U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O6.C12H16N2S
Molecular Weight 608.703
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MORANTEL PAMOATE

SMILES

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

InChI

InChIKey=YYUHRHGRIAUGKT-RCKHEGBHSA-N
InChI=1S/C23H16O6.C12H16N2S/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;1-10-6-9-15-11(10)4-5-12-13-7-3-8-14(12)2/h1-10,24-25H,11H2,(H,26,27)(H,28,29);4-6,9H,3,7-8H2,1-2H3/b;5-4+

HIDE SMILES / InChI

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

Molecular Formula C12H16N2S
Molecular Weight 220.334
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Morantel (1,4,5,6-tetrahydro-1-methyl-2-[2-(3-methyl-2-thienyl)ethenyl pyrimidine) is a tetrahydro-pyrimidine anthelmintic, differing from the related analogue pyrantel by the presence of a methyl group on the thiophene ring. Morantel tartrate, manufactured by Pfizer, Inc., was approved in the United States for use in cattle in 1981, and entered the market in early 1982. Three formulations have been approved in the United States: RUMATEL® Medicated Premix-88; RUMATEL Cattle Wormer Bolus, and PARATECT FLEX™ Diffuser, a sustained release bolus. It is intended to treat roundworms and tapeworms. Morantel is administered in lactating and non lactating cattle as morantel tartrate as a slow-release bolus (11.8 g morantel base per animal) or as a single oral dose of 6 to 7.5 mg morantel base/kg bw and in pigs at a single dose equivalent to 7.5 mg base/kg bw. In sheep, the citrate salt is administered at a single dose equivalent to 5 to 6 mg morantel base/kg bw. Morantel acts as a potent agonist at the acetylcholine receptors on the muscle cells of nematodes. Activation of the acetylcholine receptors induces a prolonged, spastic paralysis of the worms and expulsion from the host. It also been reported to block neurotransmission in vertebrates, to possess nicotine-like properties and to mimic acetylcholine at receptors in autonomic ganglia, adrenal medullae and respiratory tissues. Morantel and its salts are not used in human medicines.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Rumatel

Approved Use

Cattle: For the removal and control of mature gastrointestinal nematode infections of cattle including stomach worms (Haemonchus spp., Ostertagia spp., Trichostrongylus spp.), worms of the small intestine (Cooperia spp., Trichostrongylus spp., Nematodirus spp.), and worms of the large intestine (Oesophagostomum radiatum). Goats: For the removal and control of mature gastrointestinal nematode infections of goats including Haemonchus contortus, Ostertagia (Teladorsagia) circumcincta, and Trichostrongylusaxei.

Launch Date

7.6386238E11
PubMed

PubMed

TitleDatePubMed
The in vitro secretion of acetylcholinesterase by adult stages of Heligmosomoides polygyrus: the effects of broad-spectrum anthelmintics.
2000 Feb
Patents

Patents

Sample Use Guides

Morantel is administered in lactating and non lactating cattle as morantel tartrate as a slow-release bolus (11.8 g morantel base per animal) or as a single oral dose of 6 to 7.5 mg morantel base/kg bw and in pigs at a single dose equivalent to 7.5 mg base/kg bw. In sheep, the citrate salt is administered at a single dose equivalent to 5 to 6 mg morantel base/kg bw.
Route of Administration: Other
When the nematodes (Heligmosomoides polygyrus) were incubated in vitro with morantel (MRT) at concentrations from 1 mM to 10 nM, in RPMI medium for 2 or 6 h and then transferred to a drug-free medium (RPMI medium supplemented with 0.5% BSA) for 24 h or continuously exposed to the drug in supplement-free medium (24 h), the concentration- and time-dependent inhibitory effect on AChE secretion was observed. The concentration inhibiting the secretion of AChE by 50% (IC50) relative to drug-free controls was estimated to be 2.96 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:40 UTC 2023
Edited
by admin
on Fri Dec 15 15:08:40 UTC 2023
Record UNII
J33H52K3OO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MORANTEL PAMOATE
Common Name English
MORANTEL EMBONATE
Common Name English
PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-(2-(3-METHYL-2-THIENYL)VINYL)-, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOATE, (E)-
Common Name English
Code System Code Type Description
FDA UNII
J33H52K3OO
Created by admin on Fri Dec 15 15:08:40 UTC 2023 , Edited by admin on Fri Dec 15 15:08:40 UTC 2023
PRIMARY
SMS_ID
300000023742
Created by admin on Fri Dec 15 15:08:40 UTC 2023 , Edited by admin on Fri Dec 15 15:08:40 UTC 2023
PRIMARY
PUBCHEM
6435816
Created by admin on Fri Dec 15 15:08:40 UTC 2023 , Edited by admin on Fri Dec 15 15:08:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID00174578
Created by admin on Fri Dec 15 15:08:40 UTC 2023 , Edited by admin on Fri Dec 15 15:08:40 UTC 2023
PRIMARY
CAS
20574-52-1
Created by admin on Fri Dec 15 15:08:40 UTC 2023 , Edited by admin on Fri Dec 15 15:08:40 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY