Mefloquine

Identification

Summary

Mefloquine is an antimalarial agent used in the prophylaxis and treatment of malaria caused by Plasmodium falciparum and Plasmodium vivax.

Generic Name

Mefloquine

DrugBank Accession Number

DB00358

Background

Malaria is a protozoan disease that places an enormous burden on human health in endemic areas around the world. The 2020 World Health Organization malaria report indicates a 60% decrease in the global malaria fatality rate between 2000 to 2019.¹⁴ Despite this, malaria remains a significant cause of morbidity and mortality; 90% of deaths from malaria occur in Africa. Individuals at the highest risk for malaria are those in disease naïve populations, children under age 5, refugees in Central and Eastern Africa, nonimmune civilian and military travelers, pregnant women, and immigrants traveling to their place of origin.¹⁵

Mefloquine, commonly known as Lariam, is an antimalarial drug used for the prevention and treatment of malaria caused by infection with Plasmodium vivax and Plasmodium falciparum. The drug was initially discovered by the Walter Reed Army Institute of Research (WRAIR) during a malaria drug discovery program between 1963 until 1976. It was approved by the FDA in 1989, and was first marketed by Hoffman Laroche.⁵ This drug has been the subject of widespread controversy due to concerns regarding neurotoxic effects; product information warns of potential serious neuropsychiatric effects.^5,13

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Mefloquine (DB00358)

×

Close

Weight

Average: 378.3122
Monoisotopic: 378.116682374

Chemical Formula

C₁₇H₁₆F₆N₂O

Synonyms

• [(R*,S*)-2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol
• alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol
• Mefloquin
• Mefloquina
• Méfloquine
• Mefloquine
• Mefloquinum

External IDs

• RO 21-5998
• RO-215998
• WR 142,490

Poor quality drug data slowing you down?

Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.

Download eBook

Poor quality drug data slowing you down?

Download eBook

Pharmacology

Indication

Mefloquine is indicated for the treatment of mild to moderate cases of malaria caused by Plasmodium falciparum and Plasmodium vivax. It is effective against chloroquine-resistant forms of Plasmodium falciparum. Mefloquine is also indicated for the prophylaxis of malaria caused by Plasmodium falciparum and Plasmodium vivax, including chloroquine-resistant forms of Plasmodium falciparum.¹³

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Prophylaxis of	Malaria caused by plasmodium falciparum		••••••••••••			••••••
Treatment of	Malaria caused by plasmodium falciparum		••••••••••••			••••••
Prophylaxis of	Malaria caused by plasmodium vivax		••••••••••••			••••••
Treatment of	Malaria caused by plasmodium vivax		••••••••••••			••••••

Create Account

Contraindications & Blackbox Warnings

Prevent Adverse Drug Events Today

Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events with our Clinical API

Learn more

Pharmacodynamics

Sporozoites located in the salivary glands of mosquitoes infected with malaria parasites are introduced into the bloodstream of a human host during mosquito feeding. These sporozoites rapidly invade the liver, where they mature into liver-stage schizonts, rupturing and releasing 2,000 - 40,000 merozoites that invade red blood cells.¹⁹ Mefloquine is an antimalarial drug acting as a blood schizonticide, preventing and treating malaria.^1,3

Mechanism of action

The mechanism of action of mefloquine is not completely understood. Some studies suggest that mefloquine specifically targets the 80S ribosome of the Plasmodium falciparum, inhibiting protein synthesis and causing subsequent schizonticidal effects.⁴ There are other studies in the literature with limited in vitro data on mefloquine's mechanism of action.^8,11

Target	Actions	Organism
AFe(II)-protoporphyrin IX	binder	Plasmodium falciparum
A80S ribosomal subunit	binder	Plasmodium falciparum
UAdenosine receptor A2a	antagonist	Humans

Absorption

Mefloquine is readily absorbed from the gastrointestinal tract; food significantly increases absorption and increases bioavailability by 40%. The bioavailability of tablets compared with the oral solution preparation of mefloquine is over 85%. Cmax is achieved in 6 to 24 hours in healthy volunteers after a single dose.^7,13 Average blood concentrations range between 50 to 110 ng/ml/mg/kg.⁷ A weekly dose of 250 mg leads to steady-state plasma concentrations of 1000 to 2000 μg/L, after 7 to 10 weeks of administration.¹³

Volume of distribution

The apparent volume of distribution is in healthy adults is about 20 L/kg with wide tissue distribution.¹³ Various estimates of the total apparent volume of distribution range from 13.3 to 40.9L/kg.⁷ Mefloquine can accumulate in erythrocytes that have been infected with malaria parasites.¹³

