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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:levomethadone
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Accession:CHEBI:136003 term browser browse the term
Definition:A 6-(dimethylamino)-4,4-diphenylheptan-3-one that has (R)-configuration. It is the active enantiomer of methadone and its hydrochloride salt is used to treat adults who are addicted to drugs such as heroin and morphine.
Synonyms:exact_synonym: (6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one
 related_synonym: (-)-methadone;   (6R)-methadone;   (R)-6-(dimethylamino)-4,4-diphenyl-3-heptanone;   Formula=C21H27NO;   InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3/t17-/m1/s1;   InChIKey=USSIQXCVUWKGNF-QGZVFWFLSA-N;   L-6-(dimethylamino)-4,4-diphenyl-3-heptanone;   R-methadone;   SMILES=CCC(=O)C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1;   l-methadone;   levometadona;   levomethadonum
 xref: CAS:125-58-6;   Chemspider:20904;   DrugBank:DB13515;   Drug_Central:4586;   KEGG:D08121;   PMID:20308640;   PMID:21371149;   PMID:25669614;   PMID:27974484;   PMID:29393208;   PMID:29902789;   PMID:31842942;   PMID:32302325;   PMID:32586692;   PMID:32903474;   PMID:33345336;   PMID:33423953;   Reaxys:3213668;   Wikipedia:Levomethadone
 cyclic_relationship: is_enantiomer_of CHEBI:167308


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methadone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G ABCB1 ATP binding cassette subfamily B member 1 affects activity
increases expression		 EXP Methadone affects the activity of ABCB1 protein
Methadone results in increased expression of ABCB1 protein		 CTD PMID:19840843 NCBI chr 7:87,503,017...87,713,295
Ensembl chr 7:87,503,017...87,713,323 		JBrowse link
G BAX BCL2 associated X, apoptosis regulator affects localization EXP Methadone affects the localization of BAX protein CTD PMID:20691259 NCBI chr19:48,954,875...48,961,798
Ensembl chr19:48,954,815...48,961,798 		JBrowse link
G CCL2 C-C motif chemokine ligand 2 increases secretion ISO Methadone results in increased secretion of CCL2 protein CTD PMID:20178837 NCBI chr17:34,255,285...34,257,203
Ensembl chr17:34,255,274...34,257,208 		JBrowse link
G CCL3 C-C motif chemokine ligand 3 increases secretion ISO Methadone results in increased secretion of CCL3 protein CTD PMID:20178837 NCBI chr17:36,088,256...36,090,143
Ensembl chr17:36,088,256...36,090,169 		JBrowse link
G CX3CL1 C-X3-C motif chemokine ligand 1 increases secretion ISO Methadone results in increased secretion of CX3CL1 protein CTD PMID:20178837 NCBI chr16:57,372,490...57,385,044
Ensembl chr16:57,372,477...57,385,044 		JBrowse link
G CXCL1 C-X-C motif chemokine ligand 1 increases secretion ISO Methadone results in increased secretion of CXCL1 protein CTD PMID:20178837 NCBI chr 4:73,869,393...73,871,308
Ensembl chr 4:73,869,393...73,871,308 		JBrowse link
G CYCS cytochrome c, somatic affects localization EXP Methadone affects the localization of CYCS protein CTD PMID:20691259 NCBI chr 7:25,118,656...25,125,260
Ensembl chr 7:25,118,656...25,125,260 		JBrowse link
G CYP19A1 cytochrome P450 family 19 subfamily A member 1 multiple interactions
affects metabolic processing		 EXP Aminoglutethimide inhibits the reaction [CYP19A1 protein affects the metabolism of Methadone]; formestane inhibits the reaction [CYP19A1 protein affects the metabolism of Methadone] CTD PMID:15242824 NCBI chr15:51,208,057...51,338,596
Ensembl chr15:51,208,057...51,338,601 		JBrowse link
G CYP2D6 cytochrome P450 family 2 subfamily D member 6 increases metabolic processing
decreases activity		 ISO
EXP		 CYP2D22 protein results in increased metabolism of Methadone
Methadone results in decreased activity of CYP2D6 protein		 CTD PMID:16595712 NCBI chr22:42,126,499...42,130,810
Ensembl chr22:42,126,499...42,130,865 		JBrowse link
G CYP3A4 cytochrome P450 family 3 subfamily A member 4 affects metabolic processing
