(3S)-3-(aminomethyl)-5-methylhexanoic acid

• ChemBase编号: 115
• 分子式: C8H17NO2
• 平均质量: 159.22608
• 单一同位素质量: 159.12592879
• SMILES: OC(=O)C[C@H](CC(C)C)CN
• Canonical SMILES: NC[C@H](CC(=O)O)CC(C)C
• InChI: InChI=1S/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

名称和登记号

名称

• IUPAC标准名: (3S)-3-(aminomethyl)-5-methylhexanoic acid
• IUPAC传统名: pregabalin
• 商标名: Lyrica
• 别名: (S)-3-(Aminomethyl)-5-methylhexanoic acid; pregabalin; Pregabalin; (S)-3-(Aminomethyl)-5-methylhexanoic acid; CI-1008; PD-144723; Pregabalin; (3S)-3-(Aminomethyl)-5-methylhexanoic Acid; (S)-(+)-3-(Aminomethyl)-5-methylhexanoic Acid; (S)-3-(Ammoniomethyl)-5-methylhexanoate; CI 1008; Lyrica; PD 144723; (S)-Pregabalin

登记号

• CAS号: 148553-50-8
• MDL号: MFCD00917044
• PubChem SID: 46504934; 160963578
• PubChem CID: 5486971

理论计算性质

JChem

• Acid pKa: 4.8009205
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -1.4076396
• LogD (pH = 7.4): -1.3444575
• Log P: -1.3455846
• 摩尔折射率: 43.68 cm^3
• 极化性: 17.506392 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.35
• LOG S: -1.15
• 溶解度: 1.13e+01 g/l

分子性质

理化性质

• 溶解度: deionized water: ≥10 mg/mL; Water
• 外观: Off-White Solid; white powder
• 熔点: 194-196°C
• 疏水性(logP): 1.3

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-48/22
• 安全公开号: 22-36/37
• TSCA收录: false
• GHS危险品标识: GHS05; GHS08
• GHS警示词: Danger
• GHS危险声明: H318-H361
• GHS警示性声明: P280-P305 + P351 + P338
• 毒品管制信息: USDEA Schedule V
• 保存温度: room temp

产品相关信息

• 纯度: ≥97% (NMR); 95+%; 97%
• Empirical Formula (Hill Notation): C8H17NO2

详细说明

DrugBank - DB00230

• Drug Groups: illicit; approved; investigational
• Description: Pregabalin is an anticonvulsant drug used for neuropathic pain, as an adjunct therapy for partial seizures, and in generalized anxiety disorder. It was designed as a more potent successor to gabapentin. Pregabalin is marketed by Pfizer under the trade name Lyrica. It is considered to have a dependence liability if misused, and is classified as a Schedule V drug in the U.S. [Wikipedia]
• Indication: For management of neuropathic pain associated with diabetic peripheral neuropathy and postherpetic neuralgia.
• Pharmacology: Pregabalin is a new anticonvulsant drug indicated as an add on therapy for partial onset seizures and for certain types of neuropathic pain. It was designed as a more potent successor to a related drug, gabapentin. Pregabalin binds to the alpha2-delta subunit of the voltage-gated calcium channel in the central nervous system. While pregabalin is a structural derivative of the inhibitory neurotransmitter gamma- aminobutyric acid (GABA), it does not bind directly to GABAA, GABAB, or benzodiazepine receptors, does not augment GABAA responses in cultured neurons, does not alter rat brain GABA concentration or have acute effects on GABA uptake or degradation. However, in cultured neurons prolonged application of pregabalin increases the density of GABA transporter protein and increases the rate of functional GABA transport. Pregabalin does not block sodium channels, is not active at opiate receptors, and does not alter cyclooxygenase enzyme activity. It is inactive at serotonin and dopamine receptors and does not inhibit dopamine, serotonin, or noradrenaline reuptake.
• Affected Organisms: Humans and other mammals
• Biotransformation: Negligible
• Absorption: Well absorbed after oral administration.
• Half Life: ~6 hours
• Elimination: Pregabalin is eliminated from the systemic circulation primarily by renal excretion as unchanged drug.
• Distribution: * 0.5 L/kg
• Clearance: * Renal cl=67.0 – 80.9 mL/min [young healthy subjects]
• References: : Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - PZ0010

Biochem/physiol Actions
Pregabalin is a lipophilic GABA analog/ligand at α2δ subunit of voltage-dependent Ca2+ channels. Pregabalin is an anticonvulsant, anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - P704790

S-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

参考文献

• : Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. Pubmed
• Taylor, C.P., at al.: Epilepsy Res., 14, 11 (1993)
• Field, M.J., et al.: Pain, 80, 391 (1999)