primaquine

プリマキン

　

WordNet

1. synthetic antimalarial drug

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/02 13:34:10」(JST)

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Primaquine

Systematic (IUPAC) name
(RS)-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a607037
Pregnancy cat.	?
Legal status	US: ℞-only Unlicensed (UK)
Routes	Oral
Pharmacokinetic data
Bioavailability	96%
Metabolism	Liver
Half-life	6 hours
Excretion	?
Identifiers
CAS number	90-34-6 Y
ATC code	P01BA03
PubChem	CID 4908
DrugBank	DB01087
ChemSpider	4739 Y
UNII	MVR3634GX1 Y
KEGG	D08420 Y
ChEBI	CHEBI:8405 Y
ChEMBL	CHEMBL506 Y
Chemical data
Formula	C15H21N3O
Mol. mass	259.347 g/mol
SMILES O(c1cc(NC(C)CCCN)c2ncccc2c1)C
InChI InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3 Y Key:INDBQLZJXZLFIT-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Primaquine (or primaquine phosphate) is a medication used in the treatment of malaria and Pneumocystis pneumonia. It is a member of the 8-aminoquinoline group of drugs that includes tafenoquine and pamaquine.

Primaquine was first synthesised by Robert Elderfield of Columbia University in the 1940s. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Medical uses

Primaquine is mainly used to treat P. vivax or P. ovale malaria, specifically to clear the dormant liver forms of these parasites (hypnozoites) once the parasite has been eliminated from the bloodstream. This requires a 14 day course of primaquine. The process of clearing the hypnozoites is termed radical cure (as opposed to simply clearing the blood of parasites). If primaquine is not administered to patients with proven P. vivax or P. ovale infection, there is a very high likelihood of relapse within weeks or months (sometimes years). The interaction between primaquine and quinine or chloroquine is thought to improve the rate of radical cure. It is not known if other antimalarials such as mefloquine are likewise able to potentiate the effect of primaquine.

Interruption of transmission

A single dose of primaquine has rapid and potent gametocytocidal activity against the most mature gametocytes (stage V) of Plasmodium falciparum, a property not held by other commonly used antimalarials which have actions against earlier gametocyte stages. This leads to a rapid reduction in transmission, and primaquine given at the same time as treatment for the asexual blood stage P. falciparum is likely to be useful in controlling P. falciparum malaria in areas of low transmission. The WHO has recommended that a single dose of primaquine (0.25 mg/kg) is safe to give (even in individuals with G6PD deficiency), for the purpose of preventing transmission of falciparum malaria.

Prevention

Primaquine is not routinely used to prevent malaria in travelers, but can be used in individuals without G6PD deficiency when other alternatives are inappropriate. In areas where vivax malaria is more prevalent than falciparum malaria, primaquine may be more effective than doxycycline or mefloquine.

Pneumocystis pneumonia

Primaquine is also used in the treatment of Pneumocystis pneumonia (PCP), a fungal infection commonly occurring in people with AIDS and, more rarely, in those taking immunosuppressive drugs. To treat PCP effectively it is usually combined with clindamycin.

Adverse reactions

Common side effects of primaquine administration include nausea, vomiting and stomach cramps. Other known adverse effects that occasionally occur are headache, visual disturbances and intense itching.

The most dangerous adverse effect of primaquine is hemolysis in patients with G6PD deficiency (Africans or Caucasians of Mediterranean descent). This is associated with the administration of large doses over several days and can be fatal, although the number of reports remains small.

Primaquine causes methemoglobinemia in all patients who take it (levels of up to 18% are reported, normal level is <1%), but this seldom causes symptoms and is always self-limiting. There may be an association with NADH methemoglobin reductase deficiency.

Contraindications

In broad terms, primaquine should not be administered to anyone with glucose-6-phosphate dehydrogenase deficiency because there can be a severe reaction resulting in hemolytic anemia. However, the WHO has recommended that a single dose of primaquine (0.25 mg/kg) is safe to give even in individuals with G6PD deficiency, for the purpose of preventing transmission of falciparum malaria.

Primaquine is contraindicated in pregnancy, because the glucose-6-phosphate dehydrogenase status of the fetus would be unknown.

The packaging label states that primaquine should not be given to patients with systemic lupus erythematosus or rheumatoid arthritis, but the rationale behind this is questionable.

Dosing

Primaquine doses are always expressed as base, not as salt (15 mg base=26.3 mg phosphate salt).

Manufacturing and availability

Primaquine was first tested on humans during the Stateville Penitentiary Malaria Study in 1944. Primaquine was licensed for use in the USA by the FDA in 1952 and is available as a generic drug from a variety of manufacturers.

Primaquine is not licensed for use in the United Kingdom. It is available on a named patient basis only from certain pharmaceutical providers. Primaquine tablets available in the UK contain 7.5 mg primaquine base (13.2 mg phosphate salt). Primaquine tablets available in the U.S. contain 15 mg base (26.3 mg phosphate salt).

Veterinary use

Primaquine is the drug of choice for treating Feline Babesiosis

Appearance in the media

This was a plot point in the M*A*S*H episode "The Red/White Blues", in which Lebanese-American Max Klinger and Jewish-American Orderly Goldman developed anemia while taking primaquine, confusing the doctors who thought it was only a possibility if the person were black.

References

External links

• National Institute of Health
• AIDS Education Global Information System

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. 抗マラリア剤：概要 antimalarial drugs an overview
• 2. 旅行者におけるマラリア感染の予防 prevention of malaria infection in travelers
• 3. HIV感染患者におけるニューモシスチス感染の治療 treatment of pneumocystis infection in hiv infected patients
• 4. 非HIV感染患者におけるニューモシスチス肺炎の治療および予防 treatment and prevention of pneumocystis pneumonia in non hiv infected patients
• 5. HIV感染患者におけるニューモシスチス感染の予防 prophylaxis against pneumocystis infection in hiv infected patients

English Journal

• Efficacy and safety of atovaquone-proguanil in treating imported malaria in Japan: The second report from the research group.

• Kimura M, Koga M, Kikuchi T, Miura T, Maruyama H.SourceDepartment of Internal Medicine, Shin-Yamanote Hospital, Japan Anti-Tuberculosis Association, Tokyo, Japan.
• Parasitology international.Parasitol Int.2012 Sep;61(3):466-9. Epub 2012 Mar 29.
• Malaria remains an important health risk among travelers to tropical/subtropical regions. However, in Japan, only 2 antimalarials are licensed for clinical use - oral quinine and mefloquine. The Research Group on Chemotherapy of Tropical Diseases introduced atovaquone-proguanil in 1999, and reported
• PMID 22484597

• Extrahepatic exoerythrocytic forms of rodent malaria parasites at the site of inoculation: clearance after immunization, susceptibility to primaquine, and contribution to blood-stage infection.

• Voza T, Miller JL, Kappe SH, Sinnis P.SourceDepartment of Medical Parasitology, New York University School of Medicine, New York, New York, USA.
• Infection and immunity.Infect Immun.2012 Jun;80(6):2158-64. Epub 2012 Mar 19.
• Plasmodium sporozoites are inoculated into the skin of the mammalian host as infected mosquitoes probe for blood. A proportion of the inoculum enters the bloodstream and goes to the liver, where the sporozoites invade hepatocytes and develop into the next life cycle stage, the exoerythrocytic, or li
• PMID 22431651

Japanese Journal

• Evidence of the formation of direct covalent adducts of primaquine, 2-tert-butylprimaquine (NP-96) and monohydroxy metabolite of NP-96 with glutathione and N-acetylcysteine

• GARG Amit,PRASAD Bhagwat,TAKWANI Hardik,JAIN Meenakshi,JAIN Rahul,SINGH Saranjit
• Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 879(1), 1-7, 2011-01-01
• NAID 10029025087

• In vitro effect of current antimalarial drugs on the survival of paired Schistosoma mansoni adult worms and their egg production

• MITSUI Yoshinori,AOKI Yoshiki
• Tropical medicine and health 38(2), 69-73, 2010-06-01
• NAID 10026955873

Related Links

• Primaquine: MedlinePlus Drug Information - National Library ...

Primaquine is used alone or with another medication to treat malaria (a serious infection that is spread by mosquitoes in certain parts of the world and can cause death) and to prevent the disease from coming back in ...

• primaquine [PharmGKB]

PharmGKB contains no dosing guidelines for this drug/small molecule. To report known genotype-based dosing guidelines, or if you are interested in developing ... PharmGKB gathers information regarding PGx on FDA drug labels ...

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「プリマキン」

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primaquine

商品名

• プリマキン

会社名

• サノフィ

成分

• プリマキンリン酸塩

薬効分類

• 抗マラリア剤

薬効

• 三日熱マラリア及び卵形マラリアを効能・効果とする新有効成分含有医薬品

「G6PD deficiency primaquine and」

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Glucose-6-phosphate dehydrogenase deficiency