CAS 51773-92-3|Mefloquine hydrochloride

Introduction：Basic information about CAS 51773-92-3|Mefloquine hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Mefloquine hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles43
7. Synonyms

Common Name	Mefloquine hydrochloride
CAS Number	51773-92-3	Molecular Weight	378.312
Density	1.4±0.1 g/cm3	Boiling Point	415.7±40.0 °C at 760 mmHg
Molecular Formula	C₁₇H₁₇ClF₆N₂O	Melting Point	250-254ºC
MSDS	ChineseUSA	Flash Point	205.2±27.3 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	Mefloquine Hydrochloride
Synonym	More Synonyms

Mefloquine hydrochloride BiologicalActivity

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 channel currents with an IC50 value of approximately 1 microM. Mefloquine slowed the activation rate of KvLQT1/minK and more block was evident at lower membrane potentials compared with higher ones. HERG channel currents were about 6-fold less sensitive to block by mefloquine (IC50 = 5.6 microM). Block of HERG displayed a positive voltage dependence with maximal inhibition obtained at more depolarized potentials [1]. MQ has a highly selective cytotoxicity that inhibits PCa cell growth. MQ-mediated ROS simultaneously downregulated Akt phosphorylation and activated extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK) and adenosine monophosphate-activated protein kinase (AMPK) signaling in PC3 cells [2]. in vivo: Pregnant rats were treated orally with AS (15 and 40 mg/kg body weight (bwt)/day), MQ (30 and 80 mg/kg bwt/day) and AS/MQ (15/30 and 40/80 mg/kg bwt/day) on days 9-11 post coitum (pc). The dams were euthanized on day 12 pc and gestational and embryos histological parameters were evaluated [3].Clinical trial: Activity of Mefloquine Against Urinary Schistosomiasis . Phase 2
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Anti-infection >>ParasiteResearch Areas >>Infection
References	[1]. Kang J, Chen XL, Wang L, Interactions of the antimalarial drug mefloquine with the human cardiac potassium channels KvLQT1/minK andHERG. J Pharmacol Exp Ther. 2001 Oct;299(1):290-6. [2]. Yan KH, Yao CJ, Hsiao CH, Mefloquine exerts anticancer activity in prostate cancer cells via ROS-mediated modulation of Akt, ERK, JNK and AMPK signaling. Oncol Lett. 2013 May;5(5):1541-1545. [3]. Boareto AC, Müller JC, Louren?o EL, Effects of the combined artesunate and mefloquine antimalarial drugs on rat embryos. Hum Exp Toxicol. 2013 Feb 19. [Epub ahead of print]

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 channel currents with an IC50 value of approximately 1 microM. Mefloquine slowed the activation rate of KvLQT1/minK and more block was evident at lower membrane potentials compared with higher ones. HERG channel currents were about 6-fold less sensitive to block by mefloquine (IC50 = 5.6 microM). Block of HERG displayed a positive voltage dependence with maximal inhibition obtained at more depolarized potentials [1]. MQ has a highly selective cytotoxicity that inhibits PCa cell growth. MQ-mediated ROS simultaneously downregulated Akt phosphorylation and activated extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK) and adenosine monophosphate-activated protein kinase (AMPK) signaling in PC3 cells [2]. in vivo: Pregnant rats were treated orally with AS (15 and 40 mg/kg body weight (bwt)/day), MQ (30 and 80 mg/kg bwt/day) and AS/MQ (15/30 and 40/80 mg/kg bwt/day) on days 9-11 post coitum (pc). The dams were euthanized on day 12 pc and gestational and embryos histological parameters were evaluated [3].Clinical trial: Activity of Mefloquine Against Urinary Schistosomiasis . Phase 2

Related Catalog

Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Anti-infection >>ParasiteResearch Areas >>Infection

References

[1]. Kang J, Chen XL, Wang L, Interactions of the antimalarial drug mefloquine with the human cardiac potassium channels KvLQT1/minK andHERG. J Pharmacol Exp Ther. 2001 Oct;299(1):290-6.

[2]. Yan KH, Yao CJ, Hsiao CH, Mefloquine exerts anticancer activity in prostate cancer cells via ROS-mediated modulation of Akt, ERK, JNK and AMPK signaling. Oncol Lett. 2013 May;5(5):1541-1545.

