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 | |||||||||||||||||||||
Logarithm of the Partition Coefficient (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 | |||||||||||||||||||||||
Combinatorial Drugs (CBD) | Click to Jump to the Detailed CBD Information of This Drug | ||||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Drug-Metabolizing Enzyme (DME) |
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug Off-Target (DOT) |
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 | An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20. | ||||
10 | Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500. | ||||
11 | Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42. | ||||
12 | Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. | ||||
13 | Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol Appl Pharmacol. 2009 Nov 15;241(1):14-22. doi: 10.1016/j.taap.2009.07.012. Epub 2009 Jul 17. | ||||
14 | Understanding the mechanisms for metabolism-linked hemolytic toxicity of primaquine against glucose 6-phosphate dehydrogenase deficient human erythrocytes: evaluation of eryptotic pathway. Toxicology. 2012 Mar 29;294(1):54-60. doi: 10.1016/j.tox.2012.01.015. Epub 2012 Feb 6. | ||||
15 | Cerner Multum, Inc. "Australian Product Information.". | ||||
16 | 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] | ||||
17 | Harper KM, Knapp DJ, Criswell HE, Breese GR "Vasopressin and alcohol: A multifaceted relationship." Psychopharmacology (Berl) 235 (2018): 3363-79. [PMID: 32936259] | ||||
18 | Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA. | ||||
19 | Canadian Pharmacists Association. | ||||
20 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
21 | Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL. | ||||
22 | Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ. | ||||
23 | Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
24 | Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176] | ||||
25 | Ball P "Quinolone-induced QT interval prolongation: a not-so-unexpected class effect." J Antimicrob Chemother 45 (2000): 557-9. [PMID: 10797074] | ||||
26 | Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY. | ||||
27 | Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA. | ||||
28 | Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA. | ||||
29 | Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC. | ||||
30 | Anson BD, Weaver JG, Ackerman MJ, et al. "Blockade of HERG channels by HIV protease inhibitors." Lancet 365 (2005): 682-686. [PMID: 15721475] | ||||
31 | Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD. | ||||
32 | Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY. | ||||
33 | Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE. | ||||
34 | 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] | ||||
35 | Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO. | ||||
36 | Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
37 | Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA. | ||||
38 | Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ. | ||||
39 | Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ. | ||||
40 | Product Information. Nuplazid (pimavanserin). Accelis Pharma, East Windsor, NJ. | ||||
41 | Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA. | ||||
42 | Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA. | ||||
43 | Product Information. Barhemsys (amisulpride). Acacia Pharma, Inc, Indianapolis, IN. | ||||
44 | 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] | ||||
45 | Iannini PB "Cardiotoxicity of macrolides, ketolides and fluoroquinolones that prolong the QTc interval." Expert Opin Drug Saf 1 (2002): 121-8. [PMID: 12904146] | ||||