PYRIMETHAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H13ClN4
Molecular Weight	248.711
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C(C(N)=NC(N)=N1)C2=CC=C(Cl)C=C2

InChI

InChIKey=WKSAUQYGYAYLPV-UHFFFAOYSA-N

InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)

HIDE SMILES / InChI

Molecular Formula	C12H13ClN4
Molecular Weight	248.711
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9554869

Pyrimethamine, sold under the trade name Daraprim, is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. In addition it was approved in Chemoprophylaxis of Malaria. However, resistance to pyrimethamine is prevalent worldwide. It is not suitable as a prophylactic agent for travelers to most areas. Pyrimethamine is well absorbed with peak levels occurring between 2 to 6 hours following administration. It is eliminated slowly and has a plasma half-life of approximately 96 hours. Pyrimethamine is 87% bound to human plasma proteins. Pyrimethamine acts by selectively inhibiting malarial dihydrofolate reductase-thymidylate synthase and the rationale for its therapeutic action is based on the differential requirement between host and parasite for nucleic acid precursors involved in growth. This activity is highly selective against plasmodia and Toxoplasma gondii. Pyrimethamine possesses blood schizonticidal and some tissue schizonticidal activity against malaria parasites of humans. The action of pyrimethamine against Toxoplasma gondii is greatly enhanced when used in conjunction with sulfonamides.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydrofolate reductase 56 Target ID: CHEMBL1939 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9554869	Inhibitor 8228		1.5 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Toxoplasmosis 12 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Curative	Approved 8360	DARAPRIM Approved Use Treatment of Toxoplasmosis: DARAPRIM is indicated for the treatment of toxoplasmosis when used conjointly with a sulfonamide, since synergism exists with this combination. Treatment of Acute Malaria: DARAPRIM is also indicated for the treatment of acute malaria. It should not be used alone to treat acute malaria. Fast-acting schizonticides such as chloroquine or quinine are indicated and preferable for the treatment of acute malaria. However, conjoint use of DARAPRIM with a sulfonamide (e.g., sulfadoxine) will initiate transmission control and suppression of susceptible strains of plasmodia. Chemoprophylaxis of Malaria: DARAPRIM is indicated for the chemoprophylaxis of malaria due to susceptible strains of plasmodia. However, resistance to pyrimethamine is prevalent worldwide. It is not suitable as a prophylactic agent for travelers to most areas. Launch Date -5.34556803E11
Acute malaria 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Curative	Approved 8360	DARAPRIM Approved Use Treatment of Toxoplasmosis: DARAPRIM is indicated for the treatment of toxoplasmosis when used conjointly with a sulfonamide, since synergism exists with this combination. Treatment of Acute Malaria: DARAPRIM is also indicated for the treatment of acute malaria. It should not be used alone to treat acute malaria. Fast-acting schizonticides such as chloroquine or quinine are indicated and preferable for the treatment of acute malaria. However, conjoint use of DARAPRIM with a sulfonamide (e.g., sulfadoxine) will initiate transmission control and suppression of susceptible strains of plasmodia. Chemoprophylaxis of Malaria: DARAPRIM is indicated for the chemoprophylaxis of malaria due to susceptible strains of plasmodia. However, resistance to pyrimethamine is prevalent worldwide. It is not suitable as a prophylactic agent for travelers to most areas. Launch Date -5.34556803E11
Malaria 94 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Preventing	Approved 8360	DARAPRIM Approved Use Treatment of Toxoplasmosis: DARAPRIM is indicated for the treatment of toxoplasmosis when used conjointly with a sulfonamide, since synergism exists with this combination. Treatment of Acute Malaria: DARAPRIM is also indicated for the treatment of acute malaria. It should not be used alone to treat acute malaria. Fast-acting schizonticides such as chloroquine or quinine are indicated and preferable for the treatment of acute malaria. However, conjoint use of DARAPRIM with a sulfonamide (e.g., sulfadoxine) will initiate transmission control and suppression of susceptible strains of plasmodia. Chemoprophylaxis of Malaria: DARAPRIM is indicated for the chemoprophylaxis of malaria due to susceptible strains of plasmodia. However, resistance to pyrimethamine is prevalent worldwide. It is not suitable as a prophylactic agent for travelers to most areas. Launch Date -5.34556803E11

