(S)(+)-3-Aminomethyl-5-methyl-hecanoic acid
pregabalin
CAS: 148553-50-8
Molecular Formula: C8H17NO2
(S)(+)-3-Aminomethyl-5-methyl-hecanoic acid - Names and Identifiers
| Name | pregabalin |
| Synonyms | CI 1008 CI-1008 PD 144723 Pregablin PD-144723 pregabalin PREGABALIN TOS-BB-0910 (R)-Pregabalin (S)-Pregabalin 3-isobutyl GABA Pregabalin [USAN] (R-)-3-isobutyl GABA Pregabalin intermediate PREDNISOLONESODIUMPHOSPHATE 3-(aminomethyl)-5-methyl-(S)-Lyrica 3-(aminomethyl)-5-methyl-hexanoic acid 3-(Aminomethyl)-5-methyl-hexanoic acid 3(S)-(AMINOMETHYL)-5-METHYLHEXANOIC ACID (3S)-3-(AMINOMETHYL)-5-METHYLHEXANOIC ACID (3R)-3-(aminomethyl)-5-methylhexanoic acid 3-(aminomethyl)-5-methyl-(3S)-Hexanoic acid (S)(+)-3-Aminomethyl-5-methyl-hecanoic acid (3S)-3-(aminomethyl)-5-methyl-hexanoic acid |
| CAS | 148553-50-8 |
| EINECS | 604-639-1 |
| 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 |
| InChIKey | AYXYPKUFHZROOJ-ZETCQYMHSA-N |
(S)(+)-3-Aminomethyl-5-methyl-hecanoic acid - Physico-chemical Properties
| Molecular Formula | C8H17NO2 |
| Molar Mass | 159.23 |
| Density | 0.997±0.06 g/cm3(Predicted) |
| Melting Point | 194-196°C |
| Boling Point | 274.0±23.0 °C(Predicted) |
| Specific Rotation(α) | D23 +10.52° (c = 1.06 in water) |
| Flash Point | 9℃ |
| Solubility | deionized water: ≥10mg/mL |
| Vapor Presure | 0.00153mmHg at 25°C |
| Appearance | white powder |
| pKa | 4.23±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.464 |
(S)(+)-3-Aminomethyl-5-methyl-hecanoic acid - Risk and Safety
| Risk Codes | R63 - Possible risk of harm to the unborn child R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 3 |
| HS Code | 29224999 |
(S)(+)-3-Aminomethyl-5-methyl-hecanoic acid - Reference Information
| antiepileptic drugs | pregabalin is a non-γ-aminobutyric acid (GABA) receptor agonist or antagonist, and is a new type of calcium channel regulator, which can block voltage-dependent calcium channels and reduce the release of neurotransmitters. Clinically, it is mainly used for neuralgia related to diabetic peripheral neuropathy, post-herpetic neuralgia and adjuvant treatment of adult partial seizures, generalized anxiety disorder, central neuralgia (including spinal cord injury, stroke and multiple sclerosis associated with neuralgia) and fibromyalgia. |
| R & D process | Pregabalin is an analog of the neurotransmitter γ-aminobutyric acid (GABA), the trade name is Lyrica. In December 2004, the FDA approved pregabalin as a drug for the treatment of diabetic neuralgia and herpes zoster neuralgia. Pregabalin is the first drug recognized in the United States and Europe for the treatment of both pain. In June 2005, pregabalin was approved for adjuvant treatment of adult local epilepsy. In March 2006, the European Union approved pregabalin for the treatment of generalized anxiety disorder (GAD) and social anxiety disorder (SAD). |
| pharmacological effects | pregabalin has a good therapeutic effect on epilepsy. studies on various animal seizure models show that pregabalin can obviously prevent seizures, and its dose of active effect is 3-10 times lower than that of gabapentin. Studies have found that pregabalin can reduce the sensory and motor spinal reflex stimulated by the toe tip of the rat, reduce the related behaviors of diabetes, peripheral nerve injury or chemotherapy neuropathic animal pain models, and inhibit or reduce the pain caused by spinal irritants Related behaviors. Animal studies have found that pregabalin may have an advantage in combination with opioids. Pregabalin offers a new option for the clinical treatment of neuropathic pain. |
| indications | pregabalin is mainly used for the treatment of peripheral neuralgia and adjuvant treatment of localized epileptic seizures. |
| Mechanism of action | Pregabalin may reduce the calcium-dependent release of some neurotransmitters by regulating the function of calcium channels. Although pregabalin is a structural derivative of the inhibitory neurotransmitter γ-aminobutyric acid (GABA), it does not directly bind to GABAA, GABAB or benzodiazepine receptors, does not increase the GABAA response of cultured neurons in vitro, does not change the GABA concentration in rat brain, and has no acute effect on GABA uptake or degradation. However, studies have found that long-term exposure of neurons cultured in vitro to pregabalin increases GABA transporter density and functional GABA transport rate. Pregabalin does not block sodium channels, is inactive to opioid receptors, does not change cyclooxygenase activity, is inactive to dopamine and serotonin receptors, and does not inhibit dopamine, serotonin or norepinephrine Reuptake. |
