기본 정보
- 표준 SMILES
CC(C)C[C@H](CN)CC(=O)O- InChIKey
AYXYPKUFHZROOJ-ZETCQYMHSA-N- 분자식
- C8H17NO2
- 평균 분자량
- 159.23 g/mol
- 단동위원소 질량
- 159.12592878
개요
Pregabalin is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It is functionally related to a gamma-aminobutyric acid.
이름 및 식별자
- 우선 이름
- Pregabalin
- IUPAC
- (3S)-3-(aminomethyl)-5-methylhexanoic acid
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
148553-50-8- PubChem CID
- 5486971
- DTXSID
DTXSID1045950- ChEMBL
CHEMBL1059- ChEBI
CHEBI:64356- UNII
- 55JG375S6M
- EC Number
- 604-639-1
- Nikkaji
- J702.547E
물성
구조 계산 물성
- XLogP
- -1.6
- 극성 표면적
- 63.3 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 11
- 형식 전하
- 0
- 복잡도
- 123
실험 및 물리화학적 성질
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
DEA Schedule V Controlled Substance -> Depressants
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Antiepileptic
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Solubility
Freely soluble
Freely soluble in water and both basic and acidic solutions
1.13e+01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesics; Anticonvulsants
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
Animal Drugs
EMA approved medicines: Veterinary medicine
Active Ingredients (Pregabalin) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 199) of reports.
Danger
H318 (72.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P203, P260, P264+P265, P280, P305+P354+P338, P317, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 199 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
FDA Requirements
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.
안전 및 보호
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.
독성 정보
Interactions
Patients who require concomitant treatment with central nervous system depressants such as opiates or benzodiazepines should be informed that they may experience additive CNS side effects, such as somnolence.
The pharmacokinetic interactions of pregabalin and gabapentin were investigated in 12 healthy subjects following concomitant single-dose administration of 100-mg pregabalin and 300-mg gabapentin and in 18 healthy subjects following concomitant multiple-dose administration... Gabapentin pharmacokinetics following single- and multiple-dose administration were unaltered by pregabalin coadministration. The extent of pregabalin absorption was unaffected by gabapentin coadministration, although there was a small reduction in rate of absorption.
Pregabalin coadministration had no effect on the steady-state pharmacokinetics of norethindrone and ethinyl estradiol (1 mg/35 mug, respectively) in healthy subjects.
Multiple-dose administration of pregabalin in healthy subjects had no effect on the rate and extent of lorazepam single-dose pharmacokinetics and single-dose administration of lorazepam had no effect on the steady-state pharmacokinetics of pregabalin.
For more Interactions (Complete) data for PREGABALIN (8 total), please visit the HSDB record page.
Hepatotoxicity
Limited data is available on the hepatotoxicity of pregabalin. In prelicensure clinical trials in diabetic neuropathy and epilepsy, therapy with pregabalin was not associated with an increased frequency of serum aminotransferase elevations or liver toxicity. Since its approval and more wide scale use, however, pregabalin has been linked to rare instances of clinically apparent liver injury. Most cases were mild and frequently without jaundice. The latency to onset of injury was short, symptoms of liver injury arising within 3 to 14 days. Both cholestatic and hepatocellular patterns of injury have been reported. Signs of hypersensitivity (fever, rash, eosinophilia) and autoimmunity were not present. Some cases have been severe and associated with marked jaundice and prolongation of the prothrombin time, but all cases ultimately resolved after the medication was stopped without evidence of residual injury.
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ In a double-blind, placebo-controlled clinical trial to assess the effect of pregabalin on sperm motility, 30 healthy male subjects were exposed to pregabalin at a dose of 600 mg/day. After 3 months of treatment (one complete sperm cycle), the difference between placebo- and pregabalin-treated subjects in mean percent sperm with normal motility was <4% and neither group had a mean change from baseline of more than 2%. Effects on other male reproductive parameters in humans have not been adequately studied.
/CASE REPORTS/ /Investigators/ present a patient who, after unintended rapid up-titration of pregabalin, experienced psychotic symptoms associated with rhythmic EEG-changes resolving completely after discontinuation of pregabalin and benzodiazepine administration.
/CASE REPORTS/ /Investigators/ report two patients with refractory epilepsy who developed unilateral painful gynecomastia and lower extremity pain (one of them localized and the other one diffuse), shortly after receiving Pregabalin (PGB). Neither of them had previous endocrinologic problems or complaints about pain on their medical history. PGB was stopped in one patient and reduced in the other one, with complete disparition of the symptoms in the following weeks in both patients.
