Compound: colchicine
SMILES: O=c1c(OC)ccc-2c(c1)[C@@H](NC(=O)C)CCc3c2c(OC)c(OC)c(OC)c3
InChIKey: IAKHMKGGTNLKSZ-INIZCTEOSA-N
Synonyms: colchicine, 64-86-8, Colchisol, Colchineos, Colchicinum, Colchicina, Colcrys, (-)-colchicine, Mitigare, 7-alpha-H-Colchicine, NSC 757, NSC-757, LODOCO, Colchcine, NSC757, N-Acetyl trimethylcolchicinic acid methylether, DTXSID5024845, N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide, SML2Y3J35T, GLOPERBA, MYINFLA, (S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide, DTXCID204845, CHEBI:23359, CHEBI:27882, MITIGARE COMPONENT COLCHICINE, Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-, Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-, Acetamide, N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, Acetamide, N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-, (S)-N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)ACETAMIDE, N-((7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo(a)heptalen-7-yl)acetamide, N-((7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo(d)heptalen-7-yl)acetamide, N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide, COLCHICUM, COLCIGEL, COLCHICINUM 4x, RefChem:5703, Colchicine Tablets 0.5 mg, 200-598-5, N-(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, Benzo(a)heptalene, acetamide deriv., Colsaloid, Condylon, Colcin, Colchicin, 7alphaH-Colchicine, Kolkicin, Goutnil, (S)-colchicine, Colchicine EP Impurity B, spindle poison, MFCD00078484, N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide, (S)-Colchicine >95%, CHEMBL107, Colchicine [JAN], Colchicin [German], NCGC00025125-07, Colchysat, Colchicina [Italian], (S)-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide, Colstat, Colchicine; Thiocolchicoside Impurity A, N-[(7s)-1,2,3,10-Tetramethoxy-9-Oxo-6,7-Dihydro-5h-Benzo[d]heptalen-7-Yl]ethanamide, LOC, SMR000058323, CCRIS 691, 7.alpha.H-Colchicine, HSDB 3044, Colchicine [USP:JAN], SR-01000075794, SR-01000597576, EINECS 200-598-5, UNII-SML2Y3J35T, Artrichine;, AI3-31149, Colchicine conformational isomer, Colchisol;, Colchicine CRS, (S)-colchicina, 4lzr, (S)-colchicin, Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(.alpha.)heptalen-7-yl)-, Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-, MPC-004, CAS-64-86-8, Prestwick_695, Colchicine (Standard), Spectrum_000842, Tocris-1364, 4o2b, COLCHICINE [MI], Colchiceine methyl ether;, Prestwick0_000363, Prestwick1_000363, Prestwick2_000363, Prestwick3_000363, Spectrum2_000075, Spectrum3_000362, Spectrum4_000298, Spectrum5_000787, COLCHCINE [VANDF], COLCHICINE [HSDB], COLCHICINUM [HPUS], Colchicine (JP18/USP), Epitope ID:141498, UPCMLD-DP065, C 9754, EC 200-598-5, COLCHICINE [MART.], SCHEMBL8469, 7JX9WZ3SJ5, COLCHICINE [USP-RS], COLCHICINE [WHO-DD], COLCHICINE [WHO-IP], N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide, Lopac0_000310, BSPBio_000485, BSPBio_002083, KBioGR_000856, KBioSS_001322, Colchicine (contains 5% Ethyl Acetate at maximum), MLS001055448, MLS001304089, MLS002153786, DivK1c_000753, SPECTRUM1500205, SPBio_000289, SPBio_002406, BPBio1_000535, GTPL2367, MEGxp0_001879, COLCHICINE [EP IMPURITY], COLCHICINE [ORANGE BOOK], SCHEMBL29374654, UPCMLD-DP065:001, ACon1_000353, HMS502F15, KBio1_000753, KBio2_001322, KBio2_003890, KBio2_006458, KBio3_001303, COLCHICINE [EP MONOGRAPH], MSK7171, NINDS_000753, COLCHICINE [USP MONOGRAPH], HMS1569I07, HMS1920A08, HMS2091G16, HMS2096I07, HMS2231C05, HMS3260N22, HMS3713I07, Pharmakon1600-01500205, COLCHICINUM [WHO-IP LATIN], Colchicine, >=96.0% (HPLC), PROBEN-C COMPONENT COLCHICINE, Tox21_110947, Tox21_201547, Tox21_300582, Tox21_500310, BDBM50014846, CCG-39910, HY-16569R, NSC756702, NSC813203, s2284, COLBENEMID COMPONENT COLCHICINE, AKOS001582887, Colchicine, >=95% (HPLC), powder, Tox21_110947_1, CS-1141, DB08117, EBC-372049, FC11732, LP00310, NSC-756702, NSC-813203, SDCCGMLS-0066633.P001, SDCCGSBI-0050298.P006, (S)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide, IDI1_000753, N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-acetamide, NCGC00025125-01, NCGC00025125-02, NCGC00025125-03, NCGC00025125-04, NCGC00025125-05, NCGC00025125-06, NCGC00025125-08, NCGC00025125-09, NCGC00025125-10, NCGC00025125-11, NCGC00025125-12, NCGC00025125-13, NCGC00025125-14, NCGC00025125-15, NCGC00025125-18, NCGC00025125-20, NCGC00025125-33, NCGC00169157-01, NCGC00169157-02, NCGC00169157-03, NCGC00254359-01, NCGC00259096-01, NCGC00260995-01, AS-13686, COL-PROBENECID