increases metabolic processing		 EXP CYP3A4 protein affects the metabolism of Methadone
CYP3A4 protein results in increased metabolism of Methadone		 CTD PMID:15986265 PMID:16595712 NCBI chr 7:99,756,967...99,784,184
Ensembl chr 7:99,756,960...99,784,248 		JBrowse link
G DRD2 dopamine receptor D2 multiple interactions ISO Methadone affects the reaction [Cocaine affects the expression of DRD2 mRNA] CTD PMID:18990547 NCBI chr11:113,409,605...113,475,398
Ensembl chr11:113,409,605...113,475,691 		JBrowse link
G HCRT hypocretin neuropeptide precursor multiple interactions ISO Methadone affects the reaction [Cocaine affects the expression of HCRT mRNA] CTD PMID:18990547 NCBI chr17:42,184,060...42,185,452
Ensembl chr17:42,184,060...42,185,452 		JBrowse link
G IL10 interleukin 10 increases secretion ISO Methadone results in increased secretion of IL10 protein CTD PMID:20178837 NCBI chr 1:206,767,602...206,772,494
Ensembl chr 1:206,767,602...206,774,541 		JBrowse link
G IL1A interleukin 1 alpha increases expression ISO Methadone results in increased expression of IL1A protein CTD PMID:20178837 NCBI chr 2:112,773,925...112,784,493
Ensembl chr 2:112,773,925...112,784,493 		JBrowse link
G IL1B interleukin 1 beta increases secretion
increases expression		 ISO Methadone results in increased secretion of IL1B protein
Methadone results in increased expression of IL1B protein		 CTD PMID:20178837 NCBI chr 2:112,829,751...112,836,779
Ensembl chr 2:112,829,751...112,836,816 		JBrowse link
G IL2 interleukin 2 decreases expression EXP Methadone results in decreased expression of IL2 mRNA CTD PMID:23965172 NCBI chr 4:122,451,470...122,456,725
Ensembl chr 4:122,451,470...122,456,725 		JBrowse link
G IL4 interleukin 4 increases expression
multiple interactions		 EXP Methadone results in increased expression of IL4 mRNA; Methadone results in increased expression of IL4 protein
CTAP octapeptide inhibits the reaction [Methadone results in increased expression of IL4 mRNA]; SB 203580 inhibits the reaction [Methadone results in increased expression of IL4 mRNA]		 CTD PMID:23965172 NCBI chr 5:132,673,989...132,682,678
Ensembl chr 5:132,673,986...132,682,678 		JBrowse link
G IL6 interleukin 6 increases expression
increases secretion		 ISO Methadone results in increased expression of IL6 mRNA; Methadone results in increased expression of IL6 protein
Methadone results in increased secretion of IL6 protein		 CTD PMID:20178837 NCBI chr 7:22,727,200...22,731,998
Ensembl chr 7:22,725,884...22,732,002 		JBrowse link
G INS insulin decreases response to substance EXP Methadone results in decreased susceptibility to INS protein CTD PMID:2554359 NCBI chr11:2,159,779...2,161,209
Ensembl chr11:2,159,779...2,161,221 		JBrowse link
G KCNH2 potassium voltage-gated channel subfamily H member 2 multiple interactions
decreases activity		 EXP Chlorobutanol promotes the reaction [Methadone results in decreased activity of KCNH2 protein] CTD PMID:14527710 NCBI chr 7:150,944,961...150,978,321
Ensembl chr 7:150,944,961...150,978,321 		JBrowse link
G LEP leptin increases expression EXP Methadone results in increased expression of LEP protein CTD PMID:15717844 NCBI chr 7:128,241,278...128,257,629
Ensembl chr 7:128,241,278...128,257,629 		JBrowse link
G MAPK1 mitogen-activated protein kinase 1 increases phosphorylation EXP Methadone results in increased phosphorylation of MAPK1 protein CTD PMID:23965172 NCBI chr22:21,759,657...21,867,680
Ensembl chr22:21,759,657...21,867,680 		JBrowse link
G MAPK3 mitogen-activated protein kinase 3 increases phosphorylation EXP Methadone results in increased phosphorylation of MAPK3 protein CTD PMID:23965172 NCBI chr16:30,114,105...30,123,220
Ensembl chr16:30,114,105...30,123,506 		JBrowse link
G NFKBIA NFKB inhibitor alpha increases expression EXP Methadone results in increased expression of NFKBIA protein CTD PMID:22258905 NCBI chr14:35,401,513...35,404,749
Ensembl chr14:35,401,079...35,404,749 		JBrowse link
G OPRD1 opioid receptor delta 1 affects binding
