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64-86-8 molecular structure
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N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide

ChemBase ID: 1205
Molecular Formular: C22H25NO6
Molecular Mass: 399.437
Monoisotopic Mass: 399.16818753
SMILES and InChIs

SMILES:
O(c1c2c(CC[C@H](NC(=O)C)c3c2ccc(OC)c(=O)c3)cc(OC)c1OC)C
Canonical SMILES:
COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)OC
InChI:
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1
InChIKey:
IAKHMKGGTNLKSZ-INIZCTEOSA-N

Cite this record

CBID:1205 http://www.chembase.cn/molecule-1205.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
IUPAC Traditional name
colchicine
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
Brand Name
Colbenemid
Col-probenecid
Condylon
Proben-C
Synonyms
Colchicine
(S)-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide
Colchicin
Colchicina
Colchicinum
Colchicine
N-[(7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
(-)-Colchicine
Colchineos
Colchisol
Colcin
Colsaloid
Condylon
NSC 757
(S)-Colchicine >95%
(R)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
(+)-Colchicine
(R)-Colchicine
Colchiceine methyl ether
Artrichine
秋水仙素
秋水仙碱
CAS Number
64-86-8
75520-89-7
EC Number
200-598-5
MDL Number
MFCD00078484
Beilstein Number
2228813
Merck Index
142471
PubChem SID
24892656
160964667
24278348
PubChem CID
6167
CHEBI ID
27882
ATC CODE
M04AC01
CHEMBL
107
Chemspider ID
5933
DrugBank ID
DB01394
IUPHAR ligand ID
2367
KEGG ID
D00570
Unique Ingredient Identifier
SML2Y3J35T
Wikipedia Title
Colchicine
Medline Plus
a682711

