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Chlorphenesin Carbamate

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Synthokem Chlorphenesin Carbamate

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Also known as: 886-74-8, Maolate, Rinlaxer, 3-(4-chlorophenoxy)-2-hydroxypropyl carbamate, 3-(p-chlorophenoxy)-1,2-propanediol 1-carbamate, 3-(p-chlorophenoxy)-2-hydroxypropyl carbamate

Molecular Formula

C₁₀H₁₂ClNO₄

Molecular Weight

245.66 g/mol

InChI Key

SKPLBLUECSEIFO-UHFFFAOYSA-N

FDA UNII

G014XC07GH

Chlorphenesin Carbamate is the carbamate ester form of chlorphenesin, a preservative agent and centrally-acting muscle relaxant with some anti-bacterial and anti-fungal, muscle relaxing and potential antineoplastic activities. Although the exact mechanism of action (MoA) has yet to be fully elucidated, chlorphenesin may inhibit tumor cell proliferation and metastasis.

1 2D Structure

Chlorphenesin Carbamate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[3-(4-chlorophenoxy)-2-hydroxypropyl] carbamate

2.1.2 InChI

InChI=1S/C10H12ClNO4/c11-7-1-3-9(4-2-7)15-5-8(13)6-16-10(12)14/h1-4,8,13H,5-6H2,(H2,12,14)

2.1.3 InChI Key

SKPLBLUECSEIFO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1OCC(COC(=O)N)O)Cl

