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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16N2S.C4H6O6
Molecular Weight 370.421
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MORANTEL TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN1CCCN=C1\C=C\C2=C(C)C=CS2

InChI

InChIKey=GGXQONWGCAQGNA-UUSVNAAPSA-N
InChI=1S/C12H16N2S.C4H6O6/c1-10-6-9-15-11(10)4-5-12-13-7-3-8-14(12)2;5-1(3(7)8)2(6)4(9)10/h4-6,9H,3,7-8H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/b5-4+;/t;1-,2-/m.1/s1

HIDE SMILES / InChI

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

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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 15:20:51 UTC 2023
Edited
by admin
on Fri Dec 15 15:20:51 UTC 2023
Record UNII
5WF7E9QC3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MORANTEL TARTRATE
GREEN BOOK   MART.   MI   USAN   USP   USP-RS  
USAN  
Official Name English
NSC-758647
Code English
MORANTEL TARTRATE [MART.]
Common Name English
MORANTEL TARTRATE [USP IMPURITY]
Common Name English
MORANTEL TARTRATE [GREEN BOOK]
Common Name English
SUIMINTH
Brand Name English
(E)-1,4,5,6-Tetrahydro-1-methyl-2-[2-(3-methyl-2-thienyl)vinyl]pyrimidine tartrate (1:1)
Common Name English
MORANTEL HYDROGEN TARTRATE
Common Name English
PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-(2-(3-METHYL-2-THIENYL)ETHENYL)-, (E)-,(R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Common Name English
PARATECT
Brand Name English
MORANTEL TARTRATE [USAN]
Common Name English
MORANTEL TARTRATE [USP-RS]
Common Name English
CP-12009-18
Code English
MORANTEL TARTRATE [MI]
Common Name English
CP-12,009-18
Code English
CP-12-009-18
Code English
MORANTEL TARTRATE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.1450
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
CFR 21 CFR 520.1450C
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
CFR 21 CFR 520.1450A
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
CFR 21 CFR 556.425
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
CFR 21 CFR 558.360
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
CFR 21 CFR 520.1450B
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
Code System Code Type Description
FDA UNII
5WF7E9QC3F
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
RS_ITEM_NUM
1446906
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
SMS_ID
300000023780
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
MERCK INDEX
m7623
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY Merck Index
PUBCHEM
6433951
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID2045575
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
NSC
758647
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL1240978
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
CAS
26155-31-7
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
NCI_THESAURUS
C75222
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
RXCUI
1368899
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY RxNorm
DAILYMED
5WF7E9QC3F
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
247-481-5
Created by admin on Fri Dec 15 15:20:51 UTC 2023 , Edited by admin on Fri Dec 15 15:20:51 UTC 2023
PRIMARY
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ACTIVE MOIETY