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Chemistry

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Also known as: Metiprilone, Noludar, Metiprilon, Dimerin, Noctan, Methyprylone
Molecular Formula
C10H17NO2
Molecular Weight
183.25  g/mol
InChI Key
SIDLZWOQUZRBRU-UHFFFAOYSA-N
FDA UNII
X66M7YN35V

Methyprylon
Methyprylon is a sedative of the piperidinedione derivative family that was previously used for the treatment of insomnia. However, with the introduction of newer drugs with fewer side effects, such as benzodiazepines, the clinical use of methyprylon is now limited. Methyprylon was withdrawn from the U.S. market in June 1965 and the Canadian market in September 1990 due to adverse events.
1 2D Structure

Methyprylon

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3,3-diethyl-5-methylpiperidine-2,4-dione
2.1.2 InChI
InChI=1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13)
2.1.3 InChI Key
SIDLZWOQUZRBRU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1(C(=O)C(CNC1=O)C)CC
2.2 Other Identifiers
2.2.1 UNII
X66M7YN35V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methprylon

2. Noludar

2.3.2 Depositor-Supplied Synonyms

1. Metiprilone

2. Noludar

3. Metiprilon

4. Dimerin

5. Noctan

6. Methyprylone

7. Methyprolon

8. Methyprylon [inn]

9. 125-64-4

10. Methyprylonum

11. Methprylon

12. Nodular

13. Methyprylone [inn-french]

14. Methyprylonum [inn-latin]

15. Metiprilona [inn-spanish]

16. 3,3-diethyl-5-methylpiperidine-2,4-dione

17. Ro 1-6463

18. 2,4-piperidinedione, 3,3-diethyl-5-methyl-

19. 2,4-dioxo-3,3-diethyl-5-methylpiperidine

20. 3,3-diethyl-5-methyl-2,4-piperidinedione

21. Dea No. 2575

22. 2,4-dioxy-3,3-diethyl-5-methylpiperidine

23. 3,3-diethyl-2,4-dioxo-5-methylpiperidine

24. Nsc 30442

25. Methyprylon, (+)-

26. Methyprylon, (-)-

27. Nsc-30442

28. Cut48i42on

29. P66z3ur32t

30. X66m7yn35v

31. Metiprilona

32. 2,4-piperidinedione, 3,3-diethyl-5-methyl-, (+)-

33. 2,4-piperidinedione, 3,3-diethyl-5-methyl-, (-)-

34. 30590-00-2

35. 30590-01-3

36. Noludar (tn)

37. Hsdb 3128

38. Methyprylon (jan/inn)

39. Einecs 204-745-4

40. Unii-cut48i42on

41. Brn 0082860

42. Methyprylon [usp:inn:ban]

43. (+)-noludar

44. (?)-noludar

45. Methyprylon [mi]

46. Methyprylon [jan]

47. Methyprylon [hsdb]

48. Methyprylon [vandf]

49. Methyprylon [mart.]

50. Unii-p66z3ur32t

51. Unii-x66m7yn35v

52. Methyprylon [who-dd]

53. Schembl155838

54. 3,4-dioxo-5-methylpiperidine

55. 2, 3,3-diethyl-5-methyl-

56. Gtpl7238

57. 2,3-diethyl-5-methylpiperidine

58. Chembl1200790

59. Dtxsid7023306

60. Chebi:31837

61. Methyprylon [orange Book]

62. Nsc30442

63. Wln: T6mv Dvtj C2 C2 E1

64. Akos006239549

65. Db01107

66. D01150

67. Q409558

68. 5,5-diethyl-6-hydroxy-3-methyl-2,3,4,5-tetrahydropyridin-4-one

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 183.25 g/mol
Molecular Formula C10H17NO2
XLogP30.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass183.125928785 g/mol
Monoisotopic Mass183.125928785 g/mol
Topological Polar Surface Area46.2 Ų
Heavy Atom Count13
Formal Charge0
Complexity231
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
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)


