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
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+;
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: AChE, Heligmosomoides polygyrus Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780168 |
2.96 µM [IC50] | ||
Target ID: CHEMBL1907587 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19587280 |
60.0 µM [EC50] | ||
Target ID: nAChR, Ascaris suum ACR-16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27995347 |
|||
Target ID: acetylcholine receptors, nematodes |
|||
Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19506073 |
29.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Rumatel Approved UseCattle: 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 Date1994 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780168
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.
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ACTIVE MOIETY
SUBSTANCE RECORD