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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H23NO6
Molecular Weight 385.4104
Optical Activity UNSPECIFIED
Additional Stereochemistry Yes
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0
Stereo Comments M-helix

SHOW SMILES / InChI
Structure of COLCHICEINE

SMILES

COC1=CC2=C(C(OC)=C1OC)C3=CC=C(O)C(=O)C=C3[C@H](CC2)NC(C)=O

InChI

InChIKey=PRGILOMAMBLWNG-HNNXBMFYSA-N
InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H23NO6
Molecular Weight 385.4104
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Colchiceine, a metabolite of colchicine, commonly used to treat gout, was studied as an effective compound in the model of liver damage.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

in rats: CCl4 for 8 weeks followed by colchiceine (60 microg kg(-1)) + CCl4 for 5 weeks
Route of Administration: Oral
It was determined the cytotoxicity of colchiceine (EIN) in comparison with that of colchicine (COL); to evaluate the effect of EIN on cytochrome P450 (CYP) expression and activity. Primary human hepatocytes were the model of choice for cytotoxicity and CYP expression experiments. EIN was less toxic than COL based on both parameters within the concentration range 1-100 microM. 10 microM concentration of EIN did not induce the expression of CYP1A2, CYP2A6, CYP2C9, CYP2C19, CYP2E1 and CYP3A4 isoforms, which were evaluated at the levels of mRNAs, proteins and specific activities in culture. EIN in concentrations up to 200 microM had no effect on marker activities of CYP1A2, 2C9, 2E1 and 3A4 in human liver microsomes. It was concluded that EIN in concentrations up to 10 microM is not cytotoxic in primary human hepatocytes as revealed by albumin secretion and LDH leakage.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:51:53 GMT 2023
Edited
by admin
on Sat Dec 16 08:51:53 GMT 2023
Record UNII
HJ30158L57
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COLCHICEINE
MI  
Common Name English
O10-DEMETHYLCOLCHICINE
Common Name English
COLCHICEINE [MI]
Common Name English
NSC-33411
Code English
N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)ACETAMIDE
Systematic Name English
COLCHICINE IMPURITY F [EP IMPURITY]
Common Name English
ACETAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-
Systematic Name English
NSC-123396
Code English
Code System Code Type Description
FDA UNII
HJ30158L57
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-512-5
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
CAS
477-27-0
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
PUBCHEM
234105
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
NSC
33411
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
DRUG BANK
DB15534
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
NSC
123396
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
DAILYMED
HJ30158L57
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID60878565
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
RXCUI
2174385
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY
MERCK INDEX
m3724
Created by admin on Sat Dec 16 08:51:53 GMT 2023 , Edited by admin on Sat Dec 16 08:51:53 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> IMPURITY