Protein binding

The binding of mefloquine to plasma proteins is over 98%.^7,13

Metabolism

Mefloquine is heavily metabolized in the liver by the CYP3A4 enzyme.^12,13 Two metabolites have been identified; the main metabolite, 2,8-bis-trifluoromethyl-4-quinoline carboxylic acid, which inactive against plasmodium falciparum. The second metabolite, an alcohol, is found in small quantities.¹³

Hover over products below to view reaction partners

• Mefloquine
  • 2,8-bis-trifluoromethyl-4-quinoline carboxylic acid

Route of elimination

Mefloquine is believed to be excreted in the bile and feces. In healthy volunteers who have achieved steady-state concentrations of mefloquine, the unchanged drug was excreted at 9% of the ingested dose, and excretion of its carboxylic metabolite under was measured at 4% of the ingested dose. Concentrations of other metabolites could not be determined.^9,13

Half-life

The terminal elimination half-life of mefloquine ranges from 0.9 - 13.8 days, according to one pharmacokinetic review.⁷ In various studies of healthy adults, the mean elimination half-life of mefloquine varied between 2 and 4 weeks, with a mean half-life of approximately 21 days.¹³

Clearance

The systemic clearance of mefloquine ranges from 0.022 to 0.073 L/h/kg, with an increased clearance during pregnancy.⁷ Prescribing information mentions a clearance rate of 30 mL/min.¹³

Adverse Effects

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!

See the data

Improve decision support & research outcomes with our structured adverse effects data.

See a data sample

Toxicity

The oral TDLO of mefloquine in humans is 11 mg/kg/2W (intermittent) and 880 mg/kg in the rat. Intraperitoneal LD50 in the rat is 130 mg/kg.¹⁷ Symptoms of an overdose with mefloquine may manifest as a worsening of adverse effects. In the case of an overdose, symptomatic and supportive care should be provided. There is no known antidote for an overdose with mefloquine.¹³ Monitor cardiac function by ECG, follow neuropsychiatric status for at least 24 hours, and provide treatment as required.¹³

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Abametapir	The serum concentration of Mefloquine can be increased when it is combined with Abametapir.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Mefloquine.
Abrocitinib	The serum concentration of Mefloquine can be increased when it is combined with Abrocitinib.
Acebutolol	The risk or severity of QTc prolongation can be decreased when Mefloquine is combined with Acebutolol.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Mefloquine.

Food Interactions

• Avoid alcohol.
• Take with a full glass of water.
• Take with food. The presence of food significantly enhances the rate and extent of absorption, leading to about a 40% increase in bioavailability.

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Mefloquine hydrochloride	326VC85GV6	51742-86-0	WESWYMRNZNDGBX-YLCXCWDSSA-N

Product Images

International/Other Brands

Eloquine (Unifarm) / Facital (Zydus Cadila) / Falcital (Cadila HC) / Larimef (Ipca) / Mefax (Alkem) / Mefliam (Cipla Medpro) / Meflon (ACI) / Mefloquina (AC Farma) / Mefque (Zydus Cadila) / Mephaquin (Hisamitsu Seiyaku) / Mephaquin Lactab (Mepha) / Mequin (Atlantic) / Mqf (Sun) / Suton (Newai Chem) / Tropicur (Investi)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Lariam	Tablet	250 mg/1	Oral	Hoffmann-La Roche Inc	2003-01-10	2008-12-31
Lariam Tab 250mg	Tablet	250 mg	Oral	Hoffmann La Roche	1993-12-31	2013-05-02
Mefloquine	Tablet	250 mg	Oral	Aa Pharma Inc	2002-07-23	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Mefloquine Hydrochloride	Tablet	250 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2004-01-06	Not applicable
Mefloquine Hydrochloride	Tablet	250 mg/1	Oral	Nucare Pharmaceuticals,inc.	2004-01-06	Not applicable
Mefloquine Hydrochloride	Tablet	250 mg/1	Oral	Sandoz	2002-02-20	2016-03-31
Mefloquine Hydrochloride	Tablet	250 mg/1	Oral	Rebel Distributors	2010-04-21	Not applicable
Mefloquine Hydrochloride	Tablet	250 mg/1	Oral	A-S Medication Solutions	2004-01-06	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
MEFLOTAS TABLET 250 mg	Tablet	250 mg	Oral	APOTHECA MARKETING PTE LTD	2002-03-15	Not applicable
MEPHAQUIN LACTAB 250 mg	Tablet, film coated	250 mg	Oral	APEX PHARMA MARKETING PTE. LTD.	1988-04-26	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
อาร์ทีซูเนทและเมฟลอควินไฮโดรคลอไรด์ 100/220 มก.	Mefloquine hydrochloride (220 MG) + Artesunate (100 MG)	Tablet, film coated		บริษัท ฮีลลอล ฟาร์มาซูติคอล จำกัด จำกัด	2019-04-10	Not applicable
อาร์ทีซูเนทและเมฟลอควินไฮโดรคลอไรด์ 25/55 มก.	Mefloquine hydrochloride (55 MG) + Artesunate (25 MG)	Tablet, film coated		บริษัท ฮีลลอล ฟาร์มาซูติคอล จำกัด จำกัด	2019-04-10	Not applicable

