Primidone
- CAS No.
- 125-33-7
- Chemical Name:
- Primidone
- Synonyms
- Cyral;Sertan;roe101;Midone;Roe 101;Mizodin;Mizolin;Mysedon;Misoline;Mizoline
- CBNumber:
- CB1161900
- Molecular Formula:
- C12H14N2O2
- Molecular Weight:
- 218.25
- MDL Number:
- MFCD00038662
- MOL File:
- 125-33-7.mol
- MSDS File:
- SDS
| Melting point | 281-282°C |
|---|---|
| Boiling point | 358.94°C (rough estimate) |
| Density | 1.1402 (rough estimate) |
| refractive index | 1.6660 (estimate) |
| Flash point | 9℃ |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Very slightly soluble in water, slightly soluble in ethanol (96 per cent). It dissolves in alkaline solutions. |
| pka | 12.26±0.40(Predicted) |
| color | White to Off-White |
| Water Solubility | <0.1 g/100 mL at 19 ºC |
| Merck | 14,7746 |
| BCS Class | 2 |
| InChIKey | DQMZLTXERSFNPB-UHFFFAOYSA-N |
| CAS DataBase Reference | 125-33-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 13AFD7670Q |
| ATC code | D08AC04,N03AA03,R01AX07,R02AA18,S01AX08,S03AA05 |
| Proposition 65 List | Primidone |
| NIST Chemistry Reference | Primidone(125-33-7) |
| IARC | 2B (Vol. 108) 2016 |
| EPA Substance Registry System | Primidone (125-33-7) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H351-H361d | |||||||||
| Precautionary statements | P201-P202-P264-P270-P301+P312-P308+P313 | |||||||||
| Hazard Codes | Xn,T,F | |||||||||
| Risk Statements | 22-40-39/23/24/25-23/24/25-11 | |||||||||
| Safety Statements | 22-36-45-36/37-16-7 | |||||||||
| RIDADR | 3249 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UV9100000 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29335990 | |||||||||
| Toxicity | child,TDLo,oral,625mg/kg (625mg/kg),BEHAVIORAL: SLEEPBEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)BEHAVIORAL: GENERAL ANESTHETIC,British Medical Journal. Vol. 1, Pg. 90, 1957. | |||||||||
| NFPA 704 |
|
Primidone price More Price(34)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | PHR3109 | Primidone pharmaceutical secondary standard, certified reference material | 125-33-7 | 500MG | $200 | 2024-03-01 | Buy |
| Sigma-Aldrich | P-075 | Primidone solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? | 125-33-7 | 1mL | $72 | 2024-03-01 | Buy |
| Sigma-Aldrich | BP293 | Primidone British Pharmacopoeia (BP) Reference Standard | 125-33-7 | 100MG | $257 | 2024-03-01 | Buy |
| Sigma-Aldrich | 1562000 | Primidone United States Pharmacopeia (USP) Reference Standard | 125-33-7 | 200mg | $436 | 2024-03-01 | Buy |
| TCI Chemical | P1906 | Primidone >98.0%(HPLC)(N) | 125-33-7 | 5g | $50 | 2024-03-01 | Buy |
Primidone Chemical Properties,Uses,Production
Description
Primidone is chemically and structurally similar to phenobarbital with the exception that the carbonyl group on C2 is replaced by a methylene group. This modification leads to the production of a drug with strong anticonvulsant properties without expressed soporific effects.
Description
Primidone (Item No. 19277) is an analytical reference material categorized as a barbiturate that can be detected in urine. The physiological and toxicological properties of this compound are not known; however, it is presumed to be a modulator of GABAA receptors. This product is intended for research and forensic applications.
Chemical Properties
Crystalline Solid
Uses
Primidone is an Anticonvulsant.
Uses
Primidone is mainly used for major attacks.
Definition
ChEBI: A pyrimidone that is dihydropyrimidine-4,6(1H,5H)-dione substituted by an ethyl and a phenyl group at position 5. It is used as an anticonvulsant for treatment of various types of seizures.
brand name
Mysoline (Valeant); Mysoline (Xcel).
General Description
Odorless white crystalline powder. Slightly bitter taste. No acidic properties.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Primidone is an amide. May react with azo and diazo compounds to generate toxic gases. May react with strong reducing agents to form flammable gases. A very weak base. The Combustion generates toxic mixed oxides of nitrogen (NOx).
Fire Hazard
Flash point data for Primidone are not available; however, Primidone is probably combustible.
Biological Activity
Anticonvulsant.
