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Chemistry

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Also known as: Alvinol, Ethchlorovynol, Placidyl, Arvynol, Ethchlorvinol, Ethclorvynol
Molecular Formula
C7H9ClO
Molecular Weight
144.60  g/mol
InChI Key
ZEHYJZXQEQOSON-AATRIKPKSA-N
FDA UNII
6EIM3851UZ

Ethchlorvynol
A sedative and hypnotic that has been used in the short-term management of INSOMNIA. Its use has been superseded by other drugs.
1 2D Structure

Ethchlorvynol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
2.1.2 InChI
InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
2.1.3 InChI Key
ZEHYJZXQEQOSON-AATRIKPKSA-N
2.1.4 Canonical SMILES
CCC(C=CCl)(C#C)O
2.1.5 Isomeric SMILES
CCC(/C=C/Cl)(C#C)O
2.2 Other Identifiers
2.2.1 UNII
6EIM3851UZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ethchlorovynol

2. Ethchlorvinol

3. Placidyl

2.3.2 Depositor-Supplied Synonyms

1. Alvinol

2. Ethchlorovynol

3. Placidyl

4. Arvynol

5. Ethchlorvinol

6. Ethclorvynol

7. Roeridorm

8. Normoson

9. Serensil

10. Nostel

11. Etchlorvinolo

12. Ethchlorvinyl

13. Ethochlorvynol

14. Ethychlorvynol

15. Aethyl-chlorvynol

16. Normonson

17. Normosan

18. Placidil

19. Serenesil

20. Serenil

21. Etclorvinol

22. Ethchlorvynolum

23. 1-chloro-3-ethyl-1-penten-4-yn-3-ol

24. 113-18-8

25. 1-penten-4-yn-3-ol, 1-chloro-3-ethyl-

26. 3-(beta-chlorovinyl)-1-pentyn-3-ol

27. Beta-chlorovinyl Ethyl Ethynyl Carbinol

28. Ethyl Beta-chlorovinyl Ethynyl Carbinol

29. A 71

30. Ethchlorvynol Civ

31. Nsc 30372

32. 1-chloro-3-ethylpent-1-en-4-yn-3-ol

33. (e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol

34. 6eim3851uz

35. Nsc-30372

36. Serensiloline

37. Ethyl .beta.-chlorovinyl Ethynyl Carbinol

38. Nromoson

39. 1-chloro-3-ethyl-pent-1-en-4-yn-3-ol

40. (1e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol

41. Etclorvinol [inn-spanish]

42. Ethchlorvynolum [inn-latin]

43. Placidyl (tn)

44. Beta-chlorvinyl Ethyl Ethynyl Carbinol

45. 1-chloro-3-ethylpent-1-4-yn-3-ol

46. 5-chloro-3-ethylpent-1-yn-4-en-3-ol

47. Hsdb 3079

48. Brn 1702245

49. Unii-6eim3851uz

50. Ai3-23721

51. Ethchlorvynol (jan/usp/inn)

52. Ethchlorvynol [usp:inn:ban]

53. Dea No. 2540

54. 3-(.beta.-chlorovinyl)-1-pentyn-3-ol

55. .beta.-chlorovinyl Ethyl Ethynyl Carbinol

56. Ethchlorvynol [mi]

57. Chembl591

58. Ethchlorvynol [inn]

59. Ethchlorvynol [jan]

60. Ethchlorvynol [hsdb]

61. Ethchlorvynol [vandf]

62. Ethchlorvynol [mart.]

63. Schembl113589

64. Schembl113591

65. Ethchlorvynol [who-dd]

66. Chebi:4882

67. Gtpl7180

68. Ethchlorvynol [orange Book]

69. Ethchlorvynol Civ [usp-rs]

70. Ethchlorvynol [usp Monograph]

71. Akos015903758

72. Db00189

73. 1-chloro-3-ethyl-1-penten-4-yn-3-ol #

74. 3-(.beta.-chlorvinyl)-1-pentyn-3-ol

75. C07833

76. D00704

77. Q3085140

78. 1-penten-4-yn-3-ol, 1-chloro-3-ethyl-, (1e)-

79. 1135334-09-6

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 144.60 g/mol
Molecular Formula C7H9ClO
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count3
Exact Mass144.0341926 g/mol
Monoisotopic Mass144.0341926 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count9
Formal Charge0
Complexity154
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
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)


Used as a hypnotic in the short-term treatment of simple insomnia for periods up to 1 week in duration. /Use is included in the labeling approved by the US Food and Drug Administration/.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1364


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.1360 (1992)


ETHCHLORVYNOL IS SEDATIVE-HYPNOTIC DRUG WITH RAPID ONSET & SHORT DURATION OF ACTION ... HAS ANTICONVULSANT & MUSCLE RELAXANT PROPERTIES.

