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Chemistry

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Also known as: 64-86-8, Colchisol, Colchineos, Colchicin, Colcin, Colchicina
Molecular Formula
C22H25NO6
Molecular Weight
399.4  g/mol
InChI Key
IAKHMKGGTNLKSZ-INIZCTEOSA-N
FDA UNII
SML2Y3J35T

Colchicine
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).
Colchicine is an Alkaloid. The mechanism of action of colchicine is as a Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Interaction.
1 2D Structure

Colchicine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
2.1.2 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
2.1.3 InChI Key
IAKHMKGGTNLKSZ-INIZCTEOSA-N
2.1.4 Canonical SMILES
CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
2.1.5 Isomeric SMILES
CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
2.2 Other Identifiers
2.2.1 UNII
SML2Y3J35T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Colchicine, (+-)-isomer

2. Colchicine, (r)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 64-86-8

2. Colchisol

3. Colchineos

4. Colchicin

5. Colcin

6. Colchicina

7. Colchicinum

8. Condylon

9. Colsaloid

10. Colcrys

11. 7alphah-colchicine

12. Kolkicin

13. Goutnil

14. (s)-colchicine

15. (-)-colchicine

16. Mitigare

17. Spindle Poison

18. Nsc 757

19. N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide

20. N-acetyl Trimethylcolchicinic Acid Methylether

21. Nsc757

22. N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide

23. Nsc-757

24. (s)-n-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide

25. Mfcd00078484

26. Chembl107

27. Sml2y3j35t

28. Chebi:27882

29. Colchicine [jan]

30. Colchicin [german]

31. Ncgc00025125-07

32. Colchysat

33. Colchicina [italian]

34. 7-alpha-h-colchicine

35. Dsstox_cid_4845

36. Dsstox_rid_77551

37. Dsstox_gsid_24845

38. Colstat

39. N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide

40. Acetamide, N-((7s)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-

41. Acetamide, N-[(7s)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-

42. Colchicine (tn)

43. N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5h-benzo[d]heptalen-7-yl]ethanamide

44. 30512-31-3

45. Loc

46. Smr000058323

47. Ccris 691

48. (s)-colchicine >95%

49. 7.alpha.h-colchicine

50. Hsdb 3044

51. Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (s)-

52. Colchicine [usp:jan]

53. Sr-01000075794

54. Sr-01000597576

55. Einecs 200-598-5

56. Unii-sml2y3j35t

57. Colchcine

58. Ai3-31149

59. (s)-colchicina

60. 4lzr

61. (s)-colchicin

62. Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(.alpha.)heptalen-7-yl)-

63. Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-

64. Mpc-004

65. N-((7s)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)- Acetamide

66. Cas-64-86-8

67. (s)-n-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide

68. Prestwick_695

69. Gloperba

70. Spectrum_000842

71. Tocris-1364

72. 4o2b

73. Colchicine [mi]

74. Prestwick0_000363

75. Prestwick1_000363

76. Prestwick2_000363

77. Prestwick3_000363

78. Spectrum2_000075

79. Spectrum3_000362

80. Spectrum4_000298

81. Spectrum5_000787

82. Colchcine [vandf]

83. Colchicine [hsdb]

84. Colchicinum [hpus]

85. Colchicine (jp17/usp)

86. Upcmld-dp065

87. Benzo(a)heptalen-9(5h)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-

88. C 9754

89. Ec 200-598-5

90. Colchicine [mart.]

91. Schembl8469

92. Colchicine [usp-rs]

93. Colchicine [who-dd]

94. Colchicine [who-ip]

95. N-[(7s)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide

96. Lopac0_000310

97. Methoxylated Analogue Of Xd1

98. Bspbio_000485

99. Bspbio_002083

100. Kbiogr_000856

101. Kbioss_001322

102. Colchicine (contains 5% Ethyl Acetate At Maximum)

103. Mls001055448

104. Mls001304089

105. Mls002153786

106. Divk1c_000753

107. Spectrum1500205

108. Spbio_000289

109. Spbio_002406

