Mefloquine hydrochloride Chemical Properties

Melting point:

250-254?C

storage temp. 

2-8°C

solubility 

DMSO: 38 mg/mL, soluble

form 

solid

color 

white

λmax

222nm(Acidic H2O)(lit.)

Merck 

14,5801

BCS Class

4/2

Stability:

Temperature Sensitive

InChI

InChI=1/C17H16F6N2O.ClH/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;1H/t12-,15+;/s3

InChIKey

WESWYMRNZNDGBX-YLCXCWDSSA-N

SMILES

C12N=C(C=C([C@@H](O)[C@@]3([H])NCCCC3)C=1C=CC=C2C(F)(F)F)C(F)(F)F.Cl |&1:5,7,r|

CAS DataBase Reference

51773-92-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

VC0308000

HS Code 

2933399090

MSDS

• Language:English Provider:(2R)-(+/-)-alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride
• Language:English Provider:SigmaAldrich

Mefloquine hydrochloride Usage And Synthesis

Description

Mefloquine hydrochloride is an erythrocytic schizonticide useful, in combination with sulfadoxine and pyrimethamine, in the prophylaxis and treatment of malaria. Administered once weekly, the combination is effective against pathogens resistant to other agents.

Description

Mefloquine is an orally bioavailable quinolinemethanol derivative with antimalarial properties. It increases mean survival time and abolishes malarial infection in mice at doses of 10 and 40 mg/kg, respectively. It inhibits hemozoin formation, leading to an increase in free heme in purified trophozoites. It acts as an antagonist at the adenosine A_2A receptor, an agonist at serotonin 5-HT_2A and 5-HT_2C receptors, and has various effects on calcium homeostasis. Mefloquine increases the time mice spend in the light side of the light-dark box test and reduces immobility time in the tail suspension test, parameters typically associated with anxiolytic and antidepressant-like behavior. Formulations containing mefloquine have been used to prevent and treat malaria but have been associated with neuropsychiatric disturbances.

Chemical Properties

White Solid

Originator

Walter Reed (USA)

Uses

Mefloquine Hydrochloride (Polymorph Form E) is a polymorphic form of Mefloquine Hydrochloride (M207055), a quinoline methanol antimalarial agent.

Uses

Antimalarial;Heme polymerase inhibitor

Definition

ChEBI: Mefloquine hydrochloride is a hydrochloride.

brand name

FANSIMEF

General Description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards

Biochem/physiol Actions

Blocker of gap junction channels Cx36 and Cx50.

Clinical Use

The newest of the 4-aminoquinolines,mefloquine, is marketed as the R,S-isomer. It was developedin the 1960s as part of the U.S. Army’s WalterReed Institute for Medical Research antimalarial researchprogram. It differs significantly from the other agents in this class by having two trifluromethyl moieties at positions2’ and 8' and no electronegative substituents at eitherpositions 6' (quinine) or 7' (chloroquine). Mefloquine alsodiffers from chloroquine and its analogs by being a schizonticide acting before the parasite canenter the erythrocyte. There is some evidence that it acts byraising the pH in the parasite’s vesicles interfering with itsability to process heme. Mefloquine-resistant strains ofP. falciparum have appeared. Relapse can occur with acuteP. vivax that has been treated with mefloquine because thedrug does not eliminate the hepatic phase of this species,which can reinfect the liver.
Mefloquine is teratogenic in rats, mice, and rabbits. Thereis an FDA-required warning that this drug can cause exacerbatemental disorders and is contraindicated in patients withactive depression, a recent history of depression, generalizedanxiety disorder, psychosis, schizophrenia, and other majorpsychiatric disorders or a history of convulsions.

storage

Store at +4°C

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