C_max

Value	Dose	Co-administered	Analyte	Population
2.059 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8726001	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Zidovudine	Zidovudine	PYRIMETHAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
502.9 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8726001	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Zidovudine	Zidovudine	PYRIMETHAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
190.56 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8726001	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Zidovudine	Zidovudine	PYRIMETHAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
13% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/8578s15lbl.pdf			PYRIMETHAMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1.625 g single, oral Overdose Dose: 1.625 g Route: oral Route: single Dose: 1.625 g Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	healthy, 1 n = 1 Health Status: healthy Age Group: 1 Sex: M Population Size: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	Disc. AE: Vomiting, Convulsions... AEs leading to discontinuation/dose reduction: Vomiting Convulsions (severe) Cyanosis Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19
625 mg single, oral Overdose Dose: 625 mg Route: oral Route: single Dose: 625 mg Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	healthy, 1 n = 1 Health Status: healthy Age Group: 1 Population Size: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	Disc. AE: Convulsions, Respiratory failure... AEs leading to discontinuation/dose reduction: Convulsions Respiratory failure (grade 5) Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19
1.2 g single, oral Overdose Dose: 1.2 g Route: oral Route: single Dose: 1.2 g Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	Disc. AE: Cyanosis, Vomiting... AEs leading to discontinuation/dose reduction: Cyanosis Vomiting (severe) Convulsions Apnoea Haematemesis Cardiac failure (grade 5) Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19
400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: F Population Size: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	Disc. AE: Convulsions, Vomiting... AEs leading to discontinuation/dose reduction: Convulsions (severe) Vomiting Cyanosis Collapse Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19
625 mg single, oral Overdose Dose: 625 mg Route: oral Route: single Dose: 625 mg Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	healthy, 3 n = 1 Health Status: healthy Age Group: 3 Sex: F Population Size: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19	Disc. AE: Convulsions, Unconsciousness... AEs leading to discontinuation/dose reduction: Convulsions (grade 5) Unconsciousness (grade 5) Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1 Page: p.19
300 mg single, oral (min) Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.3	unhealthy Health Status: unhealthy Condition: Toxoplasmosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.3	Disc. AE: Convulsions, Abdominal pain... AEs leading to discontinuation/dose reduction: Convulsions Abdominal pain Nausea Vomiting (severe) Excitability Respiratory depression (grade 5) Circulatory collapse (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.3
75 mg 1 times / day multiple, oral (max) Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.2	unhealthy Health Status: unhealthy Condition: Toxoplasmosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.2	Disc. AE: Folate deficiency... AEs leading to discontinuation/dose reduction: Folate deficiency Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf Page: p.2

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579 activator 77	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 901 CYP1A2 1509 CYP2C19 1463 ALDH1 40 MATE1 304 OCT1 506 OCT2 638 BSEP 401 OATP1B1 781 OATP1B3 700	MRP5 40	CYP1A 56

