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Also known as: 1-benzhydryl-4-methylpiperazine, Marezine, 82-92-8, Nautazine, Ciclizina, Neo-devomit

Molecular Formula

C₁₈H₂₂N₂

Molecular Weight

266.4 g/mol

InChI Key

UVKZSORBKUEBAZ-UHFFFAOYSA-N

FDA UNII

QRW9FCR9P2

A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)

1 2D Structure

Cyclizine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-benzhydryl-4-methylpiperazine

2.1.2 InChI

InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

2.1.3 InChI Key

UVKZSORBKUEBAZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

QRW9FCR9P2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cyclizine Hcl

2. Cyclizine Hydrochloride

3. Hcl, Cyclizine

4. Hydrochloride, Cyclizine

5. Marezine

2.3.2 Depositor-Supplied Synonyms

1. 1-benzhydryl-4-methylpiperazine

2. Marezine

3. 82-92-8

4. Nautazine

5. Ciclizina

6. Neo-devomit

7. 1-(diphenylmethyl)-4-methylpiperazine

8. Valoid

9. N-benzhydryl-n'-methylpiperazine

10. N-methyl-n'-benzhydrylpiperazine

11. Cyclizinum

12. Cyclizinum [inn-latin]

13. Ciclizina [inn-spanish]

14. Compound 47-83

15. Piperazine, 1-(diphenylmethyl)-4-methyl-

16. (n-benzhydryl)(n'-methyl)diethylenediamine

17. Wellcome Preparation 47-83

18. 1-benzhydryl-4-methylpiperazin

19. Bw 47-83

20. Cyclizine Chloride

21. Wellcome Prepn. 47-83

22. Cyclizine (inn)

23. Nsc 26608

24. (+-)-1-diphenylmethyl-4-methylpiperazine

25. N-methyl-n'-benzyhydrylpiperazine

26. 1-diphenylmethyl-4-methylpiperazine

27. Nsc-26608

28. Qrw9fcr9p2

29. Chebi:3994

30. 1-benzhydryl-4-methyl-piperazine

31. Emoquil

32. Wellcome

33. Cyclizine [inn]

34. Ne-devomit

35. Wellcome Prepn 47-83

36. Hsdb 3309

37. Ncgc00016421-01

38. Cas-303-25-3

39. Einecs 201-445-5

40. Unii-qrw9fcr9p2

41. Brn 0230441

42. Sr-05000001595

43. Cyclizine [usp:inn:ban:dcf]

44. Emoquil (salt/mix)

45. Marzine (salt/mix)

46. Spectrum_000854

47. Specplus_000917

48. Cyclizine [mi]

49. Cyclizine [hsdb]

50. Prestwick0_000510

51. Prestwick1_000510

52. Prestwick2_000510

53. Prestwick3_000510

54. Spectrum2_001174

55. Spectrum3_000368

56. Spectrum4_000205

57. Spectrum5_001594

58. Cyclizine [vandf]

59. Chembl648

60. Cyclizine [mart.]

61. Cyclizine [who-dd]

62. Schembl4690

63. Oprea1_429421

64. Bspbio_000439

65. Bspbio_002095

66. Kbiogr_000809

67. Kbioss_001334

68. 5-23-01-00232 (beilstein Handbook Reference)

69. Divk1c_007013

70. Spectrum1500211

71. Spbio_001187

72. Spbio_002360

73. Bpbio1_000483

74. Gtpl7151

75. Dtxsid4022864

76. Kbio1_001957

77. Kbio2_001334

78. Kbio2_003902

79. Kbio2_006470

80. Kbio3_001315

81. N-benzhydryl-n-methyl Piperazine

82. Hms1920a20

83. Hms2091i08

84. Pharmakon1600-01500211

85. 1-benzhydryl-4-methylpiperazine #

86. Nsc26608

87. Wln: T6n Dntj Ayr&r& D1

88. Ccg-40322

89. Mfcd00023293

90. Nsc756710

91. Zinc19156872

92. Akos015839079

93. Db01176

94. Nsc-756710

95. Ncgc00016421-02

96. Ncgc00016421-03

97. Ncgc00016421-04

98. Ncgc00016421-09

99. Ncgc00094634-01

100. Ncgc00094634-02

101. Ls-14655

102. Sbi-0052576.p003

103. (+/-)-1-diphenylmethyl-4-methylpiperazine

104. Ab00053084

105. C06930

106. D03621

107. D81845

108. Ab00053084_08

109. L000701

110. Q867308

111. Sr-05000001595-1

112. Brd-k79501723-001-02-0

113. Brd-k79501723-003-03-4

114. Brd-k79501723-003-09-1

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₂N₂
Molecular Weight	266.4 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	266.178298710 g/mol
Monoisotopic Mass	266.178298710 g/mol
Topological Polar Surface Area	6.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	253
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Antiemetics; Histamine H1 Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

