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Chemistry

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Also known as: Valmid, Ethinamat, Etinamate, Valmidate, Valamin, Volamin
Molecular Formula
C9H13NO2
Molecular Weight
167.20  g/mol
InChI Key
GXRZIMHKGDIBEW-UHFFFAOYSA-N
FDA UNII
IAN371PP48

Ethinamate
Ethinamate is a short-acting sedative-hypnotic medication used to treat insomnia. Like many such similar medications, the regular use of ethinamate can result in the development of drug tolerance in a patient. Nevertheless, the medication itself is generally no longer effective after using it for greater than 7 days. Structurally, it does not resemble the barbituates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates.
1 2D Structure

Ethinamate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1-ethynylcyclohexyl) carbamate
2.1.2 InChI
InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
2.1.3 InChI Key
GXRZIMHKGDIBEW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C#CC1(CCCCC1)OC(=O)N
2.2 Other Identifiers
2.2.1 UNII
IAN371PP48
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-ethynylcyclohexylcarbamate

2. Ethinamat

3. Valamid

4. Valamin

5. Valmidate

2.3.2 Depositor-Supplied Synonyms

1. Valmid

2. Ethinamat

3. Etinamate

4. Valmidate

5. Valamin

6. Volamin

7. 1-ethynylcyclohexyl Carbamate

8. Valaminettae

9. Valaminetten

10. 1-ethynylcyclohexanol Carbamate

11. Usaf El-42

12. 126-52-3

13. 1-ethinylcyclohexyl Carbamate

14. Ethinamatum

15. Ethinimate

16. Etinamato

17. Cyclohexanol, 1-ethynyl-, Carbamate

18. Aethinyl-cyclohexyl-carbamat

19. Carbamic Acid, 1-ethynylcyclohexyl Ester

20. (1-ethynylcyclohexyl) Carbamate

21. Carbamate De L'ethinylcyclohexanol

22. Nsc 11538

23. Nsc-11538

24. Cyclohexanol, 1-ethynyl-, 1-carbamate

25. Chebi:4884

26. Ian371pp48

27. Valaminetta

28. Cyclohexanol, Carbamate

29. Ethinamatum [inn-latin]

30. Ethynylcyclohexyl Carbamate

31. Etinamato [inn-spanish]

32. 1-ethinylcyclohexyl Carbonate

33. Wln: L6tj Aovz A1uu1

34. Aethinyl-cyclohexyl-carbamat [german]

35. Valmid (tn)

36. Hsdb 3325

37. Carbamate De L'ethinylcyclohexanol [french]

38. Ethinamate (jan/inn)

39. Einecs 204-789-4

40. Brn 1946056

41. Unii-ian371pp48

42. Dea No. 2545

43. Ethinamate [usp:inn:ban:jan]

44. Ethinamate [mi]

45. Ethinamate [inn]

46. Ethinamate [jan]

47. Ethinamate [hsdb]

48. Ethinamate [vandf]

49. Ethinamate [mart.]

50. Chembl1576

51. Ethinamate [who-dd]

52. Schembl44635

53. Ethinamate, Analytical Standard

54. Gtpl7325

55. Zinc1385

56. Dtxsid7023013

57. Ethinamate [orange Book]

58. Nsc11538

59. Nsc30282

60. Nsc31618

61. Nsc-30282

62. Nsc-31618

63. Nsc524623

64. Cs-6642

65. Db01031

66. Nsc-524623

67. [(1-ethynylcyclohexyl)oxy]methanimidic Acid

68. Hy-101584

69. Ethynamate Ethynylcyclohexyl Carbamate

70. C07832

71. D00703

72. Q410225

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 167.20 g/mol
Molecular Formula C9H13NO2
XLogP31.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass167.094628657 g/mol
Monoisotopic Mass167.094628657 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count12
Formal Charge0
Complexity220
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Sedatives, Nonbarbiturate

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


SHORT-ACTING MILD HYPNOTIC USEFUL FOR INDUCTION OF SLEEP IN SIMPLE INSOMNIA.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1005


CONSEQUENTLY, IT MAY BE USEFUL TO INSOMNIAC WHO HAS DIFFICULTY FALLING ASLEEP BUT NOT TO ONE WHO HAS LONG PERIODS OF WAKEFULNESS DURING NIGHT. ITS EFFECT ON REM SLEEP IS UNKNOWN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 126


The primary Medication Classification of the US Veterans Administration is CN309: Sedatives/Hypnotics, Other

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1362 (1992)


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


4.2 Drug Warning

LONG-TERM USE OF LARGER THAN RECOMMENDED DOSES MAY LEAD TO PSYCHIC & PHYSICAL DEPENDENCE. ABSTINENCE SYNDROME IS SIMILAR TO THAT FOR BARBITURATES ...