110. Bpbio1_000535

111. Gtpl2367

112. Megxp0_001879

113. Colchicine [ep Impurity]

114. Colchicine [orange Book]

115. Dtxsid5024845

116. Upcmld-dp065:001

117. Acon1_000353

118. Hms502f15

119. Kbio1_000753

120. Kbio2_001322

121. Kbio2_003890

122. Kbio2_006458

123. Kbio3_001303

124. Colchicine [ep Monograph]

125. Ninds_000753

126. Colchicine [usp Monograph]

127. Hms1569i07

128. Hms1920a08

129. Hms2091g16

130. Hms2096i07

131. Hms2231c05

132. Hms3260n22

133. Hms3713i07

134. Pharmakon1600-01500205

135. Zinc621853

136. Colchicinum [who-ip Latin]

137. Colchicine, >=96.0% (hplc)

138. Mitigare Component Colchicine

139. Proben-c Component Colchicine

140. Tox21_110947

141. Tox21_201547

142. Tox21_300582

143. Tox21_500310

144. Bdbm50014846

145. Ccg-39910

146. Nsc756702

147. Nsc813203

148. S2284

149. Colbenemid Component Colchicine

150. Akos001582887

151. Colchicine, >=95% (hplc), Powder

152. Tox21_110947_1

153. Colchicine Component Of Mitigare

154. Cs-1141

155. Db08117

156. Lp00310

157. Nsc-756702

158. Nsc-813203

159. Sdccgmls-0066633.p001

160. Sdccgsbi-0050298.p006

161. Colchicine Component Of Proben-c

162. Idi1_000753

163. N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-acetamide

164. Colchicine Component Of Colbenemid

165. Ncgc00025125-01

166. Ncgc00025125-02

167. Ncgc00025125-03

168. Ncgc00025125-04

169. Ncgc00025125-05

170. Ncgc00025125-06

171. Ncgc00025125-08

172. Ncgc00025125-09

173. Ncgc00025125-10

174. Ncgc00025125-11

175. Ncgc00025125-12

176. Ncgc00025125-13

177. Ncgc00025125-14

178. Ncgc00025125-15

179. Ncgc00025125-18

180. Ncgc00025125-20

181. Ncgc00025125-33

182. Ncgc00169157-01

183. Ncgc00169157-02

184. Ncgc00169157-03

185. Ncgc00254359-01

186. Ncgc00259096-01

187. Ncgc00260995-01

188. As-13686

189. Col-probenecid Component Colchicine

190. Hy-16569

191. Nci60_041659

192. Sbi-0050298.p004

193. Colchicine Component Of Col-probenecid

194. Eu-0100310

195. Ft-0603187

196. Mls001055448-02

197. N1721

198. C-7100

199. C07592

200. D00570

201. M01514

202. Binds To Tubulin; Inhibits Microtubular Assembly

203. 078c484

204. Sr-01000075794-1

205. Sr-01000075794-3

206. Sr-01000075794-6

207. Sr-01000075794-7

208. Sr-01000597576-1

209. Sr-01000597576-3

210. Brd-k00259736-001-06-5

211. Brd-k00259736-001-10-7

212. Wln: L B677 Mv&t&j Co1 Do1 Eo1 Jmv1 No1

213. Benzo[a]heptalen-9(5h)-one,7-dihydro-1,2,3,10-tetramethoxy-

214. Colchicine, (european Pharmacopoeia (ep) Reference Standard)

215. Colchicine, United States Pharmacopeia (usp) Reference Standard

216. Colchicine, Bioreagent, Plant Cell Culture Tested, >=95% (hplc)

217. Colchicine, Pharmaceutical Secondary Standard; Certified Reference Material

218. Colchicine For System Suitability, European Pharmacopoeia (ep) Reference Standard

219. N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5h-benzo[d]heptalen-7-yl]acetamide

220. (1e)-n-[(7s)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl] Ethanimidic Acid

221. Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-,(s)-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 399.4 g/mol
Molecular Formula C22H25NO6
XLogP31
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass399.16818752 g/mol
Monoisotopic Mass399.16818752 g/mol
Topological Polar Surface Area83.1 Ų
Heavy Atom Count29
Formal Charge0
Complexity740
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameColcrys
PubMed HealthColchicine (By mouth)
Drug ClassesAntigout
Drug LabelColchicine is an alkaloid chemically described as (S)N- (5,6,7,9-tetrahydro- 1,2,3, 10-tetramethoxy-9-oxobenzo [alpha] heptalen-7-yl) acetamide with a molecular formula of C22H25NO6 and a molecular weight of 399.4. The structural formula of colchicin...
Active IngredientColchicine
Dosage FormTablet
Routeoral; Oral
Strength0.6mg
Market StatusPrescription
CompanyAr Holding; Takeda Pharms Usa

