primaquine phosphate

Names

[ CAS No. ]:
63-45-6

[ Name ]:
primaquine phosphate

[Synonym ]:
1,4-pentanediamine, N4-(6-methoxy-8-quinolinyl)-, phosphate (1:2)
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine phosphate (1:2)
N-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine phosphate (1:2)
EINECS 200-560-8
Primaquine phosphate
N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine phosphate (1:2)
Primaquine diphosphate
4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine,phosphoric acid
Primaquine diphosphate salt
1,4-Pentanediamine, N-(6-methoxy-8-quinolinyl)-, phosphate (1:2)
primaquine bis(phosphate)
MFCD00013166
Primaquine (Diphosphate)

Biological Activity

[Description]:

Primaquine is the only generally available anti-malarial that prevents relapse in vivax and ovale malaria, and the only potent gametocytocide in falciparum malaria.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[References]

[1]. Ashley EA, et al. Primaquine: the risks and the benefits. Malar J. 2014 Nov 3;13:418.

[2]. Rajgor DD, et al. Antirelapse Efficacy of Various Primaquine Regimens for Plasmodium vivax. Malar Res Treat. 2014;2014:347018.

[3]. Hanboonkunupakarn B, et al. Open-label crossover study of primaquine and dihydroartemisinin-piperaquine pharmacokinetics in healthy adult thai subjects. Antimicrob Agents Chemother. 2014 Dec;58(12):7340-6.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
451.1ºC at 760 mmHg

[ Melting Point ]:
205-206 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₅H₂₇N₃O₉P₂

[ Molecular Weight ]:
455.337

[ Flash Point ]:
226.6ºC

[ Exact Mass ]:
455.122253

[ PSA ]:
235.31000

[ LogP ]:
1.69880

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
moderately soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VA9660000

CAS REGISTRY NUMBER :: 63-45-6

LAST UPDATED :: 199509

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C15-H21-N3-O.2H3-O4-P

MOLECULAR WEIGHT :: 455.39

WISWESSER LINE NOTATION :: T66 BNJ HO1 JMY1&3Z &..H3.P-O4 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 177 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 68 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 105 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 19300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 540 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 600 mg/kg

SEX/DURATION :: female 8-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 480 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Microorganism - not otherwise specified

DOSE/DURATION :: 5 mg/L

REFERENCE :: AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 1,259,1972 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3750 No. of Facilities: 206 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 2809 (estimated) No. of Female Employees: 2111 (estimated)

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
Missing Phrase - N15.00950417

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
VA9660000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933499090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Optimization of primaquine diphosphate tablet formulation for controlled drug release using the mixture experimental design.

Pharm. Dev. Technol. 18(5) , 1247-54, (2013)

A tablet formulation based on hydrophilic matrix with a controlled drug release was developed, and the effect of polymer concentrations on the release of primaquine diphosphate was evaluated. To achie...

Development of simplified HPLC methods for the detection of counterfeit antimalarials in resource-restraint environments.

J. Pharm. Biomed. Anal. 98 , 434-45, (2014)

Regular quality control and post-marketing surveillance of pharmaceuticals has been a critical challenge for countries of the developing world ever since. Counterfeit and substandard medicines are wid...

Validation of a method for the simultaneous quantification of chloroquine, desethylchloroquine and primaquine in plasma by HPLC-DAD

J. Pharm. Biomed. Anal. 95 , 200-6, (2014)

• Chloroquine, desethyl chloroquine and primaquine level were quantified simultaneously by HPLC-DAD. • The method validation parameters were adequate according international standards. • Sample prepar...