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아르글라빈

Arglabin

HCID 5574924
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
84692-91-1
표준 SMILES
C=C1C(=O)O[C@@H]2[C@H]3C(C)=CC[C@@]34O[C@@]4(C)CC[C@@H]12
InChIKey
UVJYAKBJSGRTHA-CUZKYEQNSA-N
분자식
C15H18O3
평균 분자량
246.3 g/mol
단동위원소 질량
246.12559443

개요

Arglabin is an organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers. It has a role as a metabolite and an antineoplastic agent. It is an epoxide, a gamma-lactone, a sesquiterpene lactone and an organic heterotetracyclic compound.

이름 및 식별자

우선 이름
Arglabin
IUPAC
(1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one
현지명
아르글라빈
영어명
arglabin
분자식
C15H18O3
분자량
246.3

이름 및 동의어

Arglabin84692-91-1(+)-arglabinYS8UOP7QZ1CHEBI:73228(1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-oneDTXSID30233687(1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo(9.3.0.01,3.06,10)tetradec-12-en-8-oneRefChem:113990DTXCID60156178851-932-7Arglabin=DMA
이름 더 보기
아르글라빈CS-1320Arglabin, BRArglabin 84692-91-1Arglabin ((+)-Arglabin)Arglabin, 10 mM in DMSO(3aS)-2,3,3aβ,4,5β,6,6a,7,9aβ,9bα-Decahydro-6α,6aα-epoxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2-one(3aR,4aS)-1,4aα-Dimethyl-7-methylene-4a,5,6,6aα,9aβ,9bα-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(7H)-one
UNII-YS8UOP7QZ13H-Oxireno(8,8a)azuleno(4,5-b)furan-8(4aH)-one, 5,6,6a,7,9a,9b-hexahydro-1,4a-dimethyl-7-methylene-ARGLABINEMFCD28716120(3aR,4aS,6aS,9aS,9bR)-5,6,6a,7,9a,9b-Hexahydro-1,4a-dimethyl-7-methylene-3H-Oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one,(+)-Arglabin?SCHEMBL60010orb1217601

물성

구조 계산 물성

XLogP
1.7
극성 표면적
38.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
18
형식 전하
0
복잡도
506

물리화학적 성질

녹는점
100 · 100-102 °C
끓는 점
404.6 · 404.6±45.0 °C(Predicted)
밀도
1.22 · 1.22±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
용해도
클로로포름(약간 용해됨)
물리적 상태
고체
색상
회백색
생물학적 소스
semisynthetic (from parthenolide)
InChI
1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11-,12-,14-,15+/m0/s1
InChIKey
UVJYAKBJSGRTHA-ZCRGAIPPSA-N
SMILES
O1[C@@]32[C@@]1(CC[C@@H]4[C@H](OC(=O)C4=C)[C@@H]3C(=CC2)C)C

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (100%)

안전 데이터

wgk
WGK 3
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids

화학 및 산업

응용 분야 · 1건

개요Arglabin is a new antineoplastic agent launched in Russia for the treatment of a variety of cancers. It is a sesquiterpene gamma-lactone extracted from Artemisia glabella, a plant from Kazakstan; it was first developed in Kazakstan followed by US and other countries as an ethical pharmaceutical. Arglabin can be obtained by resin extraction from A.glabella, purification by chromatography and finally recrystallization. Arglabin is a potent and selective inhibitor of farnesyl transferase, an enzyme critical to the function of the Ras oncogene in cancer cell reproduction. It showed a strong Inhibitory effect against tumor cells proliferation in in vitro models of transformed mouse hepatocytes and splenocytes. This cytotoxic effect against tumor cells was 50-100 times higher than that on intact cells. In many patients with various cancers, Arglabin was shown to stop or inhibit the tumour development, alone or in combination with other anticancer agents, and was reportedly well tolerated with few sideeffects. Promising response rates were also reported with Arglabin after treating other 《difficult-to-treat cancers》 such as breast, ovarian, lung or colon cancers.

추가 설명 · 1건

정의ChEBI: An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the add ct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.

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데이터베이스 식별자

CAS
84692-91-1
PubChem CID
5574924
ChEMBL
CHEMBL2206431
ChEBI
CHEBI:73228
UNII
YS8UOP7QZ1
EC Number
851-932-7
Nikkaji
J264.652H