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Chemistry

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Also known as: 125-33-7, Primaclone, Mysoline, Lepimidin, 2-deoxyphenobarbital, Liskantin
Molecular Formula
C12H14N2O2
Molecular Weight
218.25  g/mol
InChI Key
DQMZLTXERSFNPB-UHFFFAOYSA-N
FDA UNII
13AFD7670Q

Primidone
A barbiturate derivative that acts as a GABA modulator and anti-epileptic agent. It is partly metabolized to PHENOBARBITAL in the body and owes some of its actions to this metabolite.
Primidone is an Anti-epileptic Agent. The physiologic effect of primidone is by means of Decreased Central Nervous System Disorganized Electrical Activity.
1 2D Structure

Primidone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
2.1.2 InChI
InChI=1S/C12H14N2O2/c1-2-12(9-6-4-3-5-7-9)10(15)13-8-14-11(12)16/h3-7H,2,8H2,1H3,(H,13,15)(H,14,16)
2.1.3 InChI Key
DQMZLTXERSFNPB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1(C(=O)NCNC1=O)C2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
13AFD7670Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Primidone

2. Apo-primidone

3. Desoxyphenobarbital

4. Liskantin

5. Misodine

6. Mizodin

7. Mylepsinum

8. Mysoline

9. Primaclone

10. Primidon Holsten

11. Resimatil

12. Sertan

2.3.2 Depositor-Supplied Synonyms

1. 125-33-7

2. Primaclone

3. Mysoline

4. Lepimidin

5. 2-deoxyphenobarbital

6. Liskantin

7. Mylepsinum

8. Lepsiral

9. Misodine

10. Mizodin

11. Mylepsin

12. Neurosyn

13. Primidon

14. Sertan

15. 2-desoxyphenobarbital

16. Hexadiona

17. Majsolin

18. Milepsin

19. Misolyne

20. Prilepsin

21. Primakton

22. Primoline

23. Prysoline

24. Resimatil

25. Midone

26. Mizolin

27. Mysedon

28. Cyral

29. Medi-pets

30. Primacone

31. Desoxyphenobarbitone

32. Pyrimidone Medi-pets

33. 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione

34. Primidona

35. Primidonum

36. Roe 101

37. 5-phenyl-5-ethyl-hexahydropyrimidine-4,6-dione

38. 4,6(1h,5h)-pyrimidinedione, 5-ethyldihydro-5-phenyl-

39. 5-ethyl-5-phenyldihydropyrimidine-4,6(1h,5h)-dione

40. Nci-c56360

41. Primidone (primaclone)

42. 5-ethyldihydro-5-phenyl-4,6(1h,5h)-pyrimidinedione

43. 5-ethyl-5-phenylhexahydropyrimidine-4,6-dione

44. 5-ethylhexahydro-4,6-dioxo-5-phenylpyrimidine

45. 5-ethylhexahydro-5-phenylpyrimidine-4,6-dione

46. Nsc 41701

47. 5-aethyl-5-phenyl-hexahydropyrimidin-4,6-dion

48. Chebi:8412

49. 5-phenyl-5-aethylhexahydropyrimidindion-(4,6)

50. Nsc-41701

51. Mls000028593

52. Primacione

53. 13afd7670q

54. Ncgc00015834-11

55. Cas-125-33-7

56. Smr000058501

57. Dsstox_cid_3510

58. Primidonum [inn-latin]

59. Dsstox_rid_77058

60. Dsstox_gsid_23510

61. Primidona [inn-spanish]

62. Hexamidine (the Antispasmodic)

63. Ccris 54

64. Mysoline (tn)

65. Hsdb 3169

66. Sr-01000003162

67. Einecs 204-737-0

68. Brn 0218034

69. Hexamidine(the Antispasmodic)

70. 5-aethyl-5-phenyl-hexahydropyrimidin-4,6-dion [german]

71. 5-phenyl-5-aethylhexahydropyrimidindion-(4,6) [german]

