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Mefloquine hydrochloride

Mefloquine hydrochloride structure

CAS No:
51773-92-3
Formula:
C17H16F6N2O.ClH
Chemical Name:
Mefloquine hydrochloride
Synonyms:
4-Quinolinemethanol,α-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-,hydrochloride (1:1),(αS)-rel-;4-Quinolinemethanol,α-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride,(R*,S*)-(±)-;4-Quinolinemethanol,α-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride,(αS)-rel-;Mefloquine hydrochloride;WR 142490;4-Quinolinemethanol,α-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride,(R*,S*)-;Loriam;Ro 21-5998/001;NSC 157387;Mefloquin hydrochloride;(±)-Mefloquine hydrochloride;68682-28-0
Categories:
Analytical Chemistry > Standard

Description

Mefloquine hydrochloride is a quinoline antimalarial drug that is structurally related to the antiarrhythmic agent quinidine. IC50 Value: 1 microM ( for K+ channel) [1]Target: AntiparasiticMefloquine is widely used in both the treatment and prophylaxis of Plasmodium falciparum malaria. MQ can induces oxidative stress in vitro. Evidence indicates that reactive oxygen species (ROS) may be used as a therapeutic modality to kill cancer cells [2].in vitro: Mefloquine inhibitedKvLQT1/minK chan

Mefloquine hydrochloride is a hydrochloride.|Mefloquine is a quinoline derivative used for the prevention and therapy of P. falciparum malaria. Mefloquine therapy is associated with a low rate of transient and asymptomatic serum enzyme elevations and is a rare cause of clinically apparent acute liver injury.|A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.

Mefloquine hydrochloride Basic Attributes

Molecular Weight：

414.77

Exact Mass：

378.116669

EC Number：

257-412-0

UNII：

326VC85GV6

DSSTox ID：

DTXSID1047819

HScode：

2933399090

Characteristics

PSA：

45.2 Å²

Appearance：

white solid

Density：

1.4±0.1 g/cm3

Melting Point：

259-260 °C (decomp)

Flash Point：

205.2±27.3 °C

Refractive Index：

1.519

Water Solubility：

DMSO: 38 mg/mL, soluble

Storage Conditions：

Refrigerator

Safety Information

Transport codes：

UN 3077 9 / PGIII

wgk germany：

hazard class code：

RTECS Number：

VC0308000

Marks：

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 94 companies from 4 notifications to the ECHA C&L Inventory.

Toxicity

Hepatotoxicity：

Chronic therapy with mefloquine is associated with asymptomatic, transient serum enzyme elevations in up to 18% of patients. These elevations are usually mild and resolve without dose modifications. Despite widespread use, mefloquine has rarely been linked to clinically apparent acute liver injury and too few reports are available to characterize the clinical features of such injury. Instances of acute hepatocellular injury as well as cholestatic hepatitis have been linked to use of mefloquine. Allergic manifestations (rash, fever, eosinophilia) and autoantibody formation are rare.

Drug Information

LiverTox Summary：

Mefloquine is a quinoline derivative used for the prevention and therapy of P. falciparum malaria. Mefloquine therapy is associated with a low rate of transient and asymptomatic serum enzyme elevations and is a rare cause of clinically apparent acute liver injury.

Drug Classes：

Antimalarial Agents

MeSH：

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

MeSH Entry Terms：

Lariam

Mefloquine hydrochloride Use and Manufacturing

Methods of Manufacturing

Solutions of (+/-)-erythro-mefloquinium chloride (2 mmol) and sodium tetraethylborate (2 mmol) in ethanol were mixed and stirred overnight. The reaction mixture was filtered to remove sodium chloride and the mother liquor was left at room temperature. After a period, crystals of (+/-)-erythro-mefloquine were collected. IR and NMR spectral data were in agreement with published data.Solution of mefloquinium chloride (2 mmol) and sodium tetraphenylborate (2 mmol) in acetone were mixed and stirred overnight. The reaction mixture was filtered to remove sodium chloride and the mother liquor was left at room temperature. After a period, crystals of (+/-)-erythro-mefloquinium tetraphenylborate monoacetone solvate, (3*Me2CO), were collected, m.p 137-139 C (with evolution of gases).

Uses

Quinoline methanol antimalarial agent.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:414.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:2
Exact Mass:414.0933598
Monoisotopic Mass:414.0933598
Topological Polar Surface Area:45.2
Heavy Atom Count:27
Complexity:483
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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CAS No.: 51773-92-3

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