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Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O6.C13H16N2O
Molecular Weight 604.6485
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OXANTEL PAMOATE

SMILES

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

InChI

InChIKey=CCOAINFUFGBHBA-UETGHTDLSA-N
InChI=1S/C23H16O6.C13H16N2O/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;1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2,4-7,10,16H,3,8-9H2,1H3/b;7-6+

HIDE SMILES / InChI

Molecular Formula C13H16N2O
Molecular Weight 216.2789
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.ncbi.nlm.nih.gov/pubmed/7639515 | https://www.ncbi.nlm.nih.gov/pubmed/19506073 | http://parasitipedia.net/index.php?option=com_content&view=article&id=2504&Itemid=2777 | https://www.ncbi.nlm.nih.gov/pubmed/20038616

Oxantel is a narrow-spectrum anthelmintic effective against whipworms in dogs and cats. It is ineffective against other roundworms, flukes, tapeworms or external parasites. Oxantel acts on the nervous system of the worms as inhibitors of acetylcholinesterase. Oxantel, a cholinergic anthelmintic and fumarate reductase inhibitor, significantly inhibited biofilm formation by P. gingivalis and disrupted established biofilms at concentrations below its MIC against planktonic cells. Oxantel was more effective against P. gingivalis in biofilm than metronidazole, a commonly used antibiotic for periodontitis. When oxantel was administrated to human beings for the treatment of trichuriasis, no drug reaction or side effects were reported, and the results of hematologic, biochemical and urinary examinations didn’t reveal any significant drug-related changes.

Originator

Curator's Comment: # Pfizer Inc.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TELOPAR

Approved Use

Oxantel is a narrow-spectrum anthelmintic effective against whipworms in dogs and cats.
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Treatment of multiple intestinal helminthiasis with oxantel and pyrantel.
1978
Efficacy and safety of albendazole plus ivermectin, albendazole plus mebendazole, albendazole plus oxantel pamoate, and mebendazole alone against Trichuris trichiura and concomitant soil-transmitted helminth infections: a four-arm, randomised controlled trial.
2015 Mar
Efficacy and safety of oxantel pamoate in school-aged children infected with Trichuris trichiura on Pemba Island, Tanzania: a parallel, randomised, controlled, dose-ranging study.
2016 Jan
Patents

Sample Use Guides

Dog: 140 mg. One tablet per 7 kg of body weight (20 mg of oxantel per 1 kg of body weight).
Route of Administration: Oral
In Vitro Use Guide
The MIC, MBC and ICs values for Oxantel determined in laboratory-adapted strain NCTC 11639 of H. pylori. MIC=0.94 mM, MBC=0.94 mM, IC50=0.31 mM, IC90=1.04 mM. For the wild-type strain UNSW 10593/5 the MIC and MBC values were 0.47 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:06 UTC 2023
Edited
by admin
on Fri Dec 15 15:26:06 UTC 2023
Record UNII
UPY1D732T0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXANTEL PAMOATE
MI   USAN  
USAN  
Official Name English
(E)-M-(2-(1,4,5,6-TETRAHYDRO-1-METHYL-2-PYRIMIDINYL)VINYL)PHENOL 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOATE) (1:1) (SALT)
Common Name English
TELOPAR
Brand Name English
CP-14445-16
Code English
OXANTEL PAMOATE [MI]
Common Name English
PHENOL, 3-(2-(1,4,5,6-TETRAHYDRO-1-METHYL-2-PYRIMIDINYL)ETHENYL), (E)-, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (1:1) (SALT)
Common Name English
NSC-759296
Code English
CP-14,445-16
Code English
Oxantel embonate [WHO-DD]
Common Name English
OXANTEL EMBONATE [MART.]
Common Name English
OXANTEL EMBONATE
MART.   WHO-DD  
Common Name English
OXANTEL PAMOATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
Code System Code Type Description
EVMPD
SUB184281
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
MERCK INDEX
m8291
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
272-332-6
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
NSC
759296
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
PUBCHEM
5281086
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
SMS_ID
100000170410
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
MESH
C037225
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
CAS
68813-55-8
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
RXCUI
1871176
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
NCI_THESAURUS
C90730
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
FDA UNII
UPY1D732T0
Created by admin on Fri Dec 15 15:26:06 UTC 2023 , Edited by admin on Fri Dec 15 15:26:06 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY