Rolipram (HCID 5092)

개요

Rolipram is a member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhibitor. It has a role as an antidepressant and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.

이름 및 식별자

우선 이름: Rolipram
IUPAC: 4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
영어명: ROLIPRAM
분자식: C16H21NO3
분자량: 275.34

이름 및 동의어

rolipram61413-54-5(R,S)-rolipram4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-oneZK 62711RolipramumZK-627114-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-oneNSC-7601254-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinoneZK 62 711

이름 더 보기

SB 95952Roliprame(¨¤)-RoliprRolipram >(±)-RolipramROLIPRAM 98+%

SB-95952ZK-62771K676NL63N7CHEBI:104872(+-)-rolipramPyrrolidone, 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-ZK62711RefChem:389268

데이터베이스 식별자

CAS: 61413-54-5
PubChem CID: 5092
DTXSID: DTXSID3044124
ChEMBL: CHEMBL63
ChEBI: CHEBI:104872
UNII: K676NL63N7
EC Number: 262-771-1
Nikkaji: J18.478K

물성

구조 계산 물성

XLogP: 2.2
극성 표면적: 47.6 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 3
회전 가능 결합 수: 4
무거운 원자 수: 20
형식 전하: 0
복잡도: 341

실험 및 물리화학적 성질

LogP2.17

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section174.11 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점: 127 · 127-133 °C
끓는 점: 418.29 °C · 418.29°C (rough estimate)
밀도: 1.0677 · 1.0677 (rough estimate)
굴절률: 1.55 · 1.5500 (estimate)
저장 조건: -20 °C · Sealed in dry,Store in freezer, under -20°C
용해도: 2 O: · H2O: 0.2 mg/mL
물리적 상태: 고체
산도 계수 (pKa): 16.02 · 16.02±0.40(Predicted)
색상: 흰색에서 황백색까지
생물학적 소스: synthetic (organic)
수용성: 2 O: · H2O: 0.2mg/mLethanol: 7mg/mLDMSO: 7.3mg/mL
Merck: 14 · 14,8251
안정성: 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChI: InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
InChIKey: HJORMJIFDVBMOB-UHFFFAOYSA-N
SMILES: O(C1CCCC1)C1C=C(C2CC(NC2)=O)C=CC=1OC

화학적 성질

Yellowish solid

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H302 (37.5%): 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 64 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (37.5%)

안전 데이터

wgk: 3
rtecs: UY5749237
ridadr: 3249
독성: LD50 oral in mouse: > 300mg/kg
HS 번호: 29337900
risk_code: 36/37/38-11
hazard_code: Xi
safety_code: 26-36
포장분류: III
위험 등급: 6.1(b)
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 2건

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.

Compounds that specifically inhibit PHOSPHODIESTERASE 4.

응용 분야

용도(±)-Rolipram is a cAMP-specific phosphodiesterase 4 (PDE4) inhibitor.

일반 설명A cell-permeable, selective inhibitor of cAMP-specific phosphodiesterase (PDE IV; IC50 = 800 nM). A rolipram-insensitive PDE IV subtype is also known to exist. Also inhibits NF-κB and NFAT activation in Jurkat and primary T cells.