2 of 2  
Drug NameColcrys
PubMed HealthColchicine (By mouth)
Drug ClassesAntigout
Drug LabelColchicine is an alkaloid chemically described as (S)N- (5,6,7,9-tetrahydro- 1,2,3, 10-tetramethoxy-9-oxobenzo [alpha] heptalen-7-yl) acetamide with a molecular formula of C22H25NO6 and a molecular weight of 399.4. The structural formula of colchicin...
Active IngredientColchicine
Dosage FormTablet
Routeoral; Oral
Strength0.6mg
Market StatusPrescription
CompanyAr Holding; Takeda Pharms Usa

4.2 Therapeutic Uses

Gout Suppressants

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Colchicine also is used in the prophylactic treatment of recurrent gouty arthritis. Colchicine has no effect on plasma concentrations or urinary excretion of uric acid; therefore, concomitant administration of allopurinol or a uricosuric agent (e.g., probenecid, sulfinpyrazone) is necessary to decrease serum urate concentrations. Prophylactic doses of colchicine should be administered before the initiation of allopurinol or uricosuric therapy because sudden changes in serum urate concentrations may precipitate acute gout attacks. After the serum urate concentration has been reduced to the desired level and acute gout attacks have not occurred for 3-6 months (some clinicians suggest 1-12 months), colchicine may be discontinued and the patient may be treated with urate lowering agents alone. Colchicine is frequently used in combination with probenecid to facilitate prophylactic therapy in patients with chronic gouty arthritis. The usefulness of the commercially available fixed-dosage preparation is limited, however, because the colchicine present exceeds the amount required by most patients. /Use Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3691-2


Colchicine is used to relieve attacks of acute gouty arthritis. Nonsteroidal anti-inflammatory agents (NSAIAs) (e.g., indomethacin, ibuprofen, naproxen, sulindac, piroxicam, ketoprofen) are as effective as, and better tolerated than, usual dosages of colchicine for short-term use in relieving acute attacks of gouty arthritis. Corticosteroids also are used to relieve acute attacks of gouty arthritis. Colchicine is considered a second-line agent; colchicine may be used for the treatment of acute gouty arthritis in patients who have not responded to or who cannot tolerate recommended therapies (i.e., NSAIAs, corticosteroids). /Use Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3691


96 patients aged 15 yr or more with complete or incomplete Behcet's disease, whose visual acuity was 20/40 or less, and who had experienced at least 2 episodes of ocular attack during the 16 wk before the study were selected. 47 patients received cyclosporin (10 mg/kg) and 49 colchicine (1 mg/kg) daily for 16 wk. The frequency of ocular attack was reduced more in the cyclosporin group than in the colchicine group (p < 0.001). The severity of ocular attacks was also less severe after cyclosporin than after colchicine (p < 0.001). Colchicine alleviated oral aphthous ulcer in 10 patients (20%). Dermal lesions were alleviated in 15% of the colchicine group. Clinical symptoms were improved in 33% for the colchicine group, and 10 cases were aggravated. OKT4/OKT8 ratios were 1.44 in the colchicine group before the study and 1.46 after treatment. Frequently observed side effects of colchicine were hirsutism (2 patients) and renal dysfunction (2 patients). Treatment was stopped because of hepatic dysfunction in 2 colchicine cases.

PMID:2566048 Masuda K et al; Lancet 1 (8647): 1093-6 (1989)


For more Therapeutic Uses (Complete) data for COLCHICINE (11 total), please visit the HSDB record page.


