U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[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

HIDE SMILES / InChI

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

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

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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
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
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
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
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
[Studies on chemical constituents from roots of Pterospermum heterophyllum].
2008 Aug
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
Betulin binds to gamma-aminobutyric acid receptors and exerts anticonvulsant action in mice.
2008 Oct
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

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 Sat Dec 16 00:42:49 GMT 2023
Edited
by admin
on Sat Dec 16 00:42:49 GMT 2023
Record UNII
6W70HN7X7O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CP BETULIN
Brand Name English
NSC-4644
Code English
LUP-20(29)-ENE-3.BETA.,28-DIOL
Common Name English
ORISTRACT BTL
Brand Name English
BETULIN [INCI]
Common Name English
BETULINOL
Common Name English
Code System Code Type Description
DAILYMED
6W70HN7X7O
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
RXCUI
2467840
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
MERCK INDEX
m2462
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY Merck Index
PUBCHEM
72326
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
CHEBI
3086
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
CAS
473-98-3
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
MESH
C002503
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
WIKIPEDIA
Betulin
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-475-5
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID101019934
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
FDA UNII
6W70HN7X7O
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY
NSC
4644
Created by admin on Sat Dec 16 00:42:49 GMT 2023 , Edited by admin on Sat Dec 16 00:42:49 GMT 2023
PRIMARY