| Pharmacokinetics | Absorption: Taking pregabalin on an empty stomach, the absorption is rapid, reaching the peak plasma concentration within 1 hour after single or multiple doses. It is estimated that the oral bioavailability of pregabalin is ≥ 90%, and it is independent of dose. After multiple doses, steady state can be achieved within 24 to 48 hours. When taken with food, the absorption rate of pregabalin is reduced, Cmax is reduced by 25-30%, and tmax is delayed to about 2.5 hours. However, taking pregabalin and food at the same time will not have a clinically significant impact on the absorption of pregabalin. Distribution: Preclinical studies have shown that pregabalin can pass the blood-brain barrier in mice, rats and monkeys. Pregabalin can pass through the placenta of rats and can appear in the milk of lactating rats. In the human body, the apparent distribution volume of pregabalin after oral administration is about 0.56L/kg. Pregabalin does not bind to plasma proteins. Metabolism: The metabolism of pregabalin in the human body is negligible. After administration of radiolabeled pregabalin, about 98% pregabalin is recovered in urine in prototype form. N-methylated derivatives, the main metabolite of pregabalin, are also found in urine and account for 0.9% of the dose. In preclinical studies, no racemization of pregabalin from S-optical enantiomer to R-optical enantiomer was found. Excretion: pregabalin is mainly removed from the systemic circulation and excreted through the kidneys in the form of a prototype drug. The average clearance half-life of pregabalin is 6.3 hours. Both pregabalin plasma clearance and renal clearance are directly proportional to creatinine clearance. For patients with renal dysfunction or undergoing hemodialysis treatment, it is necessary to adjust the dose |
| clinical application | in December 2008, the U.S. food and drug administration (FDA) approved pregabalin (trade name "lerica") for the treatment of diabetic peripheral neuralgia (DPN) and postherpetic neuralgia (PHN), the two most common neuropathic pains. Neuropathic pain is one of the most difficult to treat chronic pain syndromes. It is mainly characterized by blunt pain, burning, and tingling. There are many triggers for neuralgia. Diabetes, infection (such as herpes zoster), cancer and AIDS can cause neuralgia. About 3% of the population in Europe suffers from neuralgia. |
| drug interaction | 1. It is not metabolized by the cytochrome P450 system, so it rarely interacts with other drugs. Does not affect antiepileptic drugs (such as sodium valproate, phenytoin, lamotrigine, carbazepine, phenobarbital, topiramate), oral contraceptives, oral hypoglycemic drugs, diuretics, insulin, etc. Pharmacokinetics. 2. When this product is used with oxycodone, its recognition function is reduced and sports function damage is enhanced. 3. It has an additive effect with lorazepam and ethanol. |
| Synthesis method | Diethyl malonate and 3-methylbutyraldehyde are condensed under the action of diisopropylamine to obtain 98. The latter undergoes double bond addition with KCN and hydrolyzes and decarboxylates to obtain racemic pregabalin 96. The racemic pregabalin forms a diastereomeric salt with S-(+)-mandelic acid and undergoes crystalline resolution to obtain an optically pure S-isomer. |
| capsule preparation | the preparation method of pregabalin capsule has the following steps: ① pregabalin raw material is passed through a 30-mesh (aperture 600 μm) screen on a swing granulator, and pregabalin raw material passing through a 30-mesh sieve is passed through a 60-mesh (aperture 250 μm) screen and an 80-mesh (aperture 180 μm) screen in sequence, take pregabalin granule powder that has passed 60 mesh sieve and has not passed 80 mesh sieve for later use; (2) Lactose is sequentially passed through 80 mesh (pore size 180 μm) screen and 120 mesh (pore size 120 μm) screen on the shock sieve, and lactose granule powder that has passed 80 mesh screen and has not passed 120 mesh screen is taken for later use; (3) The pregabalin granule powder (D50 particle size is 180 μm ~ 220 μm) obtained in step (1) is first used, d90 particle size is 250 μm ~ 280 μm) and the binder are mixed evenly on a multi-directional motion mixer, then lubricant and lactose particle powder obtained in step ② (D50 particle size is 120 μm ~ 140 μm,D90 particle size is 160 μm ~ 180 μm) are added, and the mixed evenly is continued. Finally, the uniformly mixed materials are directly filled on a full-automatic capsule filling machine to obtain pregabalin capsules. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:48
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