4.3 Drug Warning

Colchicine injection has been available in the US since the 1950s and has been used for the treatment of acute attacks of gout. Colchicine injection preparations that have been commercially available have not been approved by the US Food and Drug Administration (FDA). Serious adverse events, some fatal, have been reported in patients receiving colchicine injection. Because of the potentially serious health risks associated with unapproved colchicine injection, FDA announced on February 8, 2008, that it would take enforcement action (e.g., seizure, injunction, other judicial proceeding) against all firms, including compounding pharmacies, attempting to manufacture, ship, or deliver colchicine injection. FDA will implement enforcement action against all firms attempting to manufacture or ship colchicine injection products that do not have a National Drug Code (NDC) number on or after February 8, 2008. For colchicine injection products with an NDC number, FDA will take enforcement action against all firms attempting to manufacture such products on or after March 10, 2008, and against firms that ship such products on or after August 6, 2008.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3692


Myelosuppression, leukopenia, granulocytopenia, thrombocytopenia, pancytopenia, and aplastic anemia with colchicine used in therapeutic doses have been reported.

US Natl Inst Health; DailyMed. Current Medication Information for Colcrys - Colchicine, USP (September 2009). Available from, as of September 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15266


Colchicine-induced neuromuscular toxicity and rhabdomyolysis have been reported with chronic treatment in therapeutic doses. Patients with renal dysfunction and elderly patients, even those with normal renal and hepatic function, are at increased risk.

US Natl Inst Health; DailyMed. Current Medication Information for Colcrys - Colchicine, USP (September 2009). Available from, as of September 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15266


The most common adverse reaction is diarrhea (23%). Pharyngolaryngeal pain was seen in 3% of patients treated for gout flares. Gastrointestinal tract adverse effects are the most frequent side effects in patients initiating colchicine, usually presenting within 24 hours, and occurring in up to 20% of patients given therapeutic doses. Typical symptoms include cramping, nausea, diarrhea, abdominal pain, and vomiting. These events should be viewed as dose-limiting if severe as they can herald the onset of more significant toxicity.

US Natl Inst Health; DailyMed. Current Medication Information for Colcrys - Colchicine, USP (September 2009). Available from, as of September 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15266


For more Drug Warnings (Complete) data for COLCHICINE (13 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

The lethal dose in humans has been estimated to be 65 mg.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3693


4.5 Drug Indication

Prevention of cardiovascular events


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Gout Suppressants

Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout. (See all compounds classified as Gout Suppressants.)


Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
COLCHICINE
5.2.2 FDA UNII
SML2Y3J35T
5.2.3 Pharmacological Classes
Alkaloids [CS]; Cytochrome P450 3A4 Inhibitors [MoA]; P-Glycoprotein Interactions [MoA]; Alkaloid [EPC]; Cytochrome P450 3A4 Inhibitors [MoA]
5.3 ATC Code

M04AC01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


M - Musculo-skeletal system

M04 - Antigout preparations

M04A - Antigout preparations

M04AC - Preparations with no effect on uric acid metabolism

M04AC01 - Colchicine


5.4 Absorption, Distribution and Excretion

The absorption of colchicine is rapid but variable. Peak plasma concentrations occur 0.5 to 2 hours after dosing. In plasma, 50% of colchicine is protein-bound. There is significant enterohepatic circulation. The exact metabolism of colchicine is unknown but seems to involve deacetylation by the liver. Only 10% to 20% is excreted in the urine, although this increases in patients with liver disease. The kidney, liver, and spleen also contain high concentrations of colchicine, but it apparently is largely excluded from heart, skeletal muscle, and brain. The plasma half-life of colchicine is approximately 9 hours, but it can be detected in leukocytes and in the urine for at least 9 days after a single intravenous dose.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 707


... Two cases involving suicide by the ingestion of medications marketed in France /is reported/. In case 1, only heart blood was taken after body external examination. In case 2 an autopsy was performed and heart blood, urine, gastric contents and bile were taken for toxicological analysis. Colchicine was assayed in biological specimens by an HPLC-DAD method, after extraction by dichloromethane at pH 8, adding prazepam as internal standard (IS). Analyses were performed on a Symetry C-8 column. Mobile phase was a gradient of acetonitrile/pH 3.8 phosphate buffer. Colchicine is eluted at 13.1 min and the method is linear for blood, urine and bile over the range 4-1000 ng/mL. LOQ is 4 ng/mL. The concentrations of colchicine detected are: case 1: heart blood 13 ng/mL; case 2: heart blood 66 ng/mL, urine 500 ng/mL, gastric content 12 ng/mL, bile 5632 ng/mL. Our findings are in the range of lethal concentrations previously described, but there is no correlation with the amount of ingested drug. Even after massive overdose, it could be impossible to detect colchicine in blood, and as there is a widespread enterohepatic recirculation before excretion in bile and feces, bile is the target sample to analyse. We conclude in both cases that the cause of death was suicide with colchicine. It appears very important to perform an autopsy in order to obtain bile, urine, heart blood and femoral blood.

