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Mefloquine

Mefloquine

Synopsis, Chemistry

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Also known as: Mefloquine hydrochloride, Mefloquine hcl, 51773-92-3, Mefloquine (hydrochloride), Loriam, Mefloquine hydrochloride, (+)

Molecular Formula

C₁₇H₁₇ClF₆N₂O

Molecular Weight

414.8 g/mol

InChI Key

WESWYMRNZNDGBX-YLCXCWDSSA-N

FDA UNII

326VC85GV6

A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.

1 2D Structure

Mefloquine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol;hydrochloride

2.1.2 InChI

InChI=1S/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+;/m1./s1

2.1.3 InChI Key

WESWYMRNZNDGBX-YLCXCWDSSA-N

2.1.4 Canonical SMILES

C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl

2.1.5 Isomeric SMILES

C1CCN[C@H](C1)[C@H](C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl

2.2 Other Identifiers

2.2.1 UNII

326VC85GV6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lariam

2. Mefloquine

3. Mefloquine Hydrochloride

4. Mephloquine

5. Ro 21 5998 001

6. Ro-21-5998-001

7. Ro215998001

8. Wr 142,490

9. Wr 177,602

10. Wr-142,490

11. Wr-177,602

12. Wr142,490

13. Wr177,602

2.3.2 Depositor-Supplied Synonyms

1. Mefloquine Hydrochloride

2. Mefloquine Hcl

3. 51773-92-3

4. Mefloquine (hydrochloride)

5. Loriam

6. Mefloquine Hydrochloride, (+)

7. 51742-86-0

8. 326vc85gv6

9. Ro 21-5998/001

10. Mefloquinehydrochloride

11. 5y9l3636o3

12. Ro-21-5998/001

13. (s)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2r)-piperidin-2-yl]methanol;hydrochloride

14. Dsstox_cid_27796

15. Dsstox_rid_82568

16. Dsstox_gsid_47819

17. Mls001332559

18. Nsc-157387

19. (r)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2s)-piperidin-2-ylmethanol Hydrochloride

20. (s)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2r)-piperidin-2-yl]methanol Hydrochloride

21. Wr 142490 Hydrochloride

22. Nsc 157387

23. Cas-51773-92-3

24. Mefloquine Hydrochloride [usan]

25. Mefloquin Hydrochloride

26. Ncgc00161831-02

27. Smr000875233

28. Einecs 257-412-0

29. Wr-142490

30. Tcmdc-124288

31. Unii-326vc85gv6

32. Unii-5y9l3636o3

33. Gnf-pf-5559

34. Lariam (tn)

35. Mefloquine Hydrochloride [usan:usp]

36. Ro-215998001

37. Chembl1606

38. Dl-erythro-alpha-2-piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol Monohydrochloride

39. Schembl41094

40. Mls001332560

41. Chebi:6719

42. (+/-)-mefloquine Hcl

43. Dtxsid1047819

44. Tox21_111999

45. Hy-17437a

46. Mfcd00797519

47. S4420

48. Mefloquine Hydrochloride (jp17/usp)

49. Mefloquine Hydrochloride [jan]

50. Akos015919767

51. Tox21_111999_1

52. Ac-4686

53. Ccg-268825

54. Cs-1430

55. Gs-3621

56. Nc00622

57. (r*,s*)-(1)-alpha-2-piperidyl-2,8-bis(trifluoromethyl)quinoline-4-methanol Monohydrochloride

58. Mefloquine Hydrochloride [mart.]

59. Mefloquine Hydrochloride [vandf]

60. Mefloquine Hydrochloride [usp-rs]

61. Mefloquine Hydrochloride [who-dd]

62. Mefloquine Hydrochloride [who-ip]

63. Ncgc00161831-04

64. 4-quinolinemethanol, Alpha-(2r)-2-piperidinyl-2,8-bis(trifluoromethyl)-, Monohydrochloride, (alphas)-rel-

65. 4-quinolinemethanol, Alpha-2-piperidinyl-2,8-bis(trifluoromethyl)-, Monohydrochloride, (r*,s*)-(+-)-

66. M2313

67. Sw220098-1

68. Mefloquine Hydrochloride [ep Impurity]

69. Mefloquine Hydrochloride [orange Book]

70. D00831

71. Mefloquine Hydrochloride [ep Monograph]

72. Mefloquine Hydrochloride [usp Monograph]

73. Mefloquini Hydrochloridum [who-ip Latin]

74. Mefloquine Hydrochloride, >=98% (hplc), Powder

75. Q-201345

76. Mefloquine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

77. (?s)-rel-?-(2r)-2-piperidinyl-2,3-bis(trifluoromethyl-4-quinolinemethanol Hydrochloride

78. (2,8-bis-trifluoromethylquinolin-4-yl)-piperidin-2-yl-methanol Hydrochloride(r*,s*)

79. Mefloquine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

80. Mefloquine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

81. Rel-(s)-(2,8-bis(trifluoromethyl)quinolin-4-yl)((r)-piperidin-2-yl)methanol Hydrochloride

82. (as)?-?rel-?a-?(2r)?-?2-?piperidinyl-?2,8-?bis(trifluoromethyl)?-?4-?quinolinemethanol Monohydrochloride

83. 4-quinolinemethanol, .alpha,-[(2r)-2-piperidinyl]-2,8-bis(trifluoromethyl)-, (.alpha.s)-, Hydrochloride (1:1)

84. 4-quinolinemethanol, .alpha.-(2r)-2-piperidinyl-2,8-bis(trifluoromethyl)-, Hydrochloride (1:1), (.alpha.s)-

85. 4-quinolinemethanol, .alpha.-(2r)-2-piperidinyl-2,8-bis(trifluoromethyl)-, Monohydrochloride, (.alpha.s)-

86. 4-quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-, Monohydrochloride, (r*,s*)- (+/-)-

87. 4-quinolinemethanol, A-(2r)-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride, (as)-rel-

88. Dl-erythro-.alpha.-2-piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol Monohydrochloride

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₇ClF₆N₂O
Molecular Weight	414.8 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	414.0933598 g/mol
Monoisotopic Mass	414.0933598 g/mol
Topological Polar Surface Area	45.2 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	483
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Mefloquine hydrochloride
Drug Label	Mefloquine hydrochloride is an antimalarial agent available as 250 mg tablets of mefloquine hydrochloride (equivalent to 228.0 mg of the free base) for oral administration.Mefloquine hydrochloride is a 4-quinolinemethanol derivative with the specific...
Active Ingredient	Mefloquine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	250mg
Market Status	Prescription
Company	Sandoz; Roxane; Barr

2 of 2
Drug Name	Mefloquine hydrochloride
Drug Label	Mefloquine hydrochloride is an antimalarial agent available as 250 mg tablets of mefloquine hydrochloride (equivalent to 228.0 mg of the free base) for oral administration.Mefloquine hydrochloride is a 4-quinolinemethanol derivative with the specific...
Active Ingredient	Mefloquine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	250mg
Market Status	Prescription
Company	Sandoz; Roxane; Barr

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antimalarials

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Antimalarial [EPC]