9-Cis-Retinoic Acid

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 · ALRT1057

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

Identifikatoren & physikalische Daten

CAS No.	5300-03-8
Summenformel	C20H28O2
Durchschnittliche Molmasse	300,4 g/mol
Monoisotopische Masse	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

Chemische & physikalische Eigenschaften

XLogP	6,3
Polarare Oberfläche (TPSA)	37,3
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	5
Schwere Atome	22
Formalladung	0
Komplexität	567
Arzneimittel	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Isotretinoin
Lipide	Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Color/Form	Yellow fine needles from ethanolYellow powder
Löslichkeit	Insoluble in waterIn ethanol, 7.01 mg/g at 25 °CAcetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water.
Human Drugs	Breast FeedingLactationMilk, HumanAntineoplastic AgentsDermatologic AgentsKeratolytic AgentsRetinoidsFDA approved drugs -> Active ingredient
Schmelzpunkt	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/
Siedepunkt	462.8±14.0 °C(Predicted)
Dichte	1.011±0.06 g/cm3(Predicted)
Lagerbedingungen	-20°C
pKa (Säurekonstante)	4.73±0.33(Predicted)
Aggregatzustand	Light yellow to orange crystalline powder.
Farbe	Pale Yellow to Yellow
Biologische Quelle	natural
Stabilität	Store Dry in Freezer at -20°C for up to 1 yearin Solution at -20°C for up to 3 Months.
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
CAS Datenbank	5300-03-8(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-Einstufung	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]
Regulatorische Informationen	Alitretinoin: Does not have an individual approval but may be used under an appropriate group standard
FDA-Anforderungen	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.
Brandbekämpfungsverfahren	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.
Lagerbedingungen	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).
Reinigungsverfahren	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.

Anwendungen & Verwendung

Beschreibung

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.

Verwenden

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.