PMID:15240048 Deveaux M et al; Forensic Sci Int 143 (2-3): 219-22 (2004).


After oral administration plasma concentrations reach a peak within 0.5 to 2 hours and afterwards decrease rapidly within 2 hours. The plasma half-life is 60 minutes. Colchicine may remain in tissues for as long as 10 days.

IPCS; Poisons Information Monograph (PIM) 141: Colchicine. (October 1995). Available from, as of August 25, 2009: https://www.inchem.org/documents/pims/pharm/colchic.htm


Information was available on urinary excretion in 5 cases. Concentrations in urine are 10 to 80 fold higher than those in plasma. Four to 25 per cent of the dose ingested was excreted in urine over three to ten days. Excretion was specially high during the first 24 hours following ingestion. Colchicine is eliminated in urine up to the tenth day.

IPCS; Poisons Information Monograph (PIM) 141: Colchicine. (October 1995). Available from, as of August 25, 2009: https://www.inchem.org/documents/pims/pharm/colchic.htm


For more Absorption, Distribution and Excretion (Complete) data for COLCHICINE (12 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Colchicine undergoes some hepatic metabolism. Colchicine is partially deacetylated in the liver. Large amounts of colchicine and of its metabolites undergo enterohepatic circulation. This may explain the occurrence of a second plasma peak concentration observed 5 to 6 hours after ingestion.

IPCS; Poisons Information Monograph (PIM) 141: Colchicine. (October 1995). Available from, as of August 25, 2009: https://www.inchem.org/documents/pims/pharm/colchic.htm


Three novel conjugation metabolites of colchicine were identified in rat bile facilitated by enhanced on-line liquid chromatography-accurate radioisotope counting. The known 2- and 3-demethylcolchicines (DMCs) underwent O-sulfate conjugation in addition to the previously described O-glucuronidation. 2-DMC was preferably O-glucuronidated, whereas 3-DMC predominantly yielded O-sulfation conjugates, indicating phase II conjugation regiopreferences. Moreover, M1 was identified as a novel glutathione conjugate and a possible biotransformation pathway for its formation was proposed. The known 2-DMC (M6), 3-DMC (M7), 2-DMC glucuronide (M4), and novel 3-DMC sulfate (M3) were confirmed as the major metabolites. ...

PMID:18227142 Xu L et al; Drug Metab Dispos 36 (4): 731-9 (2008).


5.6 Biological Half-Life

Following IV administration of a single therapeutic dose (as of August 2008, IV preparations are no longer commercially available in the US), colchicine is rapidly removed from the plasma; plasma half-life is about 20 minutes. The drug has a half-life of about 60 hours in leukocytes.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3694


The elimination half life is variable, ranging from 4.4 hours in normal patients to 30 hours or more in elderly patients. A therapeutic dose produced a half life of 18.8 hours in patients with renal dysfunction.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1033


After a single 2 mg intravenous dose the average plasma half life is 20 minutes. Plasma half-life is increased in severe renal disease (40 min) and decreased in severe hepatic disease (9 min).

IPCS; Poisons Information Monograph (PIM) 141: Colchicine. (October 1995). Available from, as of August 25, 2009: https://www.inchem.org/documents/pims/pharm/colchic.htm


5.7 Mechanism of Action

... HUVEC cells were exposed to various concentrations of colchicine and were harvested at different time points. Ribonucleic acid was extracted, amplified, reverse transcribed and hybridized to complementary deoxyribonucleic acid microarrrays containing more than 40,000 probes to human expressed sequence tags. This approach enabled us to have a global look at the transcriptional response induced by colchicine treatment. Colchicine changed the expression of many genes in HUVEC cells following exposure to a concentration of 100 ng/ml or higher. Following short exposure (30 or 120 min), colchicine affected genes known to be involved in the cell cycle and its regulation. However, change in expression of genes involved in neutrophil migration or other inflammatory processes were observed mainly after 12 to 24 hr. The anti-inflammatory effect of colchicine may be mediated not only through direct interaction with microtubules but also through changes at the transcriptional level. This latter effect apparently requires a higher concentration and a longer time to occur.