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


WITHDRAWAL SYMPTOMS, INCL CONVULSIONS, MAY OCCUR WHEN ETHINAMATE IS DISCONTINUED ABRUPTLY.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 227


ETHINAMATE SHOULD NOT BE TAKEN CONCURRENTLY WITH ALC OR OTHER CNS DEPRESSANTS & PATIENT ON THIS DRUG SHOULD BE WARNED AGAINST OPERATING MOTOR VEHICLE OR OPERATING HAZARDOUS MACHINERY FOR @ LEAST 4 OR 5 HR AFTER TAKING DRUG.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1005


ALTHOUGH NO MATERNAL OR FETAL ADVERSE EFFECTS HAVE BEEN REPORTED, SUFFICIENT LAB WORK HAS NOT BEEN DONE IN THIS AREA TO WARRANT ITS USE IN PREGNANT & LACTATING WOMEN. ... ETHINAMATE HAS NOT BEEN STUDIED IN CHILDREN; HENCE, IT IS NOT RECOMMENDED FOR PEDIATRIC USE. ... USED WITH CAUTION IN PATIENTS WITH HISTORY OF DRUG ABUSE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1005


For more Drug Warnings (Complete) data for ETHINAMATE (7 total), please visit the HSDB record page.


4.3 Drug Indication

Used for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ethinamate is used to treat insomnia (trouble in sleeping). However, it has generally been replaced by other medicines for the treatment of insomnia. If ethinamate is used regularly (for example, every day) to help produce sleep, it is usually not effective for more than 7 days. Structurally, it does not resemble the barbiturates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates. Continued and inappropriate use of ethinamate can lead to tolerance and physical dependence, with withdrawal symptoms very similar to those of the barbiturates.


5.2 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration.


ETHINAMATE IS INACTIVATED @ LEAST PARTLY BY LIVER, BY HYDROXYLATION OF CYCLOHEXYL RING; PRODUCT IS CONJUGATED & EXCRETED AS GLUCURONIDE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


IT IS EXTENSIVELY METABOLIZED, BUT PRELIMINARY EXPERIENCE INDICATES APPRECIABLE QUANTITIES CAN BE REMOVED BY EXTRACORPOREAL HEMODIALYSIS. ... HIGH LIPID SOLUBILITY ... .

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-224


ABSORPTION & CLEARANCE OF ETHINAMATE WAS STUDIED AFTER SINGLE ORAL DOSAGES IN THERAPEUTIC RANGE TO NONFASTING SUBJECTS. MEAN MAX PLASMA LEVEL WAS OBSERVED AFTER 1 HR (T/2 IN BLOOD 2.3 HR).

PMID:4604053 CLIFFORD JM ET AL; CLIN PHARMACOL THER 16 (2): 376 (1974)


Rapidly absorbed. ... Renal elimination. Approximately 36% of administered dose appears in urine within 24 hours.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1362 (1992)


Ethinamate is rapidly absorbed from the gastrointestinal tract and is in part metabolized by the liver. The major of three metabolites is hydroxyethinamate (yielded by hydroxylation of the cyclohexyl ring), and it is yet unclear whether this metabolite has any pharmacologic effect. Hydroxyethinamate is combined with glucuronide to form approximately equal quantities with free hydroxyethinamate. Maximum blood concentrations are reached within 60 minutes after ingestion. From the absorbed ethinamate, 10 per cent is metabolized to CO2 while the rest is excreted by the kidney, mainly as hydroxyethinamate glucuronides (89 per cent), and metabolites (9%); only 2% of free ethinamate is excreted in the urine.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 850


5.3 Metabolism/Metabolites

Hepatic.


ETHINAMATE IS INACTIVATED @ LEAST PARTLY BY LIVER, BY HYDROXYLATION OF CYCLOHEXYL RING; PRODUCT IS CONJUGATED & EXCRETED AS GLUCURONIDE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


Ethinamate is rapidly absorbed from the gastrointestinal tract and is in part metabolized by the liver. The major of three metabolites is hydroxyethinamate (yielded by hydroxylation of the cyclohexyl ring), and it is yet unclear whether this metabolite has any pharmacologic effect. Hydroxyethinamate is combined with glucuronide to form approximately equal quantities with free hydroxyethinamate.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 850


5.4 Biological Half-Life

2.5 hours


Half-life 2.5 hours. Duration of action about 3 to 5 hours.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1362 91992)


135 MINUTES

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 850


5.5 Mechanism of Action

The mechanism of action is not known. However, studies have shown that ethinamate inhibits carbonic anhydrases I and II (J Biol Chem. 1992 Dec 15;267(35):25044-50). This inhibition by ethinamate is not sufficiently strong, however, to implicate carbonic anhydrases I and II in the mechanism of action.


... ETHINAMATE ... /IS/ NON-SELECTIVE CNS /DEPRESSANT/ ... .

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 126


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