72. Unii-13afd7670q

73. Primidone [usp:inn:ban:jan]

74. Primidone Solution

75. Primidone(mysoline)

76. Primidone (mysoline)

77. Spectrum_000832

78. Tocris-0830

79. Pyrimidone 'medi-pets'

80. Primidone [inn]

81. Primidone [jan]

82. Primidone [mi]

83. Primidone [hsdb]

84. Primidone [iarc]

85. Opera_id_1083

86. Prestwick0_000933

87. Prestwick1_000933

88. Prestwick2_000933

89. Prestwick3_000933

90. Spectrum2_001293

91. Spectrum3_000553

92. Spectrum4_000485

93. Spectrum5_001144

94. Lopac-p-7295

95. Primidone [vandf]

96. Biomol-nt_000261

97. Chembl856

98. Primidone [mart.]

99. P 7295

100. Pyrimidone ''medi-pets''

101. Primidone [usp-rs]

102. Primidone [who-dd]

103. Lopac0_001021

104. Schembl34221

105. Bspbio_000866

106. Bspbio_002225

107. Kbiogr_000969

108. Kbioss_001312

109. 5-24-08-00102 (beilstein Handbook Reference)

110. Mls001055411

111. Mls001074125

112. Bidd:gt0319

113. Divk1c_000324

114. Primidone, Analytical Standard

115. Spectrum1500501

116. Spbio_001325

117. Spbio_003035

118. Primidone (jp17/usp/inn)

119. Primidone [green Book]

120. Bpbio1_000859

121. Bpbio1_000954

122. Gtpl5338

123. Zinc1979

124. Primidone [ep Impurity]

125. Primidone [orange Book]

126. Dtxsid7023510

127. Primidone [ep Monograph]

128. Hms501a06

129. Kbio1_000324

130. Kbio2_001312

131. Kbio2_003880

132. Kbio2_006448

133. Kbio3_001725

134. Primidone For Peak Identification

135. Wln: T6mv Dvmtj C2 Cr

136. Primidone [usp Monograph]

137. Ninds_000324

138. Hms1570l08

139. Hms1920j20

140. Hms2092a21

141. Hms2097l08

142. Hms2236g03

143. Hms3259k04

144. Hms3263m03

145. Hms3266h18

146. Hms3369j12

147. Hms3411n13

148. Hms3655l05

149. Hms3675n13

150. Hms3714l08

151. Hms3884a18

152. Pharmakon1600-01500501

153. Hy-b0339

154. Nsc41701

155. Tox21_110238

156. Tox21_201948

157. Tox21_303194

158. Tox21_501021

159. Bdbm50248152

160. Ccg-39231

161. Mfcd00038662

162. Nsc757291

163. S1965

164. Akos003368409

165. Tox21_110238_1

166. Db00794

167. Ks-5217

168. Lp01021

169. Nc00532

170. Nsc-757291

171. Sdccgsbi-0050994.p005

172. Idi1_000324

173. Smp1_000135

174. Ncgc00015834-01

175. Ncgc00015834-02

176. Ncgc00015834-03

177. Ncgc00015834-04

178. Ncgc00015834-05

179. Ncgc00015834-06

180. Ncgc00015834-07

181. Ncgc00015834-08

182. Ncgc00015834-09

183. Ncgc00015834-10

184. Ncgc00015834-12

185. Ncgc00015834-13

186. Ncgc00015834-14

187. Ncgc00015834-15

188. Ncgc00015834-16

189. Ncgc00015834-17

190. Ncgc00015834-19

191. Ncgc00015834-28

192. Ncgc00016377-01

193. Ncgc00023254-02

194. Ncgc00023254-04

195. Ncgc00023254-05

196. Ncgc00023254-06

197. Ncgc00023254-07

198. Ncgc00023254-08

199. Ncgc00023254-09

200. Ncgc00023254-10

201. Ncgc00257146-01

202. Ncgc00259497-01

203. Ncgc00261706-01

204. Bp166193

205. Sbi-0050994.p004

206. Ab00052079

207. Eu-0101021

208. Ft-0603328

209. Ft-0674032

210. P1906

211. Sw196576-3

212. 5-ethyldihydro-5-phenyl-4,5h)-pyrimidinedione

213. C07371

214. C71997

215. D00474

216. Ab00052079-14

217. Ab00052079_15

218. Ab00052079_16

219. 125p337

220. 4,5h)-pyrimidinedione, 5-ethyldihydro-5-phenyl-

221. A805374

222. Q420383

223. J-005215

224. Sr-01000003162-2

225. Sr-01000003162-4

226. Sr-01000003162-5

227. Sr-01000003162-8

228. Brd-k32247306-001-05-4

229. Brd-k32247306-001-17-9

230. 5-ethyl-5-phenyldihydro-4,6(1h,5h)-pyrimidinedione #

231. Primidone, European Pharmacopoeia (ep) Reference Standard

232. Primidone, United States Pharmacopeia (usp) Reference Standard

233. Primidone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

234. Primidone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 218.25 g/mol
Molecular Formula C12H14N2O2
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass218.105527694 g/mol
Monoisotopic Mass218.105527694 g/mol
Topological Polar Surface Area58.2 Ų
Heavy Atom Count16
Formal Charge0
Complexity279
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 Drug Information
1 of 4  
Drug NameMysoline
PubMed HealthPrimidone (By mouth)
Drug ClassesAnticonvulsant
Drug LabelChemical name: 5-ethyldihydro-5-phenyl-4,6 (1H, 5H)-pyrimidinedione. Structural formula:Mysoline* (primidone) is a white, crystalline, highly stable substance, M.P. 279-284C. It is poorly soluble in water (60 mg per 100 mL at 37C) and in most org...
Active IngredientPrimidone
Dosage FormTablet
RouteOral
Strength250mg; 50mg
Market StatusPrescription
CompanyValeant

2 of 4  
Drug NamePrimidone
PubMed HealthPrimidone (By mouth)
Drug ClassesAnticonvulsant
Drug LabelPrimidone, USP is a white, crystalline, highly stable substance, M.P. 279-284 C. It is poorly soluble in water (60 mg per 100 mL at 37 C) and in most organic solvents. It possesses no acidic properties, in contrast to its barbiturate analog.Chemi...
Active IngredientPrimidone
Dosage FormTablet
RouteOral
Strength250mg; 50mg
Market StatusPrescription
CompanyVintage Pharms; Hikma Pharms; Watson Labs; Amneal Pharm; Lannett; Mutual Pharm; Impax Labs

3 of 4  
Drug NameMysoline
PubMed HealthPrimidone (By mouth)
Drug ClassesAnticonvulsant
Drug LabelChemical name: 5-ethyldihydro-5-phenyl-4,6 (1H, 5H)-pyrimidinedione. Structural formula:Mysoline* (primidone) is a white, crystalline, highly stable substance, M.P. 279-284C. It is poorly soluble in water (60 mg per 100 mL at 37C) and in most org...
Active IngredientPrimidone
Dosage FormTablet
RouteOral
Strength250mg; 50mg
Market StatusPrescription
CompanyValeant

4 of 4  
Drug NamePrimidone
PubMed HealthPrimidone (By mouth)
Drug ClassesAnticonvulsant
Drug LabelPrimidone, USP is a white, crystalline, highly stable substance, M.P. 279-284 C. It is poorly soluble in water (60 mg per 100 mL at 37 C) and in most organic solvents. It possesses no acidic properties, in contrast to its barbiturate analog.Chemi...
Active IngredientPrimidone
Dosage FormTablet
RouteOral
Strength250mg; 50mg
Market StatusPrescription
CompanyVintage Pharms; Hikma Pharms; Watson Labs; Amneal Pharm; Lannett; Mutual Pharm; Impax Labs

4.2 Therapeutic Uses

Anticonvulsants

National Library of Medicine's Medical Subject Headings. Primidone. Online file (MeSH, 2018). Available from, as of August 29, 2018: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Primidone is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of August 29, 2018: https://clinicaltrials.gov/


Primidone, used alone or concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. /Included in US product labeling./