Categories

ATC Codes

P01BF02 — Artesunate and mefloquine

• P01BF — Artemisinin and derivatives, combinations
• P01B — ANTIMALARIALS
• P01 — ANTIPROTOZOALS
• P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

P01BC02 — Mefloquine

• P01BC — Methanolquinolines
• P01B — ANTIMALARIALS
• P01 — ANTIPROTOZOALS
• P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Drug Categories

• Agents Causing Muscle Toxicity
• Agents that reduce seizure threshold
• Aminoquinolines
• Anti-Infective Agents
• Antimalarial methanolquinolines
• Antimalarials
• Antiparasitic Agents
• Antiparasitic Products, Insecticides and Repellents
• Antiprotozoals
• Cholinesterase Inhibitors
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Heterocyclic Compounds, Fused-Ring
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Potential QTc-Prolonging Agents
• QTc Prolonging Agents
• Quinolines

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as 4-quinolinemethanols. These are organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

4-quinolinemethanols

Direct Parent

4-quinolinemethanols

Alternative Parents

Aralkylamines / Pyridines and derivatives / Piperidines / Benzenoids / Heteroaromatic compounds / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Aromatic alcohols / Alkyl fluorides

show 4 more

Substituents

1,2-aminoalcohol / 4-quinolinemethanol / Alcohol / Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperidine / Pyridine / Secondary alcohol / Secondary aliphatic amine / Secondary amine

show 15 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines, organofluorine compound, quinolines, secondary alcohol (CHEBI:63681)

Affected organisms

• Plasmodium falciparum

Chemical Identifiers

UNII

TML814419R

CAS number

53230-10-7

InChI Key

XEEQGYMUWCZPDN-UHFFFAOYSA-N

InChI

InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2

IUPAC Name

[2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol

SMILES

OC(C1CCCCN1)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F

References

Synthesis Reference

Asymmetric Total Synthesis of the Antimalarial Drug (+)-Mefloquine Hydrochloride via Chiral N-Amino Cyclic Carbamate Hydrazones.Org. Lett. 2011, 13, 12, 3118–3121. May 26, 2011. https://doi.org/10.1021/ol2010193