HYPNOTIC USEFUL IN MGMNT OF INSOMNIA OF VARIED ETIOLOGY. IT USUALLY INDUCES SLEEP WITHIN 45 MIN; IT PROVIDES SLEEP FOR 5-8 HR. HENCE, IT IS USEFUL AS HYPNOTIC IN PT WITH SIMPLE & NERVOUS INSOMNIA.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1007


300 MG DOSE ... SUPPRESSES REM SLEEP AS MUCH AS DOES 100 MG OF PENTOBARBITAL.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 134


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

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IB p.1900 (1992)


For more Therapeutic Uses (Complete) data for METHYPRYLON (6 total), please visit the HSDB record page.


4.2 Drug Warning

May be habit forming.

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 964


ABSTINENCE SYNDROME IS LIKE THAT OF BARBITURATES & INCL INSOMNIA, CONFUSION, HALLUCINATIONS, & CONVULSIONS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 134


PATIENTS SHOULD BE WARNED AGAINST CONCOMITANT USE OF METHYPRYLON & ALCOHOL OR OTHER CNS DEPRESSANTS. ... ITS SAFE USE DURING PREGNANCY & IN CHILDREN UNDER 3 YR OF AGE HAS NOT BEEN ESTABLISHED.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1007


SIDE EFFECTS ARE USUALLY INFREQUENT & MILD. THERE HAVE BEEN RARE CASES OF MORNING DROWSINESS, DIZZINESS ... ESOPHAGITIS ...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1007


For more Drug Warnings (Complete) data for METHYPRYLON (9 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

... IN FATAL CASES, BLOOD CONCN IN EXCESS OF 9.0 MG/100 ML HAVE BEEN REPORTED.

Sunshine, Irving (ed.) Methodology for Analytical Toxicology. Cleveland: CRC Press, Inc., 1975., p. 261


4.4 Drug Indication

For the treatment of insomnia.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Methyprylon, a piperidinedione CNS depressant, is close to barbituric acid in structure, but different enough to be called a "non-barbiturate" sedative-hynotic. Methyprylon is used for insomnia and daytime tension. Methyprylon depresses the activity of muscle tissues, the heart, and the respiratory system.


5.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CE - Piperidinedione derivatives

N05CE02 - Methyprylon


5.3 Absorption, Distribution and Excretion

DRUG IS WELL ABSORBED FROM INTESTINE.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 69


IT IS MORE WATER SOL THAN GLUTETHIMIDE, BUT IT IS NOT KNOWN WHETHER GI ABSORPTION IS CONSEQUENTLY LESS ERRATIC. ... ONLY 3% IS EXCRETED IN URINE UNCHANGED. ... ONLY 60% OF FREE METABOLITES & GLUCURONIDES IS RECOVERABLE FROM URINE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 134


THERAPEUTIC BLOOD CONCN PROBABLY DO NOT EXCEED 1.0 MG/100 ML. FOLLOWING SINGLE ORAL DOSE OF 650 MG IN ADULTS, MAX PLASMA CONCN OF APPROX 1.0 MG/100 ML IS REACHED AFTER 2 HR. IN FATAL CASES, BLOOD CONCN IN EXCESS OF 9.0 MG/100 ML HAVE BEEN REPORTED.

Sunshine, Irving (ed.) Methodology for Analytical Toxicology. Cleveland: CRC Press, Inc., 1975., p. 261


Methyprylon does not accumulate selectively in organ systems.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 852


For more Absorption, Distribution and Excretion (Complete) data for METHYPRYLON (6 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Hepatic. Methyprylon is almost completely metabolized.


