Tranilast
Grundinformationen
- CAS
70806-55-2- Standard-SMILES
COc1ccc(/C=C/C(=O)Nc2ccccc2C(=O)O)cc1OC- InChIKey
NZHGWWWHIYHZNX-CSKARUKUSA-N- Summenformel
- C18H17NO5
- Durchschnittliche Molmasse
- 327,3 g/mol
Überblick
Tranilast is an amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group. It has a role as an antineoplastic agent, a calcium channel blocker, an anti-asthmatic drug, an anti-allergic agent, a hepatoprotective agent, an aryl hydrocarbon receptor agonist and a nephroprotective agent. It is a secondary carboxamide, a member of cinnamamides, an amidobenzoic acid and a dimethoxybenzene. It is functionally related to an anthranilic acid.
Namen und Bezeichner
- Bevorzugter Name
- Tranilast
- IUPAC
- 2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid
- Englischer Name
- trans-Tranilast
- Summenformel
- C18H17NO5
- Molmasse
- 327.33
Namen und Synonyme
tranilast53902-12-8RizabenTranilastumMK-341HVF50SMY6EN-(3,4-Dimethoxycinnamoyl)anthranilic acidNSC-758970CHEBI:775722-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic AcidBENZOIC ACID, 2-((3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)AMINO)-
Weitere Namen anzeigen
Tranilast (trans-)trans-Tranilast, >98%Trans-Tranilast, 10 mM in DMSOTranilast Impurity 3 (trans-Tranilast)2-(3,4-Dimethoxycinnamoylamino)benzoic acid2-(3,4-Dimethoxy-trans-cinnamoylamino)benzoic acid(E)-2-(3-(3,4-dimethoxyphenyl)propyleneamideyl)benzenemacetic acid2-[[(2E)-3-(3,4-DiMethoxyphenyl)-1-oxo-2-propen-1-yl]aMino]benzoic AcidBenzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]-
2-{[(2e)-3-(3,4-Dimethoxyphenyl)prop-2-Enoyl]amino}benzoic Acid2-(((2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl)amino)benzoic acidBenzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-RefChem:898664MK341N (3', 4'-dimethoxycinnamoyl) anthranilic acid (N-5')1 N-(3'-4'-dimethoxycinnamoyl) anthranilic acid (N-5'), N(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5')trans-Tranilast
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,2
- Polarare Oberfläche (TPSA)
- 84,9 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 464
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 184 °C · 184 °C(Solv: water (7732-18-5); acetone (67-64-1))
- Siedepunkt
- 585.6 · 585.6±50.0 °C(Predicted)
- Dichte
- 1.299 · 1.299±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- 100 mg/mL · DMSO: 100 mg/mL (305.50 mM)
- pka
- 3.45 · 3.45±0.36(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tranilast
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Anwendungen
Verwendentrans-Tranilast is used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.
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