/CASE REPORTS/ /Investigators/ present the cases of 5 men who reported mild to moderate erectile dysfunction or impotence for the first time when treated with the new antiepileptic drug pregabalin as add-on therapy.
For more Human Toxicity Excerpts (Complete) data for PREGABALIN (7 total), please visit the HSDB record page.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Pregabalin
vLess-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Skin lesions ranging from erythema to necrosis were seen in repeated-dose toxicology studies in both rats and monkeys. The etiology of these skin lesions is unknown. At the maximum recommended human dose, there is a 2-fold safety margin for the dermatological lesions. The more severe dermatopathies involving necrosis were associated with pregabalin exposures of approximately 3 to 8 times those achieved in humans given the MRD.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Ocular lesions (characterized by retinal atrophy [including loss of photoreceptor cells] and/or corneal inflammation/mineralization) were observed in two lifetime carcinogenicity studies in Wistar rats. These findings were observed at plasma pregabalin exposures (AUC) >/=2 times those achieved in humans given the maximum recommended dose... A no-effect dose for ocular lesions was not established. Similar lesions were not observed in lifetime carcinogenicity studies in two strains of mice or in monkeys treated for 1 year.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ A dose-dependent increase in the incidence of malignant vascular tumors (hemangiosarcomas) was observed in two strains of mice (B6C3F1 and CD-1) given pregabalin (200, 1000, or 5000 mg/kg) in the diet for two years. Plasma pregabalin exposure (AUC) in mice receiving the lowest dose that increased hemangiosarcomas was approximately equal to the human exposure at the maximum recommended dose ... A no-effect dose for induction of hemangiosarcomas in mice was not established.
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ In fertility studies in which male rats were orally administered pregabalin (50 to 2500 mg/kg) prior to and during mating with untreated females, a number of adverse reproductive and developmental effects were observed. These included decreased sperm counts and sperm motility, increased sperm abnormalities, reduced fertility, increased preimplantation embryo loss, decreased litter size, decreased fetal body weights, and an increased incidence of fetal abnormalities. Effects on sperm and fertility parameters were reversible in studies of this duration (3-4 months). The no-effect dose for male reproductive toxicity in these studies was 100 mg/kg.
For more Non-Human Toxicity Excerpts (Complete) data for PREGABALIN (11 total), please visit the HSDB record page.
Populations at Special Risk
Advise diabetic patients to watch for skin damage while receiving pregabalin therapy, since increased risk of skin ulcerations associated with pregabalin therapy has been observed in animal studies.
Because there are limited data regarding use of pregabalin in patients with New York Heart Association (NYHA) class III or IV congestive heart failure, the drug should be used with caution in these patients.
Environmental Water Concentrations
While data specific to pregabalin were not located(SRC, 2007), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
Antidote and Emergency Treatment
There is no known antidote for pregabalin. Treatment is generally symptomatic and supportive. ... To enhance elimination- Hemodialysis indicated by the patients clinical state; patients with significant renal impairment may increase clearance of pregabalin approximately 50% in 4 hours. Monitoring of vital signs and observation of clinical status of the patient. Supportive care- Contacting a certified poison control center for up-to-date information on management of overdose with pregabalin.
Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat stupor and coma if they occur. Protect the patient from self-injury caused by ataxia. Treat agitation and delirium if they occur. Monitor asymptomatic patients for a minimum of 4-6 hours. Admit symptomatic patients for at least 24 hours after lamotrigine, felbamate, topiramate, or zonisamide ingestions. ... Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. ... /Anticonvulsants, Newer/
규제 정보
FDA Requirements
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.
화학 및 산업
약리 정보
ATC Code
N03AX16
N - Nervous system
QN - Nervous system
Pharmacodynamics
Although the structure of pregabalin is similar to gamma-aminobutyric acid (GABA), it does not bind to GABA receptors. Instead, it binds the alpha2-delta subunit of presynaptic voltage-gated calcium channels in the central nervous system. Pregabalin does not modulate dopamine receptors, serotonin receptors, opiate receptors, sodium channels or cyclooxygenase activity.
