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Chemistry

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Also known as: Parametadione, Paradione, 115-67-3, Isoethadione, Paramethadionum, 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
Molecular Formula
C7H11NO3
Molecular Weight
157.17  g/mol
InChI Key
VQASKUSHBVDKGU-UHFFFAOYSA-N
FDA UNII
Z615FRW64N

Paramethadione
Paramethadione is an anticonvulsant in the oxazolidinedione class. It is associated with fetal trimethadione syndrome, which is also known as paramethadione syndrome.
1 2D Structure

Paramethadione

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
2.1.2 InChI
InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3
2.1.3 InChI Key
VQASKUSHBVDKGU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1(C(=O)N(C(=O)O1)C)C
2.2 Other Identifiers
2.2.1 UNII
Z615FRW64N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-ethyl-3,5-dimethyloxazolinedione

2.3.2 Depositor-Supplied Synonyms

1. Parametadione

2. Paradione

3. 115-67-3

4. Isoethadione

5. Paramethadionum

6. 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione

7. 2,4-oxazolidinedione, 5-ethyl-3,5-dimethyl-

8. 3,5-dimethyl-5-ethyloxazolidine-2,4-dione

9. 5-ethyl-3,5-dimethyl-2,4-oxazolidinedione

10. 5-ethyl-3,5-dimethyloxazolidine-2,4-dione

11. A 348

12. Paramethadione (inn)

13. Isoethadione; Paradione

14. Nsc-760129

15. Chebi:7921

16. Z615frw64n

17. Parametadione [dcit]

18. Parametadiona

19. Parametadiona [inn-spanish]

20. Paramethadionum [inn-latin]

21. Paramethadione [inn]

22. Paradione (tn)

23. Hsdb 3245

24. Einecs 204-098-8

25. Brn 0127715

26. Unii-z615frw64n

27. Paramethadione [usp:inn:ban]

28. Paramethadione [mi]

29. Chembl1100

30. Schembl34857

31. Paramethadione [hsdb]

32. 4-27-00-03255 (beilstein Handbook Reference)

33. Paramethadione [vandf]

34. Paramethadione [mart.]

35. Gtpl7261

36. Paramethadione [who-dd]

37. Dtxsid8023420

38. Hms3264i11

39. Pharmakon1600-01505456

40. Hy-b1721

41. Paramethadione [orange Book]

42. Nsc760129

43. Akos006239791

44. Ccg-213441

45. Db00617

46. Nsc 760129

47. Ncgc00183600-01

48. Ncgc00183600-04

49. Sbi-0206930.p001

50. A-348

51. Cs-0013725

52. C07411

53. D00495

54. Ab01563081_01

55. 115p673

56. Sr-05000002060

57. Q3895202

58. Sr-05000002060-1

59. 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione #

60. Brd-a22128695-001-01-8

61. Z2327506990

62. 128557-52-8

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 157.17 g/mol
Molecular Formula C7H11NO3
XLogP30.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass157.07389321 g/mol
Monoisotopic Mass157.07389321 g/mol
Topological Polar Surface Area46.6 Ų
Heavy Atom Count11
Formal Charge0
Complexity214
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

Anticonvulsants

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


/PARAMETHADIONE & TRIMETHADIONE/...WERE MAJOR AGENTS FOR TREATMENT OF PETIT MAL EPILEPSY & ATYPICAL SPIKE-AND-WAVE ABSENCE ATTACKS BEFORE INTRODUCTION OF ETHOSUXIMIDE. THOUGH EFFECTIVE, THEIR SIDE EFFECTS MAKE THEM DRUGS OF SECOND CHOICE.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 597


MEDICATION (VET): ANTICONVULSANT. USE: NOW RARE, TO CONTROL CONVULSIONS IN ANIMALS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 413


Paramethadione and trimethadione are indicated in the control of absence (petit mal) seizures that are refractory to treatment with other medications. /Included in US product labeling./

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 243


... Its pharmacological properties, therapeutic uses, dosage, and toxicity are similar to those of trimethadione.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 478


4.2 Drug Warning

ALTHOUGH IT IS SLIGHTLY LESS POTENT, DOES NOT INDUCE MYASTHENIA GRAVIS-LIKE SYNDROME, & INDUCES PHOTOPHOBIA & SKIN RASHES IN SOMEWHAT FEWER PATIENTS, IT HAS SAME LIMITATIONS & EXHIBITS SAME SIDE REACTIONS AS.../TRIMETHADIONE/.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1016


AS WITH TRIMETHADIONE, THERE IS SUGGESTIVE EVIDENCE THAT USE OF PARAMETHADIONE DURING PREGNANCY IS ASSOCIATED WITH INCR IN INCIDENCE OF CONGENITAL ABNORMALITIES. ACCORDINGLY, PARAMETHADIONE SHOULD BE AVOIDED IN PREGNANT WOMEN IF POSSIBLE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 466