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. 365


4.2 Drug Warning

BECAUSE OF A REPORTED EFFECT TO SUPRESS THE ANTICIPATED RESPONSE TO DICUMAROL, DRUG SHOULD BE USED CAUTIOUSLY IN COMBINATION WITH DRUGS METABOLIZED BY LIVER, & IT IS CONTRAINDICATED IN INTERMITTENT PORPHYRIA.

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. 365


...SHOULD BE WARNED AGAINST OPERATING MOTOR VEHICLE OR HAZARDOUS MACHINERY WHILE ON DRUG. ... IT SHOULD NOT BE USED IN PATIENT WITH HISTORY OF DRUG ABUSE, & DRUG SHOULD BE GRADUALLY WITHDRAWN FROM PATIENT TAKING EXCESSIVE QUANTITIES. ... SAFE & EFFECTIVE USE OF THIS AGENT DURING PREGNANCY & IN PEDIATRIC-AGE PATIENTS ... NOT ... ESTABLISHED.

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


WITHDRAWAL SYMPTOMS MAY RESEMBLE TO DELIRIUM TREMENS, AND ARE SOMETIMES SUGGESTIVE OF SCHIZOPHRENIC REACTION. THEY ARE ESPECIALLY SEVERE IN ELDERLY PATIENTS.

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. 365


Ethchlorvynol crosses the placenta. ... FDA Pregnancy Category C: Animal reproduction studies have shown an adverse effect on the fetus and there are no adequate and well controlled studies in humans, but potential benefits may warrant use ... in pregnant women despite potential risks.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1360 (1992)


For more Drug Warnings (Complete) data for ETHCHLORVYNOL (13 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

The lethal dose usually ranges from 10 to 25 g, but death has followed a dose of 2.5 g in the presence of ethanol.

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. 365


4.4 Drug Indication

Used for short-term hypnotic therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ethchlorvynol is a sedative drug and schedule IV (USA) controlled substance. It produces cerebral depression, however the exact mechanism of action is not known.


5.2 MeSH Pharmacological Classification

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)


5.3 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM08 - Ethchlorvynol


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed from gastrointestinal tract.


... SLOW DISAPPEARANCE OF DRUG WAS SHOWN TO BE DUE LARGELY TO EXTENSIVE TISSUE DISTRIBUTION.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 443


AFTER ORAL INGESTION OF 1 G OF ETHCHLORVYNOL, SYMPTOMS OF CNS DEPRESSION OCCUR WITHIN 15-30 MIN. VOL OF DISTRIBUTION IS GREATER THAN VOL OF TOTAL BODY WATER. IN ACUTELY INTOXICATED PATIENT ... CONCN IN CSF REACHES 50% OF THAT IN PLASMA.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 129


DRUG IS MAINLY /METABOLIZED BY THE/ LIVER, BUT APPROX 10% OF USUAL DOSE IS EXCRETED INT URINE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 129


RAPIDLY ABSORBED FROM GI TRACT ... ORAL ADMIN OF 200 MG, 500 MG & 750 MG ... PRODUCED PEAK PLASMA LEVELS OF 0.9 TO 2.5 MCG/ML, 4.2 TO 6.5 MCG/ML & 8 MCG/ML, RESPECTIVELY, WITHIN 1 TO 2 HR ... /HUMAN/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1975


For more Absorption, Distribution and Excretion (Complete) data for ETHCHLORVYNOL (17 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

About 90% of a dose is metabolized in the liver. Some ethchlorvynol may also be metabolized in the kidneys. Ethchlorvynol and metabolites undergo extensive enterohepatic recirculation.


