CAS 58-14-0|Daraprim|Pirimecidan|Pyrimethamine|Malocide|pyrimethamine|5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine|Pyrimethamine|Daraprim|乙胺嘧啶|6-乙基-5-(4-氯苯基)-2,4-嘧啶二胺|5-[4-Chlorophe...

General Information

Structure

Molecular Formula

C₁₂H₁₃ClN₄

Molecular Mass

248.71142

Exact Mass

248.08287412

Charge

InChI

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)

InChIKey

WKSAUQYGYAYLPV-UHFFFAOYSA-N

Canonic Smiles

CCc1nc(N)nc(c1c1ccc(cc1)Cl)N

Isomeric Smiles

Clc1ccc(c2c(nc(nc2N)N)CC)cc1

Calculated Properties

JChem

Acid pKa

17.222044

H Acceptors

H Donor

LogD (pH = 5.5)

0.9725773

LogD (pH = 7.4)

2.2334282

Log P

2.7483032

Molar Refractivity

71.542

Polarizability

27.221851

Polar Surface Area

77.82

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.62

LOG S

-3.14

Solubility (Water)

1.79e-01 g/l

Data Source

Names and Identifiers

Synonyms

MalocidePyrimethaminePirimecidanDaraprimPyrimethamine乙胺嘧啶6-乙基-5-(4-氯苯基)-2,4-嘧啶二胺5-[4-Chlorophenyl]-6-ethyl-2,4-pyrimidinediamine5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidineChloridinChloridinePirimetminNSC 3061RP 4753KhloridinPirimetaminaChloridynCDPirimetaminPyrimethamine HclPrimethamineDiaminopyritaminEthylpyrimidinePyremethaminePyrimethamin5-(4-Chlorophenyl)-6-ethylpyriMidine-2,4-diaMine

IUPAC Traditional name

pyrimethamine

IUPAC name

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

Brand Name

DaraprimMalocidTinduringKhloridinMalacidPirimecidanDisuloneDaraprimeMaloprimErbaprelinaMalocideTindurinDarachlorDarapramDaraclorFansidar

Names and Identifiers

Registration numbers

CAS Number

58-14-0

PubChem CID

4993

PubChem SID

465059871609635532487038124898876

EC Number

MDL Number

Beilstein Number

Wikipedia Title

KEGG ID

CHEBI ID

DrugBank ID

Medline Plus

Chemspider ID

CHEMBL

ATC CODE

P01BD01

Unique Ingredient Identifier

Z3614QOX8W

Registration numbers

Properties

Safety Information

-20°C

Room Temperature (15-30°C)

-20°C Freezer

Harmful (Xn)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00205

Drug Groups

approved

Description

One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]

Indication

For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine

Pharmacology

Pyrimethamine is an antiparasitic compound commonly used as an adjunct in the treatment of uncomplicated, chloroquine resistant, P. falciparum malaria. Pyrimethamine is a folic acid antagonist 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. However, the 4-amino-quinoline compounds are more effective against the erythrocytic schizonts. It does not destroy gametocytes, but arrests sporogony in the mosquito. The action of pyrimethamine against Toxoplasma gondii is greatly enhanced when used in conjunction with sulfonamides.

Affected Organisms

Plasmodium

Biotransformation

Hepatic

Absorption

Well absorbed with peak levels occurring between 2 to 6 hours following administration

Half Life

96 hours

Protein Binding

87%

References

• Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. [Pubmed]

• Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y: Target guided synthesis of 5-benzyl-2,4-diamonopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases from Plasmodium falciparum. J Med Chem. 2004 Jan 15;47(2):345-54. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S2006

Research Area: Infection
Biological Activity:
Pyrimethamine is a dihydrofolate reductase(DHFR) inhibitor with an IC50 of 15.4 nM. It is a medication used for protozoal infections. It is commonly used as an antimalarial drug (for both treatment and prevention of malaria), and is also used (combined with sulfadiazine) in the treatment of Toxoplasma gondii infections in immune-compromised patients, such as HIV-positive individuals. It interferes with folic acid synthesis by inhibiting the enzyme dihydrofolate reductase (DHFR). Folic acid is needed for DNA and RNA synthesis in many species, including protozoa. [1]

MP Biomedicals

02194180

Antiprotozoal compound
For Research Use Only

Wikipedia

Pyrimethamine

Sigma Aldrich

46706

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

P997240

Dihydrofolate reductase inhibitor; generally used in combination with other antimicrobial agents. Antiprotozoal (Toxoplasma); antimalarial.

Molecule Details

References

PubChem Literature

From Data Sources

• Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. Pubmed

• http://en.wikipedia.org/wiki/Pyrimethamine

• Leport, C., et al.: Am. J. Med., 84, 94 (1983)

• McIntosh, H.M., et al.: Ann. Trop. Med., Parasitol., 93, 265 (1983)

• Plowe, C.V., et al.: Br. Med. J., 328, 545 (1983)

• Loutfy, M.A., et al.: Anal. Profiles Drug Subs., 12, 463 (1983)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

pyrimethamine

IUPAC name

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

Brand Name

DaraprimMalocidTinduringKhloridinMalacidPirimecidanDisuloneDaraprimeMaloprimErbaprelinaMalocideTindurinDarachlorDarapramDaraclorFansidar

Registration numbers

CAS Number

58-14-0

PubChem CID

4993

PubChem SID

465059871609635532487038124898876

EC Number

MDL Number

Beilstein Number

Wikipedia Title

KEGG ID

CHEBI ID

DrugBank ID

Medline Plus

Chemspider ID

CHEMBL

ATC CODE

P01BD01

Unique Ingredient Identifier

Z3614QOX8W

References

PubChem Literature

From Data Sources

• Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. Pubmed

• http://en.wikipedia.org/wiki/Pyrimethamine

• Leport, C., et al.: Am. J. Med., 84, 94 (1983)

• McIntosh, H.M., et al.: Ann. Trop. Med., Parasitol., 93, 265 (1983)

• Plowe, C.V., et al.: Br. Med. J., 328, 545 (1983)

• Loutfy, M.A., et al.: Anal. Profiles Drug Subs., 12, 463 (1983)

Bioactivity

PubChem BioAssay

Properties

Safety Information

-20°C

Room Temperature (15-30°C)

-20°C Freezer

Harmful (Xn)

Molecule Details

DrugBank

DB00205

Drug Groups

approved

Description

One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]

Indication

For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine

Pharmacology

Affected Organisms

Plasmodium

Biotransformation

Hepatic

Absorption

Well absorbed with peak levels occurring between 2 to 6 hours following administration

Half Life

96 hours

Protein Binding

87%

References

• Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S2006

MP Biomedicals

02194180

Antiprotozoal compound
For Research Use Only

Wikipedia

Pyrimethamine

Sigma Aldrich