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Baricitinib

HCID 44205240
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1187594-09-7
표준 SMILES
CCS(=O)(=O)N1CC(CC#N)(n2cc(-c3ncnc4[nH]ccc34)cn2)C1
InChIKey
XUZMWHLSFXCVMG-UHFFFAOYSA-N
분자식
C16H17N7O2S
평균 분자량
371.4 g/mol
단동위원소 질량
371.11644378

개요

Baricitinib is a pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine substituted by a 1-[3-(cyanomethyl)-1-(ethanesulfonyl)azetidin-3-yl]-1H-pyrazol-4-yl group at position 5. It is an FDA approved selective Janus Kinase 1 and 2 (JAK1 and JAK2) inhibitor used for the treatment of rheumatoid arthritis. It has a role as an antiviral agent, an immunosuppressive agent, an antirheumatic drug, an anti-inflammatory agent and an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor. It is a nitrile, a member of pyrazoles, a sulfonamide, a pyrrolopyrimidine and a member of azetidines.

이름 및 식별자

우선 이름
Baricitinib
IUPAC
2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile
영어명
Baricitinib
분자식
C16H17N7O2S
분자량
371.42

이름 및 동의어

Baricitinib1187594-09-7olumiantLY3009104INCB028050INCB 028050INCB-0280502-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrileLY-3009104LY 3009104ISP4442I3YDTXCID5074719
이름 더 보기
Baricitinib-API1-(Ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyriMidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrileBarrickiniBaricitinib (LY3009104, INCB028050)CS-574BaricinixBaritinibBarectinib
CHEBI:95341DTXSID30152228L04AA373-Azetidineacetonitrile, 1-(ethylsulfonyl)-3-(4-(7H-pyrrolo(2,3-d)pyrimidin-4-yl)-1H-pyrazol-1-yl)-baricitinibum(1-(Ethylsulfonyl)-3-(4-(7H-pyrrolo(2,3-d)pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile{1-(ethylsulfonyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]azetidin-3-yl}acetonitrile2-(3-(4-(7H-pyrrolo(2,3-d)pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile

데이터베이스 식별자

CAS
1187594-09-7

물성

구조 계산 물성

XLogP
-0.5
극성 표면적
129 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
7
회전 가능 결합 수
5
무거운 원자 수
26
형식 전하
0
복잡도
678

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Antirheumatic Agents; Enzyme Inhibitors; Janus Kinase Inhibitors; JAK Inhibitors; Signal Transduction Inhibitors; Protein Kinase Inhibitors

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

물리화학적 성질

녹는점
212 · 212-215°C
밀도
1.56 · 1.56
저장 조건
-20 °C · -20°C
용해도
DMSO(최대 30mg/ml) 또는 DMF(최대 50mg/ml)에 용해됩니다.
산도 계수 (pKa)
11.66 · 11.66±0.50(Predicted)
물리적 상태
고체
색상
흰색 또는 황백색
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 DMF 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChI
InChI=1S/C16H17N7O2S/c1-2-26(24,25)22-9-16(10-22,4-5-17)23-8-12(7-21-23)14-13-3-6-18-15(13)20-11-19-14/h3,6-8,11H,2,4,9-10H2,1H3,(H,18,19,20)
InChIKey
XUZMWHLSFXCVMG-UHFFFAOYSA-N
SMILES

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P318, P319, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (50%)

독성 정보

Hepatotoxicity · 1건

In the large prelicensure clinical trials in rheumatoid arthritis, serum aminotransferase elevations occurred in up to 17% of baricitinib treated subjects compared to 11% in placebo recipients. The elevations were typically mild and transient and values above 3 times the upper limit of normal (ULN) occurred in 1% to 2% of patients. The elevations occasionally led to early discontinuations, but more often resolved even without dose adjustment. In prelicensure studies in rheumatoid arthritis, alopecia areata and other rheumatic and immune-mediated disorders, there were no instances of clinically apparent liver injury attributed to baricitinib. Since approval and more wide scale availability of baricitinib, there have been no published reports of hepatotoxicity associated with its use.

Adverse Effects · 1건

Baricitinib is generally considered a safe and well-tolerated medication. However, it increases the risk of severe infections due to its immunosuppressive properties. During clinical trials, the most frequently reported adverse events in alopecia areata patients included upper respiratory tract infections, acne vulgaris, headaches, urinary tract infections, and folliculitis. In addition, there is an increased incidence of herpes zoster infections.

화학 및 산업

약리 정보

ATC Code · 3건

L04AA37

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingBaricitinib is approximately 50% bound to plasma proteins and 45% bound to serum proteins.
Pharmacodynamics · 1건

Baricitinib is a disease-modifying antirheumatic drug (DMARD) used to ameliorate symptoms and slow down the progression of rheumatoid arthritis. In animal models of inflammatory arthritis, baricitinib was shown to have significant anti-inflammatory effects but also led to the preservation of cartilage and bone, with no detectable suppression of humoral immunity or adverse hematologic effects. Baricitinib decreased the levels of immunoglobulins and serum C-reactive protein in patients with rheumatoid arthritis.

