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
[H][C@]12[C@@H](CC[C@]1(CO)CC[C@]3(C)[C@]2([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(C)=C
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 | 9 / 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 |
|||
Curative | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Disc. AE: Soft tissue infection, aggravated condition... Other AEs: Pain of skin, Wound inflammation... AEs leading to discontinuation/dose reduction: Soft tissue infection (serious, 6 patients) Other AEs:aggravated condition (serious, 6 patients) wound infection (serious, 6 patients) Wound necrosis (serious, 6 patients) Pain of skin (2 patients) Sources: Wound inflammation (1 pt) Pruritic rash (1 pt) Wound complication (1 pt) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pruritic rash | 1 pt | 72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Wound complication | 1 pt | 72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Wound inflammation | 1 pt | 72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Pain of skin | 2 patients | 72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Soft tissue infection | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Wound necrosis | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
aggravated condition | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
wound infection | serious, 6 patients Disc. AE |
72 % 1 times / day multiple, topical (unknown) Studied dose Dose: 72 %, 1 times / day Route: topical Route: multiple Dose: 72 %, 1 times / day Sources: |
unhealthy, ADULT n = 20 Health Status: unhealthy Condition: burns Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
Chemical characterization of fine particle emissions from fireplace combustion of woods grown in the northeastern United States. | 2001 Jul 1 |
|
Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. | 2001 May |
|
Ethnopharmacology and bioinformatic combination for leads discovery: application to phospholipase A(2) inhibitors. | 2001 Nov |
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Diterpenoids from the stem bark of Croton zambesicus. | 2002 Jun |
|
Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. | 2002 Nov |
|
[Synthesis and pharmacological activity of betulin dinicotinate]. | 2002 Nov-Dec |
|
Pentacyclic triterpenoids from Ilex macropoda. | 2002 Oct |
|
Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium. | 2002 Oct |
|
[Study on chemical constituents of rhizome of Anemone raddeana]. | 2002 Sep |
|
Triterpenoids from the stembark of Pyrus communis. | 2003 Dec |
|
New triterpenoids from Gentiana lutea. | 2003 Jan |
|
Cytotoxic triterpenes from the twigs of Celtis philippinensis. | 2003 Jan |
|
New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata. | 2003 Mar |
|
Cytotoxic lupane-type triterpenoids from Acacia mellifera. | 2004 Apr |
|
Determination of betulin in Grewia tiliaefolia by HPTLC. | 2004 Jan |
|
In vitro androgenicity in pulp and paper mill effluents. | 2004 Oct |
|
Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. | 2005 Feb |
|
[Synthesis and antitumor activity of cyclopropane derivatives of betulinic and betulonic acids]. | 2005 May-Jun |
|
Unusual naphthoquinones, catechin and triterpene from Byrsonima microphylla. | 2005 Oct |
|
Correlation of cytotoxic activity of betulinines and their hydroxy analogues. | 2005 Oct 1 |
|
Protective effects of betulin and betulinic acid against ethanol-induced cytotoxicity in HepG2 cells. | 2005 Sep-Oct |
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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 |
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Structure-activity relationships of triterpenoid saponins on fruiting body induction in Pleurotus ostreatus. | 2006 Aug |
|
Antiproliferative terpenoids from almond hulls (Prunus dulcis): identification and structure-activity relationships. | 2006 Feb 8 |
|
Streblus asper Lour. (Shakhotaka): A Review of its Chemical, Pharmacological and Ethnomedicinal Properties. | 2006 Jun |
|
Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2. | 2006 Mar 1 |
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Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents. | 2006 Oct 1 |
|
Pharmacological properties of the ubiquitous natural product betulin. | 2006 Sep |
|
Boc-lysinated-betulonic acid: a potent, anti-prostate cancer agent. | 2006 Sep 15 |
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Triterpenic and other lipophilic components from industrial cork byproducts. | 2006 Sep 6 |
|
Betulin binds to melanocortin receptors and antagonizes alpha-melanocyte stimulating hormone induced cAMP generation in mouse melanoma cells. | 2007 Sep-Oct |
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[Studies on chemical constituents from roots of Pterospermum heterophyllum]. | 2008 Aug |
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Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa. | 2008 Jan |
|
Potential anti-tumor-promoting activity of 3alpha-hydroxy-D:A-friedooleanan-2-one from the stem bark of Mallotus philippensis. | 2008 Mar |
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Betulin binds to gamma-aminobutyric acid receptors and exerts anticonvulsant action in mice. | 2008 Oct |
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Interaction of the globular domain of human C1q with Salmonella typhimurium lipopolysaccharide. | 2008 Sep |
|
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 Feb |
|
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 Feb |
|
Analysis of pentacyclic triterpenes by LC-MS. A comparative study between APCI and APPI. | 2009 Jan |
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
Created
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admin
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Edited
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Record UNII |
6W70HN7X7O
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Record Status |
Validated (UNII)
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Record Version |
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Betulin
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