Mechanism of Action
Although the mechanism of action has not been fully elucidated, studies involving structurally related drugs suggest that presynaptic binding of pregabalin to voltage-gated calcium channels is key to the antiseizure and antinociceptive effects observed in animal models. By binding presynaptically to the alpha2-delta subunit of voltage-gated calcium channels in the central nervous system, pregabalin modulates the release of several excitatory neurotransmitters including glutamate, substance-P, norepinephrine, and calcitonin gene related peptide. In addition, pregabalin prevents the alpha2-delta subunit from being trafficked from the dorsal root ganglia to the spinal dorsal horn, which may also contribute to the mechanism of action. Although pregabalin is a structural derivative of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA), it does not bind directly to GABA or benzodiazepine receptors.
Pregabalin is an anticonvulsant that is structurally related to the inhibitory CNS neurotransmitter gamma-aminobutyric acid (GABA). Pregabalin also has demonstrated analgesic activity. Although pregabalin was developed as a structural analog of GABA, the drug does not bind directly to GABA-A, GABA-B, or benzodiazepine receptors; does not augment GABA-A responses in cultured neurons; and does not alter brain concentrations of GABA in rats or affect 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 binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in CNS tissues. ... In vitro, pregabalin reduces the calcium-dependent release of several neurotransmitters, including glutamate, norepinephrine, and substance P, possibly by modulation of calcium channel function.
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.
Pregabalin is a potent ligand for the alpha-2-delta subunit of voltage-gated calcium channels in the central nervous system that exhibits potent anticonvulsant, analgesic, and anxiolytic activity in a range of animal models. ... Potent binding to the alpha-2-delta site reduces depolarization-induced calcium influx with a consequential modulation in excitatory neurotransmitter release. Pregabalin has no demonstrated effects on GABAergic mechanisms. ...
For more Mechanism of Action (Complete) data for PREGABALIN (6 total), please visit the HSDB record page.
Biological Half-Life
The elimination half life of pregabalin is 6.3 hours.
Pregabalin is eliminated from the systemic circulation primarily by renal excretion as unchanged drug with a mean elimination half-life of 6.3 hours in subjects with normal renal function.
Metabolism/Metabolites
Less than 2% of pregabalin is metabolized and it is excreted virtually unchanged in the urine.
Pregabalin undergoes negligible metabolism in humans. Following a dose of radiolabeled pregabalin, approximately 90% of the administered dose was recovered in the urine as unchanged pregabalin. The N-methylated derivative of pregabalin, the major metabolite of pregabalin found in urine, accounted for 0.9% of the dose. In preclinical studies, pregabalin (S-enantiomer) did not undergo racemization to the R-enantiomer in mice, rats, rabbits, or monkeys.
MeSH Pharmacological Classification
Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
Drugs used to prevent SEIZURES or reduce their severity.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
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.
Absorption, Distribution and Excretion
After oral dosing administered in the fasted state, pregabalin absorption is rapid, and extensive. Pregabalin oral bioavailability is reported to be ≥90% regardless of the dose. Cmax is attained within 1.5 hours after single or multiple doses, and steady state is attained within 24-48 hours with repeated administration. Both Cmax and AUC appear to be dose proportional. Food decreases the rate of pregabalin absorption and as a result, lowers the Cmax by an estimated 25-30% and increases the Tmax to approximately 3 hours. However, the effect of food does not appear to impact the total absorption of pregabalin in a way that is clinically relevant. As a result, pregabalin can be administered with or without food.
Pregabalin is almost exclusively eliminated in the urine. Further, based on preclinical studies, pregabalin does not appear to undergo racemization to the R enantiomer in the body.
After oral administration of pregabalin, the reported apparent volume of distribution is roughly 0.5 L/kg. Although pregabalin is not very lipophilic, it is able to cross the blood brain barrier(BBB). System L transporters facilitate the transport of large amino acids across the BBB and it has been confirmed that pregabalin is a substrate. This information suggests that system L transporters are responsible for pregabalin uptake into the BBB. In rat models, pregabalin has been shown to cross the placenta.
In young healthy subjects the mean renal clearance is estimated to be 67.0 to 80.9 mL mL/min. Given pregabalin's lack of plasma protein binding, this clearance rate suggests that renal tubular reabsorption is involved.
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.
용도 및 제조
Uses
MEDICATION
THERAP CAT: Anticonvulsant
Use (kg) in Switzerland (2009): >1000
관련 반응
연결된 노트
불러오는 중…