Triptolide
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Triptolide
structure -
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CAS No:
38748-32-2
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Formula:
C20H24O6
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Chemical Name:
Triptolide
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Synonyms:
Trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one,3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-,(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-;Triptolide;(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-Decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one;Triptolid;[3bS-(3bα,4aα,5aR*,6β,6aβ,7aβ,7bα,8aR*,8bβ)]-3b,4,4a,6,6a,7a,7b,8b,9,10-Decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one;(-)-Triptolide;PG 490;NSC 163062
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CAS No:
Description
Triptolide is a diterpenoid triepoxide extracted from the root of Tripterygium wilfordii with immunosuppressive, anti-inflammatory and antiproliferative effects. Triptolide is a NF-κB activation inhibitor.
Triptolide is an organic heteroheptacyclic compound, an epoxide, a gamma-lactam and a diterpenoid. It has a role as an antispermatogenic agent and a plant metabolite.|Triptolide has been used in trials studying the treatment of HIV, Crohn's Disease, Intestinal Diseases, Gastrointestinal Diseases, and Digestive System Diseases, among others.
Characteristics
84.1
0.2
white to off-white solid
1.5±0.1 g/cm3
226-227 °C
601.7ºC at 760 mmHg
220.7±25.0 °C
1.647
DMSO: soluble
2-8°C
LD50 i.p. in mice: 1.93 mg/kg (Chen)
D25 -154°
Safety Information
6.1
2811
3
22-24/25
YK7751000
P201, P202, P260, P264, P270, P271, P281, P284, P301+P310, P304+P340, P308+P313, P310, P320, P321, P330, P403+P233, P405, P501
H300
|Danger|H300 (60%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P281, P284, P301+P310, P304+P340, P308+P313, P310, P320, P321, P330, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Agents, either mechanical or chemical, which destroy spermatozoa in the male genitalia and block spermatogenesis. (See all compounds classified as Antispermatogenic Agents.)
PG490
Triptolide Use and Manufacturing
Labelled Triptolite (T815600), diterpenoid triepoxide with immunosuppressant and antitumor properties.
Computed Properties
Molecular Weight:360.4
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:360.15728848
Monoisotopic Mass:360.15728848
Topological Polar Surface Area:84.1
Heavy Atom Count:26
Complexity:819
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It has strong anti-inflammatory and immunosuppressive effects. In terms of anti-inflammatory effects, it can antagonize and inhibit the release of inflammatory mediators and the degree of experimental inflammatory response. In terms of immunosuppressive effects, it can inhibit T cell function, delayed allergic reactions, interleukin-1 secretion, and the division and reproduction of mitogens and antigen-stimulated T cells.
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