N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine

• ChemBase ID: 958
• Molecular Formular: C15H21N3O
• Molecular Mass: 259.34674
• Monoisotopic Mass: 259.16846231
• SMILES: O(c1cc(NC(CCCN)C)c2ncccc2c1)C
• Canonical SMILES: NCCCC(Nc1cc(OC)cc2c1nccc2)C
• InChI: InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
• InChIKey: INDBQLZJXZLFIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
• IUPAC Traditional name: primaquine
• Brand Name: Neo-Quipenyl; Primachin
• Synonyms: Primaquine; 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine Phosphate; 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline Phosphate; (+/-)-Primaquine Phosphate; 6-Methoxy-8-[4-amino-1-methylbutylamino]quinoline Phosphate; NSC 27296; Neo-Quipenyl Phosphate; Primachin Phosphate; Primaquin Phosphate; SN 13272; WR 2975; dl-Primaquine Phosphate; Primaquine Diphosphate

Database IDs

• CAS Number: 90-34-6; 63-45-6
• MDL Number: MFCD00598906
• PubChem SID: 160964421; 46508222
• PubChem CID: 4908
• CHEBI ID: 8405
• ATC CODE: P01BA03
• CHEMBL: 506
• Chemspider ID: 4739
• DrugBank ID: DB01087
• KEGG ID: D08420
• Unique Ingredient Identifier: MVR3634GX1
• Wikipedia Title: Primaquine
• Medline Plus: a607037

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.10915
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3967301
• LogD (pH = 7.4): -0.96040577
• Log P: 1.642921
• Molar Refractivity: 78.5149 cm^3
• Polarizability: 31.37844 Å^3
• Polar Surface Area: 60.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.76
• LOG S: -3.66
• Solubility (Water): 5.64e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Orange Solid
• Melting Point: 190-194°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 96%
• Half Life: 6 hours
• Metabolism: Liver
• Legal Status: Rx-only (US); Unlicensed (UK)

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB01087

• Drug Groups: approved
• Description: 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)
• Indication: For the treatment of malaria.
• Pharmacology: Primaquine is an antimalarial agent and is the essential co-drug with chloroquine in treating all cases of malaria. In the blood, malaria parasites break down a part of the red blood cells known as haemoglobin. When this happens haemoglobin is divided into two parts; haem and globin. Haem is toxic to the malaria parasite. To prevent it from being damaged, the malaria parasite produces an chemical which converts the toxic haem into a non-toxic product. Primaquine acts by interfering with a part of the parasite (mitochondria) that is responsible for supplying it with energy. Without energy the parasite dies. This stops the infection from continuing and allows the person to recover. Primaquine kills the intrahepatic form of Plasmodium vivax and Plasmodium ovale, and thereby prevents the development of the erythrocytic forms that are responsible for relapses (it also kills gametocytes). Primaquine is not used in the prevention of malaria, only in the treatment. It has insignificant activity against the asexual blood forms of the parasite and therefore it is always used in conjunction with a blood schizonticide and never as a single agent. Primaquine has gametocytocidal activity against all plasmodia, including P. falciparum.
• Affected Organisms: Plasmodium
• Half Life: 3.7-7.4 hours
• References: Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. [Pubmed] ; ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. [Pubmed] ; Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. [Pubmed] ; Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. [Pubmed] ; Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. [Pubmed]
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - P733500

Antimalarial.

REFERENCES

• Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. Pubmed
• ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. Pubmed
• Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. Pubmed
• Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. Pubmed
• Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. Pubmed
• Marrs, T., et al.: Toxicol Lett., 36, 281 (1987)
• Karbwang, J., et al.: Clin. Pharmacokinetic., 27, 104 (1987)
• Noedl, H., et al.: Antimicrob. Agents Chemother., 45, 2106 (2010)