multiple interactions		 ISO Methadone binds to OPRD1 protein
[Methadone binds to OPRD1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRD1 protein] which results in decreased uptake of Serotonin		 CTD PMID:7562497 NCBI chr 1:28,812,170...28,871,267
Ensembl chr 1:28,812,170...28,871,267 		JBrowse link
G OPRK1 opioid receptor kappa 1 affects binding
multiple interactions		 ISO Methadone binds to OPRK1 protein
[Methadone binds to OPRK1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRK1 protein] which results in decreased uptake of Serotonin		 CTD PMID:7562497 NCBI chr 8:53,225,724...53,251,637
Ensembl chr 8:53,225,724...53,251,637 		JBrowse link
G OPRM1 opioid receptor mu 1 multiple interactions
affects binding		 ISO [Methadone binds to OPRM1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRM1 protein] which results in decreased uptake of Serotonin CTD PMID:7562497 NCBI chr 6:154,010,496...154,246,867
Ensembl chr 6:154,010,496...154,246,867 		JBrowse link
G ORM2 orosomucoid 2 affects binding
multiple interactions		 EXP Methadone binds to ORM2 protein alternative form
Methadone inhibits the reaction [Imipramine binds to ORM2 protein alternative form]		 CTD PMID:8946472 NCBI chr 9:114,329,869...114,333,251
Ensembl chr 9:114,329,869...114,333,251 		JBrowse link
G PLD2 phospholipase D2 increases activity EXP Methadone results in increased activity of PLD2 protein CTD PMID:23965172 NCBI chr17:4,807,152...4,823,430
Ensembl chr17:4,807,152...4,823,434 		JBrowse link
G PRL prolactin affects secretion
increases secretion
increases expression		 EXP Methadone affects the secretion of PRL protein
Methadone results in increased secretion of PRL protein
Methadone results in increased expression of PRL protein		 CTD PMID:2554359 PMID:16675813 PMID:21094671 NCBI chr 6:22,287,246...22,302,835
Ensembl chr 6:22,287,244...22,302,826 		JBrowse link
G TLR4 toll like receptor 4 affects binding
increases expression
affects response to substance
multiple interactions		 EXP
ISO		 Methadone binds to TLR4 protein
Methadone results in increased expression of TLR4 mRNA; Methadone results in increased expression of TLR4 protein
Methadone affects the susceptibility to TLR4 protein
Naloxone affects the reaction [Methadone binds to TLR4 protein]		 CTD PMID:20178837 NCBI chr 9:117,704,403...117,724,735
Ensembl chr 9:117,704,175...117,724,735 		JBrowse link
G TNF tumor necrosis factor increases secretion
increases expression		 ISO Methadone results in increased secretion of TNF protein
Methadone results in increased expression of TNF protein		 CTD PMID:20178837 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 26034
    role 25961
      biological role 25929
        pharmacological role 22058
          analgesic 15532
            opioid analgesic 674
              levomethadone 32
                methadone + 32
Path 2
Term Annotations click to browse term
  CHEBI ontology 26034
    subatomic particle 26009
      composite particle 26009
        hadron 26020
          baryon 26009
            nucleon 26009
              atomic nucleus 26009
                atom 26009
                  main group element atom 25834
                    p-block element atom 25834
                      carbon group element atom 25434
                        carbon atom 25403
                          organic molecular entity 25392
                            heteroorganic entity 24766
                              organochalcogen compound 24378
                                organooxygen compound 24054
                                  carbonyl compound 23563
                                    ketone 19347
                                      dialkyl ketone 51
                                        heptan-3-one 32
                                          6-(dimethylamino)-4,4-diphenylheptan-3-one 32
                                            levomethadone 32
                                              methadone + 32
paths to the root