Primidone

Modify Date: 2024-01-02 08:49:04

Primidone Structure
Primidone structure
 Common Name Primidone
CAS Number 125-33-7 Molecular Weight 218.25200
Density 1.138g/cm3 Boiling Point 520.7ºC at 760mmHg
Molecular Formula C12H14N2O2 Melting Point 281-282°C
MSDS Chinese USA Flash Point 228.2ºC
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Warning

 Use of Primidone


Primidone is an anticonvulsant of the pyrimidinedione class.Target: GABA ReceptorPrimidone is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (minor) and phenylethylmalonamide (PEMA) (major), are also anticonvulsants. It is believed to work via interactions with voltage-gated sodium channels which inhibit high-frequency repetitive firing of action potentials [1]. The effect of primidone in essential tremor is not mediated by PEMA.[76] The major metabolite, phenobarbital, is also a potent anticonvulsant in its own right and likely contributes to primidone's effects in many forms of epilepsy [2]. Primidone and the other enzyme-inducing anticonvulsants can cut the half-life of antipyrine roughly in half (6.2 ± 1.9 h vs. 11.2 ± 4.2 h), and increases the clearance rate by almost 70%. Phenobarbital reduces the half-life to 4.8 ± 1.3 and increases the clearance by almost 109% [3].

 Names

Name primidone
Synonym More Synonyms

 Primidone Biological Activity

Description Primidone is an anticonvulsant of the pyrimidinedione class.Target: GABA ReceptorPrimidone is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (minor) and phenylethylmalonamide (PEMA) (major), are also anticonvulsants. It is believed to work via interactions with voltage-gated sodium channels which inhibit high-frequency repetitive firing of action potentials [1]. The effect of primidone in essential tremor is not mediated by PEMA.[76] The major metabolite, phenobarbital, is also a potent anticonvulsant in its own right and likely contributes to primidone's effects in many forms of epilepsy [2]. Primidone and the other enzyme-inducing anticonvulsants can cut the half-life of antipyrine roughly in half (6.2 ± 1.9 h vs. 11.2 ± 4.2 h), and increases the clearance rate by almost 70%. Phenobarbital reduces the half-life to 4.8 ± 1.3 and increases the clearance by almost 109% [3].
Related Catalog
References

[1]. Macdonald, R.L. and K.M. Kelly, Antiepileptic drug mechanisms of action. Epilepsia, 1995. 36 Suppl 2: p. S2-12.

[2]. Calzetti, S., et al., Phenylethylmalonamide in essential tremor. A double-blind controlled study. J Neurol Neurosurg Psychiatry, 1981. 44(10): p. 932-4.

[3]. Perucca, E., et al., A comparative study of the relative enzyme inducing properties of anticonvulsant drugs in epileptic patients. Br J Clin Pharmacol, 1984. 18(3): p. 401-10.

 Chemical & Physical Properties

Density 1.138g/cm3
Boiling Point 520.7ºC at 760mmHg
Melting Point 281-282°C
Molecular Formula C12H14N2O2
Molecular Weight 218.25200
Flash Point 228.2ºC
Exact Mass 218.10600
PSA 58.20000
LogP 1.19550
Vapour Pressure 6.08E-11mmHg at 25°C
Index of Refraction 1.528
Storage condition Store at RT
Water Solubility <0.1 g/100 mL at 19 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UV9100000
CHEMICAL NAME :
4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-
CAS REGISTRY NUMBER :
125-33-7
BEILSTEIN REFERENCE NO. :
0218034
LAST UPDATED :
199712
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C12-H14-N2-O2
MOLECULAR WEIGHT :
218.28
WISWESSER LINE NOTATION :
T6MV DVMTJ C2 CR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
38 gm/kg/7Y-I
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
280 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
332 mg/kg
TOXIC EFFECTS :
Behavioral - anticonvulsant
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
340 mg/kg
TOXIC EFFECTS :
Behavioral - anticonvulsant
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10500 mg/kg/14D-C
TOXIC EFFECTS :
Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17062 mg/kg/13W-C
TOXIC EFFECTS :
Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27440 mg/kg/14D-C
TOXIC EFFECTS :
Behavioral - ataxia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
89 gm/kg/13W-C
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
2 gm/kg/4D-I
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10350 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10350 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other neonatal measures or effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2025 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - Apgar score (human only)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
10640 mg/kg
SEX/DURATION :
female 1-38 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - drug dependence Reproductive - Effects on Newborn - physical
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
330 mg/kg
SEX/DURATION :
female 6-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
990 mg/kg
SEX/DURATION :
female 6-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
875 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
275 mg/kg
SEX/DURATION :
female 6-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
Sperm Morphology

MUTATION DATA

TYPE OF TEST :
Micronucleus test
TEST SYSTEM :
Rodent - hamster Embryo
DOSE/DURATION :
250 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 392,61,1997 *** REVIEWS *** TOXICOLOGY REVIEW DICPBB Drug Intelligence and Clinical Pharmacy. (POB 42435, Cincinnati, OH 45242) V.3- 1969- Volume(issue)/page/year: 8,690,1974 TOXICOLOGY REVIEW AUHPAI Australian Journal of Hospital Pharmacy. (B.R. Miller, POB 125, Heidelberg, Vic., Australia) V.1- 1971- Volume(issue)/page/year: 4(1),5,1974 TOXICOLOGY REVIEW DRUGAY Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. (ADIS Press International Inc., Suite B-30, Oxford Ct. Business Center, 582 Middletown Blvd., Langhorne, PA 19047) V.1- 1971- Volume(issue)/page/year: 8,354,1974 TOXICOLOGY REVIEW PRSMA4 Proceedings of the Royal Society of Medicine. (New York, NY) V.1-70, 1907-77. For publisher information, see JRSMD9. Volume(issue)/page/year: 63,48,1970 TOXICOLOGY RIVIEW BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,442,1973 TOXICOLOGY REVIEW AJDCAI American Journal of Diseases of Children. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1-80(3), 1911-50; V.100- 1960- Volume(issue)/page/year: 131,1337,1977 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4105 No. of Facilities: 416 (estimated) No. of Industries: 3 No. of Occupations: 6 No. of Employees: 11085 (estimated) No. of Female Employees: 6869 (estimated)

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H302-H351
Precautionary Statements P280-P301 + P312 + P330
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases S22-S36-S45
RIDADR 3249
WGK Germany 3
RTECS UV9100000
Packaging Group III
Hazard Class 6.1(b)

 Synthetic Route

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 Synonyms

Prysoline
Primidon
Mysoline
Misodine
MFCD00038662
Sertan
Primidone
EINECS 204-737-0
5-ethyl-5-phenyl-dihydro-pyrimidine-4,6-dione
Mylepsinum
Liskantin
Mizodin
5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
Primaclone
5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione
2-Deoxyphenobarbital
2-Desoxyphenobarbital,5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione
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Related Compounds: More...
Primidone-d5
30003-49-7
Primidone-d5
73738-06-4
Primidone Impurity F
1189504-46-8
primidone impurity D
80544-75-8
2-Ethyl-2-phenyl-N,N'-propanediamide primidone met lsu
55268-56-9
Chemsrc provides Primidone(CAS#:125-33-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Primidone are included as well.>> amp version: Primidone

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