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
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(=O)O[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O
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 |
|||
Target ID: GO:0034205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25880304 |
|||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24667059 |
40.0 µM [IC50] | ||
Target ID: CHEMBL614392 |
|||
Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24051027 |
|||
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
by
admin
on
Edited
Mon Mar 31 20:46:01 GMT 2025
by
admin
on
Mon Mar 31 20:46:01 GMT 2025
|
| Record UNII |
PKO39VY215
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
166062
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
18405
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | RxNorm | ||
|
16830-15-2
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
C63665
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
DTXSID30937476
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
1043331
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
m2092
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | Merck Index | ||
|
PKO39VY215
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
SUB12949MIG
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
DB14081
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
11954171
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
100000077438
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
C004446
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
PKO39VY215
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
240-851-7
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY | |||
|
36002
Created by
admin on Mon Mar 31 20:46:01 GMT 2025 , Edited by admin on Mon Mar 31 20:46:01 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Centella asiatica aerial parts.
|