About 90% of a dose is metabolized in the liver. Some ethchlovynol may also be metabolized in the kidneys.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1360 (1992)


Although the metabolic fate of ethchlorvynol has not been fully elucidated, there is evidence that the drug is extensively metabolized, probably in the liver. There is also some evidence that the kidneys may play an essential role in metabolism of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1365


Metabolism in liver originally was assumed to be negligible, but this has been somewhate disproved since it was later found that ethchlorvynol is readily metabolized in liver. Although metabolites have not yet been identified, it would appear that glucuronide conjugation occurs as well as hydroxylation with reduction of unsaturated bonds in the chemical structure.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 826


Approximately 90% of the drug will undergo biotransformation, probably in the liver, since ethchlorvynol is concentrated in bile to three times as much as in serum.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 826


5.6 Biological Half-Life

Plasma half-life is approximately 10 to 20 hours, terminal half-life is 21-100 hours.


AFTER EQUILIBRIUM FOLLOWING HYPNOTIC DOSES, BLOOD LEVEL FALLS RAPIDLY, WITH AVG T/2 OF 5.6 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 129


... HALF-LIFE FOR ... DISTRIBUTION ... 5 TO 6 HR ... HALF-LIFE FOR ... ELIMINATION /IS/ 70 HR /HUMAN/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1975


Plasma half-life is approximately 10 to 20 hours.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IA p.1360 (1992)


100 hr (overdose) /From table/

Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 942


A 33 year old obese, hypothyroid, white male with several medical problems was admitted to University Hospital in September 1984 for treatment of drug intoxication. Admitting medications included ethchlorvynol in addition to other central nervous system depressants. Initial serum concn were reported at 70 ug/ml in this somnolent yet totally conscious adult. Established therapeutic concn are 2-8 ug/ml, with toxic exceeding 20 ug/ml. A tolerance phenomenon seemed evident. Serum ethchlorvynol concn were monitored daily during early hospitalization and continued to be substantially greater than reported toxic concn. Kinetic values were as follows: total body clearance 9.92 ml/min, volume of distribution 68.0 liters, and half-life 78 hr. These values are unique in that they were calculated from a patient who had not suffered an acute overdose, thereby differing markedly from previously published values. The influence of hypothyroidism and hyperlipidemia on these markedly different values appears to be significant. Ethchlorvynol should probably be added to the list of drugs influenced by thyroid disease.

PMID:3822854 Kolpek JH et al; Pharmacotherapy 6 (6): 323-7 (1986)


5.7 Mechanism of Action

Although the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates. Barbiturates bind at a distinct binding sites associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.


MOST OF MODERN SEDATIVE-HYPNOTIC AGENTS ARE GENERAL DEPRESSANTS. THEY DEPRESS WIDE RANGE OF CELLULAR FUNCTIONS IN MANY VITAL ORGAN SYSTEMS. /HYPNOTICS & SEDATIVES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 102


The mechanism of action of the drug is not known. In doses used for hypnosis, ethchlorvynol produces cerebral depression and quiet, deep sleep. Higher doses may lead to general anesthesia and concurrent depression of respiratory and vasomotor centers; death may result from respiratory failure, hypotension, or complications of prolonged coma. The effect of ethchlorvynol or rapid eye movement (REM) or other stages of sleep has not yet been established. In experimental animals, ethchlorvynol exhibits anticonvulsant and muscle relaxant activity.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1364


Intravenous injection of ethchlorvynol (ECV) leads to hypoxemia and a permeability pulmonary edema. Whether the hypoxemia is directly attributable to the pulmonary edema or caused by release of mediators has not been explored. Three groups of dogs were studied: (1) ethchlorvynol, (2) indomethacin--ethchlorvynol, and (3) ketanserin--ethchlorvynol. In group 1, 25 to 30 mg/kg of ethchlorvynol caused a significant fall in PaO2 at 4 min (92 +/- 12.6 to 77 +/- 21 mm Hg, p <0.05), which persisted throughout the experiment. The P(A-a)O2 gradient widened significantly at 3 min (22 +/- 11 to 31 +/- 16.8 mm Hg, p <0.05) and remained abnormal for the remainder of the experiment. There was no significant fall in PaO2 in groups 2 and 3. Lung tissue water to dry weight ratio increased significantly in all groups at 60 min. Lung tissue water to dry weight ratios were normal at 10 min after ethchlorvynol injection in additional groups. It was concluded that ethchlorvynol causes hypoxemia, which is mediated by cyclooxygenase products and 5-hydroxytryptamine. This hypoxemia can be prevented by the administration of drugs that block these products.

PMID:3096135 Millen JE, Glauser FL; Am J Med Sci 292 (5): 293-8 (1986)


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