PYRIMETHAMINE TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H13ClN4.C4H6O6
Molecular Weight	398.798
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CCC1=NC(N)=NC(N)=C1C2=CC=C(Cl)C=C2

InChI

InChIKey=NFFRTUJRKBKQES-LREBCSMRSA-N

InChI=1S/C12H13ClN4.C4H6O6/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7;5-1(3(7)8)2(6)4(9)10/h3-6H,2H2,1H3,(H4,14,15,16,17);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

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

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 61 Target ID: CHEMBL1939 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9554869	Inhibitor 8504		1.5 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Toxoplasmosis 13 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Curative	Approved 8583	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 1953
Acute malaria 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Curative	Approved 8583	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 1953
Malaria 96 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	Preventing	Approved 8583	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 1953

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
96 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/8578s15lbl.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		PYRIMETHAMINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
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	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		PYRIMETHAMINE plasma	Homo sapiens population: UNKNOWN age: ADULT 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	healthy, 1 Health Status: healthy Age Group: 1 Sex: M Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1	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
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	healthy, 1 Health Status: healthy Age Group: 1 Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1	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
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	healthy, 2 Health Status: healthy Age Group: 2 Sex: M Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1	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
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	healthy, 2 Health Status: healthy Age Group: 2 Sex: F Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1	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
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	healthy, 3 Health Status: healthy Age Group: 3 Sex: F Sources: http://apps.who.int/iris/bitstream/handle/10665/65774/WHO_MAL_79.907.pdf?sequence=1	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
300 mg single, oral 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	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
75 mg 1 times / day multiple, oral 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/08578slr016_daraprim_lbl.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP1A2 2153 CYP2C19 2057 ALDH1 41 MATE1 415 OCT1 620 OCT2 779 BSEP 550 OATP1B1 1079 OATP1B3 961	MRP5 41	CYP1A 59

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	inconclusive [Activation 10 uM]
ALDH1 41	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	inconclusive [Activation 39.8107 uM]
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation 5.0119 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation 7.9433 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYifX0%3D	inconclusive [Activation >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	no [Activation >10 uM]
CYP1A 122	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12451431/	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2In19	no
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	weak [IC50 200.1 uM]
MATE1 416	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00205, https://pubmed.ncbi.nlm.nih.gov/28971610/	yes [IC50 0.131 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31427432/	yes [IC50 1.8 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28971610/	yes [IC50 4.55 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00205, https://pubmed.ncbi.nlm.nih.gov/26721703/	yes [IC50 45.1 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
MRP5 41	substrate 4014 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
eMolecules	511729	https://www.emolecules.com/cgi-bin/more?vid=511729
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