Mechanism of Action · 1건

As members of the tyrosine kinase family, Janus kinases (JAKs) are intracellular enzymes that modulate signals from cytokines and growth factor receptors involved in hematopoiesis, inflammation, and immune cell function. Upon binding of extracellular cytokines and growth factors, JAKs phosphorylate and activate Signal Transducers and Activators of Transcription (STATs). STATs modulate intracellular activity, including gene transcription of inflammatory mediators that promote an autoimmune response, such as IL-2, IL-6, IL-12, IL-15, IL-23, IFN-γ, GM-CSF, and interferons. The JAK-STAT pathway has been implicated in the pathophysiology of rheumatoid arthritis, as it is associated with an overproduction of inflammatory mediators. There are four JAK proteins: JAK 1, JAK 2, JAK 3 and TYK2. JAKs form homodimers or heterodimers and pair differently in different cell receptors to transmit cytokine signaling. Baricitinib is a selective and reversible inhibitor of JAK1 and JAK2 with less affinity for JAK3 and TYK2; however, the relevance of inhibition of specific JAK enzymes to therapeutic effectiveness is not currently known. Baricitinib inhibits the activity of JAK proteins and modulates the signaling pathway of various interleukins, interferons, and growth factors. It was also shown to decrease the proliferation of JAK1/JAK2 expression in mutated cells and induce cell apoptosis.

Biological Half-Life

관련 반응

14건
반응 기록 만들기
HRID 135641 반응식
HRID 135641생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 288286 반응식
HRID 288286생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 298779 반응식
HRID 298779생성물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 1151841 반응식
HRID 1151841생성물로Training data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1692964 반응식
HRID 1692964생성물로uspto-grants-2012_04
HRID 1692965 반응식
HRID 1692965반응물로uspto-grants-2012_04
HRID 1692972 반응식
HRID 1692972반응물로uspto-grants-2012_04
HRID 1692977 반응식
HRID 1692977생성물로uspto-grants-2012_04
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
PubChem CID
44205240
DTXSID
DTXSID30152228
ChEMBL
CHEMBL2105759
ChEBI
CHEBI:95341
UNII
ISP4442I3Y
EC Number
691-421-4
Nikkaji
J3.196.953K
N1(S(CC)(=O)=O)CC(N2C=C(C3N=CN=C4NC=CC4=3)C=N2)(CC#N)C1
Toxicity Summary
Signs and Symptoms of Overdose
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Baricitinib

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
WGK 3
HS 번호
29350090
Hazard Classifications
Repr. 1BSTOT RE 1STOT SE 3
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
The elimination half-life in patients with rheumatoid arthritis is approximately 12 hours. The elimination half-life was 10.8 hours in intubated patients with COVID-19 who received baricitinib via nasogastric (NG) or orogastric (OG) tube.
Metabolism/MetabolitesBaricitinib is metabolized by CYP3A4. Approximately 6% of the orally administered dose was identified as metabolites in urine and feces; however, no metabolites of baricitinib were quantifiable in plasma.
FDA Pharmacological Classification · 6건

ISP4442I3Y

BARICITINIB

Established Pharmacologic Class [EPC] - Janus Kinase Inhibitor

Mechanisms of Action [MoA] - Janus Kinase Inhibitors

Baricitinib is a Janus Kinase Inhibitor. The mechanism of action of baricitinib is as a Janus Kinase Inhibitor.

BARICITINIB

Absorption, Distribution and Excretion · 4건

The absolute bioavailability of baricitinib is approximately 80%. The Cmax was reached after one hour of oral drug administration. A high-fat meal decreased the mean AUC and Cmax of baricitinib by approximately 11% and 18%, respectively, and delayed Tmax by 0.5 hours.

Baricitinib is predominantly excreted via renal elimination. It is cleared via filtration and active secretion. Approximately 75% of the administered dose was eliminated in the urine, with 20% of that dose being the unchanged drug. About 20% of the dose was eliminated in the feces, with 15% of that dose being an unchanged drug.

Following intravenous administration, the volume of distribution was 76 L, indicating distribution into tissues.

The total body clearance of baricitinib was 8.9 L/h in patients with rheumatoid arthritis. The total body clearance and half-life of baricitinib was 14.2 L/h in intubated patients with COVID-19 who received baricitinib via nasogastric (NG) or orogastric (OG) tube.

응용 분야

용도Baricitinib is a JAK1 and JAK2 inhibitor and have been used as a promising treatment for rheumatoid arthritis.

상·하류 제품 정보

상류 원료

(4-(1-(3-(cyanomethyl)-1-(ethylsulfonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate에탄술포닐클로라이드2-(1-(에틸술포닐)아제티딘-3-일리덴)아세토니트릴2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile1-Boc-3-(시아노메틸렌)아제티딘4-Chloro-7H-pyrrolo[2,3-d]pyrimidine수산화나트륨물메틸알콜테트라하이드로푸란

하류 제품

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