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	inconclusive [Activation 10 uM]
ALDH1 40	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	inconclusive [Activation 39.8107 uM]
CYP3A4 1909	activator 210 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation 5.0119 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation 7.9433 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation >10 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	no [Activation >10 uM]
CYP1A 121	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12451431/	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	no
BSEP 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	weak [IC50 200.1 uM]
MATE1 306	inhibitor 3240 Sources: https://go.drugbank.com/drugs/DB00205, https://pubmed.ncbi.nlm.nih.gov/28971610/	yes [IC50 0.131 uM]
OCT1 523	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/31427432/	yes [IC50 1.8 uM]
OCT2 639	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/28971610/	yes [IC50 4.55 uM]
CYP2C8 955	inhibitor 3240 Sources: https://go.drugbank.com/drugs/DB00205, https://pubmed.ncbi.nlm.nih.gov/26721703/	yes [IC50 45.1 uM]
OATP1B1 796	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 709	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
MRP5 40	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/12869626/	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8673	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8673
ChemicalBook	CB8461315	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8461315
MolPort	MolPort-001-783-655	https://www.molport.com/shop/molecule-link/MolPort-001-783-655
Selleck Chemicals	Pyrimethamine	http://www.selleckchem.com/products/Pyrimethamine.html
ZINC	ZINC000000057464	http://zinc15.docking.org/substances/ZINC000000057464
eMolecules	511729	https://www.emolecules.com/cgi-bin/more?vid=511729

PubMed

Title	Date	PubMed

[Pyrimethamine-induced megaloblatic anemia in florid toxoplasmosis].	1976 Feb 13	1256293
In vivo assessment of antimicrobial agents against Toxoplasma gondii by quantification of parasites in the blood, lungs, and brain of infected mice.	1990 Aug	2221854
Pneumocystis carinii dihydrofolate reductase used to screen potential antipneumocystis drugs.	1991 Jul	1929292
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
The effect of artesunate combined with standard antimalarials against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum in vitro.	1999 Jul-Aug	10674097
Anti-toxoplasma activities of antiretroviral drugs and interactions with pyrimethamine and sulfadiazine in vitro.	2000 Sep	10952623
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.	2001 Jan	11124226
Activity of gatifloxacin alone or in combination with pyrimethamine or gamma interferon against Toxoplasma gondii.	2001 Jan	11120943
A trial of proguanil-dapsone in comparison with sulfadoxine-pyrimethamine for the clearance of Plasmodium falciparum infections in Tanzania.	2001 Jul-Aug	11579891
[Therapeutic potential of protein kinase CK2 modulators].	2002	12611170
Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance.	2002 Feb 10	11807801
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.	2002 Jun	12019133
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.	2003 Aug	12730611
Effect of immunomodulator daraprim on potentiation of vaccine protection of leishmania major in BALB/c mice.	2003 Mar	17301350
[Disulone].	2004 Dec	15692440
Patterns of resistance and DHFR/DHPS genotypes of Plasmodium falciparum in rural Tanzania prior to the adoption of sulfadoxine-pyrimethamine as first-line treatment.	2004 Jun	15099990
Dapsone hypersensitivity syndrome masquerading as a viral exanthem: three cases and a mini-review.	2004 May	15175785
Pyrimethamine (2,4-diamino-5-p-chlorophenyl-6-ethylpyrimidine) induces apoptosis of freshly isolated human T lymphocytes, bypassing CD95/Fas molecule but involving its intrinsic pathway.	2005 Dec	16157660
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Sulfonamide crystals and acute renal failure.	2006 Jun	16732870
Presumed dapsone-induced drug hypersensitivity syndrome causing reversible hypersensitivity myocarditis and thyrotoxicosis.	2006 Nov	17160201
Suppression of telomerase activity by pyrimethamine: implication to cancer.	2007 Oct	18392083
A comparison of vitamin A and leucovorin for the prevention of methotrexate-induced micronuclei production in rat bone marrow.	2008 Dec	19061007
Anti-toxoplasmosis effects of oleuropein isolated from Fraxinus rhychophylla.	2008 Dec	19043212
Impact of placental Plasmodium falciparum malaria on pregnancy and perinatal outcome in sub-Saharan Africa: part III: placental malaria, maternal health, and public health.	2008 Mar	18604306
Changes in malaria indices between 1999 and 2007 in The Gambia: a retrospective analysis.	2008 Nov 1	18984187
Antifolate activity of pyrimethamine enhances temozolomide-induced cytotoxicity in melanoma cells.	2009 May	19435820
Self-reported data: a major tool to assess compliance with anti-malarial combination therapy among children in Senegal.	2009 Nov 17	19922609
Cost effectiveness of seasonal intermittent preventive treatment using amodiaquine & artesunate or sulphadoxine-pyrimethamine in Ghanaian children.	2010 Aug 17	20808923
In vitro and in vivo characterization of the antimalarial lead compound SSJ-183 in Plasmodium models.	2013	24255594
A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain.	2013 Dec 12	24120516
Synthesis, characterization and antimalarial activity of quinoline-pyrimidine hybrids.	2013 Jan 1	23168082

