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76584-70-8

76584-70-8 Structure

76584-70-8 Structure
IdentificationMore
[Name]

Divalproex sodium
[CAS]

76584-70-8
[Synonyms]

DIVALPROEX SODIUM
Valproate semisodium
SEMISODIUMVALPROATE
Dipropylacetic acid hemisodium salt
Sodium 2-propylpentanoate 2-propylpentanoic acid
SODIUM DIVALPROATE
Valproate Semisodium(Divalproate sodium, Divalproex sodium)
[EINECS(EC#)]

202-303-5
[Molecular Formula]

C16H31NaO4
[MDL Number]

MFCD00879852
[Molecular Weight]

310.4
[MOL File]

76584-70-8.mol
Chemical PropertiesBack Directory
[Melting point ]

222 °C
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[color ]

White
[Major Application]

pharmaceutical (small molecule)
[InChI]

InChI=1S/C8H16O2.Na.H/c1-3-5-7(6-4-2)8(9)10;;/h7H,3-6H2,1-2H3,(H,9,10);;
[InChIKey]

WGNTXHWGJLKAFJ-UHFFFAOYSA-N
[SMILES]

C(C(=O)O)(CCC)CCC.[NaH]
[CAS DataBase Reference]

76584-70-8(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

WGK 3
[HS Code ]

2915900000
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

Divalproex is a prodrug form of valproic acid (Item No. 13033) that contains valproic acid and valproate sodium. Formulations containing divalproex exhibit delayed gastrointestinal absorption and are converted to valproic acid in the intestine, which reduces gastric irritation and nervous system side effects. Formulations containing divalproex are widely used for the treatment of seizures and bipolar disorder.
[Chemical Properties]

White Solid
[Originator]

Depakote,Abbott
[Uses]

Anticonvulsant; Bipolar Agent
[Uses]

Antiepileptic; Anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.
[Uses]

Divalproex sodium consists of a compound of sodium valproate and valproic acid in a 1:1 molar relationship in an enteric coated form. In rare cases, it is also used as a treatment for major depressive disorder, and increasingly taken long-term for prevent
[Definition]

ChEBI: A mixture of valproic acid and its sodium salt in a 1:1 molar ratio. It is used for the management and treatment of seizure disorders, mania, and prophylactic treatment of migraine headache.
[Manufacturing Process]

Dipropyl acetic acid or valproic acid may be prepared the next way. Propylbromide is mixed with cyanacetic acid in the presence of sodium ethylate, made from absolute ethanol and sodium. By that prepared α,α- dipropylcyanacetic acid ethyl ester is saponified with equimolecular amounts of NaOH to give dipropylacetonitril. The desired dipropylacetic acid is produced by saponification of dipropylacetonitryl with aquatic NaOH. It is colorless liquid. BP 219°-220°C.
Sodium salt of this acid may be prepared by adding of equivalent of NaOH.
[Brand name]

Depakote (Abbott).
[Therapeutic Function]

Anticonvulsant
[Clinical Use]


Treatment of manic episodes associated with bipolar disorder
Migraine prophylaxis (unlicensed)
[Drug interactions]

Potentially hazardous interactions with other drugs
Antibacterials: metabolism possibly inhibited by erythromycin; avoid with pivmecillinam; concentration reduced by carbapenems - avoid.
Antidepressants: avoid with St John’s wort.
Antiepileptics: concentration reduced by carbamazepine; concentration of active carbamazepine metabolite increased; increased concentration of lamotrigine, phenobarbital, rufinamide and possibly ethosuximide; sometimes reduces concentration of active metabolite of oxcarbazepine; alters phenytoin concentration; phenytoin and phenobarbital reduce valproate concentration; hyperammonaemia and CNS toxicity with topiramate.
Antipsychotics: increased neutropenia with olanzapine; possibly increases or decreases concentration of clozapine; possibly increases quetiapine concentration.
Ciclosporin: variable ciclosporin blood level response.
Sodium oxybate: concentration of sodium oxybate increased.
Ulcer-healing drugs: metabolism inhibited by cimetidine, increased concentration.
[Metabolism]

Valproic acid is extensively metabolised in the liver, a large part by glucuronidation (up to 60
%) and the rest by a variety of complex pathways (up to 45
%). It is excreted in the urine almost entirely in the form of its metabolites; small amounts are excreted in faeces and expired air.
[References]

[1] MCGRAW D. Therapeutic drug monitoring with valproate-Why product selection is an important factor[J]. Mental Health Clinician, 2014, 19 1: 31-34. DOI: 10.9740/mhc.n186966
Spectrum DetailBack Directory
[Spectrum Detail]

Divalproex sodium(76584-70-8)MS
Divalproex sodium(76584-70-8)1HNMR
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