PMID:16188942 Ben-Chetrit E et al; Rheumatology (Oxford) 45 (3):274-82 (2006).


Colchicine, long used to treat gout, arrests microtubule assembly and inhibits many cellular functions. At micromolar concentrations, it suppresses monosodium urate crystal-induced NACHT-LRR-PYD-containing protein-3 (NALP3) inflammasome-driven caspase-1 activation, IL-1beta processing and release, and L-selectin expression on neutrophils. At nanomolar concentrations, colchicine blocks the release of a crystal-derived chemotactic factor from neutrophil lysosomes, blocks neutrophil adhesion to endothelium by modulating the distribution of adhesion molecules on the endothelial cells, and inhibits monosodium urate crystal-induced production of superoxide anions from neutrophils. Cyto-chrome P450 3A4, the multidrug transporter P-glycoprotein, and the drugs that bind these proteins influence its pharmacokinetics and pharmacodynamics. Trial evidence supports its efficacy in acute gout and in preventing gout flares, but it has narrow therapeutic index, and overdosage is associated with gastrointestinal, hepatic, renal, neuromuscular, and cerebral toxicity; bone marrow damage; and high mortality.

PMID:18638431 Nuki G; Curr Rheumatol Rep 10 (3): 218-27 (2008).


The actions of colchicine were examined with the two-electrode voltage-clamp technique and radioligand binding assays in mouse and human 5-hydroxytryptamine(3A) receptors (5-HT(3A)Rs) expressed in Xenopus laevis oocytes. Colchicine inhibited 5-hydroxytryptamine (5-HT)-evoked currents in oocytes expressing mouse 5-HT(3A)Rs, with an IC(50) of 59.5 +/- 3 uM. In contrast to the mouse receptor, coapplication of colchicine with 5-HT (<1 uM) strongly enhanced 5-HT-evoked currents in oocytes expressing human 5-HT(3A)Rs. Colchicine applied alone did not induce a detectable current. In the presence of 0.5 microM 5-HT, the potentiation was concentration-dependent and reached the maximum (approximately 100%) when 750 microM colchicine was applied. However, colchicine-dependent inhibition can be observed at 5-HT concentrations > 1 uM. In oocyte membranes expressing mouse or human receptors, binding studies with colchicine (25 nM-1 mM) revealed no displacement of 1-methyl-N-((1R,3r,5S)-9-methyl-9 azabicyclo [3.3.1]nonan-3yl)-1H-indazole-3 carboxamide ([(3)H]BRL-43694), suggesting that actions of colchicine do not occur at the ligand binding domain. Functional effects of colchicine on both receptors occurred in the absence of preincubation and after cold temperature incubation, suggesting that the microtubule-depolymerizing effects of colchicine play no role in modulation of receptor function. Studies with interspecies chimeric receptors demonstrated that the distal one third of the N terminus is responsible for the bidirectional modulation by colchicine. Collectively, these results suggest that colchicine modulates receptor function through loops C and/or F through a gating mechanism.

PMID:19188483 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2672862 de Oliveira-Pierce AN et al; J Pharmacol Exp Ther 329 (2): 838-47 (2009).


Colchicine exerts a variety of pharmacological effects, but how these occur or how they relate to its activity in gout is not well understood. It has antimitotic effects, arresting cell division in GI by interfering with microtubule and spindle formation (an effect shared with vinca alkaloids). This effect is greatest on cells with rapid turnover (e.g., neutrophils and GI epithelium). Although somewhat controversial, colchicine may alter neutrophil motility in ex vivo assays. Colchicine also renders cell membranes more rigid and decreases the secretion of chemotactic factors by activated neutrophils.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 707


For more Mechanism of Action (Complete) data for COLCHICINE (8 total), please visit the HSDB record page.


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05-Jan-2021
14-Aug-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(KGS)
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(USD/KGS)
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DOSAGE - CAPSULE;ORAL - 0.6MG

USFDA APPLICATION NUMBER - 204820

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DOSAGE - SOLUTION;ORAL - 0.6MG/5ML

USFDA APPLICATION NUMBER - 210942

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DOSAGE - TABLET;ORAL - 0.6MG

USFDA APPLICATION NUMBER - 22352

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