CAS 125-33-7|Primidone
Introduction：Basic information about CAS 125-33-7|Primidone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | ChineseUSA | Flash Point | 228.2ºC |
| Symbol | GHS07, GHS08 | Signal Word | Warning |
Names
| Name | primidone |
|---|---|
| Synonym | More Synonyms |
Primidone BiologicalActivity
| 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 | Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorSignaling Pathways >>Neuronal Signaling >>GABA ReceptorResearch Areas >>Neurological Disease |
| 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 |
| InChIKey | DQMZLTXERSFNPB-UHFFFAOYSA-N |
| SMILES | CCC1(c2ccccc2)C(=O)NCNC1=O |
| Storage condition | Store at RT |
| Water Solubility | <0.1 g/100 mL at 19 ºC |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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 |
|---|---|
| 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) |
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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 |