NEPHROPATHIES HAVE DEVELOPED...ESP IN PATIENTS RECEIVING...PARAMETHADIONE. THESE REACTIONS MAY DEVELOP INSIDIOUSLY, & URINALYSES SHOULD BE MADE BEFORE & PERIODICALLY DURING TREATMENT. DEVELOPMENT OF ANY SIGNIFICANT RENAL ABNORMALITY IS INDICATION FOR DISCONTINUING THE DRUG.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 458


SINCE EARLY RECOGNITION OF /BLOOD/ DYSCRASIA & DISCONTINUANCE OF...DRUG ARE ESSENTIAL, PT SHOULD BE ADVISED TO REPORT PROMPTLY SUCH SYMPTOMS AS SORE THROAT, FEVER, EASY BRUISING, PETECHIAE, EPISTAXIS, OR OTHER SIGNS OF INFECTION OR BLEEDING TENDENCY. /ANTICONVULSANTS /

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 458


For more Drug Warnings (Complete) data for PARAMETHADIONE (15 total), please visit the HSDB record page.


4.3 Drug Indication

Used for the control of absence (petit mal) seizures that are refractory to treatment with other medications.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Paramethadione is an oxazolidinedione anticonvulsant similar to trimethadione that acts on the central nervous system (CNS) to reduce the number of absence seizures (often seen in epileptics). Absence seizures involve an interruption to consciousness where the person experiencing the seizure seems to become vacant and unresponsive for a short period of time (usually up to 30 seconds). Paramethadione acts on thalamic neurons in the thalamic reticular nucleus (which studies have shown to be associated with absence seizures, von Krosigk et al., 1993).


5.2 ATC Code

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AC - Oxazolidine derivatives

N03AC01 - Paramethadione


5.3 Absorption, Distribution and Excretion

Absorption

Rapid via the digestive tract.


PARAMETHADIONE IS COMPLETELY N-DEMETHYLATED TO 5-ETHYL-5-METHYL-OXAZOLIDINE-2,4-DIONE AND SLOWLY EXCRETED BY KIDNEYS.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 78


5.4 Metabolism/Metabolites

Primarily hepatic (mainly via cytochrome P450 isozyme 2C9), paramethadione is completely demethylated to 5-ethyl-5-methyl-2,4-oxazolidinedione, the active metabolite.


PARAMETHADIONE IS COMPLETELY N-DEMETHYLATED TO 5-ETHYL-5-METHYL-OXAZOLIDINE-2,4-DIONE...

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 78


PARAMETHADIONE IS N-DEMETHYLATED BY HEPATIC MICROSOMAL ENZYMES TO ACTIVE METABOLITE THAT IS SLOWLY EXCRETED IN URINE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 216


PARAMETHADIONE IS N-DEMETHYLATED BY HEPATIC MICROSOMAL ENZYMES TO ACTIVE METABOLITE... METABOLITE ACCUMULATES DURING CHRONIC MEDICATION & IS PROBABLY RESPONSIBLE FOR MOST OF ANTICONVULSANT ACTIVITY OF PARENT DRUG...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 216


5.5 Biological Half-Life

12 to 24 hours (however the half-life for the active metabolite is not known)


Paramethadion - 12 to 24 hours; active metabolite - unknown.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 243


5.6 Mechanism of Action

Dione anticonvulsants such as paramethadione reduce T-type calcium currents in thalamic neurons (including thalamic relay neurons). This inhibits corticothalamic transmission and raises the threshold for repetitive activity in the thalamus. This results in a dampening of the abnormal thalamocortical rhythmicity proposed to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram (EEG) during absence seizures.


Dione anticonvulsants reduce T-type calcium currents in thalamic neurons, including thalamic relay neurons. this raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram (EEG) with absence seizures, is dampened. The maximal seizure pattern in patients undergoing electroconvulsive therapy is not modified. /Dione anticonvulsants/

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 243


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Paramethadione manufacturers, exporters & distributors 1

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API | Excipient name

Paramethadione

Synonyms

Parametadione, Paradione, 115-67-3, Isoethadione, Paramethadionum, 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione

Cas Number

115-67-3

Unique Ingredient Identifier (UNII)

Z615FRW64N

About Paramethadione

Paramethadione is an anticonvulsant in the oxazolidinedione class. It is associated with fetal trimethadione syndrome, which is also known as paramethadione syndrome.

Paramethadione Manufacturers

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

Paramethadione Suppliers

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

Paramethadione GMP

Paramethadione 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 Paramethadione 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 Paramethadione GMP manufacturer or Paramethadione GMP API supplier for your needs.

Paramethadione CoA

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

Paramethadione CoA mostly includes findings from lab analyses of a specific batch. For each Paramethadione 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.

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