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Primaquine diphosphate

Primaquine diphosphate structure

CAS No:
63-45-6
Formula:
C15H21N3O.2H3O4P
Chemical Name:
Primaquine diphosphate
Synonyms:
1,4-Pentanediamine,N4-(6-methoxy-8-quinolinyl)-,phosphate (1:2);Quinoline,8-[(4-amino-1-methylbutyl)amino]-6-methoxy-,phosphate (1:2);Quinoline,8-[(4-amino-1-methylbutyl)amino]-6-methoxy-,diphosphate;8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline di(dihydrogen phosphate);8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline diphosphate;Primaquine diphosphate;Primaquine phosphate;WR 2975;NSC 149765;Pharmaniaga;Camden;Malquine;Primaquine bisphosphate;84902-21-6
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

orange powder

Primaquine is an aminoquinoline that has been used for the prevention and therapy of malaria for more than 50 years. Primaquine is not associated with serum enzyme elevations during therapy and has yet to be linked to instances of clinically apparent acute liver injury.|An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)

Primaquine diphosphate Basic Attributes

Molecular Weight：

455.34

Exact Mass：

455.122

EC Number：

200-560-8

DSSTox ID：

DTXSID6045248

HScode：

29334900

Characteristics

PSA：

216

XLogP3：

1.69880

Appearance：

orange powder

Melting Point：

197-198 °C

Boiling Point：

451.1°C at 760 mmHg

Flash Point：

226.6ºC

Water Solubility：

water: soluble 50mg/mL, clear, orange to red

Storage Conditions：

Refrigerator

Toxicity：

Oral-rat LD50: 177 mg/kg; Oral-Mouse LD50: 68 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Collision Cross Section：

161.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

VA9660000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P264, P270, P301+P310, P321, P330, P405, P501

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

highly toxic

Hepatotoxicity：

Despite use for more than 50 years, primaquine has not been linked to significant serum aminotransferase elevations or to clinically apparent acute liver injury. Primaquine can cause hemolysis in patients with G6PD deficiency, which can result in mild jaundice.

Drug Information

LiverTox Summary：

Drug Classes：

Antimalarial Agents

MeSH：

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

MeSH Entry Terms：

Diphosphate, Primaquine

Primaquine diphosphate Use and Manufacturing

Uses

Primaquine is an established antimalarial drug used in the treatment of persistent liver forms of P. vivax or P. ovale infection for its ability to kill late-stage gametocytes and hypnozoites. In historical terms, this aminoquinoline was the stimulus for the discovery of glucose-6-phosphate (G6P) dehydrogenase deficiency as it induced hemolytic anemia in patients lacking the G6P-metabolizing enzyme.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:455.34
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:6
Exact Mass:455.12225344
Monoisotopic Mass:455.12225344
Topological Polar Surface Area:216
Heavy Atom Count:29
Complexity:312
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product can kill the tissue-stage strains of Plasmodium vivax, Plasmodium malariae, Plasmodium falciparum and Plasmodium ovale, especially Plasmodium vivax. It can also kill the gametocytes of various Plasmodium parasites, and has a particularly strong effect on Plasmodium falciparum, preventing it from developing in the mosquito body, thereby blocking transmission. This product has a very weak effect on the erythrocytic stage. It may be related to the interference with DNA synthesis. When the red-stage malaria parasites and tissue cells were cultured in a primaquine solution for 8 hours, electron microscopic observation showed that primaquine could change the mitochondrial morphology of the malaria parasite, manifested as mitochondrial swelling and the appearance of cytoplasmic vacuoles. This drug can inhibit the oxidation of mitochondria and significantly reduce the oxygen uptake of malaria parasites. Primaquine is metabolized in the body and converted into quinoline quinone derivatives with strong oxidative properties, which can convert reduced glutathione (GSH) in erythrocytes into oxidized glutathione (GSSH). When the latter is reduced, it needs to consume reduced coenzyme II (NADPH). Since the infrared stage of malarial parasites consumes coenzyme II (NADP) during their development in the hepatic parenchymal cells, primaquine interferes with the reduction process of coenzyme II, causing a decrease in coenzyme II and seriously disrupting the sugar metabolism and oxidation process of malarial parasites.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Primaquine Phosphate Tablets
Ingredients	Primaquine phosphate
Indication	1. This product acts on the erythrocytic stage of Plasmodium vivax. When used in combination with chloroquine, which acts on the erythrocytic stage, it can cure Plasmodium vivax malaria. 2. Mepaline (Adipine) and proguanil can inhibit the metabolism of primaquine. Therefore, when primaquine is used together with these two drugs, its blood concentration is greatly increased, the maintenance time is also prolonged, and the toxicity is increased, but the efficacy is not increased. 3. It should not be used in combination with other drugs that have hemolytic effects and inhibit bone marrow hematopoietic function.
Specifications	13.2 mg (equivalent to 7.5 mg of primaquine)
Manufacturer	SPH Zhongxi Pharmaceutical Co., Ltd.

Primaquine phosphate
Manufacturer	Chongqing Southwest NO.2 Pharmaceutical FACTORY Co., Ltd.

Primaquine Phosphate Tablets
Ingredients	Primaquine phosphate
Indication	1. This product acts on the erythrocytic stage of Plasmodium vivax. When used in combination with chloroquine, which acts on the erythrocytic stage, it can cure Plasmodium vivax malaria. 2. Mepaline (Adipine) and proguanil can inhibit the metabolism of primaquine. Therefore, when primaquine is used together with these two drugs, its blood concentration is greatly increased, the maintenance time is also prolonged, and the toxicity is increased, but the efficacy is not increased. 3. It should not be used in combination with other drugs that have hemolytic effects and inhibit bone marrow hematopoietic function.
Specifications	13.2mg
Manufacturer	Shandong Xinhua Pharmaceutical Company Limited

See More Related Drugs

Registered Holders

MATRIX PHARMACORP PRIVATE LTD

United States
Active
IPCA LABORATORIES LIMITED

Brazil
Active
Chongqing Southwest NO.2 Pharmaceutical FACTORY Co., Ltd.

China
Active

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ISO high pure 99% Primaquine diphosphate powder CAS 63-45-6 Pharmaceutical Raw material

CAS No.: 63-45-6

Grade: Pharmaceutical Grade

Content: 99%

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Primaquine diphosphate

CAS No.: 63-45-6

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Content: 98%

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