Pharmacokinetics
Approximately 60 to 80% of an oral dose of primidone is absorbed and slowly metabolized by the liver to phenobarbital and phenylethylmalonamide (PEMA). All three molecules have antiseizure effects, but PEMA appears to be weaker and to
be the more toxic metabolite. During chronic therapy, approximately 15 to 25% of an oral dose of primidone is excreted in the
urine unchanged, 15 to 25% metabolized to phenobarbital, and 50 to 70% excreted as PEMA (half-life, 24–48 hours). The
phenobarbital metabolite may be excreted in the urine unchanged, as its p-hydroxy metabolite, and as glucuronide or sulfate
conjugates. Following an oral dose, the peak plasma levels for primidone are reached in approximately 4 hours, with a reported
half-life of 10 to 12 hours. Plasma concentrations in the range of 8 to 12 μg/mL control seizures and minimize adverse effects.
Primidone shows antiseizure activity before the phenobarbital levels reach therapeutic range. Only after chronic dosing of
primidone are the levels of phenobarbital significant, suggesting autoinduction. Serum levels of chronically administered
primidone exceed those of its metabolite, phenobarbital, thus demonstrating that it has antiseizure activity independent of
phenobarbital. When primidone is coadministered with enzyme-inducing AEDs, the levels of its phenobarbital metabolite may be
two- to threefold higher than those in the noninduced state. Protein binding of primidone and PEMA is negligible, and the
phenobarbital metabolite is approximately 50% protein bound.
Primidone use is associated with decreases in CBZ, lamotrigine, valproate, tiagabine, and zonisamide serum levels. Primidone
levels are increased by nicotinamide and isoniazid. Hydantoins increase the plasma concentrations of primidone, phenobarbital,
and PEMA. CBZ increases levels of phenobarbital derived from primidone. Primidone levels are decreased by succinimides,
CBZ, and acetazolamide.
Clinical Use
Primidone is the 2-deoxy derivative of phenobarbital and is approved by the U.S. FDA for initial or adjunctive treatment of simple partial, complex partial, and tonic-clonic seizures. It is less effective against these types of seizures than is phenytoin or CBZ, and it shares the antiseizure and sedative actions of phenobarbital. Although not approved for the purpose, it often is used to treat benign familial tremor (essential tremor).
Side effects
As with phenobarbital, serious toxicity for primidone is rare, although it may cause disabling sedation, irritability, and decreased mental functioning in a number of persons. Ataxia, dysphoria, idiosyncratic rash, leukopenia, agranulocytosis, lymphadenopathy, hepatitis, and a systemic lupus erythematosus–like syndrome have been reported adverse effects for primidone. Deficiencies of folic acid and of vitamins D and K are possible with long-term therapy of primidone, as is a folateresponsive megaloblastic anemia. Measurement of the complete blood cell count should be performed at 6-month intervals.
Safety Profile
Poison by ingestion and intraperitoneal routes. Human teratogenic effects include developmental abnormalities of the craniofacial area, skin and skin appendages, and cardlovascular system. Human reproductive effects: effects on newborn, including unusual growth statistics, drug dependence, physical and other neonatal changes. Experimental teratogenic and reproductive effects. Human mutation data reported. An addictive drug. When heated to decomposition it emits toxic fumes of NOx. See also BARBITURATES.
Synthesis
Primidone, 5-ethyl-5-phenylhexahydropyrimidinedione-4,6 (9.2.1) is synthesized by reacting ethylphenylmalonic acid diamide with formamide [5,6]. An alternative method is the electrolytic reduction of phenobarbital or the catalytic reduction of the appropriate 2-thiobarbituric acid [7].
Veterinary Drugs and Treatments
Primidone is indicated for seizure control (idiopathic epilepsy, epileptiform convulsions) in the dog. Because it is rapidly converted into phenobarbital in this species (see Pharmacokinetics below), and has a greater incidence of hepatotoxicity and behavioral effects, most neurologists do not recommend its use. However, some clinicians feel that some animals not responding to phenobarbital do benefit from primidone therapy, perhaps as a result that PEMA has been demonstrated to potentiate the anticonvulsant activity of phenobarbital in animals. When compared with phenobarbital, increased incidence of hepatotoxicity associated with primidone is considered the major limitation to long-term therapy with this agent. Primidone is considered more toxic in rabbits and cats than in humans or dogs.
Drug interactions
Potentially hazardous interactions with other drugs
Aminophylline and theophylline: metabolism of
aminophylline and theophylline increased, reduced
effect.
Anthelmintics: concentration of albendazole and
praziquantel reduced.
Anti-arrhythmics: reduced concentration of
disopyramide and possibly propafenone; possibly
reduced concentration of dronedarone - avoid.
Antibacterials: reduced concentration of
chloramphenicol, doxycycline, metronidazole,
telithromycin and rifampicin - avoid with
telithromycin.
Anticoagulants: increased metabolism of coumarins
(reduced effect); possibly reduced concentration of
apixaban and edoxaban and possibly rivaroxaban.
Antidepressants: antagonise anticonvulsant effect;
reduces concentration of paroxetine, reboxetine,
mianserin and tricyclics; concentration reduced by St
John’s wort - avoid.