NIH; DailyMed. Current Medication Information for Primidone Tablet (Updated: July 26, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1a817f7-c190-4825-94eb-442f477187e3


/EXPL THER/ OBJECTIVES: Cerebellar tremor is a disabling sign of multiple sclerosis (MS), and various kinds of treatments have been proposed with different results. Primidone is one of the medications, mostly advised for essential tremor. The aim of our study was to determine the tolerability and efficacy of primidone in reducing severe cerebellar tremor in patients with MS. METHODS: Ten patients with severe cerebellar tremor were enrolled in this study. Primidone started with dose of 31.5 mg and gradually increased up to maximum of 750 mg/d. The severity of tremor was assessed with Activity of Daily Living (ADL), Nine-Hole Peg Test (NHPT), and Fahn Tremor Rating Scale (FTRS) at baseline and 2 follow-up studies after 6 and 12 weeks. RESULTS: All outcome measures including ADL, FTRS, and NHPT of dominant and nondominant hands improved. The mean ADL changed from 51.8 at baseline to 36.8 after 12 weeks. FTRS was 14.8 at baseline, which reduced to 9.5 during this period. These changes were statistically significant. Although the time of the NHPT showed some improvement, it did not reach a statistically significant point after 6 weeks.The drug was well tolerated in all patients, and mild drowsiness reported by the patients disappeared at the end of the study. CONCLUSIONS: Our study showed that primidone is tolerable in MS patients and effectively reduces severe cerebellar tremor in such patients.

PMID:22821064 Naderi F et al; Clin Neuropharmacol 35 (5): 224-6 (2012)


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


4.3 Drug Warning

Primidone is contraindicated in: 1) patients with porphyria and 2) patients who are hypersensitive to phenobarbital

NIH; DailyMed. Current Medication Information for Primidone Tablet (Updated: July 26, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1a817f7-c190-4825-94eb-442f477187e3


The abrupt withdrawal of antiepileptic medication may precipitate status epilepticus. The therapeutic efficacy of a dosage regimen takes several weeks before it can be assessed.

NIH; DailyMed. Current Medication Information for Primidone Tablet (Updated: July 26, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1a817f7-c190-4825-94eb-442f477187e3


Antiepileptic drugs (AEDs), including primidone, increase the risk of suicidal thoughts or behavior in patients taking these drugs for any indication. Patients treated with any AED for any indication should be monitored for the emergence or worsening of depression, suicidal thoughts or behavior, and/or any unusual changes in mood or behavior.

NIH; DailyMed. Current Medication Information for Primidone Tablet (Updated: July 26, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1a817f7-c190-4825-94eb-442f477187e3


The most frequently occurring early side effects are ataxia and vertigo. These tend to disappear with continued therapy, or with reduction of initial dosage. Occasionally, the following have been reported: nausea, anorexia, vomiting, fatigue, hyperirritability, emotional disturbances, sexual impotency, diplopia, nystagmus, drowsiness, and morbilliform skin eruptions. Granulocytopenia, agranulocytosis, and red-cell hypoplasia and aplasia, have been reported rarely. These and, occasionally, other persistent or severe side effects may necessitate withdrawal of the drug. Megaloblastic anemia may occur as a rare idiosyncrasy to primidone and to other anticonvulsants. The anemia responds to folic acid without necessity of discontinuing medication.

NIH; DailyMed. Current Medication Information for Primidone Tablet (Updated: July 26, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1a817f7-c190-4825-94eb-442f477187e3


For more Drug Warnings (Complete) data for Primidone (12 total), please visit the HSDB record page.


4.4 Drug Indication

Primidone is commonly indicated for the management of grand mal, psychomotor, and focal epileptic seizures. In addition, it has also been studied and utilized as an effective management of essential tremor.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Primidone alters sodium and calcium channel transport, reducing the frequency of nerve firing, which may be responsible for its effect on convulsions and essential tremor. Primidone has a wide therapeutic window as doses of 50-1000mg/day were effective. Patients should be counselled regarding the risk of status epilepticus with abrupt cessation of primidone.


