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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
Structure of BETULIN

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

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment: Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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)
Soft tissue infection (serious, 6 patients)
wound infection (serious, 6 patients)
aggravated condition (serious, 6 patients)
Other AEs:
Pruritic rash (1 pt)
Wound inflammation (1 pt)
Wound complication (1 pt)
Pain of skin (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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

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
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
by admin
on Mon Mar 31 20:39:36 GMT 2025
Edited
by admin
on Mon Mar 31 20:39:36 GMT 2025
Record UNII
6W70HN7X7O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CP BETULIN
Preferred Name English
BETULIN
INCI   MI  
INCI  
Official Name English
LUP-20(29)-ENE-3,28-DIOL, (3.BETA.)-
Common Name English
BETULINIC ALCOHOL
Common Name English
LUP-20(30)-ENE-3.BETA.,28-DIOL
Common Name English
(+)-BETULIN
Common Name English
BETULINE
Common Name English
BETULIN [MI]
Common Name English
NSC-4644
Code English
LUP-20(29)-ENE-3.BETA.,28-DIOL
Common Name English
ORISTRACT BTL
Brand Name English
BETULINOL
Common Name English
Code System Code Type Description
DAILYMED
6W70HN7X7O
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
RXCUI
2467840
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
MERCK INDEX
m2462
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY Merck Index
PUBCHEM
72326
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
CHEBI
3086
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
CAS
473-98-3
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
MESH
C002503
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
WIKIPEDIA
Betulin
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-475-5
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID101019934
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
FDA UNII
6W70HN7X7O
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
NSC
4644
Created by admin on Mon Mar 31 20:39:36 GMT 2025 , Edited by admin on Mon Mar 31 20:39:36 GMT 2025
PRIMARY
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TARGET -> INHIBITOR
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BINDER->LIGAND
TARGET -> INHIBITOR
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