Details of the Drug
General Information of Drug (ID: DMWQ16I)
Drug Name |
Primaquine
|
|||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Synonyms |
Kanaprim; Primachin; Primachina; Primachinum; Primaquin; Primaquina; Primaquinum; Primachina [DCIT]; SN 13272; WR 2975; Dl-Primaquine; Kanaprim (TN); Neo-Quipenyl; Primaquina [INN-Spanish]; Primaquine (INN); Primaquine Bis-Phosphoric Acid; Primaquine [INN:BAN]; Primaquinum [INN-Latin]; SN 13,272; TG1-296; TG1-297; Ethylbutylamino)-6-methoxyquinoline; S. N. 13272; N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy; N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine; Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-(6CI,8CI); (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; (+)-Primaquine; (+/-)-Primaquine; (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; (-)-Primaquine; 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-(9CI); 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline; 6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline; 6-Methoxy-8-[4-amino-1-methylbutylamino]quinoline; 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline; 8-(4-Amino-1-m; 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline
|
|||||||||||||||||||
Indication |
|
|||||||||||||||||||
Therapeutic Class |
Antimalarials
|
|||||||||||||||||||
Drug Type |
Small molecular drug
|
|||||||||||||||||||
Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 259.35 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 2.2 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 6 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 2 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 4 | |||||||||||||||||||
ADMET Property |
|
|||||||||||||||||||
Chemical Identifiers |
|
|||||||||||||||||||
Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
|
|||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Drug-Metabolizing Enzyme (DME) |
|
|||||||||||||||||||||||||||||||
Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Same Disease as Primaquine
Coadministration of a Drug Treating the Disease Different from Primaquine (Comorbidity)
|
Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
1 | FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 008316. | ||||
---|---|---|---|---|---|
2 | BDDCS applied to over 900 drugs | ||||
3 | Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches | ||||
4 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
5 | Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose | ||||
6 | Primaquine-induced differential gene expression analysis in mice liver using DNA microarrays. Toxicology. 2007 Sep 24;239(1-2):96-107. | ||||
7 | Primaquine metabolism by human liver microsomes: effect of other antimalarial drugs. Biochem Pharmacol. 1992 Aug 4;44(3):587-90. | ||||
8 | Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. | ||||
9 | Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65. | ||||
10 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
11 | Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. | ||||
12 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
13 | Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. | ||||
14 | Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98. | ||||
15 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
16 | The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76. | ||||
17 | Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. | ||||
18 | Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. | ||||
19 | Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8. | ||||
20 | Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. | ||||
21 | Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. | ||||
22 | PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. | ||||
23 | The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184. | ||||
24 | The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46. | ||||
25 | Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. | ||||
26 | Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509. | ||||
27 | Cerner Multum, Inc. "Australian Product Information.". | ||||
28 | Abernethy DR, Wesche DL, Barbey JT, et al. "Stereoselective halofantrine disposition and effect: concentration-related QTc prolongation." Br J Clin Pharmacol 51 (2001): 231-7. [PMID: 11298069] | ||||
29 | Harper KM, Knapp DJ, Criswell HE, Breese GR "Vasopressin and alcohol: A multifaceted relationship." Psychopharmacology (Berl) 235 (2018): 3363-79. [PMID: 32936259] | ||||
30 | Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA. | ||||
31 | Canadian Pharmacists Association. | ||||
32 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
33 | Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL. | ||||
34 | Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ. | ||||
35 | Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
36 | Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176] | ||||
37 | Ball P "Quinolone-induced QT interval prolongation: a not-so-unexpected class effect." J Antimicrob Chemother 45 (2000): 557-9. [PMID: 10797074] | ||||
38 | Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY. | ||||
39 | Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA. | ||||
40 | Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA. | ||||
41 | Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC. | ||||
42 | Anson BD, Weaver JG, Ackerman MJ, et al. "Blockade of HERG channels by HIV protease inhibitors." Lancet 365 (2005): 682-686. [PMID: 15721475] | ||||
43 | Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD. | ||||
44 | Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY. | ||||
45 | Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE. | ||||
46 | Ohnishi K, Yoshida H, Shigeno K, et al. "Prolongation of the QT interval and ventricular tachycardia in patients treated with arsenic trioxide for acute promyelocytic leukemia." Ann Intern Med 133 (2000): 881-5. [PMID: 11103058] | ||||
47 | Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO. | ||||
48 | Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
49 | Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA. | ||||
50 | Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ. | ||||
51 | Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ. | ||||
52 | Product Information. Nuplazid (pimavanserin). Accelis Pharma, East Windsor, NJ. | ||||
53 | Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA. | ||||
54 | Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA. | ||||
55 | Product Information. Barhemsys (amisulpride). Acacia Pharma, Inc, Indianapolis, IN. | ||||
56 | Goto M, Sato M, Kitzazawa H, et.al "Papaverine-induced QT interval prolongation and ventricular fibrillation in a patient with a history of drug-induced QT prolongation." Intern Med 53 (2014): 1629-31. [PMID: 25088875] | ||||
57 | Iannini PB "Cardiotoxicity of macrolides, ketolides and fluoroquinolones that prolong the QTc interval." Expert Opin Drug Saf 1 (2002): 121-8. [PMID: 12904146] | ||||