Cat. No.: HY-12651D

(R)-Primaquine

Name: (R)-Primaquine
Brand: MedChemExpress
SKU: HY-12651D
Price: 255.00 USD
Availability: InStock
Rating: 5 (1 reviews)

(Synonyms: (-)-Primaquine)

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(R)-Primaquine ((−)-Primaquine) is the R-configured enantiomer of Primaquine (HY-12651A). (R)-Primaquine is an antimalarial agent. The V_max and K_m values of (R)-Primaquine metabolism by recombinant human CYP2D6 are 0.42 μmol/min/mg and 21.6 μM, respectively. (R)-Primaquine can be used in malaria-related research.

For research use only. We do not sell to patients.

Purity : 99.59%
CAS No.: 57152-56-4
Formula: C₁₅H₂₁N₃O
Molecular Weight:259.35

Storage:

Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

(R)-Primaquine Chemical Structure

CAS No.: 57152-56-4

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Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- Cellular Effect
- In Vitro
- Parmacokinetics
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

All Parasite Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
NHDF	IC₅₀	50 μM Compound: 41	Cytotoxicity against NHDF assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against NHDF assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 28671460]

In Vitro

(R)-Primaquine (20 μM; 120 min) is metabolized by recombinant human CYP2D6 with a V_max of 0.42 μmol/min/mg and K_m of 21.6 μM, preferentially forming 4-OH-PQ (22% of total conversion), higher levels of 3-OH-PQ, and specific dihydroxylated metabolites, while being depleted at a slower rate (30% depletion of 20 μM in 120 min) than (+)-(S)-primaquine^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Parmacokinetics

Species	Dose	Route	T_1/2	C_max	T_max	AUC_0-∞	MRT	V	CL
Rhesus monkey^[4]	3.0 mg/kg	p.o.	4.9 h	357 μg/L	4.7 h	4128 h·μg/L	8.5 h	8.1 L/kg	1.3 L/h/kg
Rhesus monkey^[4]	4.5 mg/kg	p.o.	46.5 h	1232 μg/L	3.3 h	15585 h·μg/L	8.9 h	4.6 L/kg	0.6 L/h/kg

In Vivo

Parasitic InfectionFungal InfectionOthers

Parasitic Infection

(R)-Primaquine ((−)-Primaquine) (11.1-100 mg/kg; p.o.; once daily; for 3 consecutive days) exhibits dose-dependent blood schizonticidal activity against Plasmodium berghei in Swiss Webster mice. At a dose of 100 mg/kg/day administered for 3 days, it achieves 100% suppression of parasitemia, 100% survival rate, and a 40% cure rate^[3].
(R)-Primaquine (10-160 mg/kg; p.o.; daily administration; for 3 consecutive days) exhibits causal prophylactic activity against liver-stage Plasmodium berghei infection induced by sporozoites in ICR mice, with an ED₈₀ of 63.7 mg/kg/day, and achieves 100% protection at 80 mg/kg/day.^[3]

Fungal Infection

(R)-Primaquine (2-10 mg/kg; p.o.; daily administration; for 21 consecutive days) shows no efficacy against Pneumocystis carinii infection in immunosuppressed BALB/c mice when administered at the highest dose of 10 mg/kg/day for 21 days^[3].

Others

(R)-Primaquine (6.25-12.5 mg/kg; intraperitoneal injection; twice daily for 7 consecutive days) causes only mild hemolysis in G6PD-deficient human erythrocytes transplanted into NOD-SCID mice. At doses up to 12.5 mg/kg/day administered for 7 days, its hemolytic activity is significantly lower than that of (S)-primaquine^[3].
(R)-Primaquine (4.86 mg/kg; p.o.; once daily; for 3 consecutive days) is well tolerated in female Beagle dogs after administration at a dose of 4.86 mg/kg/day for 3 days, with no significant systemic toxicity, methemoglobinemia, or organ damage observed^[3].
(R)-Primaquine (1.3-4.5 mg/kg/day; oral administration; once daily; for 7 consecutive days) induces dose-dependent increases in methemoglobin, reticulocytes, and alanine transaminase (ALT) in healthy G6PD-normal rhesus monkeys, and no severe reversible hepatotoxicity is observed at doses up to 4.5 mg/kg/day^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Swiss Webster (male, 18 to 20 g, intraperitoneally inoculated with Plasmodium berghei NK-65 strain parasitized red blood cells)^[3]
Dosage:

11.1 mg/kg/day; 33.3 mg/kg/day; 100 mg/kg/day
Administration:

p.o.; daily; 3 days (days 0 to 2)
Result:

At 100 mg/kg/day, achieved 100% parasitemia suppression and cured 2/5 mice by day 28.

Animal Model:

ICR (female, inoculated with Plasmodium berghei ANKA strain sporozoites isolated from Anopheles dirus mosquitoes)^[3]
Dosage:

10 mg/kg/day; 80 mg/kg/day; 160 mg/kg/day
Administration:

p.o.; daily; 3 days (days -1 to 1)
Result:

Resulted in 0% of mice surviving to day 31 at 10 mg/kg/day.
Resulted in 100% of mice surviving to day 31 at 80 mg/kg/day.
Resulted in 80% of mice surviving to day 31 (1/5 mice died due to toxicity) at 160 mg/kg/day.
Had an ED₈₀ (80% effective dose) of 63.7 mg/kg/day for 3 days.

