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Gabapentin hydrochloride(CAS No. 60142-96-3)

Gabapentin hydrochloride C9H17NO2 (cas 60142-96-3) Molecular Structure

60142-96-3 Structure

Identification and Related Records

【Name】
Gabapentin hydrochloride
【Iupac name】
2-[1-(aminomethyl)cyclohexyl]acetic acid
【CAS Registry number】
60142-96-3
【Synonyms】
1-(Aminomethyl)cyclohexaneacetic acid
Cyclohexaneacetic acid, 1-(aminomethyl)-
Gabapentino [Spanish]
Neurontin (TN)
Go 3450
CI 945
Cyclohexaneacetic acid,1-(aminomethyl)-
Gabapentine
2-[1-(aminomethyl)cyclohexyl]acetic acid
GOE 2450
2-[1-(azaniumylmethyl)cyclohexyl]acetate
Gabapentin
Gabapentino [INN-Spanish]
Gabapentine [INN-French]
Garbapentin
Gabapetine
【EINECS(EC#)】
262-076-3
【Molecular Formula】
C9H17NO2 (Products with the same molecular formula)
【Molecular Weight】
207.7
【Inchi】
InChI=1/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
【Canonical SMILES】
C1CCC(CC1)(CC(=O)O)CN
【MOL File】
60142-96-3.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline powder
【Density】
1.058 g/cm3
【Melting Point】
162℃
【Boiling Point】
314.4 °C at 760 mmHg
【Refractive Index】
1.484
【Flash Point】
144 °C
【Water】
H2O: 10 mg/mL
【Solubilities】
H2O:10mg/mL
【Color/Form】
off-white
【Stability】
Stable at normal temperatures and pressures.
【Storage temp】
Keep tightly closed.
【Computed Properties】
Molecular Weight:171.23678 [g/mol]
Molecular Formula:C9H17NO2
XLogP3:-1.1
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:3
Exact Mass:171.125929
MonoIsotopic Mass:171.125929
Topological Polar Surface Area:63.3
Heavy Atom Count:12
Formal Charge:0
Complexity:162
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
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 Ring Count:1
Effective Rotor Count:4.2
Conformer Sampling RMSD:0.6
CID Conformer Count:21

Safety and Handling

【Hazard Codes】
T:;
【Risk Statements】
R61
【Safety Statements 】
53-26-36/37/39-45-36
【Safety】

Hazard Codes: ToxicT,IrritantXi
Risk Statements: 61-36/37/38
R61:May cause harm to the unborn child.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 53-26-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: GU6496000

【Transport】
Not reg
【Formulations/Preparations】
Oral: Capsules: 100 mg Neurontin, (Pfizer), 300 mg Neurontin, (Pfizer), 400 mg Neurontin, (Pfizer).
Oral: Solution: 250 mg/5 mL Neurontin, (Pfizer).
Oral: Tablets: 100 mg, Gabapentin Tablets, (Greenstone, IVAX, Purepac, Teva), Gabarone (IVAX); 300 mg, Gabapentin Tablets, (Greenstone, IVAX, Purepac, Teva), Gabarone, (IVAX); 400 mg, Gabapentin Tablets, (Greenstone, IVAX, Purepac, Teva), Gabarone, (IVAX).
Oral: Tablets, film-coated: 600 mg Neurontin, (Pfizer); 800 mg Neurontin, (Pfizer).
Trade name: Neurontin (Warner-Lambert).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl gabapentin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

? Gabapentin (CAS NO.60142-96-3), its Synonyms are 1-(Aminomethyl)cyclohexaneacetic acid ; Aclonium ; Cyclohexaneacetic acid, 1-(aminomethyl)- ; Gabapentine ; Gabapentino ; Gabapentinum .

