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Zolpidem tartrate(CAS No. 99294-93-6)

Zolpidem tartrate 2(C19H21N3O).C4H6O6 (cas 99294-93-6) Molecular Structure

99294-93-6 Structure

Identification and Related Records

【Name】
Zolpidem tartrate
【CAS Registry number】
99294-93-6
【Synonyms】
N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide 2,3-dihydroxybutanedioate (2:1)
(2R,3R)-2,3-Dihydroxybutandis?ure--N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamid(1:2)
Bilcam
Cymerion
Dalparan
Durnit
Eudorm
Ivadal
Myslee
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide L-(+)-Tartrate (2:1)
N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide 2,3-dihydroxybutanedioate (2:1)
Niotal
SL 800750-23N
Stilnoct
Stilnox
Stimox
Sumenan
Zolpidem L-(+)-hemitartrate
【Molecular Formula】
2(C19H21N3O).C4H6O6 (Products with the same molecular formula)
【Molecular Weight】
764.88
【Inchi】
InChI=1/C19H21N3O.C4H6O6/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19;5-1(3(7)8)2(6)4(9)10/h5-10,12H,11H2,1-4H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
【MOL File】
99294-93-6.mol

Chemical and Physical Properties

【Appearance】
White to off-white crystalline powder
【Density】
g/cm3
【Melting Point】
196 deg C /Zolpidem/
【Boiling Point】
°Cat760mmHg
【Flash Point】
°C
【Solubilities】
Solubility in water (20 deg C): 23 mg/ml
【Computed Properties】
Molecular Weight:457.47638 [g/mol]
Molecular Formula:C23H27N3O7
H-Bond Donor:4
H-Bond Acceptor:7
Rotatable Bond Count:6
Exact Mass:457.1849
MonoIsotopic Mass:457.1849
Topological Polar Surface Area:153
Heavy Atom Count:33
Formal Charge:0
Complexity:551
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
Xi
【Risk Statements】
R36/37/38
【Safety Statements 】
26-36
【Safety】

Hazard Codes of Zolpidem tartrate (CAS NO.99294-93-6):? Xi
Risk Statements:? 36/37/38
36/37/38:? Irritating to eyes, respiratory system and skin?
Safety Statements:? 26-36
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?

【Formulations/Preparations】
The main ingredient in the drug Ambien ... (tablets)
Ivadal; Niotal; Stilnoct; Stilnox
【Exposure Standards and Regulations】
Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule IV includes zolpidem, DEA Code #2783; Drug class: depressants.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl zolpidem tartrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Octanol/Water Partition Coefficient】
log Kow = 2.42 /Zolpidem/
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: J.P. Kaplan, P. George, EP 50563; eidem, US 4382938 (1982, 1983 both to Synthelabo)

Biomedical Effects and Toxicity

【Therapeutic Uses】
Zolpidem is indicated for short-term treatment of insomnia. A decrease in sleep latency and increase in the duration of sleep for up to 5 weeks have been demonstrated in controlled clinical studies with zolpidem. Failure of insomnia to remit after 7 to 10 days of treatment may indicate the presence of a primary psychiatric or medical illness. Worsening of insomnia or the emergence of new abnormalities of thinking or behavior may be the consequence of an unrecognized psychiatric or physical disorder. /Included in US product labeling/ /Salt not specified/
Selective benzodiazepine receptor agonist not related chemically to benzodiazepines; sedative; hypnotic. /Salt not specified/
... A case of antipsychotic-induced parkinsonism that was managed with zolpidem /was reported/. ... A 34-yr-old white man who had had antipsychotic-induced parkinsonism with symptoms of repetitive persistent gross tremors of the hands for numerous years was unresponsive to traditional antiparkinsonian medications. With the initiation of zolpidem ... the tremors decreased significantly. ... When zolpidem was started ..., the motor exam score on the Unified Parkinson's Disease Rating Scale decreased from 29 at baseline to a score of 9 after one month of use. After 4 months of zolpidem use, the patient's mental status decompensated, & clozapine was initiated. As the patient experienced excessive sedation, zolpidem was discontinued while clozapine was maintained to help with the psychosis &, potentially, the tremors. The tremors reemerged with a motor exam score of 30. Zolpidem was reinitiated ..., & the patient's tremors have been stable for 2 years. ... Further investigation is needed to study the use of nontraditional medications in patients requiring ...antipsychotic medication who have refractory parkinsonian symptoms. /Salt not specified/ [Farver DK, Khan MH; Ann Pharmacother 35(4): 435-437 (2001)]
【Biomedical Effects and Toxicity】
A peak blood level of 200 ng/mL was reached 30 min after oral admin of 20 mg zolpidem. After oral admin zolpidem is rapidly & completely absorbed from the GI tract. Although some first-pass biotransformation of the drug results in a bioavailability of about 70%, after doses of 7-20 mg, zolpidem is 92% bound to plasma proteins. The apparent volume of distribution after a 5 mg iv dose was 0.5 L/kg. Brain concns reach one third to one half of those achieved in the plasma. Zolpidem is completely metabolized.
The excretion of zolpidem in breast milk represents 0.004 to 0.019% of an admin dose. /Salt not specified/
Zolpidem is eliminated almost entirely by conversion to inactive products in the liver, largely through oxidation of the methyl groups on the phenyl & imidazopyridine rings to the corresponding carboxylic acids. Its half-life in plasma is approx 2 hr in individuals with normal hepatic blood flow or function. This value may be increased twofold or more in those with cirrhosis, & it also tends to be greater in older patients; adjustment of dosage often is necessary in both categories of patients. Although little or no unchanged zolpidem is found in the urine, the elimination of the drug is slower in patients with chronic renal insufficiency, largely owing to an incr in its apparent volume of distribution. /Salt not specified/
Solid dispersions & physical mixtures of Zolpidem in polyethylene glycol 4000 (PEG 4000) & 6000 (PEG 6000) were prepared with the aim to incr its aqueous solubility. ... Physical determinations/revealed/ no drug-polymer interactions ... Both solubility & dissolution rate of the drug in these formulations were increased. Each individual dissolution profile of PEG based formulation fitted Baker-Lonsdale & first order kinetic models. Finally, significant differences in ataxic induction time were observed between Zolpidem orally administered as suspension of drug alone & as solid dispersion or physical mixture. These formulations, indeed, showed almost 2- to 3-fold longer ataxic induction times suggesting that, in the presence of PEG, the intestinal membrane permeability is probably the rate-limiting factor of the absorption process. /Salt not specified/ [Trapani G, et al; Int J Pharm 184(1): 121-130 (1999)] PubMed Abstract
Nursing mothers: Studies in lactating mothers indicate that the half-life of zolpidem is similar to that in young normal volunteers (2.6 + or - 0.3 hr). Between 0.004 and 0.019% of the total administered dose is excreted into milk, but the effect of zolpidem on the infant is unknown. /Salt not specified/
Zolpidem ... was identified in the blood of 29 subjects arrested for impaired driving. ... In 5 separate cases, where zolpidem was the only drug detected (0.08-1.40 mg/l, mean 0.65 mg/l, median 0.47 mg/l), signs of impairment included slow & slurred speech, slow reflexes, disorientation, lack of balance & coordination, & "blacking out." ... /Salt not specified/ [Logan BK, Couper FJ; J Forensic Sci 46(1): 105-110 (2001)] PubMed Abstract

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