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Proguanil

Synopsis, Chemistry

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TABLET;ORAL - 250MG;100MG, TABLET;ORAL - 62.5MG;25MG

TABLET;ORAL - 250MG;100MG
TABLET;ORAL - 62.5MG;25MG

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Also known as: Proguanil hydrochloride, Chloroguanide hydrochloride, 637-32-1, Diguanyl, Chlorguanide hydrochloride, Chloroquanil

Molecular Formula

C₁₁H₁₇Cl₂N₅

Molecular Weight

290.19 g/mol

InChI Key

SARMGXPVOFNNNG-UHFFFAOYSA-N

FDA UNII

R71Y86M0WT

A biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.

1 2D Structure

Proguanil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydrochloride

2.1.2 InChI

InChI=1S/C11H16ClN5.ClH/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9;/h3-7H,1-2H3,(H5,13,14,15,16,17);1H

2.1.3 InChI Key

SARMGXPVOFNNNG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl.Cl

2.1.5 Isomeric SMILES

CC(C)N=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

R71Y86M0WT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bigumal

2. Chlorguanid

3. Chloriguane

4. Chloroguanide

5. Chloroguanide Hydrochloride

6. Hydrochloride, Chloroguanide

7. Hydrochloride, Proguanil

8. Paludrin

9. Proguanil

10. Proguanil Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Proguanil Hydrochloride

2. Chloroguanide Hydrochloride

3. 637-32-1

4. Diguanyl

5. Chlorguanide Hydrochloride

6. Chloroquanil

7. Proguanil Hcl

8. Proguanilhydrochloride

9. 1-(p-chlorophenyl)-5-isopropylbiguanide Hydrochloride

10. Drinupal

11. Guanatol

12. Palusil

13. Gw Ah7673a

14. Tirian Hydrochloride

15. Proguanil (hydrochloride)

16. 336u50

17. Palusil Hydrochloride

18. Drinupal Hydrochloride

19. Guanatol Hydrochloride

20. Gwah7673a

21. Gw-ah7673a

22. R71y86m0wt

23. M-4888

24. Nsc-12977

25. Nsc-26614

26. Rp-3359

27. Bigumalum

28. Sn-12837

29. 3359 Rp

30. Dsstox_cid_27756

31. Dsstox_rid_82533

32. Dsstox_gsid_47776

33. 336-u-50

34. Sn 12,837

35. 1-(4-chlorophenyl)-5-isopropylbiguanide Hydrochloride

36. M 4888

37. Chloroguanidine Hydrochloride

38. Imidodicarbonimidic Diamide, N-(4-chlorophenyl)-n'-(1-methylethyl)-,monohydrochloride

39. N-(4-chlorophenyl)-n(sup5)-isopropyldiguanide Hydrochloride

40. Ncgc00016528-01

41. Cas-637-32-1

42. Einecs 211-283-7

43. Nsc 12977

44. Nsc 26614

45. Unii-r71y86m0wt

46. Sr-05000001973

47. Proguanil Hydrochloride [usan]

48. 1-(4-chlorophenyl)-3-(n-propan-2-ylcarbamimidoyl)guanidine;hydrochloride

49. Proguanil Chloride

50. Paludrine (tn)

51. Proguanil Hydrochloride [usan:usp]

52. N-4-chlorophenyl-n(sup 5)-isopropyldiguanide Hydrochloride

53. Proguanili Hydrochloridum

54. Biguanide, 1-(p-chlorophenyl)-5-isopropyl-, Monohydrochloride

55. Imidodicarbonimidic Diamide, N-(4-chlorophenyl)-n'-(1-methylethyl)-, Monohydrochloride

56. Schembl218859

57. Ambz0378

58. Proguanil For System Suitability

59. Chembl1201059

60. Dtxsid7047776

61. Hy-b0806a

62. Hms1571g19

63. Pharmakon1600-01504211

64. Proguanil Hydrochloride (jan/usp)

65. Tox21_110476

66. Ccg-39555

67. Nsc758688

68. Proguanil Hydrochloride [jan]

69. Akos024255720

70. Tox21_110476_1

71. Am85857

72. Chlorguanide Hydrochloride [mi]

73. Hs-0102

74. Nsc-758688

75. Proguanil Hydrochloride [mart.]

76. Proguanil Hydrochloride [usp-rs]

77. Proguanil Hydrochloride [who-dd]

78. Proguanil Hydrochloride [who-ip]

79. Ncgc00016528-05

80. Proguanil Hydrochloride, >=95% (hplc)

81. Cs-0031267

82. Proguanil Hydrochloride [orange Book]

83. Proguanil Hydrochloride [ep Monograph]

84. D02487

85. Proguanil Hydrochloride [usp Monograph]

86. Malarone Component Proguanil Hydrochloride

87. Proguanili Hydrochloridum [who-ip Latin]

88. 637p321

89. A923181

90. Proguanil Hydrochloride Component Of Malarone

91. Sr-05000001973-3

92. W-109585

93. Malarone Pediatric Component Proguanil Hydrochloride

94. Proguanil Hydrochloride Component Of Malarone Pediatric

95. 1-(p-chlorophenyl)-5-isopropylbiguanide Monohydrochloride

96. Proguanil Hydrochloride, British Pharmacopoeia (bp) Reference Standard

97. Proguanil Hydrochloride, European Pharmacopoeia (ep) Reference Standard

98. Proguanil Hydrochloride, United States Pharmacopeia (usp) Reference Standard

99. (1e)-1-[amino-[(4-chlorophenyl)amino]methylidene]-2-propan-2-ylguanidine Hydrochloride

100. Proguanil For System Suitability, European Pharmacopoeia (ep) Reference Standard

101. Proguanil Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

102. Imidodicarbonimidic Diamide, N-(4-chlorophenyl)-n'-(1-methylethyl)-, Hydrochloride (1:1)

2.4 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇Cl₂N₅
Molecular Weight	290.19 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	289.0861010 g/mol
Monoisotopic Mass	289.0861010 g/mol
Topological Polar Surface Area	88.8 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	292
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 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.)

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

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