Mafoprazine

Mafoprazine
Clinical data
Trade names	Mafropan
AHFS/Drugs.com	Monograph
Identifiers
	IUPAC name N-[4-[3-[4-(2-fluorophenyl)piperazin-1-yl]propoxy]-3-methoxyphenyl]acetamide;
CAS Number	80428-29-1 ;
PubChem CID	71241;
ChemSpider	64374 ;
UNII	D7UUO54C6N;
KEGG	C18361 ;
ChEMBL	ChEMBL2105101 ;
CompTox Dashboard (EPA)	DTXSID50230310 ;
Chemical and physical data
Formula	C22H28FN3O3
Molar mass	401.482 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(OCCCN2CCN(CC2)C3=C(F)C=CC=C3)C=CC(NC(C)=O)=C1;
	InChI InChI=1S/C22H28FN3O3/c1-17(27)24-18-8-9-21(22(16-18)28-2)29-15-5-10-25-11-13-26(14-12-25)20-7-4-3-6-19(20)23/h3-4,6-9,16H,5,10-15H2,1-2H3,(H,24,27) ; Key:PHOCQBYGUQPMIB-UHFFFAOYSA-N ;

Mafoprazine is an antipsychotic of the phenylpiperazine class which is used in veterinary medicine.^[1] Intramuscular injections of mafoprazine mesylate are used for the sedation of pigs either on its own,^[2] or in combination with sodium pentobarbital^[3] or thiopental.^[4]

Pharmacology

Mafoprazine
Site	K_i (nM)	Species	Ref
D₂	10.7	Rat	^[5]^[6]
α₁	12.7	Rat	^[5]^[6]
α₂	101.0	Rat	^[5]^[6]

It demonstrates activity as a D₂ dopamine receptor antagonist, an α₁ adrenergic receptor antagonist, and an α₂ adrenergic receptor agonist.^[5]

The affinity of mafoprazine for D₂ dopamine receptors is 6 and 16 times lower than that of chlorpromazine and haloperidol, respectively, but 2 times higher than that of azaperone.^[5]

The K_i for various receptors was determined using rat neuronal receptor binding assays.^{[citation needed]}

History

Mafoprazine was first synthesized in 1988.^[5] It is sold as Mafropan® by DS Pharma Animal Health Co. Ltd., Osaka, Japan.

References

^ "Mafoprazine | Chemical Substance Information". J-GLOBAL. Japan Science and Technology Agency. J-GLOBAL ID: 200907023639364356.
^ Heishima K, Kuo K, Kimura M, Mori T (2019). "Animal Lymphocyte Metaphase Chromosome Preparation". Radiation Cytogenetics. Methods in Molecular Biology. Vol. 1984. pp. 7–22. doi:10.1007/978-1-4939-9432-8_2. ISBN 978-1-4939-9430-4. PMID 31267415. S2CID 195787061.
^ Azizi AF, Miyazaki R, Yumito T, Ohashi Y, Uno S, Miyajima U, et al. (January 2018). "Effect of maternal supplementation with seaweed powder on immune status of liver and lymphoid organs of piglets". The Journal of Veterinary Medical Science. 80 (1): 8–12. doi:10.1292/jvms.17-0537. PMC 5797852. PMID 29142150.
^ Umeyama K, Watanabe K, Watanabe M, Horiuchi K, Nakano K, Kitashiro M, et al. (April 2016). "Generation of heterozygous fibrillin-1 mutant cloned pigs from genome-edited foetal fibroblasts". Scientific Reports. 6 (1): 24413. Bibcode:2016NatSR...624413U. doi:10.1038/srep24413. PMC 4830947. PMID 27074716. S2CID 22352477.
^ ^a ^b ^c ^d ^e ^f Fukuchi I, Kawashima K, Matsuoka Y, Ishida R (May 1988). "Neurochemical study of mafoprazine, a new phenylpiperazine derivative". Japanese Journal of Pharmacology. 47 (1): 51–61. doi:10.1254/jjp.47.51. PMID 3411821. S2CID 13158367.
^ ^a ^b ^c "MAFOPRAZINE". NCATS Inxight Drugs. U.S. National Center for Advancing Translational Sciences (NCATS).

[1] "Mafoprazine | Chemical Substance Information". J-GLOBAL. Japan Science and Technology Agency. J-GLOBAL ID: 200907023639364356.

[2] Heishima K, Kuo K, Kimura M, Mori T (2019). "Animal Lymphocyte Metaphase Chromosome Preparation". Radiation Cytogenetics. Methods in Molecular Biology. Vol. 1984. pp. 7–22. doi:10.1007/978-1-4939-9432-8_2. ISBN 978-1-4939-9430-4. PMID 31267415. S2CID 195787061.

[3] Azizi AF, Miyazaki R, Yumito T, Ohashi Y, Uno S, Miyajima U, et al. (January 2018). "Effect of maternal supplementation with seaweed powder on immune status of liver and lymphoid organs of piglets". The Journal of Veterinary Medical Science. 80 (1): 8–12. doi:10.1292/jvms.17-0537. PMC 5797852. PMID 29142150.

[4] Umeyama K, Watanabe K, Watanabe M, Horiuchi K, Nakano K, Kitashiro M, et al. (April 2016). "Generation of heterozygous fibrillin-1 mutant cloned pigs from genome-edited foetal fibroblasts". Scientific Reports. 6 (1): 24413. Bibcode:2016NatSR...624413U. doi:10.1038/srep24413. PMC 4830947. PMID 27074716. S2CID 22352477.

[F1988-5] ^ ^a ^b ^c ^d ^e ^f Fukuchi I, Kawashima K, Matsuoka Y, Ishida R (May 1988). "Neurochemical study of mafoprazine, a new phenylpiperazine derivative". Japanese Journal of Pharmacology. 47 (1): 51–61. doi:10.1254/jjp.47.51. PMID 3411821. S2CID 13158367.

[drugsncats-6] "MAFOPRAZINE". NCATS Inxight Drugs. U.S. National Center for Advancing Translational Sciences (NCATS).

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