Antiepileptics: concentration increased by
fosphenytoin, oxcarbazepine, phenytoin, stripentol
and valproate and possibly carbamazepine, also active
metabolite of oxcarbazepine reduced and valproate
concentration reduced, concentration of fosphenytoin
and phenytoin usually reduced but can also be
increased; concentration of ethosuximide, rufinamide
and topiramate possibly reduced; concentration of
lamotrigine, tiagabine and zonisamide reduced.
Antifungals: possibly reduced concentration
of isavuconazole, itraconazole, posaconazole
and voriconazole - avoid concomitant use with
voriconazole; reduced absorption of griseofulvin
(reduced effect).
Antimalarials: avoid with piperaquine with
artenimol; anticonvulsant effect antagonised by
mefloquine
Antipsychotics: antagonise anticonvulsant effect;
metabolism of haloperidol increased; possibly
reduces aripiprazole concentration - increase
aripiprazole dose; concentration of both drugs
reduced with chlorpromazine; possibly reduces
clozapine concentration; possibly reduces lurasidone
concentration - avoid.
Antivirals: concentration of abacavir, boceprevir,
darunavir, dolutegravir, fosamprenavir, indinavir,
lopinavir, rilpivirine and saquinavir possibly reduced;
avoid with boceprevir and rilpivirine; concentration
of daclatasvir, dasabuvir, ombitasvir, paritaprevir
and simeprevir possibly reduced - avoid; avoid with
elvitegravir, etravirine, ledipasvir, sofosbuvir and
telaprevir.
Calcium-channel blockers: effects of calcium-channel
blockers probably reduced - avoid with isradipine
and nimodipine.
Cannabis extract: concentration possibly reduced by
primidone - avoid.
Ciclosporin: reduced ciclosporin levels.
Cobicistat: concentration of cobicistat possibly
reduced.
Corticosteroids: metabolism of corticosteroids
accelerated, reduced effect.
Cytotoxics: possibly reduced concentration
of axitinib, increase axitinib dose; possibly
reduced concentration of bortezomib, bosutinib,
cabozantinib, ceritinib, crizotinib, dasatinib,
ponatinib and vandetanib - avoid; avoid with
cabazitaxel, dabrafenib, gefitinib and panobinostat;
concentration of irinotecan and its active metabolite
and possibly etoposide reduced; possible increased
hypersensitivity reactions with procarbazine.
Diuretics: concentration of eplerenone reduced -
avoid; increased risk of osteomalacia with carbonic
anhydrase inhibitors.
Guanfacine: concentration of guanfacine possibly
reduced - increase dose of guanfacine.
Hormone antagonists: possibly reduced
concentration of abiraterone - avoid; metabolism of
toremifene accelerated.
Metabolism
Partially metabolised to phenobarbital and phenylethylmalonamide in the liver, both of which are active and have longer half-lives compared to primidone (metabolites may accumulate in renal impairment). It is excreted in urine as unchanged drug and metabolites.
Primidone Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21695 | 55 |
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | fandachem@gmail.com | China | 9352 | 55 |
| Xiamen AmoyChem Co., Ltd | +86-592-6051114 +8618959220845 | sales@amoychem.com | China | 6387 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 47465 | 58 |
| HANGZHOU CLAP TECHNOLOGY CO.,LTD | 86-571-88216897,88216896 13588875226 | sales@hzclap.com | CHINA | 6313 | 58 |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 29474 | 58 |
| AFINE CHEMICALS LIMITED | 0571-85134551 | info@afinechem.com | CHINA | 15377 | 58 |
| Hebei Guanlang Biotechnology Co,.LTD | +8619930503252 | daisy@crovellbio.com | China | 5964 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| Shaanxi Didu New Materials Co. Ltd | +86-89586680 +86-13289823923 | 1026@dideu.com | China | 9309 | 58 |
View Lastest Price from Primidone manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2023-03-06 | Primidone
125-33-7
|
US $10.70 / g/Bag | 10g | 99% | 10000kg | Hebei Guanlang Biotechnology Co,.LTD | |
 |
2021-08-12 | Primidone
125-33-7
|
US $15.00-10.00 / KG | 1KG | 99%+ HPLC | Monthly supply of 1 ton | Zhuozhou Wenxi import and Export Co., Ltd | |
 |
2021-07-23 | Primidone USP/EP/BP
125-33-7
|
US $1.10 / g | 1g | 99.9% | 100 Tons min | Dideu Industries Group Limited |
-
- Primidone
125-33-7
- US $10.70 / g/Bag
- 99%
- Hebei Guanlang Biotechnology Co,.LTD
-
- Primidone
125-33-7
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd
-
- Primidone USP/EP/BP
125-33-7
- US $1.10 / g
- 99.9%
- Dideu Industries Group Limited