5.2 MeSH Pharmacological Classification

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)


Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PRIMIDONE
5.3.2 FDA UNII
13AFD7670Q
5.3.3 Pharmacological Classes
Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]
5.4 ATC Code

N03AA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AA - Barbiturates and derivatives

N03AA03 - Primidone


5.5 Absorption, Distribution and Excretion

Absorption

Oral primidone is up to 80% bioavailable with a Tmax if 2-4h. A 500mg oral dose of primidone Reaches a Cmax of 2.70.4g/mL with a Tmax of 0.5-7h. Data regarding the AUC of primidone is not readily available.


Route of Elimination

Primidone is 72.9-80.6% recovered in urine.


Volume of Distribution

The volume of distribution of primidone is 0.5-0.8L/kg.


Clearance

Primidone is cleared at a rate of 30mL/min.


Mice were treated with a teratogenic dose of primidone (100 mg/kg) by gastric intubation at three different times during pregnancy, viz. days 6-14, days 12-14 on day 14 only. Blood samples were taken on day 14 at 1, 4, 8 and 24 hr after dosage. Primidone and its metabolites phenylethylmalondiamide (PEMA), and phenobarbitone, were assayed by GLC. There was no accumulation of the parent compound or the metabolites after repeated administration of primidone; each of the substances was cleared from the plasma within 24 hr. The rate of metabolism of primidone increased with prolonged treatment. The peak concentration of the metabolites was higher in the two multiple-dose groups than in the single dose group. The concentration of PEMA exceeded that of primidone between 3-8 hr and then began to decrease in the multiple-dose groups, a similar pattern was established for phenobarbitone also, although the concentrations were lower than those of PEMA.

PMID:910462 McElhatton PR et al; Xenobiotica 7 (10): 617-22 (1977)


The placental transfer of primidone and metabolites was investigated in 14 women treated for epilepsy with primidone (and additionally phenytoin, ethosuximide or valproate in 5 women) throughout pregnancy. Primidone, PEMA /phenylethylmalonamide/, phenobarbital, and polar metabolites (p-hydroxyphenobarbital and p-hydroxyphenobarbital glucuronide) were found in similar concentrations in maternal and cord blood at birth.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V108 196 (2016)


The pharmacokinetics of primidone (PRM) after oral administration of a single 500 mg dose was studied in 7 patients with acute viral hepatitis and 7 healthy control subjects. The elimination half-life and the apparent clearance of unchanged PRM in the patients were 18.0 +/- 3.1 hr and 42 +/- 14 mL/kg/hr, respectively (mean +/- SD) and did not differ significantly from the values in the controls (half-life 17.0 +/- 2.4 hr; clearance 35 +/- 8 mL/kg/hr). The metabolite phenylethylmalonamide (PEMA) was detected in the serum of all normal subjects within 2-24 hr. By contrast, serum levels of this metabolite were undetectable (less than 2 umol/L) in all but one of the patients. Serum levels of phenobarbital (PB) remained below the limit of detection (less than 2 umol/L) in all subjects. The findings indicate that accumulation of PRM with its attendant toxicity is unlikely to occur in epileptic patients who develop acute viral hepatitis, despite evidence that the metabolism of the drug is affected by this condition. The possibility of impaired conversion to PB and its implications are discussed.

PMID:6519155 Pisani F et al; Eur J Clin Pharmacol 27 (4): 465-9 (1984)


Primidone is slowly absorbed after oral administration in the dog, with peak levels occurring 2-4 hours after dosing.

Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1212


For more Absorption, Distribution and Excretion (Complete) data for Primidone (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Primidone is metabolized to phenobarbitol and phenylethylmalonamide (PEMA). This metabolism is largely mediated by CYP2C9, CYP2C19, and CYP2E1.


