Primaquine
- CAS No.
- 90-34-6
- Chemical Name:
- Primaquine
- Synonyms
- PRIMAQUIN;primaquine;Primaquine USP/EP/BP;8-(4-Amino-1-methylbutylamino);n4-(6-methoxy-8-quinolinyl)-4-pentanediamine;N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine;N'-(6-Methoxy-8-quinolinyl)pentane-1,4-diamine;N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediaMine;4-[(6-Methoxyquinolin-8-yl)amino]pentan-1-amine;4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
- CBNumber:
- CB0875785
- Molecular Formula:
- C15H21N3O
- Molecular Weight:
- 259.35
- MOL File:
- 90-34-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/4/23 13:52:06
| Melting point | 25°C |
|---|---|
| Boiling point | bp0.2 175-179° |
| Density | 1.0313 (rough estimate) |
| refractive index | 1.5600 (estimate) |
| storage temp. | Refrigerator |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | pKa 3.74/9.99(H2O,t =25) (Uncertain) |
| form | Oil |
| color | Dark Yellow to Dark Orange |
| Water Solubility | 718.4g/L(25 ºC) |
| CAS DataBase Reference | 90-34-6 |
| NIST Chemistry Reference | 1,4-Pentanediamine, n(4)-(6-methoxy-8-quinolinyl)-(90-34-6) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335 |
| Precautionary statements | P261-P305+P351+P338 |
| Toxicity | LD50 oral in mouse: 100mg/kg |
Primaquine Chemical Properties,Uses,Production
Uses
Primaquine is the most effective and most toxic drug from the whole series of known
8-aminoquinolines. It is generally used for treating exoerythrocyte forms of malaria caused
by P. vivax and P. ovale. It also acts on the sexual forms of the plasmodia, which die in the
human body upon using this drug.
Primaquine is used for treating and preventing late relapses of 3- and 4-day malaria as
well as tropic malaria. Synonyms of this drug are avlon and others.
Indications
Primaquine is the least toxic and most effective of the 8- aminoquinoline antimalarial compounds. The mechanism by which 8-aminoquinolines exert their antimalarial effects is thought to be through a quinoline–quinone metabolite that inhibits the coenzyme Q–mediated respiratory chain of the exoerythrocytic parasite.
Definition
ChEBI: A N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at N4 position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.
Antimicrobial activity
Primaquine is highly active against the hepatic stages of the malaria life cycle, including the latent hypnozoite stage of P. vivax. It has poor activity against erythrocytic stages of malaria parasites, other than gametocytes. The isomers have similar antiplasmodial activity but differ in toxicity. It exhibits activity against Pneumocystis jirovecii and, in experimental models, against Babesia spp. and the intracellular stages of Leishmania spp. and Trypanosoma cruzi.
Acquired resistance
Failure rates of up to 35% have been reported in South East Asia in patients treated with a standard course for P. vivax infections.
Pharmaceutical Applications
A synthetic 8-aminoquinoline, formulated as the diphosphate for oral administration.
Mechanism of action
Moving the side chain from the fourth position of the quinoline ring to the eighth position completely changes the compound’s spectrum of activity. Unlike the 4-substituted aminoquinolines, primaquine has practically no effect on erythrocyte forms of the malaria parasite. Its activity is limited to tissue forms of the parasite in mammals and in the mosquitoes themselves. This makes primaquine an especially valuable drug, allowing radical recovery and simultaneous prevention, which is usually not achieved by using erythrocyte drugs. The place of action of primaquine is the mitochondria of the malarial parasite. It seems likely that primaquine interferes in the process of electron transfer, causing damage to mitochondrial enzymatic systems. This is expressed in the swelling and vacuolization of the parasite’s mitochondria. Host mitochondria are not affected.
Pharmacokinetics
Oral absorption: >75%
Cmax 45 mg oral: 0.2 mg/L after 2–3 h
Plasma half-life: 4–10 h
Volume of distribution: 2 L/kg
Plasma protein binding: Extensive
Bioavailability is variable after oral administration. There is
extensive tissue distribution. About 60% of the dose is metabolized
to carboxyprimaquine, which can reach levels 50 times
that of the parent drug; this metabolite has a half-life of 16 h,
a low tissue distribution and is detectable at 120 h. Methoxy
and hydroxy metabolites are also detectable. Less than 4% of
the original dose is excreted unchanged in urine.
Clinical Use
Radical cure of malaria caused by P. vivax or P. ovale
Mild or moderately severe infections with Pn. jirovecii (in combination with
clindamycin).
Because of its gametocytocidal properties, primaquine has
been used rarely in a single dose to prevent the spread of chloroquine-
resistant P. falciparum.
Side effects
At standard doses side effects are mild: abdominal cramps, anemia, leukocytosis and methemoglobinemia. However, primaquine is often associated with serious adverse effects due to the toxic metabolites 5-hydroxyprimaquine or 6-methoxy- 8-aminoquinoline which are considered to be directly responsible for complications such as hemolytic anemia. Toxicity is worse in people deficient of glucose-6-phosphate dehydrogenase (G6PD) or glutathione synthetase. Adverse effects can be further increased by the repeated administration of high doses, due to its limited oral bioavailability.
Primaquine Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21673 | 55 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29897 | 58 | Inquiry |
| Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | China | 39916 | 58 | Inquiry |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | China | 49391 | 58 | Inquiry |
| Finetech Industry Limited | +86-27-87465837 +8618971612321 | China | 9626 | 58 | Inquiry |
| Hong Kong Excellence Biotechnology Co., Ltd. | +86-86-18838029171 +8618126314766 | China | 887 | 58 | Inquiry |
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