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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H34O6
Molecular Weight 442.5455
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINOBUFAGIN

SMILES

CC(=O)O[C@]1([H])[C@]([H])(c2ccc(=O)oc2)[C@@]3(C)CC[C@@]4([H])[C@@]([H])(CC[C@]5([H])C[C@]([H])(CC[C@@]54C)O)[C@]63[C@]1([H])O6

InChI

InChIKey=SCULJPGYOQQXTK-OLRINKBESA-N
InChI=1S/C26H34O6/c1-14(27)31-22-21(15-4-7-20(29)30-13-15)25(3)11-9-18-19(26(25)23(22)32-26)6-5-16-12-17(28)8-10-24(16,18)2/h4,7,13,16-19,21-23,28H,5-6,8-12H2,1-3H3/t16-,17+,18+,19-,21+,22-,23-,24+,25-,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H34O6
Molecular Weight 442.5455
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Cinobufagin is a bufadienolide compound extracted from the dried venom secreted by the parotid glands of toads and one of the glycosides in the traditional Chinese medicine ChanSu, with potential antineoplastic activity. Cinobufagin has been shown to have clinical applications in cancer treatment as well as immunomodulatory and analgesic properties. Cinobufagin induces apoptosis of osteosarcoma cells through inactivation of Notch signaling. Cinobufagin induces autophagy-mediated cell death in human osteosarcoma U2OS cells through the ROS/JNK/p38 signaling pathway. Cinobufagin significantly relieved cancer pain in mice and raised their pain threshold, mainly upregulating the expression levels of beta-Endorphin and μ- opioid receptor in the hind paw tumor and adjacent tissue. In combination with gemcitabine-oxaliplatin cinobufagin was used in clinical trial for the treatment of locally advanced or metastatic gallbladder carcinoma.

Originator

Sources: DOI: 10.1002/jlac.19284650103

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: POMC/β-endorphin/μ-opioid receptor pathway
Target ID: ROS/JNK/p38 signaling pathway
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Induction of cytochrome P450 3A by Shexiang Baoxin Pill and its main components.
2012 Jan 25
Patents

Sample Use Guides

2-3 h infusion (20 mL/m2) (0.5 g/mL) in 500 mL of 50 g/L glucose solution on days 3-11
Route of Administration: Intravenous
The survival rates of cinobufagin (0–300 nM) in 143B cells after 24, 48 and 72 h were investigated. Cinobufagin (100 nM) inhibited ~ 50% proliferation of 143 cells and the half-maximal inhibitory concentration (IC50) values were ~ 98–103 nM after 48 h treatment.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:36:54 UTC 2021
Edited
by admin
on Sat Jun 26 03:36:54 UTC 2021
Record UNII
T9PSN4R8IR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINOBUFAGIN
Common Name English
BUFA-20,22-DIENOLIDE, 16-(ACETYLOXY)-14,15-EPOXY-3-HYDROXY-, (3- .BETA.,5-.BETA.,15-.BETA.,16-.BETA.)-
Systematic Name English
CINOBUFAGIN [WHO-DD]
Common Name English
NSC-90325
Code English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
NCI_THESAURUS C45653
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
Code System Code Type Description
PUBCHEM
11969542
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
PRIMARY
FDA UNII
T9PSN4R8IR
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
PRIMARY
WIKIPEDIA
Cinobufagin
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
PRIMARY
CAS
470-37-1
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
PRIMARY
NCI_THESAURUS
C95021
Created by admin on Sat Jun 26 03:36:54 UTC 2021 , Edited by admin on Sat Jun 26 03:36:54 UTC 2021
PRIMARY NCIT
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY