Colchicine

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(New page: Pronouncation: (KOHL-chih-seen) Class: Agent for gout Trade Names: Colchicine - Tablets 0.6 mg ==Pharmacology== Inhibits inflammation and reduces pain and swelling associated with gou...)
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Pronouncation: (KOHL-chih-seen)
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<table align='right' border=1><tr><td><jmol><jmolApplet><size>200</size><script>spin on;color atoms amino;</script><uploadedFileContents>1385.SDF</uploadedFileContents><color>black</color></jmolApplet></jmol></td></tr></table>
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[http://crdd.osdd.net/raghava/biadb/str.php?id=1385&show=SHOW-3D Show 3-D Structure]
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Class: Agent for gout
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[http://crdd.osdd.net/raghava/biadb/str.php?id=1385&show=SHOW-2D Show 2-D Structure]
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Trade Names:
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{{Drugbox
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| IUPAC_name        =4-(dipropylsulfamoyl)benzoic acid;N-(1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl)acetamide
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| PubChem          = 24848032
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| DrugBank          =
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| ChemSpiderID      =
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| chemical_formula  =C<sub>3</sub><sub>5</sub>H<sub>4</sub><sub>4</sub>N<sub>2</sub>O<sub>1</sub><sub>0</sub>S
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| molecular_weight  = 684.79626
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| smiles            = N/A
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| synonyms          =
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| density          =
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| melting_point    =
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| boiling_point    =
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| solubility        =
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| bioavailability  =
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| protein_bound    =
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| metabolism        =
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| elimination_half-life =
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}}
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Colchicine - Tablets 0.6 mg
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==Description==
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==Pharmacology==
 
