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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2S.C6H8O7
Molecular Weight 412.457
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MORANTEL CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1CCCN=C1\C=C\C2=C(C)C=CS2

InChI

InChIKey=OLOCXIJVDIVAHH-FXRZFVDSSA-N
InChI=1S/C12H16N2S.C6H8O7/c1-10-6-9-15-11(10)4-5-12-13-7-3-8-14(12)2;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,9H,3,7-8H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b5-4+;

HIDE SMILES / InChI
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

1994
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.
Name Type Language
MORANTEL CITRATE
MART.  
Common Name English
EXHELM
Brand Name English
MORANTEL CITRATE [MART.]
Common Name English
PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-((1E)-2-(3-METHYL-2-THIENYL)ETHENYL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
5702276
Created by admin on Sat Dec 16 04:51:03 GMT 2023 , Edited by admin on Sat Dec 16 04:51:03 GMT 2023
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EPA CompTox
DTXSID90219780
Created by admin on Sat Dec 16 04:51:03 GMT 2023 , Edited by admin on Sat Dec 16 04:51:03 GMT 2023
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FDA UNII
VC8Z4SS5QX
Created by admin on Sat Dec 16 04:51:03 GMT 2023 , Edited by admin on Sat Dec 16 04:51:03 GMT 2023
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CAS
69525-81-1
Created by admin on Sat Dec 16 04:51:03 GMT 2023 , Edited by admin on Sat Dec 16 04:51:03 GMT 2023
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SMS_ID
300000023775
Created by admin on Sat Dec 16 04:51:03 GMT 2023 , Edited by admin on Sat Dec 16 04:51:03 GMT 2023
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