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

• ChemBase编号: 958
• 分子式: C15H21N3O
• 平均质量: 259.34674
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
• IUPAC传统名: primaquine
• 商标名: Neo-Quipenyl; Primachin
• 别名: 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

登记号

• CAS号: 90-34-6; 63-45-6
• MDL号: MFCD00598906
• PubChem SID: 160964421; 46508222
• PubChem CID: 4908
• CHEBI ID: 8405
• ATC码: P01BA03
• CHEMBL: 506
• Chemspider ID: 4739
• DrugBank ID: DB01087
• KEGG ID: D08420
• 美国药典/FDA物质标识码: MVR3634GX1
• 维基百科标题: Primaquine
• Medline Plus: a607037

理论计算性质

JChem

• Acid pKa: 17.10915
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -1.3967301
• LogD (pH = 7.4): -0.96040577
• Log P: 1.642921
• 摩尔折射率: 78.5149 cm^3
• 极化性: 31.37844 Å^3
• 极化表面积: 60.17 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.76
• LOG S: -3.66
• 溶解度: 5.64e-02 g/l

分子性质

理化性质

• 溶解度: DMSO
• 外观: Orange Solid
• 熔点: 190-194°C
• 疏水性(logP): 2.1

安全信息

• 保存条件: Refrigerator
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 给药途径: Oral
• 生物利用度: 96%
• 半衰期: 6 hours
• 代谢: Liver
• 法定药品分级: Rx-only (US); Unlicensed (UK)

产品相关信息

• 纯度: 95+%

详细说明

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.

参考文献

• 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)