[3]. Boareto AC, Müller JC, Louren?o EL, Effects of the combined artesunate and mefloquine antimalarial drugs on rat embryos. Hum Exp Toxicol. 2013 Feb 19. [Epub ahead of print]

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	415.7±40.0 °C at 760 mmHg
Melting Point	250-254ºC
Molecular Formula	C₁₇H₁₇ClF₆N₂O
Molecular Weight	378.312
Flash Point	205.2±27.3 °C
Exact Mass	378.116669
PSA	45.15000
LogP	2.87
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.519
InChIKey	WESWYMRNZNDGBX-YLCXCWDSSA-N
SMILES	Cl.OC(c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)C1CCCCN1
Storage condition	Refrigerator
Water Solubility	DMSO: 38 mg/mL, soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC0308000

CHEMICAL NAME :: 4-Quinolinemethanol, 2,8-bis(trifluoromethyl)-alpha-2-piperidinyl-, monohydrochloride, (R*,S*)-, (+-)-

CAS REGISTRY NUMBER :: 51773-92-3

LAST UPDATED :: 199603

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C17-H16-F6-N2-O.Cl-H

MOLECULAR WEIGHT :: 414.81

WISWESSER LINE NOTATION :: T66 BNJ CXFFF EYQ- BT6MTJ& JXFFF &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 96 mg/kg/52D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - excitement Behavioral - aggression

REFERENCE :: AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 154,2360,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 15 mg/kg/3W-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - coma

REFERENCE :: MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 161,453,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 11 mg/kg/2W-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 114,994,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 18 mg/kg/5W-I

TOXIC EFFECTS :: Peripheral Nerve and Sensation - paresthesis Behavioral - general anesthetic

REFERENCE :: AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 117,1058,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 880 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: ACTRAQ Acta Tropica. (Schwabe & Co., Steintorstr. 13, CH-4010 Basel, Switzerland) V.1- 1944- Volume(issue)/page/year: 37,232,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 130 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: ACTRAQ Acta Tropica. (Schwabe & Co., Steintorstr. 13, CH-4010 Basel, Switzerland) V.1- 1944- Volume(issue)/page/year: 37,232,1980

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;
Risk Phrases	R22
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
RTECS	VC0308000

Articles43

Preliminary investigation of the contribution of CYP2A6, CYP2B6, and UGT1A9 polymorphisms on artesunate-mefloquine treatment response in Burmese patients with Plasmodium falciparum malaria.

Am. J. Trop. Med. Hyg. 91(2) , 361-6, (2014)

CYP2A6, CYP2B6, and UGT1A9 genetic polymorphisms and treatment response after a three-day course of artesunate-mefloquine was investigated in 71 Burmese patients with uncomplicated Plasmodium falcipar...

Studying the effect of chloroquine on sporozoite-induced protection and immune responses in Plasmodium berghei malaria.

Malaria Journal 14 , 130, (2015)

Sporozoite immunization of animals and humans under a chemo-prophylactic cover of chloroquine (CPS-CQ) efficiently induces sterile protection against malaria. In humans, CPS-CQ is strikingly more effi...

Comparison between Flow Cytometry, Microscopy, and Lactate Dehydrogenase-Based Enzyme-Linked Immunosorbent Assay for Plasmodium falciparum Drug Susceptibility Testing under Field Conditions.

J. Clin. Microbiol. 53 , 3296-303, (2015)

Flow cytometry is an objective method for conducting in vitro antimalarial sensitivity assays with increasing potential for application in field sites. We examined in vitro susceptibility to seven ant...

Synonyms

Mefloquine hydrochloride

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

EINECS 257-412-0

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

4-quinolinemethanol, a-2-piperidinyl-2,8-bis(trifluoromethyl)-

[2,8-Bis(trifluoromethyl)-4-quinolinyl](2-piperidinyl)methanol

MFCD00797519

(AS)-rel-a-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride

4-Quinolinemethanol, α-2-piperidinyl-2,8-bis(trifluoromethyl)-

α-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol

Mefloquine (hydrochloride)

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