Related Searches: Pregabalin

Pregabalin(CAS No. 148553-50-8)

Pregabalin C8H17NO2 (cas 148553-50-8) Molecular Structure

148553-50-8 Structure

Identification and Related Records

【Name】
Pregabalin
【Iupac name】
(3S)-3-(aminomethyl)-5-methylhexanoic acid
【CAS Registry number】
148553-50-8
【Synonyms】
Hexanoic acid, 3-(aminomethyl)-5-methyl-, (S)-
3-isobutyl GABA
(R-)-3-isobutyl GABA
CI 1008
PD 144723
CI-1008
Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3S)-
Lyrica
Pregablin
(3S)-3-(aminomethyl)-5-methylhexanoic acid
(S)-(+)-3-Aminomethyl-5-methylhexanoic acid
【Molecular Formula】
C8H17NO2 (Products with the same molecular formula)
【Molecular Weight】
159.23
【Inchi】
InChI=1/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
【Canonical SMILES】
CC(C)CC(CC(=O)O)CN
【Isomers smiles】
CC(C)C[C@@H](CC(=O)O)CN
【MOL File】
148553-50-8.mol

Chemical and Physical Properties

【Appearance】
White or almost white crystalline powder
【Density】
0.997 g/cm3
【Melting Point】
194-196°C
【Boiling Point】
274 °C at 760 mmHg
【Vapour】
0.00153mmHg at 25°C
【Refractive Index】
1.464
【Flash Point】
119.5 °C
【Solubilities】
Freely soluble in water and both basic and acidic solutions
In water, 1.2X10+4 mg/L at 25 deg C (est)
【Color/Form】
White to off-white crystalline solid
【Spectral properties】
Specific optical rotation = +10.52 deg/D (c = 1.00 in water)
【Computed Properties】
Molecular Weight:159.22608 [g/mol]
Molecular Formula:C8H17NO2
XLogP3-AA:-1.6
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:5
Exact Mass:159.125929
MonoIsotopic Mass:159.125929
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Formal Charge:0
Complexity:123
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:2
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:11

Safety and Handling

【Formulations/Preparations】
Lyrica
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pregabalin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule V includes pregabalin, DEA Code #2782; Drug class: Depressants.
【Octanol/Water Partition Coefficient】
log Kow = -1.78 (est)
【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

【Usage】

S-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
- Drugs used to prevent SEIZURES or reduce their severity.
【Therapeutic Uses】
Pregabalin is indicated for management of post-herpetic neuralgia. /Included in US product label/
Pregabalin is indicated for management of neuropathic pain associated with diabetic peripheral neuropathy. /Included in US product labe/
Pregabalin is indicated as an adjunctive therapy for adult patients with partial onset seizures. /Included in US product label/
The U.S. Food and Drug Administration ... has approved Lyrica (pregabalin), the first drug to treat fibromyalgia, a disorder characterized by pain, fatigue and sleep problems.
【Biomedical Effects and Toxicity】
Pregabalin is well absorbed after oral administration ...
Following oral administration of pregabalin capsules under fasting conditions, peak plasma concentrations occur within 1.5 hours. Pregabalin oral bioavailability is >/=90% and is independent of dose. Following single- (25 to 300 mg) and multiple-dose (75 to 900 mg/day) administration, maximum plasma concentrations (C max ) and area under the plasma concentration-time curve (AUC) values increase linearly. Following repeated administration, steady state is achieved within 24 to 48 hours. Multiple-dose pharmacokinetics can be predicted from single-dose data.
The rate of pregabalin absorption is decreased when given with food, resulting in a decrease in Cmax of approximately 25% to 30% and an increase in Tmax to approximately 3 hours. However, administration of pregabalin with food has no clinically relevant effect on the total absorption of pregabalin. Therefore, pregabalin can be taken with or without food.
Pregabalin does not bind to plasma proteins. The apparent volume of distribution of pregabalin following oral administration is approximately 0.5 L/kg. Pregabalin is a substrate for system L transporter which is responsible for the transport of large amino acids across the blood brain barrier. Although there are no data in humans, pregabalin has been shown to cross the blood brain barrier in mice, rats, and monkeys. In addition, pregabalin has been shown to cross the placenta in rats and is present in the milk of lactating rats.
Elimination /is primarily/ renal approximately 90% /is excreted/ as unchanged drug, 0.9% as major metabolite N-methylated derivative of pregabalin.
Mean renal clearance was estimated to be 67.0 to 80.9 mL/min in young healthy subjects. Because pregabalin is not bound to plasma proteins this clearance rate indicates that renal tubular reabsorption is involved. Pregabalin elimination is nearly proportional to creatinine clearance.
Pregabalin clearance is nearly proportional to creatinine clearance. Dosage reduction in patients with renal dysfunction is necessary. Pregabalin is effectively removed from plasma by hemodialysis. Following a 4-hour hemodialysis treatment, plasma pregabalin concentrations are reduced by approximately 50%.
Pregabalin demonstrates highly predictable and linear pharmacokinetics. ... Absorption is extensive, rapid, and proportional to dose. Time to maximal plasma concentration is approximately 1 hr and steady state is achieved within 24-48 hr. ... High bioavailability, and dose-proportional maximal plasma concentrations and total exposures predict a dose-response relationship in clinical practice ... Administration with food has no clinically relevant effect on the amount of pregabalin absorbed, providing for a dosing regimen uncomplicated by meals. Pregabalin does not bind to plasma proteins and is excreted virtually unchanged (PubMed Abstract

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