PROFILPELAJAR.COM

Oxamniquine
Clinical data
Trade names	Vansil
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	By mouth
ATC code	P02BA02 (WHO) QP52AA02 (WHO);
Pharmacokinetic data
Bioavailability	Readily absorbed when taken by mouth
Metabolism	Liver
Elimination half-life	1 to 2.5h
Excretion	Kidney
Identifiers
	IUPAC name (RS)-1,2,3,4-Tetrahydro-2-isopropylaminomethyl-7-nitro-6-quinolylmethanol;
CAS Number	21738-42-1 ;
PubChem CID	4612;
DrugBank	DB01096 ;
ChemSpider	4451 ;
UNII	0O977R722D;
KEGG	D00460 ;
ChEBI	CHEBI:7819 ;
ChEMBL	ChEMBL847 ;
PDB ligand	OAQ (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3023398 ;
ECHA InfoCard	100.040.491
Chemical and physical data
Formula	C14H21N3O3
Molar mass	279.340 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])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)

Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni.^[1] Praziquantel, however, is often the preferred treatment.^[2] It is given by mouth and used as a single dose.^[2]

Common side effects include sleepiness, headache, nausea, diarrhea, and reddish urine.^[1] It is typically not recommended during pregnancy, if possible.^[1] Seizures may occur and therefore caution is recommended in people with epilepsy.^[1] It works by causing paralysis of the parasitic worms.^[3] It is in the anthelmintic family of medications.^[4]

Oxamniquine was first used medically in 1972.^[5] It is on the World Health Organization's List of Essential Medicines.^[6] It is not commercially available in the United States.^[4] It is more expensive than praziquantel.^[7]

Medical uses

Oxamniquine is used for treatment of schistosomiasis. According to one systematic review, praziquantel is the standard treatment for S. mansoni infections and oxamniquine also appears effective.^[8]

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.^{[citation needed]}

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.^{[citation needed]}

A reddish discoloration of urine, probably due to a metabolite of oxamniquine, has been reported.^{[citation needed]}

Oxamniquine is not recommended during pregnancy.^[1]

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.^{[citation needed]}

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.

Mechanism of action

It 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, 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.^[9]

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 inhibiting the synthesis 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.^{[citation needed]}

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 enzymatic hydroxylation via 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).^{[citation needed]}

Brand names

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

Stereochemistry

Oxamniquine contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1: 1 mixture of ( R ) - and the ( S ) - form:

Enantiomers of oxamniquine
(R)-isomer	(S)-isomer

References

^ ^a ^b ^c ^d ^e World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 94. hdl:10665/44053. ISBN 978-9-2415-4765-9.
^ ^a ^b Fenwick A, Utzinger J (2010). "Helminthic Diseases: Schistosomiasis". In Griffiths J, Maguire JH, Heggenhougen K, Quah SR (eds.). Public Health and Infectious Diseases. Elsevier. p. 351. ISBN 978-0-12-381507-1. Archived from the original on 20 December 2016.
^ Kuhlmann FM, Fleckenstein JM (2016). "Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (4th ed.). Elsevier Health Sciences. p. 1371. ISBN 978-0-7020-6338-1. Archived from the original on 20 December 2016.
^ ^a ^b "Oxamniquine medical facts from Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
^ Jordan P (1985). "Drug Trials: Oxamniquine". Schistosomiasis: The St Lucia Project. CUP Archive. p. 298. ISBN 978-0-521-30312-5. Archived from the original on 10 September 2017.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Chapter 2: Bayer & E. Merck: Discovery and development of praziquantel*: Competing drugs for schistosomiasis treatment". International Strategies for Tropical Disease Treatments: Experiences with Praziquantel. EDM Research Series No. 026. WHO Essential Medicines. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
^ Danso-Appiah A, Olliaro PL, Donegan S, Sinclair D, Utzinger J (February 2013). "Drugs for treating Schistosoma mansoni infection". The Cochrane Database of Systematic Reviews. 2013 (2): CD000528. doi:10.1002/14651858.CD000528.pub2. PMC 6532716. PMID 23450530.
^ Martindale - The extra pharmacopoeia ; [evaluated information on the world's drugs and medicines] (31st ed.). London: Royal Pharmaceutical Society. 1996. p. 121. ISBN 978-0-85369-342-0.

External links

"Oxamniquine". Drugs.com. Archived from the original on 5 March 2016. Retrieved 23 January 2018.
"Schistosomiasis treatment". Institute of Tropical Medicine. Antwerp. Archived from the original on 22 November 2004.

[WHO2008-1] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 94. hdl:10665/44053. ISBN 978-9-2415-4765-9.

[Grif2010-2] Fenwick A, Utzinger J (2010). "Helminthic Diseases: Schistosomiasis". In Griffiths J, Maguire JH, Heggenhougen K, Quah SR (eds.). Public Health and Infectious Diseases. Elsevier. p. 351. ISBN 978-0-12-381507-1. Archived from the original on 20 December 2016.

[3] Kuhlmann FM, Fleckenstein JM (2016). "Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (4th ed.). Elsevier Health Sciences. p. 1371. ISBN 978-0-7020-6338-1. Archived from the original on 20 December 2016.

[CONS2016-4] "Oxamniquine medical facts from Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

[5] Jordan P (1985). "Drug Trials: Oxamniquine". Schistosomiasis: The St Lucia Project. CUP Archive. p. 298. ISBN 978-0-521-30312-5. Archived from the original on 10 September 2017.

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[7] "Chapter 2: Bayer & E. Merck: Discovery and development of praziquantel*: Competing drugs for schistosomiasis treatment". International Strategies for Tropical Disease Treatments: Experiences with Praziquantel. EDM Research Series No. 026. WHO Essential Medicines. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

[pmid23450530-8] Danso-Appiah A, Olliaro PL, Donegan S, Sinclair D, Utzinger J (February 2013). "Drugs for treating Schistosoma mansoni infection". The Cochrane Database of Systematic Reviews. 2013 (2): CD000528. doi:10.1002/14651858.CD000528.pub2. PMC 6532716. PMID 23450530.

[9] Martindale - The extra pharmacopoeia ; [evaluated information on the world's drugs and medicines] (31st ed.). London: Royal Pharmaceutical Society. 1996. p. 121. ISBN 978-0-85369-342-0.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

PROFILPELAJAR.COM

Oxamniquine

Medical uses

Side effects

Pharmacokinetics

Mechanism of action

History

Brand names

Stereochemistry

References

External links

Read other articles:

Huitzilíhuitl

Joko Fitrianto

Domain Satsuma

KZPS

2004 en France

Field hockey at the 2006 Asian Games

Bicara Cinta

Elezioni regionali in Calabria del 1995

List of tallest buildings in Taiwan

Visitazione (Raffaello)

土库曼斯坦总统

Witte Brigade

乌克兰总理

مادة متحللة

Boeing F/A-18E/F Super Hornet

Girl

Venice Preserv'd

Military ranks of the Kingdom of Hungary

قائمة القرون

Diète fédérale