【Octanol/Water Partition Coefficient】
log Kow = -1.10
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

G. Satzinger et al., DE patent 2460891 (1976 to Godecke); eidem, US patent 4024175 (1977 to Warner-Lambert).
Synthesis: The synthesis is started with the Guareschi salt (obtained from cyclohexanone and cyanoacetate), which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid. The anhydride can be treated either with methanol to yield the half ester or with hydroxylamine to afford the N-hydroximide. The half ester is converted to the azide and subjected to a Curtius-type rearrangement to give the isocyanate which is hydrolyzed to gabapentin. Gabapentin is also obtained from the corresponding N-hydroxyimide via a Lossen-type rearrangement by conversion of /the/ N-hydroxyimide to N-benzenesulfonyloximide and following reaction with triethylamine to the urethane ester.
【Usage】

Amino acid structurally related to -Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant

Biomedical Effects and Toxicity

【Biological Activity】
Anticonvulsant with several possible mechanisms of action. Increases GABA in the brain and binds to a novel site associated with voltage-sensitive Ca 2+ channels. Prevents neuronal death and is antinociceptive and anxiolytic.
【Pharmacological Action】
- Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
- Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
- Drugs used to prevent SEIZURES or reduce their severity.
- Agents that are used to treat bipolar disorders or mania associated with other affective disorders.
- Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.
- A class of drugs that act by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools. Since they are inducers of vascular and other smooth muscle relaxation, they are used in the drug therapy of hypertension and cerebrovascular spasms, as myocardial protective agents, and in the relaxation of uterine spasms.
- Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.
【Therapeutic Uses】
Analgesics; Anticonvulsants; Antiparkinson Agents; Calcium Channel Blockers; Anti-Anxiety Agents, Excitatory Amino Acid Antagonist' Antimanic
Medication: Anticonvulsant
Gabapentin is indicated as an adjunct to other anticonvulsant medications (in the treatment of partial seizures with or without secondary generalization in adults and adolescents) with epilepsy. Gabapentin is also indicated as adjunctive therapy for the treatment of partial seizures in pediatric patients 3 years of age and older with epilepsy. /Included in US product labeling/
Gabapentin is indicated for the management of postherpetic neuralgia in adults. /Included in US product labeling/
Gabapentin is indicated for the treatment of diabetic peripheral neuropathic pain. /NOT included in US product labeling/
Used in dogs with seizure refractory to other drugs
【Biomedical Effects and Toxicity】
Volume of distribution (VolD) is approximately 50 to 60 L. Gabapentin penetrates the blood-brain barrier, yielding cerebrospinal fluid (CSF) concentrations approximately equal to 20% of corresponding steady-state plasma trough concentrations in patients with epilepsy. Brain tissue concentrations in one patient undergoing temporal lobectomy were approximately 80% of corresponding plasma concentrations.
Gabapentin is absorbed in part by the L-amino and acid transport system, which is a carrier-mediated, saturable transport system; as the dose increase, bioavailability decreases. Bioavailability ranges from approximately 60% for a 900 mg dose per day to approximately 27% for a 4800 mg dose per day. Food has a slight effect on the rate and extent of absorption of gabapentin (14% increase in AUC).
Time to peak concentration: 2 to 4 hours
Protein binding: Very low - less than 3% circulates bound to plasma protein.
Elimination: Renal: Entire absorbed dose, as unchanged drug. Gabapentin clearance is directly proportional to creatinine clearance. higher oral clearance values were observed in children
Gabapentin is distributed into human breast milk following oral administration. A nursed infant could be exposed to a maximum dose of approximately 1 mg/kg/day.
Absorption:; Food has no effect on its rate and extent of absorption.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a log Kow of -1.10(2) and a regression-derived equation(3), indicates that gabapentin is expected to have very high mobility in soil(SRC). Estimated pKa values for gabapentin are 3.68 (carboxylic acid) and 10.70 (primary amine)(4), indicating that this compound will exist primarily as a zwitterion in the environment. Volatilization of gabapentin from moist soil surfaces is not expected to be an important fate process(SRC) since ionic compounds do not volatilize. Gabapentin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-10 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a log Kow of -1.10(2) and a regression-derived equation(3), indicates that gabapentin is not expected to adsorb to suspended solids and sediment(SRC). Estimated pKa values for gabapentin are 3.68 (carboxylic acid) 10.70 (primary amine)(4), indicating that this compound will exist primarily as a zwitterion in the environment. Volatilization from water surfaces is not expected(SRC) since ionic compounds do not volatilize. According to a classification scheme(5), an estimated BCF of
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), gabapentin, which has an estimated vapor pressure of 2.9X10-10 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase gabapentin may be removed from the air by wet or dry deposition(SRC). Gabapentin does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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