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Inhibits inflammation and reduces pain and swelling associated with gouty arthritis.
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==General Properties==
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<b>*Molecular Weight</b>
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==Pharmacokinetics==
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684.79626
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'''Absorption'''
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<b>*Molecular Formula</b>
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Rapidly absorbed. T max is 0.5 to 2 h.
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C<sub>3</sub><sub>5</sub>H<sub>4</sub><sub>4</sub>N<sub>2</sub>O<sub>1</sub><sub>0</sub>S
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'''Distribution'''
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<b>*IUPAC NAME</b>
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Large amounts present in bile and intestinal secretions. High concentrations also found in kidney, liver, and spleen. About 50% protein bound. Vd is 1 to 3 L/kg.
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4-(dipropylsulfamoyl)benzoic acid;N-(1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl)acetamide
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'''Metabolism'''
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<b>*Canonical Smiles</b>
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Undergoes enterohepatic recirculation. Deacetylated primarily by the liver.
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CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O.CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
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'''Elimination'''
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<b>*Isomeric Smiles</b>
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Plasma t ½ to 10 to 60 min. Excreted via biliary and renal routes; 10% to 20% excreted unchanged in urine.
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N/A
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==Indications and Usage==
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<b>*XLogP</b>
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Treatment and relief of pain in attacks of acute gouty arthritis; regular prophylaxis between attacks and is often effective in aborting an attack when taken at the first sign of articular discomfort.
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N/A
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'''Unlabeled Uses'''
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<b>*Topological Polar Surface Area</b>
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Familial Mediterranean fever; hepatic cirrhosis; primary biliary cirrhosis; treatment of Behcet disease; scleroderma; Sweet syndrome
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158
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'''Contraindications'''
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==External Links==
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Serious GI, renal, hepatic, or cardiac disorders; blood dyscrasias.
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=24848032 Pubchem]
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==Dosage and Administration==
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[http://crdd.osdd.net/raghava/biadb/detail.php?id=1385 Link to BIAdb Database]
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'''Acute Gouty Arthritis'''
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'''Adults'''
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Initial dose (give at first sign of attack) PO 1.2 mg; then 0.6 every h or 1.2 mg every 2 h until pain is relieved or diarrhea ensues. Total dose is usually 4 to 8 mg. Wait 3 days before initiating a second course of therapy.
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'''Prophylaxis'''
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'''Adults'''
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PO 0.6 mg/day for 3 to 4 days/wk if fewer than 1 attack/yr; if more than 1 attack/yr, 0.6 mg/day. Severe cases may require 1.2 to 1.8 mg/day.
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'''Surgical Patients'''
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'''Adults'''
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PO 0.6 mg 3 times daily for 3 days before and 3 days after surgery.
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==Storage/Stability==
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'''Oral'''
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Store tablets in airtight, light-resistant container.
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'''Drug Interactions'''
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None well documented.
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'''Laboratory Test Interactions'''
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May cause false-positive results in urine tests for RBCs and hemoglobin.
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==Adverse Reactions==
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'''Dermatologic'''
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Dermatoses; purpura; alopecia.
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'''GI'''
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Nausea; vomiting; diarrhea; abdominal pain.
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'''Hematologic'''
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Bone marrow depression with aplastic anemia; agranulocytosis, leukopenia or thrombocytopenia (long-term therapy).
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'''Hepatic'''
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Elevated alkaline phosphatase and AST.
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'''Miscellaneous'''
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Reversible azoospermia; myopathy; peripheral neuritis.
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==Precautions==
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'''Monitor'''
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'''Blood counts'''
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Check blood counts periodically in patients undergoing long-term therapy.
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'''Toxicity signs'''
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Assess for signs of toxicity (eg, abdominal pain, alopecia, nausea, vomiting, diarrhea, myopathy, peripheral neuritis). Notify health care provider immediately if these signs occur.
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'''Uric acid/Creatinine'''
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Monitor serum uric acid and creatinine throughout therapy.
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'''Pregnancy'''
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Category C (oral).
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'''Lactation'''
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Undetermined.
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'''Children'''
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Safety and efficacy not established.
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'''Elderly'''
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Administer with great caution to elderly and debilitated patients.
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'''Hepatic Function'''
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Increased colchicine toxicity may occur.
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'''GI reactions'''
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Drug may cause nausea, vomiting, diarrhea, and abdominal pain that may aggravate pre-existing peptic ulcer or spastic colon. Discontinue drug if these symptoms appear.
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'''Myopathy and neuropathy'''
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Myoneuropathy may occur and cause weakness in patients with impaired kidney function; serum creatine kinase may be elevated. Usually resolves in 3 to 4 wk after drug withdrawal.
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'''Vitamin B 12 malabsorption'''
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Colchicine induces reversible malabsorption of vitamin B 12 with long-term use.
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==Overdosage==
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'''Symptoms'''
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Nausea, severe abdominal pain, vomiting, diarrhea, shock, ST segment elevation, paralysis, respiratory failure, liver damage, renal failure, leukopenia, thrombocytopenia, coagulopathy, alopecia, stomatitis.
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==Patient Information==
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* Instruct patient to take colchicine regularly to prevent acute attacks.
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* Instruct patient not to exceed 8 mg in course of therapy for acute attack. To minimize cumulative toxicity, patient should wait 3 days before starting second course.
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* Advise patient with gout to drink at least 2,000 mL of fluid daily, unless contraindicated.
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* Reinforce health care provider's instructions about weight loss, diet, and alcohol intake.
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* Advise patient to have extra supply of drug on hand in case health care provider gives instructions to increase dosage.
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* Instruct patient to stop taking drug if nausea, vomiting, diarrhea, or abdominal pain occurs, especially if patient has history of spastic colon or ulcers.
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Revision as of 00:00, 15 January 2001

Show 3-D Structure

Show 2-D Structure

Colchicine
Systematic (IUPAC) name
4-(dipropylsulfamoyl)benzoic acid;N-(1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl)acetamide
Identifiers
CAS number  ?
ATC code  ?
PubChem 24848032
Chemical data
Formula C35H44N2O10S
Mol. mass 684.79626
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

Description

General Properties

*Molecular Weight

684.79626

*Molecular Formula

C35H44N2O10S

*IUPAC NAME

4-(dipropylsulfamoyl)benzoic acid;N-(1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl)acetamide

*Canonical Smiles

CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O.CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC

*Isomeric Smiles

N/A

*XLogP

N/A

*Topological Polar Surface Area

158

External Links

Link to BIAdb Database