US4507482

General References

1. Nevin RL: A serious nightmare: psychiatric and neurologic adverse reactions to mefloquine are serious adverse reactions. Pharmacol Res Perspect. 2017 Aug;5(4). doi: 10.1002/prp2.328. [Article]
2. Palmer KJ, Holliday SM, Brogden RN: Mefloquine. A review of its antimalarial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 Mar;45(3):430-75. doi: 10.2165/00003495-199345030-00009. [Article]
3. Tickell-Painter M, Maayan N, Saunders R, Pace C, Sinclair D: Mefloquine for preventing malaria during travel to endemic areas. Cochrane Database Syst Rev. 2017 Oct 30;10:CD006491. doi: 10.1002/14651858.CD006491.pub4. [Article]
4. Wong W, Bai XC, Sleebs BE, Triglia T, Brown A, Thompson JK, Jackson KE, Hanssen E, Marapana DS, Fernandez IS, Ralph SA, Cowman AF, Scheres SHW, Baum J: Mefloquine targets the Plasmodium falciparum 80S ribosome to inhibit protein synthesis. Nat Microbiol. 2017 Mar 13;2:17031. doi: 10.1038/nmicrobiol.2017.31. [Article]
5. Croft AM: A lesson learnt: the rise and fall of Lariam and Halfan. J R Soc Med. 2007 Apr;100(4):170-4. doi: 10.1177/014107680710011411. [Article]
6. Croft AM, Herxheimer A: Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement? BMC Public Health. 2002 Mar 25;2:6. doi: 10.1186/1471-2458-2-6. [Article]
7. Karbwang J, White NJ: Clinical pharmacokinetics of mefloquine. Clin Pharmacokinet. 1990 Oct;19(4):264-79. doi: 10.2165/00003088-199019040-00002. [Article]
8. Sheridan CM, Garcia VE, Ahyong V, DeRisi JL: The Plasmodium falciparum cytoplasmic translation apparatus: a promising therapeutic target not yet exploited by clinically approved anti-malarials. Malar J. 2018 Dec 12;17(1):465. doi: 10.1186/s12936-018-2616-7. [Article]
9. Schwartz DE, Eckert G, Ekue JM: Urinary excretion of mefloquine and some of its metabolites in African volunteers at steady state. Chemotherapy. 1987;33(5):305-8. doi: 10.1159/000238513. [Article]
10. Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [Article]
11. Gillespie RJ, Adams DR, Bebbington D, Benwell K, Cliffe IA, Dawson CE, Dourish CT, Fletcher A, Gaur S, Giles PR, Jordan AM, Knight AR, Knutsen LJ, Lawrence A, Lerpiniere J, Misra A, Porter RH, Pratt RM, Shepherd R, Upton R, Ward SE, Weiss SM, Williamson DS: Antagonists of the human adenosine A2A receptor. Part 1: Discovery and synthesis of thieno[3,2-d]pyrimidine-4-methanone derivatives. Bioorg Med Chem Lett. 2008 May 1;18(9):2916-9. doi: 10.1016/j.bmcl.2008.03.075. Epub 2008 Mar 30. [Article]
12. Fontaine F, de Sousa G, Burcham PC, Duchene P, Rahmani R: Role of cytochrome P450 3A in the metabolism of mefloquine in human and animal hepatocytes. Life Sci. 2000 Apr 21;66(22):2193-212. [Article]
13. FDA Approved Products: Lariam (mefloquine hydrochloride) oral tablets [Link]
14. WHO international: 2020 World Malaria Report [Link]
15. NIH StatPearls: Malaria [Link]
16. FDA Approved Products: Mefloquine hydrochloride tablets USP [Link]
17. Cayman Chem MSDS: Mefloquine [Link]
18. CDC: Malaria [Link]
19. Medical Microbiology 4th edition: Malaria [Link]

External Links

Human Metabolome Database

HMDB0014502

KEGG Drug

D04895

KEGG Compound

C07633

PubChem Compound

4046

PubChem Substance

46505610

ChemSpider

3906

BindingDB

50022889

RxNav

6694

ChEBI

63681

ChEMBL

CHEMBL416956

Therapeutic Targets Database

DAP001310

PharmGKB

PA450348

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Mefloquine

FDA label

Download (394 KB)

MSDS

Download (107 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Malaria / Parasitic Diseases	1
4	Completed	Treatment	Falciparum / Malaria	1
4	Completed	Treatment	Healthy Subjects (HS)	1
4	Completed	Treatment	Malaria	3
4	Completed	Treatment	Malaria caused by Plasmodium falciparum	1

Pharmacoeconomics

Manufacturers

• Hoffmann la roche inc
• Barr laboratories inc
• Roxane laboratories inc
• Sandoz inc
• United states army walter reed army institute research
• West ward pharmaceutical corp

Packagers

• A-S Medication Solutions LLC
• Barr Pharmaceuticals
• Dispensing Solutions
• F Hoffmann La Roche Ltd.
• F Hoffmann-La Roche Ltd.
• Nucare Pharmaceuticals Inc.
• PD-Rx Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Roxane Labs
• Sandoz
• West-Ward Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral	250 MG
Tablet	Oral	250 mg/1
Tablet, film coated	Oral	250 mg
Tablet, film coated

Prices

Unit description	Cost	Unit
Lariam 25 250 mg tablet Box	322.77USD	box
Lariam 250 mg tablet	12.41USD	tablet
Mefloquine hcl 250 mg tablet	10.8USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	250-254	https://www.chemicalbook.com/ChemicalProductProperty_US_CB6252498.aspx
boiling point (°C)	415.7±40.0 °C	https://www.chemicalbook.com/ChemicalProductProperty_US_CB0233114.aspx
water solubility	1.806 mg/mL	https://onlinelibrary.wiley.com/doi/full/10.1002/jps.22249
logP	3.9	https://onlinelibrary.wiley.com/doi/full/10.1002/jps.22249
pKa	8.6	https://www.chemicalbook.com/ChemicalProductProperty_US_CB0233114.aspx