Physiologically based pharmacokinetic modeling of the parent chemical primidone and its two metabolites phenobarbital and phenylethylmalonamide (PEMA) was applied to investigate the differences of primidone metabolism among humans, rats, and mice. The model simulated previously published pharmacokinetic data of the parent chemical and its metabolites in plasma and brain tissues from separate studies of the three species. Metabolism of primidone and its metabolites varied widely among a sample of three human subjects from two separate studies. Estimated primidone metabolism, as expressed by the maximal velocity Vmax, ranged from 0 to 0.24 mg/kg/min for the production of phenobarbital and from 0.003 to 0.02 mg/kg/min for the production of PEMA among three human subjects. Further model simulations indicated that rats were more efficient at producing and clearing phenobarbital and PEMA than mice. However, the overall metabolism profile of primidone and its metabolites in mice indicated that mice were at higher risk of toxicity owing to higher residence of phenobarbital in their tissues and owing to the carcinogenic potential of phenobarbital as illustrated in long-term bioassays. ...

PMID:9616196 El-Masri HA, Portier CJ; Drug Metab Dispos 26 (6): 585-94 (1998)


The placental transfer of primidone and metabolites was investigated in 14 women treated for epilepsy with primidone (and additionally phenytoin, ethosuximide or valproate in 5 women) throughout pregnancy. Primidone, PEMA /phenylethylmalonamide/, phenobarbital, and polar metabolites (p-hydroxyphenobarbital and p-hydroxyphenobarbital glucuronide) were found in similar concentrations in maternal and cord blood at birth.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V108 196 (2016)


The pharmacokinetics and metabolism of primidone at steady-state were studied in 10 elderly patients aged 70-81 years and eight control subjects aged 18-26 years. Primidone half-lives and clearance values (mean +/- s.d.) were similar in the elderly and in the young (12.1 +/- 4.6 vs 14.7 +/- 3.5 hr and 34.8 +/- 9.0 vs 33.2 +/- 7.2 mL/kg/hr respectively. The serum concentrations of the metabolites phenylethylmalonamide (PEMA) and phenobarbitone relative to those of parent drug were higher in the elderly than in the young, the difference being significant (P less than 0.01) in the case of PEMA. The renal clearances of primidone, phenobarbitone and PEMA were moderately decreased in the elderly but this reduction was statistically significant only for PEMA. Elderly patients excreted a reduced proportion of unchanged primidone and an increased proportion of PEMA in urine. Ageing is associated with a greater accumulation of PEMA, which is unlikely to have a major clinical significance.

PMID:2291873 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1368252 Martines C et al; Br J Clin Pharmacol 30 (4): 607-11 (1990)


Although phenobarbital was not detected after administration of single doses of primidone, long-term administration of primidone (at various doses) in 46 epilepsy patients showed serum accumulation of phenobarbital, and PEMA /phenylethylmalonamide/. Although there was significant inter-individual variability, concentrations of the two metabolites showed correlation with those of the parent drug, and concentrations of phenobarbital were consistently higher than those of PEMA. Two of the subjects had been on a daily dose of primidone (750 mg in divided doses) for more than 3 years. After a single dose of 750 mg in this study, peak serum concentrations of primidone were achieved rapidly (by 0.5 hour), and declined slowly (half-lives, 5.3 and 7.0 hours). In both subjects, peak concentrations of metabolites, PEMA (12 and 10 ug/mL) and phenobarbital (33 and 11 ug/mL), remained relatively constant. In the cerebrospinal fluid, binding to protein by PEMA and by primidone was negligible, and approximately 60% by phenobarbital.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V108 195 (2016)


For more Metabolism/Metabolites (Complete) data for Primidone (9 total), please visit the HSDB record page.


5.7 Biological Half-Life

The half life of primidone is 7-22h in adults, 5-11h in children, and 8-80h in newborns.


The pharmacokinetics and metabolism of primidone at steady-state were studied in 10 elderly patients aged 70-81 years and eight control subjects aged 18-26 years. Primidone half-lives and clearance values (mean +/- s.d.) were similar in the elderly and in the young (12.1 +/- 4.6 vs 14.7 +/- 3.5 hr and 34.8 +/- 9.0 vs 33.2 +/- 7.2 mL/kg/hr respectively. ...

