Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H50O2 |
| Molecular Weight | 442.7168 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12
InChI
InChIKey=FVWJYYTZTCVBKE-ROUWMTJPSA-N
InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
| Molecular Formula | C30H50O2 |
| Molecular Weight | 442.7168 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800035982
https://www.ncbi.nlm.nih.gov/pubmed/16716572
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800035982
https://www.ncbi.nlm.nih.gov/pubmed/16716572
Betulin is an extract from bark of the white birch tree, which has been known since the 18th century and is chemically defined. Betulin was discovered by German-Russian chemist Johann Tobias Lowitz. He was the first scientist to study and characterise betulin, and in doing was one of the first to isolate an active plant ingredient. In numerous scientific studies, the natural active ingredient betulin has been found to have anti-inflammatory, anti-bacterial and regenerating properties. Birken AG creates a patented process for extracting high-quality betulin from birch bark. Betulin works as keratinocyte modulator and transient receptor potential channel stimulant. An extensive study program including three clinical phase III trials was initiated to develop the drug candidate Oleogel-S10, Betulin-based oleogel, as the lead indication for accelerated wound healing of partial thickness wounds. In addition, Oleogel-S10 obtained the Orphan Drug Designation for the treatment of hereditary skin disorder Epidermolysis bullosa (EB) from the European Commission. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27492128 |
15.2 µM [IC50] | ||
Target ID: CHEMBL392 |
5.2 µM [IC50] | ||
Target ID: CHEMBL613834 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27492128 |
3.1 µM [IC50] | ||
Target ID: CHEMBL2366922 |
17.08 µM [IC50] | ||
Target ID: CHEMBL2045 |
0.67 µM [Ki] | ||
Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26118418 |
4.17 µM [IC50] | ||
Target ID: CHEMBL360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25725435 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Curative | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Wound necrosis, Soft tissue infection... Other AEs: Pruritic rash, Wound inflammation... AEs leading to discontinuation/dose reduction: Wound necrosis (serious, 6 patients) Other AEs:Soft tissue infection (serious, 6 patients) wound infection (serious, 6 patients) aggravated condition (serious, 6 patients) Pruritic rash (1 pt) Sources: Wound inflammation (1 pt) Wound complication (1 pt) Pain of skin (2 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Pruritic rash | 1 pt | 72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Wound complication | 1 pt | 72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Wound inflammation | 1 pt | 72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Pain of skin | 2 patients | 72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Soft tissue infection | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Wound necrosis | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| aggravated condition | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| wound infection | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Efficacy and mechanism of action of KHBJ-9B, a new herbal medicine, and its major compound triterpenoids in human cartilage culture and in a rabbit model of collagenase-induced osteoarthritis. | 2009-02 |
|
| Anti-cancer effect of Betulin on a human lung cancer cell line: a pharmacoproteomic approach using 2 D SDS PAGE coupled with nano-HPLC tandem Mass Spectrometry. | 2009-02 |
|
| Treatment of actinic keratoses with a novel betulin-based oleogel. A prospective, randomized, comparative pilot study. | 2009-02 |
|
| Analysis of pentacyclic triterpenes by LC-MS. A comparative study between APCI and APPI. | 2009-01 |
|
| Identification of new molecules extracted from Quercus suber L. cork. | 2008-11 |
|
| Betulin binds to gamma-aminobutyric acid receptors and exerts anticonvulsant action in mice. | 2008-10 |
|
| Comparison with various parts of Broussonetia papyrifera as to the antinociceptive and anti-inflammatory activities in rodents. | 2008-09 |
|
| Interaction of the globular domain of human C1q with Salmonella typhimurium lipopolysaccharide. | 2008-09 |
|
| [Transformation of betulin diacetate by the Prins reaction]. | 2008-08-13 |
|
| [Studies on chemical constituents from roots of Pterospermum heterophyllum]. | 2008-08 |
|
| Investigation of Indian diospyros species for antiplasmodial properties. | 2008-06 |
|
| Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents. | 2008-05-05 |
|
| alpha-Glucosidase inhibitory activity of triterpenoids from Cichorium intybus. | 2008-05 |