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.057998  H Acceptors
H Donor LogD (pH = 5.5) 1.4619884 
LogD (pH = 7.4) 1.4619886  Log P 1.4619886 
Molar Refractivity 111.3756 cm3 Polarizability 41.70993 Å3
Polar Surface Area 83.09 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.59  LOG S -4.16 
Solubility (Water) 2.76e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
45 mg/mL at 25 oC [SEIDELL,A (1941)] expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
ethanol: soluble50 mg/mL expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
white to yellow powder expand Show data source
Yellow Solid expand Show data source
Melting Point
106-132°C expand Show data source
150-152°C expand Show data source
150-160 °C (dec.)(lit.) expand Show data source
155-157°C expand Show data source
ca 150°C dec. expand Show data source
Optical Rotation
[α]24/D -443°, c = 1.7 in H2O expand Show data source
Hydrophobicity(logP)
1.30 [HANSCH,C ET AL. (1995)] expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
Storage Warning
Light Sensitive expand Show data source
RTECS
GH0700000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
1544 expand Show data source
UN1544 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
I expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
46-28 expand Show data source
R:26/28 expand Show data source
Safety Statements
53-16-26-28-36/37-45 expand Show data source
53-45 expand Show data source
S:13-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
151 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300 + H330-H318-H340 expand Show data source
H300-H340 expand Show data source
GHS Precautionary statements
P201-P260-P264-P280-P284-P301 + P310 expand Show data source
P281-P301+P310-P321-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 1544 6.1/PG 1 expand Show data source
Admin Routes
Oral tablets expand Show data source
Excretion
Primarily feces, urine 10-20% expand Show data source
Half Life
9.3 - 10.6 hours expand Show data source
Legal Status
RX/POM expand Show data source
Pregnancy Category
X expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669) expand Show data source
Mechanism of Action
Exact mechanism unknown expand Show data source
Interferes with kinin formation expand Show data source
Leukocyte migration inhibitor expand Show data source
Phagocytosis inhibitor expand Show data source
Reduces phagocytosis with inflammatory expand Show data source
Response abatement expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥96.0% (HPLC) expand Show data source
95% expand Show data source
95% (dry wt.) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
plant cell culture tested expand Show data source
Impurities
≤10% ethyl acetate + H2O expand Show data source
≤3% water expand Show data source
10% ethyl acetate and chloroform expand Show data source
Biological Source
Chief alkaloid from Colchicum autumnale, many other Colchicum spp., several Merendera spp., Gloriosa superba and others (Liliaceae) expand Show data source
Application(s)
Antirheumatic expand Show data source
Cytostatic expand Show data source
Immunosuppressive expand Show data source
Potential HIV inhibitor expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C22H25NO6 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02101406 external link
Special Shipping Requirements: Hazardous Material. Contact Customer Service for details. $8.00 additional service charge per shipment.
MP Biomedicals - 05208170 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB01394 external link
Item Information
Drug Groups approved
Description A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (periodic disease). [PubChem]
Indication For treatment and relief of pain in attacks of acute gouty arthritis.
Pharmacology Colchicine is a highly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the "Meadow saffron"). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. Its present medicinal use is mainly in the treatment of gout; as well, it is being investigated for its potential use as an anti-cancer drug. It can also be used as initial treatment for pericarditis and preventing recurrences of the condition.
Toxicity The onset of toxic effects is usually delayed for several hours or more after the ingestion of an acute overdose. Nausea, vomiting, abdominal pain, and diarrhea occur first. The diarrhea may be bloody due to hemorrhagic gastroenteritis. Burning sensations of the throat, stomach, and skin may be prominent symptoms. Extensive vascular damage may result in shock. Kidney damage, evidenced by hematuria and oliguria, may occur. Muscular weakness may be marked, and ascending paralysis of the central nervous system may develop; the patient usually remains conscious. Delirium and convulsions may occur. Death due to respiratory arrest may result. Although death from the ingestion of as little as 7 mg has been reported, much larger doses have been survived .
Affected Organisms
Humans and other mammals
Biotransformation Probably hepatic. Although colchicine metabolites have not been identified in humans, metabolism by mammalian hepatic microsomes has been demonstrated in vitro.
Absorption Colchicine is rapidly absorbed after oral administration, probably from the jejunum and ileum. However, the rate and extent of absorption are variable, depending on the tablet dissolution rate; variability in gastric emptying, intestinal motility, and pH at the absorption site; and the extent to which colchicine is bound to microtubules in gastrointestinal mucosal cells.
Half Life Elimination half-life is approximately 1 hour in healthy subjects, although a study with an extended sampling time reported mean terminal elimination half-life values of approximately 9 to 10.5 hours. Other studies have reported half-life values of approximately 2 hours in patients with alcoholic cirrhosis and approximately 2.5 hours in patients with familial Mediterranean fever.
Protein Binding Low to moderate (30 to 50%).
Elimination In healthy volunteers (n=12) 40 – 65% of 1 mg orally administered colchicine was recovered unchanged in urine.
Enterohepatic recirculation and biliary excretion are also postulated to play a role in colchicine elimination.
Distribution * 5 to 8 L/kg [healthy young volunteers]
Clearance * 0.17 L/hr/kg [familial Mediterranean fever patients with end-stage renal disease]
* 0.73 L/hr/kg [familial Mediterranean fever patients with normal renal function]
External Links
Wikipedia
RxList
Drugs.com
DrugBank - DB08117 external link
Drug information: experimental
Sigma Aldrich - C9754 external link
Packaging
1, 5 g in poly bottle
100, 500 mg in poly bottle
Biochem/physiol Actions
Antimitotic agent that disrupts microtubules by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.
Sigma Aldrich - C3915 external link
Biochem/physiol Actions
Colchicine is an inhibitor of microtubule polymerization which blocks chromosome segregation during meiosis. Consequently, Colchicine is used to induce polyploidy (tetraploid) in plant cells.
Sigma Aldrich - 855774 external link
Application
For a review summarizing the metabolism and pharmacokinetics of this alkaloid, see Z. Gastroenterol. .1,2
Sigma Aldrich - 27650 external link
Other Notes
Binds specifically with tubulin thus interfering with microtubule organization.1
Toronto Research Chemicals - C640000 external link
An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pa
Toronto Research Chemicals - C640001 external link
The R-enantiomer of Colchicine (C640000). An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lin

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
  • • Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
  • • Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
  • • Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
  • • Jordan, A., et al.: Med. Res. Rev
  • • Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
  • • Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
  • • Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
  • • Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
  • • Jordan, A., et al.: Med. Res. Rev
  • • J.Am.Coll.Cardiol. (26, No. 6, 1549-57, 1995)
  • • Local delivery of biodegradable microparticles containing colchicine or a colchicine analogue: effects on restenosis and implications for catheter-based drug delivery.
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PATENTS

PATENTS

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INTERNET

INTERNET

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