Patents

Sample Use Guides

In Vivo Use Guide

Toxoplasmosis: The adult starting dose is 50 to 75 mg of the drug daily, together with 1 to 4 g daily of a sulfonamide of the sulfapyrimidine type, e.g., sulfadoxine. This dosage is ordinarily continued for 1 to 3 weeks, depending on the response of the patient and tolerance to therapy. The dosage may then be reduced to about one half that previously given for each drug and continued for an additional 4 to 5 weeks. The pediatric dosage of DARAPRIM (PYRIMETHAMINE) is 1 mg/kg/day divided into 2 equal daily doses; after 2 to 4 days this dose may be reduced to one half and continued for approximately 1 month. The usual pediatric sulfonamide dosage is used in conjunction with DARAPRIM. Treatment of Acute Malaria: at a dosage of 25 mg daily for 2 days with a sulfonamide will initiate transmission control and suppression of non-falciparum malaria. The adult dosage for acute malaria is 50 mg for 2 days; children 4 through 10 years old may be given 25 mg daily for 2 days. In any event, clinical cure should be followed by the once-weekly regimen described below for chemoprophylaxis. Regimens which include suppression should be extended through any characteristic periods of early recrudescence and late relapse, i.e., for at least 10 weeks in each case. For Chemoprophylaxis of Malaria: Adults and pediatric patients over 10 years — 25 mg (1 tablet) once weekly. Children 4 through 10 years — 12.5 mg (1/2 tablet) once weekly. Infants and children under 4 years — 6.25 mg (1/4 tablet) once weekly.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:51:55 UTC 2023` Edited by `admin` on `Wed Jul 05 22:51:55 UTC 2023`
Record UNII	Z3614QOX8W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRIMETHAMINE

Official Name

English

PYRIMETHAMINE [MART.]

Common Name

English

PYRIMETHAMINE [WHO-IP]

Common Name

English

FANSIDAR COMPONENT PYRIMETHAMINE

Common Name

English

RP-4753

Code

English

2,4-DIAMINO-5-(P-CHLOROPHENYL)-6-ETHYLPYRIMIDINE

Common Name

English

PYRIMETHAMINE [VANDF]

Common Name

English

CHLORIDINE

Common Name

English

DARAPRIM

Brand Name

English

Pyrimethamine [WHO-DD]

Common Name

English

PYRIMETHAMINE COMPONENT OF FANSIDAR

Common Name

English

WR-2978

Code

English

PYRIMETHAMINE [JAN]

Common Name

English

PYRIMETHAMINE [USP MONOGRAPH]

Common Name

English

PYRIMETHAMINE [IARC]

Common Name

English

pyrimethamine [INN]

Common Name

English

PYRIMETHAMINE [MI]

Common Name

English

PYRIMETHAMINE [GREEN BOOK]

Common Name

English

GNF-PF-5586

Code

English

TCMDC-125860

Code

English

PYRIMETHAMINE [EP MONOGRAPH]

Common Name

English

PYRIMETHAMINE [USP-RS]

Common Name

English

PYRIMETHAMINUM [WHO-IP LATIN]

Common Name

English

2,4-PYRIMIDINEDIAMINE, 5-(4-CHLOROPHENYL)-6-ETHYL-

Systematic Name

English

NSC-3061

Code

English

PYRIMETHAMINE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548044