FROM URINE OF HUMAN SUBJECTS ... TAKEN METHYPRYLON ... NEW METABOLITE HAS BEEN ... IDENTIFIED AS 2,4,6-TRIOXO-3,3-DIETHYL-5-METHYLPIPERIDINE. 2,4-DIOXO-3,3-DIETHYL-5-METHYLTETRAHYDROPYRIDINE, 2,4-DIOXO-3,3-DIETHYL-5-HYDROXYMETHYLTETRAHYDROPYRIDINE, & 4,6-DIOXO-5,5-DIETHYL-TETRAHYDRONICOTINIC ACID ... ESTABLISHED AS METABOLITES ...

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. 155


While the metabolic degradation of methyprylon is known, it is not certain in which organ this takes place. Methyprylon is dehydrogenated to 5-methyl-pyrithyldione, then partially oxidized to hydroxy derivatives, and finally oxidized to 5-carboxy-pyrithyldione. The hydroxy derivatives are bound approximately 38% to human plasma proteins. Other less important metabolites may arise, but the metabolites are partly conjugated to glucuronide, with approximately 97% of the parent drug being metabolized. Intact methyprylon (3%) and its metabolites (60%) are recovered in the urine, while approximately 20% is found in the feces, demonstrating that enterohepatic circulation of the drug occurs.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 851


5.5 Biological Half-Life

6-16 hours


PLASMA T1/2 IS 4 HR, BUT IT IS LONGER IN ACUTE INTOXICATION.

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. 366


Plasma half-life is 6 to 16 hours. Onset of action within 45 minutes. Duration of action 5 to 8 hours.

United States Pharmacopeial Convention; USP Dispensing Information 12th ed Vol IB p.1900 (1992)


Biologic half-life is not well defined, but varies between 4 and 16 hours, although a longer action has been observed in severely poisoned patients.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 851


5.6 Mechanism of Action

Methyprylon binds at a distinct binding site 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.


INCREASED STEROID HYDROXYLATION IS PROBABLY ONE IMPORTANT MECHANISM OF ACTION OF SO-CALLED CATATOXIC STEROIDS. SUCH CMPD HAVE BEEN REPORTED TO PROTECT ANIMALS AGAINST ACUTE TOXIC EFFECTS OF EXTRAORDINARY VARIETY OF DRUGS ... METHYPRYLON.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 608


METHYPRYLON STIMULATES HEPATIC MICROSOMAL ENZYME SYSTEM & DELTA-ALA SYNTHETASE ...

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. 366


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API | Excipient name

Methyprylon

Synonyms

Metiprilone, Noludar, Metiprilon, Dimerin, Noctan, Methyprylone

Cas Number

125-64-4

Unique Ingredient Identifier (UNII)

X66M7YN35V

About Methyprylon

Methyprylon is a sedative of the piperidinedione derivative family that was previously used for the treatment of insomnia. However, with the introduction of newer drugs with fewer side effects, such as benzodiazepines, the clinical use of methyprylon is now limited. Methyprylon was withdrawn from the U.S. market in June 1965 and the Canadian market in September 1990 due to adverse events.

Methyprylon Manufacturers

A Methyprylon manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Methyprylon, including repackagers and relabelers. The FDA regulates Methyprylon manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Methyprylon API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Methyprylon Suppliers

A Methyprylon supplier is an individual or a company that provides Methyprylon active pharmaceutical ingredient (API) or Methyprylon finished formulations upon request. The Methyprylon suppliers may include Methyprylon API manufacturers, exporters, distributors and traders.

Methyprylon GMP

Methyprylon Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Methyprylon GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Methyprylon GMP manufacturer or Methyprylon GMP API supplier for your needs.

Methyprylon CoA

A Methyprylon CoA (Certificate of Analysis) is a formal document that attests to Methyprylon's compliance with Methyprylon specifications and serves as a tool for batch-level quality control.

Methyprylon CoA mostly includes findings from lab analyses of a specific batch. For each Methyprylon CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Methyprylon may be tested according to a variety of international standards, such as European Pharmacopoeia (Methyprylon EP), Methyprylon JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Methyprylon USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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