Glycopyrrolate
GLYCOPYRRONIUM · GLYCOPYROLATE · Glycopyrronium impurity N · robinul · Glycopyrrone bromide · Glycopyrronium for peak identification · Glycopyrronium for peak identification CRS · Pyrrolidinium, 3-(cyclopentylhydroxyphenylacetyl)oxy-1,1-dimethyl-, bromide
식별자 및 물리적 특성
| CAS No. | 596-51-0 |
|---|---|
| 분자식 | C19H28BrNO3 |
| 평균 분자량 | 398.3 g/mol |
| SMILES | C[N+]1(C)CCC(OC(=O)C(O)(c2ccccc2)C2CCCC2)C1.[Br-] |
| InChIKey | VPNYRYCIDCJBOM-UHFFFAOYSA-M |
| PubChem CID | 11693 |
| ChEMBL | CHEMBL1201027 |
| ChEBI | CHEBI:90972 |
| EC No. | 209-887-0 |
| DTXSID | DTXSID6023109 |
화학 및 물리적 성질
| 극성 표면적 | 46.5 |
|---|---|
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 24 |
| 형식 전하 | 0 |
| 복잡도 | 424 |
| Human Drugs | Breast FeedingLactationMilk, HumanAdjuvants, AnesthesiaBronchodilator AgentsMuscarinic AntagonistsParasympatholyticsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Animal Drugs | Active Ingredients (Glycopyrrolate) -> FDA Greenbook |
| Collision Cross Section | 203.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 녹는점 | 192-195°C |
| 밀도 | 1.3222 (rough estimate) |
| 굴절률 | 1.6200 (estimate) |
| 저장 조건 | 2-8°C |
| 용해도 | H2O: ≥24mg/mL |
| 물리적 상태 | 가루 |
| 색상 | 흰색에서 황갈색까지 |
| 용해도 | H2O: ≥24mg/mL |
| Merck | 14,4501 |
| 안정성 | 흡습성 |
| InChI | InChI=1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H31H/q+1/p-1 |
| InChIKey | VPNYRYCIDCJBOM-UHFFFAOYSA-M |
| SMILES | C(O)(C(=O)OC1CC[N+](C)(C)C1)(C1=CC=CC=C1)C1CCCC1.[Br-] |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | WarningH302 (23.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Glycopyrronium bromide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| 기타 안전 정보 | IMAP assessments - Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (23.5%) |
| Hepatotoxicity | Like other anticholinergic agents, glycopyrrolate has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. A major reason for its safety may relate to the low daily dose. |
| 유해 작용 | Potential adverse reactions associated with glycopyrrolate administration include anticholinergic symptoms such as mydriasis, hyperthermia, tachycardia, and cardiac arrhythmia. They may also include blurred vision, constipation, cycloplegia, dry mouth, dry skin, flushing, photophobia, urinary retention, and xerophthalmia. |
| 독성 요약 | Acute toxicity with glycopyrrolate is secondary to an extension of the pharmacologic effects on the muscarinic cholinergic receptors. Muscarinic receptor sites are located in the brain's cerebral cortex, thalamus, hippocampus, and reticular activating system. They are also present in the postganglionic parasympathetic nervous system and other sites like sweat glands. Anticholinergic agents block the effects of acetylcholine by competitively binding and blocking muscarinic receptors. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)GlycopyrrolatevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UY4337630 |
| 독성 | LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.in male rats (mg/kg): 1150 orally (Franko) |
| 관세 코드 | 29339900 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26 |
| 위험 등급 | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Glycopyrrolate is an antagonist of muscarinic acetylcholine receptors (mAChRs; Kis = 0.42, 1.77, 0.52, 0.78, and 1.29 nM for the M1-M5 receptors, respectively). It induces relaxation of precontracted isolated human bronchi when used at concentrations of 0.01, 0.1, or 1 μM. Glycopyrrolate reduces post-prandial gastric antral motility in dogs when administered at a dose of 0.01 mg/kg. It inhibits salivation in a rat model of sialorrhea induced by pilocarpine with an ED50 value of 0.74 μg/kg. Formulations containing glycopyrrolate have been used in the treatment of sialorrhea, peptic ulcers, and chronic obstructive pulmonary disease (COPD).
용도
Glycopyrrolate inhibits secretion of digestive juices and restores normal stomach function. It is used for treating stomach ulcers, inflamed intestine, and also as a pre-operational drug for inhibiting excess stomach secretion.
용도
A synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.
일반 설명
Glycopyrrolate, 3-hydroxy-1,1-dimethylpyrrolidinium bromide -cyclopentylmandelate(Robinul), occurs as a white, crystalline powder that is solublein water or alcohol but practically insoluble in chloroformor ether.Glycopyrrolate is a typical anticholinergic and possesses,at adequate dosage levels, the atropine-like effectscharacteristic of this class of drugs. It has a spasmolyticeffect on the musculature of the GI tract as well as the genitourinarytract. It diminishes gastric and pancreatic secretionsand the quantity of perspiration and saliva. Its sideeffects are also typically atropine-like (i.e., dryness of themouth, urinary retention, blurred vision, constipation).Glycopyrrolate is a more potent antagonist on M1 than onM2 and M3 receptors. The low affinity of M2 receptorsmay, in part, explain the low incidence of tachycardiaduring use of this drug as an antispasmodic.77 Because ofits quaternary ammonium character, glycopyrrolate rarelycauses CNS disturbances, although in sufficiently highdosage, it can bring about ganglionic and myoneural junctionblock.