2.2 Other Identifiers

2.2.1 UNII

G014XC07GH

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 886-74-8

2. Maolate

3. Rinlaxer

4. 3-(4-chlorophenoxy)-2-hydroxypropyl Carbamate

5. 3-(p-chlorophenoxy)-1,2-propanediol 1-carbamate

6. 3-(p-chlorophenoxy)-2-hydroxypropyl Carbamate

7. Chlorphensin Carbamate

8. Chlorphenesincarbamate

9. 3-(4-chlorophenoxy)-1,2-propanediol-1-carbamate

10. U-19,646

11. 1,2-propanediol, 3-(4-chlorophenoxy)-, 1-carbamate

12. Nsc 82943

13. Carbamic Acid, 3-(p-chlorophenoxy)-2-hydroxypropyl Ester

14. [3-(4-chlorophenoxy)-2-hydroxypropyl] Carbamate

15. 3-(p-chlorophenoxy)-1,2-propanediol-1-carbamate

16. U 19646

17. 1,2-propanediol, 3-(p-chlorophenoxy)-, 1-carbamate

18. Nsc-82943

19. Hqc4wi89yg

20. 1,2-propanediol,3-(4-chlorophenoxy)-, 1-carbamate

21. Carbamic Acid 3-(p-chlorophenoxy)-2-hydroxypropyl Ester

22. 57u5yi11wp

23. Chebi:3643

24. Chlorphenesin Carbamate, (-)-

25. 1,2-propanediol-3-(p-chlorophenoxy)-1-carbamate

26. Nsc82943

27. Kolpicortin-sine

28. (3-p-chlorophenoxy)-2-hydroxypropylcarbamate

29. U-19646

30. 1,2-propanediol, 3-(4-chlorophenoxy)-, 1-carbamate, (-)-

31. Maolate; Nsc 82943; Rhnesicn; Rinlaxer; U 19646; U-19,646

32. 126632-50-6

33. Hsdb 3031

34. Chlorphenesin Carbamate [usan:jan]

35. Einecs 212-954-7

36. Brn 1978575

37. Unii-57u5yi11wp

38. Ncgc00016548-01

39. Cas-886-74-8

40. Prestwick_882

41. Maolate (tn)

42. Prestwick0_000234

43. Prestwick1_000234

44. Prestwick2_000234

45. Prestwick3_000234

46. Unii-hqc4wi89yg

47. Dsstox_cid_2803

48. Wln: Zvo1yq1or Dg

49. Dsstox_rid_76735

50. Dsstox_gsid_22803

51. Schembl34492

52. Bspbio_000307

53. Mls002154243

54. Spbio_002228

55. Bpbio1_000339

56. Chembl607710

57. G014xc07gh

58. Dtxsid5022803

59. Glxc-26272

60. Hms1568p09

61. Hms2095p09

62. Hms2232o23

63. Hms3371a08

64. Hms3712p09

65. Chlorphenesin Carbamate [mi]

66. Tox21_110487

67. Chlorphenesin Carbamate [jan]

68. Chlorphenesin Carbamate [hsdb]

69. Chlorphenesin Carbamate [usan]

70. Chlorphenesin Carbamate (jp17/usan)

71. Ccg-220234

72. Chlorphenesin Carbamate [mart.]

73. Chlorphenesin Carbamate [vandf]

74. Chlorphenesin Carbamate, (+)-

75. Db14656

76. Chlorphenesin Carbamate [who-dd]

77. 1, 3-(p-chlorophenoxy)-, 1-carbamate

78. Ncgc00179607-01

79. Ncgc00179607-03

80. 1, 3-(4-chlorophenoxy)-, 1-carbamate

81. Smr001233511

82. Chlorphenesin Carbamate [green Book]

83. Db-057097

84. Hy-107944

85. Chlorphenesin Carbamate [orange Book]

86. Cs-0030953

87. Ft-0602972

88. C07930

89. D00770

90. [3-(4-chlorophenoxy)-2-hydroxy-propyl] Carbamate

91. Sr-01000841824

92. 3-[(4-chlorophenyl)oxy]-2-hydroxypropyl Carbamate

93. Sr-01000841824-2

94. W-100393

95. Brd-a39230911-001-03-7

96. Q27106156

97. 1,2-propanediol, 3-(4-chlorophenoxy)-, 1-carbamate, (+)-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₂ClNO₄
Molecular Weight	245.66 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	245.0454856 g/mol
Monoisotopic Mass	245.0454856 g/mol
Topological Polar Surface Area	81.8 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	219
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

IT IS EMPLOYED TO DIMINISH SKELETAL MUSCLE SPASMS RESULTING FROM TRAUMA , INFLAMMATION, VERTEBRAL DISK SYNDROME, OSTEOARTHRITIS, AND RHEUMATOID ARTHRITIS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 860

APPLICATION: CENTRALLY ACTIVE SKELETAL MUSCLE RELAXANT SIMILAR IN ITS ACTIONS TO METHOCARBAMOL...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 860

IT MAY BE USEFUL AS TEMPORARY ADJUNCT TO PHYSIOTHERAPY & OTHER APPROPRIATE MEASURES IN THE TREATMENT OF THE DISCOMFORT PRODUCED BY SKELETAL MUSCLE SPASM OF LOCAL ORIGIN.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1026

MEDICATION (VET): /USED/ AS AN ADJUNCT TO OTHER THERAPY FOR ACUTE INFLAMMATORY OR TRAUMATIC SKELETAL MUSCLE INVOLVEMENT INCLUDING SPRAINS & INTERVERTEBRAL DISC SYNDROMES.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 108

THESE DRUGS MAY TEMPORARILY ABATE SOME OF THE SYMPTOMS OF CEREBRAL PALSY, BUT THEY HAVE MINOR ROLE IN OVERALL MGMNT OF THIS DISEASE... ALL CENTRALLY ACTING MUSCLE RELAXANTS PRODUCE SOME SEDATION, AT LEAST AT HIGHEST DOSES EMPLOYED CLINICALLY. /MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 241

4.2 Drug Warning

PERSONS TAKING DRUG SHOULD NOT DRIVE, OPERATE MACHINERY, OR UNDERTAKE ACTIVITIES THAT REQUIRE ALERTNESS, JUDGMENT, OR MENTATION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 860

...PROBABLY HAS AN ADDICTION LIABILITY, AS DO OTHER CARBAMATES.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 860

VET: DO NOT ADMIN TO ANY ANIMAL WITH SIGNIFICANT LIVER PATHOLOGY. LIVER FUNCTION MAY BE ADVERSELY AFFECTED DURING ITS USE.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 108

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

ORAL DOSES ARE READILY ABSORBED /IN ANIMALS/.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 108

MUCH OF DOSE OF CHLORPHENESIN CARBAMATE...IS RAPIDLY EXCRETED IN URINE OF RATS & OF MAN.

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. 175

AFTER ORAL ADMIN OF (14)C-LABELED CHLORPHENESIN CARBAMATE TO RATS, IT WAS ABSORBED FROM GI TRACT; EXCRETED IN URINE ABOUT 90%; 36% IN BILE. RADIOACTIVITY WAS DISTRIBUTED IN ALMOST ALL TISSUES, HIGHEST IN LIVER, BRAIN & SPINAL CORD.

NOZU T ET AL; OYO YAKURI 14(1) 1 (1977)

5.2 Metabolism/Metabolites

MAJOR METABOLITE (49% OF DOSE) IS ETHER GLUCURONIDE OF CHLORPHENESIN CARBAMATE...

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. 175

5% APPEARED IN URINE AS P-CHLOROPHENOXYLACTIC ACID, 17% AS P-CHLOROPHENOXYACETIC ACID, AND 9% AS SULFATE CONJUGATE OF P-CHLOROPHENOL...

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. 175

MAJOR METABOLITES IN A 48-HR URINE SAMPLE FROM RATS GIVEN (14)C-LABELED CHLORPHENESIN CARBAMATE WERE GLUCURONIDE, P-CHLOROPHENOXYLACTIC ACID, P-CHLOROPHENOXYACETIC ACID, & P-CHLOROPHENOL.

NOZU T ET AL; OYO YAKURI 14(1) 1 (1977)

5.3 Mechanism of Action

MUSCLE RELAXANTS CAUSE SKELETAL MUSCULAR RELAXATION, WITHOUT LOSS OF CONSCIOUSNESS, AS RESULT OF SELECTIVE ACTION UPON CNS. ... PROMINENT EFFECT OF MUSCLE RELAXANTS IS TO DEPRESS SPINAL POLYSYNAPTIC REFLEXES PREFERENTIALLY OVER MONOSYNAPTIC REFLEXES. ... MECHANISM OF ACTION...REMAIN TO BE ELUCIDATED. /MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 239

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