9-CIS-레티노산

9-CIS-레티노산 · Alitretinoin · Panretin · Tretinoin EP Impurity D · (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid · Toctino · LGD 1057 · Panretyn

https://huagongshe.com/ko/chemical/449171

식별자 및 물리적 특성

CAS No.	5300-03-8
분자식	C20H28O2
평균 분자량	300.4 g/mol
단동위원소 질량	300.20893014 g/mol
SMILES	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C(=O)O)C(C)(C)CCC1
InChIKey	SHGAZHPCJJPHSC-ZVCIMWCZSA-N
PubChem CID	449171
ChEMBL	CHEMBL705
ChEBI	CHEBI:50648
EC No.	610-929-9
DTXSID	DTXSID6040404
현지명	9-CIS-레티노산

화학 및 물리적 성질

XLogP	6.3
극성 표면적	37.3
수소 결합 공여자 수	1
수소 결합 수용자 수	2
회전 가능 결합 수	5
무거운 원자 수	22
형식 전하	0
복잡도	567
의약품	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Isotretinoin
지질	Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Color/Form	Yellow fine needles from ethanolYellow powder
용해도	Insoluble in waterIn ethanol, 7.01 mg/g at 25 °C아세토니트릴(매우 약간), 클로로포름(약간 용해됨), DMSO(약간 용해됨)
Human Drugs	Breast FeedingLactationMilk, HumanAntineoplastic AgentsDermatologic AgentsKeratolytic AgentsRetinoidsFDA approved drugs -> Active ingredient
녹는점	189-190 °C190-191 °C189-191°C
Physical Description	Solid
Stability/Shelf Life	Stable under recommended storage conditions.
Collision Cross Section	200.01 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]
Other Experimental Properties	log Kow = 6.30 /all-trans-Retinoic acid/
끓는 점	462.8±14.0 °C(Predicted)
밀도	1.011±0.06 g/cm3(Predicted)
저장 조건	-20°C
pKa(산도 계수)	4.73±0.33(Predicted)
물리적 상태	연한 노란색에서 주황색의 결정성 분말.
색상	연한 노란색에서 노란색까지
생물학적 소스	natural
용해도	클로로포름(50mg/ml), DMSO(~25mg/ml), 에탄올(25mg/ml) 및 아세톤(25mg/ml)에 용해됩니다. 물에 불용성.
안정성	최대 1년 동안 -20°C의 냉장고에 보관하세요. 최대 3개월 동안 -20°C에서 용액에 보관하세요
InChI	InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChIKey	SHGAZHPCJJPHSC-ZVCIMWCZSA-N
SMILES	C(O)(=O)/C=C(/C=C/C=C(\C=C\C1C(C)(C)CCCC=1C)/C)\C

화학적 성질

Pale Yellow Solid

안전 및 규제

GHS 분류	DangerH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
규제 정보	Alitretinoin: Does not have an individual approval but may be used under an appropriate group standard
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including alitretinoin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and Categories	Skin Irrit. 2 (100%)Acute Tox. 4 (100%)
Hazardous Reactivities and Incompatibilities	Incompatible materials: Strong oxidizing agents.
Firefighting Hazards	Hazardous decomposition products formed under fire conditions - Carbon oxides.
소화 절차	Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for fire fighting if necessary.
보관 조건	Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature -20 °C.Store at 25 deg C (77 °F)excursions permitted to 15-30 °C (59-86 °F).
정리 방법	ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

용도

개요

Alitretinoin was introduced in the US for the topical treatment of cutaneous lesions in patients with Kaposi's sarcoma (KS), the most frequent malignancy observed in AIDS patients. It is a derivative of 9-cis-retinoic acid (9- cis-RA) identified as an endogenous hormone in mammalian tissues. Alitretinoin binds to all isoforms of the intracellular retinoid X (RXR) and retinoid A (RAR) receptors thus inducing cell differentiation, increasing cell apoptosis and inhibiting cellular proliferation in experimental models of human cancer. In an international phase III trial in patients with KS, 42% of 82 patients treated with 0.1% gel formulation experienced complete or partial responses cf 7% for controls. Alitretinoin is the first topical therapy for KS and is expected to be a new option to its traditional management.

용도

9-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. 9-cis-Retinoic acid is an inhibitor of Cox-2 and an activator of RAR α, RAR β, RAR γ and RXR.