Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C48H78O19 |
Molecular Weight | 959.1215 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 27 / 27 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]8(O[C@@H]1[C@@H](CO)O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@]34CC[C@@H](C)[C@H](C)[C@@]3([H])C5=CC[C@]6([H])[C@@]7(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]7([H])CC[C@@]6(C)[C@]5(C)CC4)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O
InChI
InChIKey=WYQVAPGDARQUBT-FGWHUCSPSA-N
InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22+,24-,25-,26-,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,44+,45+,46-,47-,48+/m1/s1
Molecular Formula | C48H78O19 |
Molecular Weight | 959.1215 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 27 / 27 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.mims.com/indonesia/drug/info/madecassolCurator's Comment: Description was created based on several sources, including
http://www.indena.com/pdf/asiaticoside_st_pc.pdf
https://www.ncbi.nlm.nih.gov/pubmed/10350364
Sources: http://www.mims.com/indonesia/drug/info/madecassol
Curator's Comment: Description was created based on several sources, including
http://www.indena.com/pdf/asiaticoside_st_pc.pdf
https://www.ncbi.nlm.nih.gov/pubmed/10350364
Asiaticoside is a triterpene found in Centella that exhibits anti-inflammatory, neuroprotective, cognition enhancing, antipyretic, antioxidative, pro-angiogenic, anticancer chemotherapeutic, and chemopreventive activities. Asiaticoside inhibits melanogenesis by decreasing DNA binding by MITF; as a result, it is occasionally used in skin whitening treatments. Asiaticoside induces apoptosis, increases activation of caspase 3, decreases release of TNF-α and IL-1β, and suppresses tumor development and size in animal models of breast cancer. In animal models of cerebral ischemia/reperfusion, asiaticoside improves memory and learning deficits and decreases levels of IL-6, TNF-α, and IL-1β. Additionally, asiaticoside decreases LPS-induced inflammation and fever, suppresses activity of myeloperoxidase, and increases activity of heme oxygenase 1 (HO-1) in vivo. Asiaticoside exhibits significant wound healing activity in normal as well as delayed healing models, increasing cell migration, attachment, and growth in vitro. Asiaticoside is an active ingredient of Madecassol, marketed in Korea as wound healing agent for traumatic or surgical wounds, burns, skin grafts, fistulas, abnormal retractile or decubitus scars, cutaneomucous lesions in ENT, gynaecology, ulcerous lesions in leprosy, striae distensae, cellulitis, varicose leg ulcers, haemorrhoid..
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0032964 |
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Target ID: GO:0034205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25880304 |
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Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24667059 |
40.0 µM [IC50] | ||
Target ID: CHEMBL614392 |
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Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24051027 |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21349323 |
385.24 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Madecassol Approved UseWound healing agent for traumatic or surgical wounds, burns, skin grafts, fistulas, abnormal retractile or decubitus scars, cutaneomucous lesions in ENT, gynaecology, ulcerous lesions in leprosy, striae distensae, cellulitis, varicose leg ulcers, haemorrhoid. |
|||
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.mims.com/indonesia/drug/info/madecassol
Apply 1-2 times daily. Debride and disinfect the wound before application.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22628285
A significant reduction of MMP-1 mRNA expression was noted at the
highest concentration of asiaticoside (100 ug/mL) whereas a significant increase of TIMP-1 mRNA expression was observed at lower concentrations (25 and 50 ug/mL) in human periodontal ligament cells..
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 01:11:44 GMT 2023
by
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on
Sat Dec 16 01:11:44 GMT 2023
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Record UNII |
PKO39VY215
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Record Status |
Validated (UNII)
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Centella asiatica aerial parts.
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