COMPONENT COLCHICINE, HY-16569, IC181038, NCI60_041659, SBI-0050298.P004, COLCHICINE IMPURITY B [EP IMPURITY], EU-0100310, MLS001055448-02, NS00002718, C07592, D00570, M01514, binds to tubulin; inhibits microtubular assembly, SR-01000075794-1, SR-01000075794-3, SR-01000075794-6, SR-01000075794-7, SR-01000597576-1, SR-01000597576-3, BRD-K00259736-001-06-5, BRD-K00259736-001-10-7, BRD-K00259736-001-16-4, WLN: L B677 MV&T&J CO1 DO1 EO1 JMV1 NO1, Benzo[a]heptalen-9(5H)-one,7-dihydro-1,2,3,10-tetramethoxy-, Colchicine, (European Pharmacopoeia (EP) Reference Standard), Colchicine, United States Pharmacopeia (USP) Reference Standard, Colchicine, BioReagent, plant cell culture tested, >=95% (HPLC), Colchicine, Pharmaceutical Secondary Standard; Certified Reference Material, Colchicine for system suitability, European Pharmacopoeia (EP) Reference Standard, (1e)-N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl] ethanimidic acid, 30512-31-3, ACETAMIDE, N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-,(S)-, 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-[(7S,12aM)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9- tetrahydrobenzo[a]heptalen-7-yl]acetamide, N-[(7S,12aP)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9- tetrahydrobenzo[a]heptalen-7-yl]acetamide (conformational isomer), N-[(7S,12aP)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
Theoretical properties:
molecular_formula: C22H25NO6
molecular_weight: 399.4 g/mol
exact_mass: 399.16818752 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 29
topological_polar_surface_area: 83.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pale yellow scales or powder; pale yellow needles when crystallized from ethyl acetate
color: Pale yellow scales or powder; pale yellow needles when crystallized from ethyl acetate
odor: Odorless or nearly so
melting_point: 288 to 302 °F (EPA, 1998)
solubility: greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
Descriptions:
{"pubchem": "Colchicine can cause developmental toxicity and male reproductive toxicity according to state or federal government labeling requirements.", "chebi": "A colchicine that has (<i>S</i>)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.", "chembl": "COLCHICINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Colchicine is a medication used to prevent and treat gout, to treat familial Mediterranean fever and Beh\u00e7et's disease, and to reduce the risk of myocardial infarction. The American College of Rheumatology recommends colchicine, nonsteroidal anti-inflammatory drugs (NSAIDs) or steroids in the treatment of gout. Other uses for colchicine include the management of pericarditis. \nColchicine is taken by mouth. The injectable route of administration for colchicine can be toxic. In 2008, the US Food and Drug Administration removed all injectable colchicine from the US market.\nColchicine has a narrow therapeutic index, so overdosing is a significant risk. Common side effects of colchicine include gastrointestinal upset, particularly at high doses. Severe side effects may include pancytopenia (low blood cell counts) and rhabdomyolysis (damage to skeletal muscle), and the medication can be deadly in overdose. Whether colchicine is safe for use during pregnancy is unclear, but its use during breastfeeding appears to be safe. Colchicine works by decreasing inflammation via multiple mechanisms.\nColchicine, in the form of autumn crocus (Colchicum autumnale) crude extract, was used as early as 1500 BC to treat joint swelling. It was approved for medical use in the United States in 1961. It is available as a generic medication. In 2023, it was the 215th most commonly prescribed medication in the United States, with more than 2 million prescriptions.\nColchicine is used in plant breeding to induce polyploidy, in which the number of chromosomes in plant cells are doubled. This helps produce larger, hardier, faster-growing, and in general, more desirable plants than the normally diploid parents."}