PMID:2291873 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1368252 Martines C et al; Br J Clin Pharmacol 30 (4): 607-11 (1990)


In a ... study in eight epileptic patients (aged 18-26 years) receiving long-term treatment with primidone (mean daily dose, 422 +/- 115 mg per day), the half-life for primidone was 14.7 +/- 3.5 hours.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V108 195 (2016)


The pharmacokinetics of primidone (PRM) after oral administration of a single 500 mg dose was studied in 7 patients with acute viral hepatitis and 7 healthy control subjects. The elimination half-life and the apparent clearance of unchanged PRM in the patients were 18.0 +/- 3.1 hr and 42 +/- 14 mL/kg/hr, respectively (mean +/- SD) and did not differ significantly from the values in the controls (half-life 17.0 +/- 2.4 hr; clearance 35 +/- 8 mL/kg/hr). ...

PMID:6519155 Pisani F et al; Eur J Clin Pharmacol 27 (4): 465-9 (1984)


Serum half lives of primidone, PEMA /phenylethamalonamide/, and phenobarbital have been reported to be 1.85 hr, 7.1 hr, and 41 hr, respectively.

Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1212


For more Biological Half-Life (Complete) data for Primidone (6 total), please visit the HSDB record page.


5.8 Mechanism of Action

Primidone and its metabolites, phenobarbital and phenylethylmalonamide (PEMA), are active anticonvulsants. Primidone does not directly interact with GABA-A receptors or chloride channels but phenobarbital does. Primidone alters transmembrane sodium and calcium channel transport, reducing the frequency of nerve firing, which may be responsible for the primidones effect on convulsions and essential tremor.


The melastatin-related transient receptor potential (TRP) channel TRPM3 is a nonselective cation channel expressed in nociceptive neurons and activated by heat. Because TRPM3-deficient mice show inflammatory thermal hyperalgesia, pharmacological inhibition of TRPM3 may exert antinociceptive properties. Fluorometric Ca influx assays and a compound library containing approved or clinically tested drugs were used to identify TRPM3 inhibitors. Biophysical properties of channel inhibition were assessed using electrophysiological methods. The nonsteroidal anti-inflammatory drug diclofenac, the tetracyclic antidepressant maprotiline, and the anticonvulsant primidone were identified as highly efficient TRPM3 blockers with half-maximal inhibition at 0.6 to 6 uM and marked specificity for TRPM3. Most prominently, primidone was biologically active to suppress TRPM3 activation by pregnenolone sulfate (PregS) and heat at concentrations markedly lower than plasma concentrations commonly used in antiepileptic therapy. Primidone blocked PregS-induced Cai influx through TRPM3 by allosteric modulation and reversibly inhibited atypical inwardly rectifying TRPM3 currents induced by coapplication of PregS and clotrimazole. In vivo, analgesic effects of low doses of primidone were demonstrated in mice, applying PregS- and heat-induced pain models, including inflammatory hyperalgesia. Thus, applying the approved drug at concentrations that are lower than those needed to induce anticonvulsive effects offers a shortcut for studying physiological and pathophysiological roles of TRPM3 in vivo.

PMID:28106668 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5402713 Krugel U et al; Pain 158 (5): 856-867 (2017)


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NANTONG JINGHUA PHARMACEUTICAL CO.,LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"RUBICON RESEARCH","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"115","totalValueFC":"116181.7","currency":"USD","unitRateINR":"9711.8","date":"11-Jul-2024","totalValueINR":"9711750","totalValueInUsd":"116181.7","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"4453022","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Micronized","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"NO.20, 3 HAIBIN ROAD, YANHAIECONOMIC DEVELOPMENT ZONE, RUDONGNANTONG, JIANGSU, CHINA,226407 CN","customerAddress":"221, GOREGAON-MULUND LINK ROAD,"}]
13-Jan-2021
16-Sep-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DOSAGE - TABLET;ORAL - 250MG

USFDA APPLICATION NUMBER - 9170

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DOSAGE - TABLET;ORAL - 50MG

USFDA APPLICATION NUMBER - 9170

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