Animal Model:

BALB/c (female, 6 to 8 weeks old, immunosuppressed with dexamethasone, transtracheally inoculated with Pneumocystis carinii organisms)^[3]
Dosage:

2 mg/kg/day; 5 mg/kg/day; 10 mg/kg/day
Administration:

p.o.; daily; 21 days via drinking water
Result:

Resulted in 0/10 mice cured of P. carinii infection at all tested doses.

Animal Model:

NOD.CB17-Prkdcscid/J (NOD-SCID) (female, 8 to 9 weeks old, intraperitoneally transfused with African variant G6PD-deficient human red blood cells)^[3]
Dosage:

6.25 mg/kg/day; 12.5 mg/kg/day
Administration:

i.p.; twice daily; 7 days
Result:

Produced substantially less erythrocyte loss than (S)-Primaquine; no significant loss at 6.25 mg/kg/day versus PBS.

Animal Model:

Beagle (female)^[3]
Dosage:

4.86 mg/kg/day
Administration:

p.o.; daily; 3 days
Result:

All animals survived; body-weight loss was approximately 3-8%, with clinical chemistry and hematology remaining near baseline.

Animal Model:

Macaca mulatta (Indian-origin, male, non-malaria-naive, median age 10.8 years, median weight 9.3 kg, G6PD-normal)^[4]
Dosage:

1.3 mg/kg/day; 3.0 mg/kg/day; 4.5 mg/kg/day
Administration:

p.o.; daily; 7 days
Result:

Generally tolerated at 1.3 and 3.0 mg/kg/day; caused severe reversible hepatotoxicity in 2/3 animals at 4.5 mg/kg/day.

Animal Model:

Macaca mulatta (Indian-origin, malaria-naive, median age 4 years, median weight 5.4 kg, G6PD-normal)^[4]
Dosage:

1.3 mg/kg/day (in combination with 10 mg/kg/day Chloroquine (HY-17589A) base); 0.6 mg/kg/day (in combination with 10 mg/kg/day chloroquine base)
Administration:

p.o.; daily; 7 days
Result:

Produced lower mean methemoglobin increases than (S)-Primaquine at 1.3 and 3.0 mg/kg/day.

Chemical Information

CAS No. 57152-56-4
Appearance Solid-Liquid Mixture
Molecular Weight 259.35
Formula C₁₅H₂₁N₃O
Color Light yellow to brown
SMILES

COC(C=C1N[C@@H](CCCN)C)=CC2=C1N=CC=C2
Synonyms

(-)-Primaquine
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Pure form	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL (385.58 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.8558 mL

19.2790 mL

38.5579 mL

5 mM

0.7712 mL

3.8558 mL

7.7116 mL

10 mM

0.3856 mL

1.9279 mL

3.8558 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Dilution Calculator

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (284 KB)
SDS (254 KB)
- English - EN (254 KB)
- Français - FR (254 KB)
- Deutsch - DE (254 KB)
- Norwegian - NO (254 KB)
- Español - ES (254 KB)
- Swedish - SV (254 KB)
- Italian - IT (254 KB)
- Korean - KR (254 KB)
- Portuguese - PT (254 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Fasinu PS, et al. Enantioselective metabolism of primaquine by human CYP2D6. Malaria journal. 2014 Dec 17;13:507. [Content Brief]

[2]. Chairat K, et al. Enantiospecific pharmacokinetics and drug-drug interactions of primaquine and blood-stage antimalarial drugs. The Journal of antimicrobial chemotherapy. 2018 Nov 01;73(11):3102-3113. [Content Brief]

[3]. Nanayakkara NP, et al. Scalable preparation and differential pharmacologic and toxicologic profiles of primaquine enantiomers. Antimicrobial agents and chemotherapy. 2014 Aug;58(8):4737-44. [Content Brief]

[4]. Saunders D, et al. Pharmacokinetics and pharmacodynamics of (+)-primaquine and (-)-primaquine enantiomers in rhesus macaques (Macaca mulatta). Antimicrobial agents and chemotherapy. 2014 Dec;58(12):7283-91. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.8558 mL	19.2790 mL	38.5579 mL	96.3948 mL
	5 mM	0.7712 mL	3.8558 mL	7.7116 mL	19.2790 mL
	10 mM	0.3856 mL	1.9279 mL	3.8558 mL	9.6395 mL
	15 mM	0.2571 mL	1.2853 mL	2.5705 mL	6.4263 mL
	20 mM	0.1928 mL	0.9639 mL	1.9279 mL	4.8197 mL
	25 mM	0.1542 mL	0.7712 mL	1.5423 mL	3.8558 mL
	30 mM	0.1285 mL	0.6426 mL	1.2853 mL	3.2132 mL
	40 mM	0.0964 mL	0.4820 mL	0.9639 mL	2.4099 mL
	50 mM	0.0771 mL	0.3856 mL	0.7712 mL	1.9279 mL
	60 mM	0.0643 mL	0.3213 mL	0.6426 mL	1.6066 mL
	80 mM	0.0482 mL	0.2410 mL	0.4820 mL	1.2049 mL
	100 mM	0.0386 mL	0.1928 mL	0.3856 mL	0.9639 mL

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(R)-Primaquine

All Parasite Isoforms