / InChI
Molecular Formula C11H14N2S
Molecular Weight 206.307
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE
Molecular Formula C23H16O6
Molecular Weight 388.3695
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/monograph/pyrantel-pamoate.html

Pyrantel is an anthelmintic, which acts as an agonist of nicotinic receptors (AChRs) of nematodes and exerts its therapeutic effects by depolarizing their muscle membranes. It is used to treat a number of parasitic worm infections. This includes ascariasis, hookworm infections, enterobiasis (pinworm infection), trichostrongyliasis and trichinellosis. Common adverse reactions include diarrhea, nausea, vomiting, dizziness, headache and somnolence.

Originator

Approval Year

1971
86
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Strongid

Approved Use

Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies.

Launch Date

1990
Curative
Approved
8429
Strongid

Approved Use

Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies.

Launch Date

1990
Curative
Approved
8429
Strongid

Approved Use

Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies.

Launch Date

1990
Curative
Approved
8429
Strongid

Approved Use

Pyrantel pamoate is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); large roundworms (Parascaris equorum) and tapeworms (Anoplocephala perfoliata) in horses and ponies.

Launch Date

1990
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.09 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11348490/
13.3 mg/kg single, oral
dose: 13.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRANTEL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.06 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11348490/
13.3 mg/kg single, oral
dose: 13.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRANTEL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.43 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11348490/
13.3 mg/kg single, oral
dose: 13.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRANTEL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A1
349

CYP2C8
693

CYP1A2
1054

CYP2A6
543

CYP1B1
92

CYP2B6
664

CYP2C19
991

CYP2E1
667

CYP3A5
395

CYP4A11
119
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1054
 no
CYP1B1
92
 no
CYP2A6
543
 no
CYP2B6
664
 no
CYP2C19
991
 no
CYP2E1
667
 no
CYP3A4
1737
 no
CYP3A5
395
 no
CYP4A11
119
 no
CYP1A1
349
 yes
CYP2C8
693
 yes
CYP2C9
1037
 yes
CYP2D6
1217
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:8654
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8654
MolPort
MolPort-002-707-681
https://www.molport.com/shop/molecule-link/MolPort-002-707-681
ZINC
ZINC000000097996
http://zinc15.docking.org/substances/ZINC000000097996
PubMed

PubMed

TitleDatePubMed
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
Patents

Patents

CN104292242A
3
US5036069
3
US7001889
3

Sample Use Guides

In Vitro Use Guide
A modified methyl-thiazolyltetrazolium (MTT) reduction assay revealed good in vitro anthelmintic efficacies against Haemonchus contortus infective larvae for pyrantel tartrate at effective dose 0.1 ug/ul – 0.9 ug/ul.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:09:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:05 GMT 2023
Record UNII
81BK194Z5M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRANTEL PAMOATE
GREEN BOOK   MI   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CP 10423-16
Code English
Pyrantel embonate [WHO-DD]
Common Name English
PYRANTEL PAMOATE [GREEN BOOK]
Common Name English
PYRANTEL EMBONATE [EP MONOGRAPH]
Common Name English
CP-10,423-16
Code English
PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-(2-(2-THIENYL)ETHENYL)-, (E)-, COMPD. WITH 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACID) (1:1)
Common Name English
PYRANTEL PAMOATE [VANDF]
Common Name English
PYRANTEL PAMOATE [MI]
Common Name English
CP-10423-18
Code English
PYRANTEL (AS PAMOATE)
Common Name English
PYRANTELI EMBONAS [WHO-IP LATIN]
Common Name English
PYRANTEL EMBONATE
EP   MART.   WHO-DD   WHO-IP  
Common Name English
PYRANTEL PAMOATE [USP-RS]
Common Name English
PYRANTEL EMBONATE [WHO-IP]
Common Name English
CP-10423-16
Code English
(E)-1,4,5,6-TETRAHYDRO-1-METHYL-2-(2-(2-THIENYL)VINYL)PYRIMIDINE 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOATE) (1:1)
Common Name English
NSC-355080
Code English
PYRANTEL PAMOATE [USAN]
Common Name English
PYRANTEL PAMOATE [USP MONOGRAPH]
Common Name English
PYRANTEL PAMOATE [JAN]
Common Name English
PYRANTEL EMBONATE [MART.]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 357.152
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 520.1872
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 520.2043
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 357.180
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 357.150
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 520.2044
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 357.110
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 520.2042
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
CFR 21 CFR 520.2041
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID40897057
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
MERCK INDEX
m9336
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PYRANTEL PAMOATE
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
DAILYMED
81BK194Z5M
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
MESH
D011716
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PYRANTEL PAMOATE
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY Description: A pale yellow or yellow powder. Solubility: Practically insoluble in water and methanol R; soluble in dimethyl sulfoxide R; slightly soluble in dimethylformamide R. Category: Anthelmintic. Storage: Pyrantel embonate should be kept in a well-closed container, protected from light. Definition: Pyrantel embonate contains not less than 98.0% and not more than 102.0% of C11H14N2S,C23H16O6, calculated with reference to the dried substance.
SMS_ID
100000089059
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
RXCUI
8985
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY RxNorm
PUBCHEM
5281033
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
FDA UNII
81BK194Z5M
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-837-1
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
NCI_THESAURUS
C75232
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
NSC
355080
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1626223
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
RS_ITEM_NUM
1584003
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
DRUG BANK
DBSALT001530
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
CAS
22204-24-6
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
EVMPD
SUB04132MIG
Created by admin on Fri Dec 15 15:09:05 GMT 2023 , Edited by admin on Fri Dec 15 15:09:05 GMT 2023
PRIMARY
Related Record Type Details
Structure of PAMOIC ACID
PARENT -> SALT/SOLVATE
Structure of PYRANTEL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1,2-DIMETHYL-
IMPURITY -> PARENT
Structure of PAMOIC ACID
IMPURITY -> PARENT
NO peak value listed in USP-NF
Structure of THIOPHENE-2-CARBOXALDEHYDE
IMPURITY -> PARENT
Structure of PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-((1Z)-2-(2-THIENYL)ETHENYL)-
PARENT -> IMPURITY
Structure of N-(3-METHYLAMINOPROPYL)-2-THIOPHENEACRYLAMIDE
IMPURITY -> PARENT
PEAK VALUE OF 0.2 IN USP-NF
Structure of PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-((1Z)-2-(2-THIENYL)ETHENYL)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of PYRANTEL
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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