Predicted Properties

Property	Value	Source
Water Solubility	0.038 mg/mL	ALOGPS
logP	3.1	ALOGPS
logP	4.11	Chemaxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.79	Chemaxon
pKa (Strongest Basic)	9.46	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	45.15 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	82.58 m3·mol-1	Chemaxon
Polarizability	31.73 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9959
Blood Brain Barrier	+	0.9445
Caco-2 permeable	-	0.5753
P-glycoprotein substrate	Substrate	0.6796
P-glycoprotein inhibitor I	Non-inhibitor	0.7395
P-glycoprotein inhibitor II	Inhibitor	0.5419
Renal organic cation transporter	Non-inhibitor	0.6446
CYP450 2C9 substrate	Non-substrate	0.8711
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.6524
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8533
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9163
Ames test	Non AMES toxic	0.809
Carcinogenicity	Non-carcinogens	0.9437
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.9133 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9035
hERG inhibition (predictor II)	Inhibitor	0.8204

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001i-9025000000-bd2efec95144343a1b49
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-fbf2aeded2dfd72b12cc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-80124d44202ceb51cd8f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-056r-0019000000-058b877884ff2a12697b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-9802e87bc5e9b018960e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-2079000000-2074dcdbbe3118e6698d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00fr-3095000000-9abd434b780d3e233ae9
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	177.5304226	predicted	DarkChem Lite v0.1.0
[M-H]-	176.25337	predicted	DeepCCS 1.0 (2019)
[M+H]+	177.9182226	predicted	DarkChem Lite v0.1.0
[M+H]+	178.61137	predicted	DeepCCS 1.0 (2019)
[M+Na]+	177.3850226	predicted	DarkChem Lite v0.1.0
[M+Na]+	185.99881	predicted	DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Details1. Fe(II)-protoporphyrin IX

Kind

Small molecule

Organism

Plasmodium falciparum

Pharmacological action

Yes

Actions

Binder

References

1. Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [Article]
2. Gildenhuys J, Sammy CJ, Muller R, Streltsov VA, le Roex T, Kuter D, de Villiers KA: Alkoxide coordination of iron(III) protoporphyrin IX by antimalarial quinoline methanols: a key interaction observed in the solid-state and solution. Dalton Trans. 2015 Oct 14;44(38):16767-77. doi: 10.1039/c5dt02671g. Epub 2015 Sep 3. [Article]

2. 80S ribosomal subunit

Kind

Group

Organism

Plasmodium falciparum

Pharmacological action

Yes

Actions

Binder

This represents the 80S ribosomal subunit of Plasmodium falciparum.

References

1. Wong W, Bai XC, Sleebs BE, Triglia T, Brown A, Thompson JK, Jackson KE, Hanssen E, Marapana DS, Fernandez IS, Ralph SA, Cowman AF, Scheres SHW, Baum J: Mefloquine targets the Plasmodium falciparum 80S ribosome to inhibit protein synthesis. Nat Microbiol. 2017 Mar 13;2:17031. doi: 10.1038/nmicrobiol.2017.31. [Article]
2. Melnikov S, Manakongtreecheep K, Soll D: Revising the Structural Diversity of Ribosomal Proteins Across the Three Domains of Life. Mol Biol Evol. 2018 Jul 1;35(7):1588-1598. doi: 10.1093/molbev/msy021. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	61	N/A	N/A	A15758
Ki (nM)	2534	N/A	N/A	A15758
Ki (nM)	124	N/A	N/A	A15758
Ki (nM)	6553	N/A	N/A	A15758

Details

Binding Properties3. Adenosine receptor A2a

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Antagonist

General Function

Identical protein binding

Specific Function

Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.

Gene Name

ADORA2A

Uniprot ID

P29274

Uniprot Name

Adenosine receptor A2a

Molecular Weight

44706.925 Da

References

1. Gillespie RJ, Adams DR, Bebbington D, Benwell K, Cliffe IA, Dawson CE, Dourish CT, Fletcher A, Gaur S, Giles PR, Jordan AM, Knight AR, Knutsen LJ, Lawrence A, Lerpiniere J, Misra A, Porter RH, Pratt RM, Shepherd R, Upton R, Ward SE, Weiss SM, Williamson DS: Antagonists of the human adenosine A2A receptor. Part 1: Discovery and synthesis of thieno[3,2-d]pyrimidine-4-methanone derivatives. Bioorg Med Chem Lett. 2008 May 1;18(9):2916-9. doi: 10.1016/j.bmcl.2008.03.075. Epub 2008 Mar 30. [Article]

×

Identify potential medication risks

Easily compare up to 40 drugs with our drug interaction checker.

Get severity rating, description, and management advice.

Learn more

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54