ANTIHISTAMINE USED AS HYDROCHLORIDE & LACTATE IN PREVENTION & TREATMENT OF MOTION SICKNESS (NAUSEA, VOMITING & VERTIGO). IT IS ALSO PROBABLY EFFECTIVE FOR CONTROL OF POSTOPERATIVE NAUSEA & VOMITING.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 747

DURATION OF ACTION IS ABOUT 4 HR.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1096

...LARGE SCALE STUDY, INCL PREGNANT WOMEN RECEIVING CYCLIZINE DURING 1ST TRIMESTER, FAILED TO CONFIRM THAT DRUG HAD ANY TERATOGENIC EFFECT IN MAN WITH DOSES EMPLOYED.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1096

For more Therapeutic Uses (Complete) data for CYCLIZINE (7 total), please visit the HSDB record page.

4.2 Drug Warning

.../DO NOT/ EXCEED 4 TABLETS/DAY. /HYDROCHLORIDE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 747

.../IT/ SHOULD NOT BE USED IN WOMEN DURING PREGNANCY & THOSE LIKELY TO BECOME PREGNANT UNLESS SPECIFICALLY DIRECTED BY PHYSICIAN.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 747

IN 1965 AN AD HOC COMMITTEE OF US FDA CONCLUDED THAT EVIDENCE OF TERATOGENIC EFFECTS IN HUMAN...WAS NOT SIGNIFICANT, BUT IT MADE NO SPECIFIC MENTION OF EYES.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 341

...OFFSPRING OF PROBABLY SEVERAL THOUSAND WOMEN WHO HAD RECEIVED APPROX 150 MG CYCLIZINE/DAY DURING PREGNANCY...HAD A VARIETY OF NONOCULAR ABNORMALITIES, BUT STATISTICAL SIGNIFICANCE IN RELATION TO CYCLIZINE WAS UNCERTAIN.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 341

For more Drug Warnings (Complete) data for CYCLIZINE (8 total), please visit the HSDB record page.

4.3 Minimum/Potential Fatal Human Dose

5. 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG; BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150) LB.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-231

4.4 Drug Indication

For prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness, and vertigo (dizziness caused by other medical problems).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cyclizine is a piperazine-derivative antihistamine used as an antivertigo/antiemetic agent. Cyclizine is used in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness. Additionally, it has been used in the management of vertigo in diseases affecting the vestibular apparatus. Although the mechanism by which cyclizine exerts its antiemetic and antivertigo effects has not been fully elucidated, its central anticholinergic properties are partially responsible. The drug depresses labyrinth excitability and vestibular stimulation, and it may affect the medullary chemoreceptor trigger zone. It also possesses anticholinergic, antihistaminic, central nervous system depressant, and local anesthetic effects.

5.2 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

5.3 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AE - Piperazine derivatives

R06AE03 - Cyclizine

5.4 Absorption, Distribution and Excretion

BENZHYDROLPIPERAZINES & THEIR N-DEALKYLATION PRODUCTS ARE DISTRIBUTED IN ALL TISSUES OF RAT & ARE TRANSFERRED TO FETUS. /BENZYHYDROLPIPERAZINES/

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 194

5.5 Metabolism/Metabolites

Cyclizine is metabolised to its N-demethylated derivative, norcyclizine, which has little antihistaminic (H1) activity compared to Cyclizine.

OXIDATIVE N-DEALKYLATION IS MAIN METABOLIC PATHWAY OF BENZHYDROLPIPERAZINES; CYCLIZINE.../IS/ TRANSFORMED INTO NORCYCLIZINE...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 192

WITH A PURIFIED MIXED FUNCTION OXIDASE FROM LIVER MICROSOMES IN PRESENCE OF REDUCED PYRIDINE NUCLEOTIDE & O2.../CYCLIZINE IS/ OXIDIZED TO N-OXIDE.

Casarett, L.J., and J. Doull. Toxicology: The Basic Science of Poisons. New York: MacMillan Publishing Co., 1975., p. 120

5.6 Biological Half-Life

20 hours

5.7 Mechanism of Action

Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmful substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medulla region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibular apparatus to the vomiting centre. Motion sickness principally involves overstimulation of these pathways due to various sensory stimuli. Hence the action of cyclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since cyclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked.

.../IT SEEMS/ THAT STIMULATION OF VESTIBULAR APPARATUS IS NECESSARY & SUFFICIENT...& THAT VESTIBULAR CEREBELLAR MIDBRAIN "INTEGRATIVE VOMITING CENTER" & MEDULLARY CHEMORECEPTIVE TRIGGER ZONE ARE...INVOLVED /IN MOTION SICKNESS/. IT IS...PROBABLE THAT EFFECTIVE ANTIHISTAMINES EXERT.../ACTION/ IN THESE CENTERS. /ANTIHISTAMINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 606

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