PubMed

Title	Date	PubMed
Antimycobacterial activity of nitrogen heterocycles derivatives: bipyridine derivatives. Part III.	2014-03-03	24268596
A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain.	2013-12-12	24120516
Male and female Plasmodium falciparum mature gametocytes show different responses to antimalarial drugs.	2013-07	23629698
A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents.	2013-03-01	23352268
Toxoplasma gondii: the effect of fluconazole combined with sulfadiazine and pyrimethamine against acute toxoplasmosis in murine model.	2013-03	23270807
Synthesis, characterization and antimalarial activity of quinoline-pyrimidine hybrids.	2013-01-01	23168082
In vitro and in vivo characterization of the antimalarial lead compound SSJ-183 in Plasmodium models.	2013	24255594
Malarial dihydrofolate reductase as a paradigm for drug development against a resistance-compromised target.	2012-10-16	23035243
Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease.	2012-10	22700542
Identification of a new chemical class of antimalarials.	2012-09-01	22732921
Antiplasmodial and analgesic activities of Clausena anisata.	2012-03	22305787
Use of the NP-40 detergent-mediated assay in discovery of inhibitors of beta-hematin crystallization.	2011-07	21518844
Crystal structure of β-hexosaminidase B in complex with pyrimethamine, a potential pharmacological chaperone.	2011-03-10	21265544
Toxoplasma gondii: inhibitory activity and encystation effect of securinine and pyrrolidine derivatives on Toxoplasma growth.	2011-02	20833168
Turning science into health solutions: KEMRI's challenges as Kenya's health product pathfinder.	2010-12-13	21144070
Images in clinical tropical medicine. Pseudochondritis in leprosy.	2010-12	21118916
Evaluation of the effect of pyrimethamine, an anti-malarial drug, on HIV-1 replication.	2010-11	20800626
Pyrimethamine induces oxidative stress in Plasmodium yoelii 17XL-infected mice: a novel immunomodulatory mechanism of action for an old antimalarial drug?	2010-11	20193682
Multiple-ring enhancing lesions in an immunocompetent adult.	2010-09	20927299
Cost effectiveness of seasonal intermittent preventive treatment using amodiaquine & artesunate or sulphadoxine-pyrimethamine in Ghanaian children.	2010-08-17	20808923
Cerebellar toxoplasmosis in HIV/AIDS: a case report.	2010-06-15	20544640
Structure-activity relationships of carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase.	2010-05-15	20456959
Active case detection, treatment of falciparum malaria with combined chloroquine and sulphadoxine/pyrimethamine and vivax malaria with chloroquine and molecular markers of anti-malarial resistance in the Republic of Vanuatu.	2010-04-06	20370920
Potent and specific inhibition of mMate1-mediated efflux of type I organic cations in the liver and kidney by pyrimethamine.	2010-04	20065018
Original quinazoline derivatives displaying antiplasmodial properties.	2010-02	19926173
The human proton-coupled folate transporter (hPCFT): modulation of intestinal expression and function by drugs.	2010-02	19762432
Self-reported data: a major tool to assess compliance with anti-malarial combination therapy among children in Senegal.	2009-11-17	19922609
Factors related to compliance to anti-malarial drug combination: example of amodiaquine/sulphadoxine-pyrimethamine among children in rural Senegal.	2009-06-04	19497103
Antifolate activity of pyrimethamine enhances temozolomide-induced cytotoxicity in melanoma cells.	2009-05	19435820
Update on the treatment of ocular toxoplasmosis.	2009	19319237
A comparison of vitamin A and leucovorin for the prevention of methotrexate-induced micronuclei production in rat bone marrow.	2008-12	19061007
Anti-toxoplasmosis effects of oleuropein isolated from Fraxinus rhychophylla.	2008-12	19043212
Changes in malaria indices between 1999 and 2007 in The Gambia: a retrospective analysis.	2008-11-01	18984187
HIV, TB, Malaria, Filaria and Kala azar.	2008-10	21593967
Pyrimethamine induces apoptosis of melanoma cells via a caspase and cathepsin double-edged mechanism.	2008-07-01	18593930
ECVAM retrospective validation of in vitro micronucleus test (MNT).	2008-07	18326866
Impact of placental Plasmodium falciparum malaria on pregnancy and perinatal outcome in sub-Saharan Africa: part III: placental malaria, maternal health, and public health.	2008-03	18604306
Pyrimethamine treatment does not ameliorate lymphoproliferation or autoimmune disease in MRL/lpr-/- mice or in patients with autoimmune lymphoproliferative syndrome.	2007-12	17674358
R2(2)(8) motifs in Aminopyrimidine sulfonate/carboxylate interactions: crystal structures of pyrimethaminium benzenesulfonate monohydrate (2:2:1) and 2-amino-4,6-dimethylpyrimidinium sulfosalicylate dihydrate (4:2:2).	2007-11-13	17999751
Suppression of telomerase activity by pyrimethamine: implication to cancer.	2007-10	18392083
Age interactions in the development of naturally acquired immunity to Plasmodium falciparum and its clinical presentation.	2007-07-31	17676985
Impact of placental Plasmodium falciparum malaria on pregnancy and perinatal outcome in sub-Saharan Africa: I: introduction to placental malaria.	2007-06	18160989
[Acute renal failure due to sulfadiazine crystalluria].	2007-05	17907889
Pneumocystis carinii dihydrofolate reductase used to screen potential antipneumocystis drugs.	1991-07	1929292
Activity of minocycline against Toxoplasma gondii infection in mice.	1991-05	1885421
Sulfadiazine-induced crystalluria in AIDS patients with toxoplasma encephalitis.	1991-05	1863412
In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs.	1990-08	2221857
In vivo assessment of antimicrobial agents against Toxoplasma gondii by quantification of parasites in the blood, lungs, and brain of infected mice.	1990-08	2221854
Resolution of acute renal failure in toxoplasmic encephalitis despite continuance of sulfadiazine.	1990-07-01	2385768
In vitro and in vivo effects of doxycycline on Toxoplasma gondii.	1990-05	2360817

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 `Mon Mar 31 22:29:58 GMT 2025` Edited by `admin` on `Mon Mar 31 22:29:58 GMT 2025`
Record UNII	971V2RD6H5
Record Status	`Validated (UNII)`
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Name

Type

Language

PYRIMETHAMINE TARTRATE

Common Name

English

PYRIMETHAMINE BITARTRATE

Preferred Name

English

2,4-PYRIMIDINEDIAMINE, 5-(4-CHLOROPHENYL)-6-ETHYL-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

Pyrimethamine bitartrate [WHO-DD]

Common Name

English

2,4-PYRIMIDINEDIAMINE, 5-(4-CHLOROPHENYL)-6-ETHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Common Name

English

5-(4-CHLOROPHENYL)-6-ETHYLPYRIMIDINE-2,4-DIAMINE 2,3-DIHYDROXYBUTANEDIOATE(1:1)

Systematic Name

English

5-(4-CHLOROPHENYL)-6-ETHYL-2,4-PYRIMIDINEDIAMINE 2,3-DIHYDROXYSUCCINATE (1:1)

Systematic Name

English

NSC-65379

Code

English

Code System Code Type Description

EPA CompTox

DTXSID70289906