|
| An ethnobotanical study of medicinal plants in Mana Angetu district, southeastern Ethiopia. | 2008-04-28 |
|
| The use of primary hepatocytes from brown trout (Salmo trutta lacustris) and the fish cell lines RTH-149 and ZF-L for in vitro screening of (anti)estrogenic activity of wood extractives. | 2008-04 |
|
| Potential anti-tumor-promoting activity of 3alpha-hydroxy-D:A-friedooleanan-2-one from the stem bark of Mallotus philippensis. | 2008-03 |
|
| Effects of the wood extractives dehydroabietic acid and betulinol on reproductive physiology of zebrafish (Danio rerio)-a two-generation study. | 2008-02-18 |
|
| [Effect of nitrogen-containing derivatives of the plant triterpenes betulin and glycyrrhetic acid on the growth of MT-4, MOLT-4, CEM, and Hep G2 tumor cells]. | 2008-01-05 |
|
| Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa. | 2008-01 |
|
| A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework. | 2007-12-05 |
|
| Phytochemical and antinociceptive properties of Matayba elaeagnoides Radlk. barks. | 2007-10-05 |
|
| Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3beta-O-monodesmosidic saponins starting from betulin. | 2007-09-15 |
|
| Reciprocal regulation of endothelial nitric-oxide synthase and NADPH oxidase by betulinic acid in human endothelial cells. | 2007-08 |
|
| Betulin binds to melanocortin receptors and antagonizes alpha-melanocyte stimulating hormone induced cAMP generation in mouse melanoma cells. | 2007-07-03 |
|
| Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycin-resistant enterococci (VRE). | 2007-06 |
|
| Ethnobotanical remarks on Central and Southern Italy. | 2007-05-30 |
|
| Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates. | 2007-05-15 |
|
| In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae). | 2007-05 |
|
| Triterpenoid pyrazines and benzopyrazines with cytotoxic activity. | 2007-04 |
|
| Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities. | 2007-03 |
|
| A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis. | 2007-03 |
|
| Simultaneous determination of betulin and betulinic acid in white birch bark using RP-HPLC. | 2007-02-19 |
|
| Physical, chemical and pharmacological characterization of a new oleogel-forming triterpene extract from the outer bark of birch (betulae cortex). | 2006-12 |
|
| Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents. | 2006-10-01 |
|
| Boc-lysinated-betulonic acid: a potent, anti-prostate cancer agent. | 2006-09-15 |
|
| Triterpenic and other lipophilic components from industrial cork byproducts. | 2006-09-06 |
|
| Pharmacological properties of the ubiquitous natural product betulin. | 2006-09 |
|
| Structure-activity relationships of triterpenoid saponins on fruiting body induction in Pleurotus ostreatus. | 2006-08 |
|
| Streblus asper Lour. (Shakhotaka): A Review of its Chemical, Pharmacological and Ethnomedicinal Properties. | 2006-06 |
|
| Protection of betulin against cadmium-induced apoptosis in hepatoma cells. | 2006-03-01 |
|
| Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2. | 2006-03-01 |
|
| Acyl-CoA: cholesterol acyltransferase inhibitors from Ilex macropoda. | 2006-03 |
|
| Antiproliferative terpenoids from almond hulls (Prunus dulcis): identification and structure-activity relationships. | 2006-02-08 |
|
| [Treatment of actinic keratoses with birch bark extract: a pilot study]. | 2006-02 |
|
| A disease epidemic on Zizyphus mucronata in the Kruger National Park caused by Coniodictyum chevalieri. | 2006 |
|
| Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry. | 2006 |
|
| [Antimycobacterial activity of a dry birch bark extract on a model of experimental pulmonary tuberculosis]. | 2006 |
|
| Lupane-triterpenes from Bupleurum flavum. | 2005-12 |
|
| [Chemical constituents from the mangrove plant Ceriops tagal]. | 2005-10 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
Patents
Sample Use Guides
About 1 cm of Oleogel-S10 string (approximately 100 mg) per cm² (i.e. approximately 1 mm thick) was
applied to one half of STSG donor site by applying it onto the wound-facing side of the wound dressing.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25725435
Betulin displayed a MIC of 12.5 ug/mL and an IC50 of 2.4 ug/mL against M. tuberculosis (H37Ra).
| Substance Class |
Chemical
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| Record UNII |
6W70HN7X7O
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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BINDER->LIGAND |
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TARGET -> INHIBITOR |
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ACTIVE MOIETY |
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