Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/08/25 11:15:57」(JST)

wiki en

Oxamniquine is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine is a potent single-dose agent for treatment of S. mansoni infection in man, and it causes worms to shift from the mesenteric veins to the liver, where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs.^[1]

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.^[2]

Medical uses

Oxamniquine is used for treatment of schistosomiasis. According to one systematic review, it is equally effective as praziquantel for treating S. mansoni infections.^{[citation needed]}

Contraindications

Oxamniquine should not be taken during pregnancy.^{[citation needed]}

Side effects

It is generally well tolerated following oral doses. Dizziness with or without drowsiness occurs in at least a third of patients, beginning up to three hours after a dose, and usually lasts for up to six hours. Headache and gastrointestinal effects, such as nausea, vomiting, and diarrhoea, are also common.

Allergic-type reactions, including urticaria, pruritic skin rashes, and fever, may occur. Liver enzyme values have been raised transiently in some patients. Epileptiform convulsions have been reported, especially in patients with a history of convulsive disorders. Hallucinations and excitement have occurred rarely.

A reddish discoloration of urine, probably due to a metabolite of oxamniquine, has been reported.

Pharmacokinetics

Peak plasma concentrations are achieved one to three hours after a dose, and the plasma half-life is 1.0 to 2.5 hours.

It is extensively metabolised to inactive metabolites, principally the 6-carboxy derivative, which are excreted in the urine. About 70% of a dose of oxamniquine is excreted as the 6-carboxy metabolite within 12 hours of a dose; traces of the 2-carboxy metabolite have also been detected in the urine.

Mode of action

Oxamniquine is a semisynthetic tetrahydroquinoline and possibly acts by DNA binding, resulting in contraction and paralysis of the worms and eventual detachment from terminal venules in the mesentry, and death. Its biochemical mechanisms are hypothesized to be related to an anticholinergic effect, which increases the parasite’s motility, as well as to synthesis inhibition of nucleic acids. Oxamniquine acts mainly on male worms, but also induces small changes on a small proportion of females. Like praziquantel, it promotes more severe damage of the dorsal tegument than of the ventral surface. The drug causes the male worms to shift from the mesenteric circulation to the liver, where the cellular host response causes its final elimination. The changes caused in the females are reversible and are due primarily to the discontinued male stimulation rather than the direct effect of oxamniquine.

History

Oxamniquine was first described by Kaye and Woolhouse in 1972 as a metabolite of the compound UK 3883 (2-isopropylaminomethyl-6-methyl-7-nitro-1,2,3,4-tetrahydroquinoline). Initially, it was prepared by microbiological hydroxylation in the presence of the fungus Aspergillus sclerotiorum. In 1979, Pfizer at Sandwich was presented with the Queen's Award for Technological Achievement in recognition of the outstanding contribution made to tropical medicine by MANSIL (oxamniquine).

Brand names

Vansil; (Pfizer) 250 mg capsules, syrup 250 mg/5 mL
Mansil; 250 mg Tablets

References

^ Martidale, The Extra Pharmacopoeia, 31st ed, p121
^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

AHFS Database

External links

Drugs.com
Schistosomiasis treatment

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 駆虫薬療法 anthelminthic therapies
2. 住血吸虫症の治療および予防 treatment and prevention of schistosomiasis
3. 非肝硬変性門脈圧亢進症 noncirrhotic portal hypertension

English Journal

Efficient linkage mapping using exome capture and extreme QTL in schistosome parasites.

Chevalier FD, Valentim CL, LoVerde PT, Anderson TJ1.
BMC genomics.BMC Genomics.2014 Jul 21;15:617. doi: 10.1186/1471-2164-15-617.
BACKGROUND: Identification of parasite genes that underlie traits such as drug resistance and host specificity is challenging using classical linkage mapping approaches. Extreme QTL (X-QTL) methods, originally developed by rodent malaria and yeast researchers, promise to increase the power and simpl
PMID 25048426

Schistosomiasis control: praziquantel forever?

Cioli D1, Pica-Mattoccia L2, Basso A3, Guidi A4.
Molecular and biochemical parasitology.Mol Biochem Parasitol.2014 Jun;195(1):23-9. doi: 10.1016/j.molbiopara.2014.06.002. Epub 2014 Jun 21.
Since no vaccine exists against schistosomiasis and the molluscs acting as intermediate hosts are not easy to attack, chemotherapy is the main approach for schistosomiasis control. Praziquantel is currently the only available antischistosomal drug and it is distributed mainly through mass administra
PMID 24955523

Japanese Journal

Oxamniquine cures Schistosoma mansoni infection in a focus in which cure rates with praziquantel are unusually low

STELMA FF.
J Infect Dis 176, 304-307, 1997
NAID 30041940481

Effect of praziquantel and oxamniquine treatment on human isotype responses to Schistosoma mansoni : elevated IgE to adult worm

WEBSTER M
Parasite Immunol 19, 333-335, 1997
NAID 30014502395

Related Pictures

★リンクテーブル★

リンク元	「駆虫薬」「オキサムニキン」「オキサムニクイン」

「駆虫薬」

Oxamniquine
Systematic (IUPAC) name
	(RS)-1,2,3,4-Tetrahydro-2-isopropylaminomethyl-7-nitro-6-quinolylmethanol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	It is not known whether it will harm an unborn baby (FDA Pregnancy Category C);
Routes of; administration	oral
Legal status
Legal status	Not commercially available in the United States;
Pharmacokinetic data
Bioavailability	Readily absorbed after oral doses
Metabolism	hepatic
Biological half-life	1 to 2.5h
Excretion	mainly in urine
Identifiers
CAS Number	21738-42-1
ATC code	P02BA02 (WHO) QP52AA02 (WHO)
PubChem	CID 4612
DrugBank	DB01096
ChemSpider	4451
UNII	0O977R722D
KEGG	D00460
ChEBI	CHEBI:7819
ChEMBL	CHEMBL847
PDB ligand ID	OAQ (PDBe, RCSB PDB)
Chemical data
Formula	C14H21N3O3
Molar mass	279.3
Chirality	Racemic mixture
	SMILES [O-][N+](=O)c1c(cc2c(c1)NC(CC2)CNC(C)C)CO ;
	InChI InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3 ; Key:XCGYUJZMCCFSRP-UHFFFAOYSA-N ;
(what is this?) (verify)

　　[★]

英: anthelmintic, anthelmintics
ラ: anthelmintica
関

http://en.wikipedia.org/wiki/Anthelmintic

antiplatyhelmintic agents	Antitrematodals (schistosomicides)	binds tubulin	benzimidazole (Triclabendazole#)
		acetylcholinesterase inhibitor	phosphonic acid (metrifonate)
		Other/unknown	quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen)
	anticestodals (taeniacides)	binds tubulin	benzimidazole (albendazole#)
	anticestodals (taeniacides)	Other/unknown	salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen)
antinematodal agents (macrofilaricides)		binds tubulin	benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole)
		chloride channel	macrolide (ivermectin#)
		NMDA	tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel)
		Other/unknown	piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine