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- Proguanil
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/29 14:36:44」(JST)
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Proguanil
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| Systematic (IUPAC) name |
| 1-(4-chlorophenyl)-2-(N'-propan-2-ylcarbamimidoyl) guanidine |
| Clinical data |
| Trade names |
Paludrine |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
| Pregnancy cat. |
? |
| Legal status |
? |
| Routes |
Oral |
| Pharmacokinetic data |
| Half-life |
~20 h |
| Identifiers |
| CAS number |
500-92-5 Y |
| ATC code |
P01BB01 |
| PubChem |
CID 4923 |
| DrugBank |
DB01131 |
| ChemSpider |
4754 Y |
| UNII |
S61K3P7B2V Y |
| KEGG |
D08428 Y |
| ChEBI |
CHEBI:8455 Y |
| ChEMBL |
CHEMBL1377 Y |
| Chemical data |
| Formula |
C11H16ClN5 |
| Mol. mass |
253.731 g/mol |
SMILES
- Clc1ccc(NC(=N/C(=N/C(C)C)N)N)cc1
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InChI
-
InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17) Y
Key:SSOLNOMRVKKSON-UHFFFAOYSA-N Y
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Y (what is this?) (verify)
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Proguanil (chlorguanide, chloroguanide) is a prophylactic antimalarial drug.[1][2] When taken, it is converted to the active metabolite cycloguanil. Proguanil is effective against sporozoites. Proguanil hydrochloride is marketed as Paludrine by AstraZeneca.
It has been used for malarial prophylaxis in children with sickle cell disease living in malaria-endemic areas for many years.
Contents
- 1 Mechanism
- 2 Combinations
- 3 Precautions
- 4 References
- 5 External links
Mechanism[edit]
It works by stopping the malaria parasites, Plasmodium falciparum and Plasmodium vivax, from reproducing once they are inside red blood cells, by inhibiting the enzyme dihydrofolate reductase, which catalyzes the formation of tetrahydrofolate, the main one-carbon unit carrier in the body, required for dTMP and purine base synthesis.
Combinations[edit]
Proguanil is usually taken in combination with another antimalarial drug, such as atovaquone[3] (e.g., in the drug Malarone) or chloroquine.[4]
Malarone has fewer side effects than mefloquine, but can be more expensive because it is taken daily.
Proguanil is taken with atovaquone for chloroquine-resistant and multidrug resistant strains of P. falciparum and P. vivax. Proguanil combined with atovaquone is sold under the tradename Malarone (GlaxoSmithKline).
Precautions[edit]
General precautions regarding proguanil involve watching out for feelings of sullenness and anxiety to a level outside the ordinary, when taking it over a period of several months.[citation needed] These may come on gradually and may not be immediately attributable to anything in particular.
References[edit]
- ^ Carrington HC, Crowther AF, Davey DG, Levi AA, Rose FL (1951). "A metabolite of paludrine with high antimalarial activity". Nature 168 (4288): 1080. PMID 14910643.
- ^ Crowther AF, Levi AA (1953). "Proguanil, the isolation of a metabolite with high antimalarial activity". Br J Pharmacol Chemother 8 (1): 93–97. PMID 13066702.
- ^ Sutherland CJ, Laundy M, Price N, et al. (November 2008). "Mutations in the Plasmodium falciparum cytochrome b gene are associated with delayed parasite recrudescence in malaria patients treated with atovaquone-proguanill". Malar. J. 7 (1): 240. doi:10.1186/1475-2875-7-240. PMC 2640403. PMID 19021900.
- ^ Payen C, Monnin L, Pulce C, Descotes J (December 2008). "Bone marrow aplasia following acute poisoning with chloroquine-proguanil". Clin Toxicol (Phila) 46 (10): 1085–7. doi:10.1080/15563650601182925. PMID 19065311.
External links[edit]
- http://healthlink.mcw.edu/article/979237802.html
- Malarone official website
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Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
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Alveo-
late |
Apicom-
plexa |
Conoidasida/
(Coccidiostats) |
| Cryptosporidiosis |
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| Isosporiasis |
- trimethoprim/sulfamethoxazole#
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| Toxoplasmosis |
- pyrimethamine
- sulfadiazine
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|
|
| Aconoidasida |
| Malaria |
Individual
agents |
Hemozoin
inhibitors |
| aminoquinolines |
- (4-): amodiaquine#
- chloroquine#
- (8-): primaquine#
- pamaquine
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|
| 4-methanolquinolines |
- mefloquine#
- quinine#
- quinidine
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| Other |
|
|
|
| Antifolates |
DHFR inhibitors
(antifols) |
- proguanil#
- chlorproguanil
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|
| Sulfonamides |
- sulfadoxine
- sulfamethoxypyrazine
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|
| Coformulation |
- sulfadoxine/pyrimethamine (SP)#
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|
|
Sesquiterpene
lactones |
- artemether#
- artesunate#
- dihydroartemisinin
- artemotil
- artemisinin
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| Other |
- atovaquone (with proguanil as Malarone)
- tetracycline
- doxycycline#
- clindamycin
- pyronaridine
- piperaquine
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Combi-
nations |
| Fixed-dose (coformulated) ACTs |
- artemether/lumefantrine#
- artesunate/amodiaquine (ASAQ)
- artesunate/mefloquine (ASMQ)
- dihydroartemisinin/piperaquine
- artesunate/pyronaridine
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Other combinations
(not co-formulated) |
- artesunate/SP
- artesunate/mefloquine
- quinine/tetracycline
- quinine/doxycycline
- quinine/clindamycin
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| Babesiosis |
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Cilio-
phora |
- Balantidiasis: Tetracycline
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Hetero-
kont |
- Blastocystosis: Metronidazole
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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English Journal
- Artemether-Lumefantrine Compared to Atovaquone-Proguanil as a Treatment for Uncomplicated Plasmodium falciparum Malaria in Travelers.
- Grynberg S1, Lachish T1, Kopel E1, Meltzer E1, Schwartz E2.
- The American journal of tropical medicine and hygiene.Am J Trop Med Hyg.2015 Jan 7;92(1):13-7. doi: 10.4269/ajtmh.14-0249. Epub 2014 Nov 4.
- Atovaquone-proguanil (AP) and artemether-lumefantrine (AL) are both treatments for uncomplicated Plasmodium falciparum malaria, but comparative clinical trials are lacking. We performed a retrospective analysis, comparing treatment failure and fever clearance time in non-immune travelers with uncomp
- PMID 25371188
- Atovaquone Tolerance in Plasmodium falciparum Parasites Selected for High-Level Resistance to a Dihydroorotate Dehydrogenase Inhibitor.
- Guler JL1, White J 3rd1, Phillips MA2, Rathod PK3.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jan;59(1):686-9. doi: 10.1128/AAC.02347-14. Epub 2014 Oct 20.
- Atovaquone is a component of Malarone, a widely prescribed antimalarial combination, that targets malaria respiration. Here we show that parasites with high-level resistance to an inhibitor of dihydroorotate dehydrogenase demonstrate unexpected atovaquone tolerance. Fortunately, the tolerance is dim
- PMID 25331708
- Randomized trial of artesunate-amodiaquine, atovaquone-proguanil, and artesunate-atovaquone-proguanil for the treatment of uncomplicated falciparum malaria in children.
- Tahar R1, Almelli T2, Debue C2, Foumane Ngane V3, Djaman Allico J4, Whegang Youdom S3, Basco LK5.
- The Journal of infectious diseases.J Infect Dis.2014 Dec 15;210(12):1962-71. doi: 10.1093/infdis/jiu341. Epub 2014 Jun 18.
- BACKGROUND: Artemisinin-based combination therapies (ACTs) are recommended for the treatment of acute uncomplicated falciparum malaria in many malaria-endemic countries. Despite the emergence of artemisinin resistance, few alternative non-ACTs, including atovaquone-proguanil, are currently available
- PMID 24943722
Japanese Journal
- Fluvoxamine inhibits the CYP2C19-catalyzed bioactivation of chloroguanide
- Chloroguanide metabolism in relation to the effiency in malaria prophylaxis and the S-mephenytoin oxidation in Tanzanians
Related Links
- Proguanil (chlorguanide, chloroguanide) is a prophylactic antimalarial drug. When taken, it is converted to the active metabolite cycloguanil. Proguanil is effective against sporozoites. Proguanil hydrochloride is marketed as Paludrine by ...
- 6 Jun 2009 ... Anti Malarial Drugs: Chloroguanide (Proguanil). More popularly known as proguanil, this drug was developed by British antimalarial research in 1945. It is a biguanide derivative that is converted to an active metabolite called ...
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