DT-Web

DB01245 - Decamethonium


Identification
Name Decamethonium
Accession Number DB01245 (APRD00696)
Type small molecule
Description Decamethonium is a short acting depolarizing muscle relaxant or neuromuscular blocking agent, and is used in anesthesia to induce paralysis. It is similar to acetylcholine and acts as a partial agonist of the nicotinic acetylcholine receptor.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 258.4863
Groups approved
Monoisotopic Weight 258.303499226
Pharmacology
Indication For use as a skeletal muscle relaxant
Mechanism of action Binds to the nicotinic acetycholine receptors (by virtue of its similarity to acetylcholine) in the motor endplate and blocks access to the receptors. In the process of binding, the receptor is actually activated - causing a process known as depolarization. Since it is not degraded in the neuromuscular junction, the depolarized membrance remains depolarized and unresponsive to any other impulse, causing muscle paralysis.
Absorption Rapidly absorbed.
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity LD50=190 mg/kg (orally in mice). Prolonged apnoea, neuromuscular paralysis and cardiac arrest may occur.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Neuronal acetylcholine receptor subunit alpha-2
Name Neuronal acetylcholine receptor subunit alpha-2
Gene Name CHRNA2
Pharmacological action yes
Actions partial agonist
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Lee C, Jones T: Molecular conformation-activity relationship of decamethonium congeners. Br J Anaesth. 2002 May;88(5):692-9. - Pubmed
  • Maneckjee R, Minna JD: Opioids induce while nicotine suppresses apoptosis in human lung cancer cells. Cell Growth Differ. 1994 Oct;5(10):1033-40. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.6071
Acetylcholinesterase
Name Acetylcholinesterase
Gene Name ACHE
Pharmacological action unknown
Actions inhibitor
References
  • Robaire B, Kato G: Effects of edrophonium, eserine, decamethonium, d-tubocurarine, and gallamine on the kinetics of membrane-bound and solubilized eel acetylcholinesterase. Mol Pharmacol. 1975 Nov;11(6):722-34. - Pubmed
  • Sinha BK, Chignell CF: Synthesis and biological activity of spin-labeled analogs of biotin, hexamethonium, decamethonium, dichlorisoproterenol, and propranolol. J Med Chem. 1975 Jul;18(7):669-73. - Pubmed
  • Wu CS, Yang JT: Tacrine protection of acetylcholinesterase from inactivation by diisopropylfluorophosphate: a circular dichroism study. Mol Pharmacol. 1989 Jan;35(1):85-92. - Pubmed
  • Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. - Pubmed
  • Hallek M, Szinicz L: Effects of some mono- and bisquaternary ammonium compounds on the reactivatability of soman-inhibited human acetylcholinesterase in vitro. Biochem Pharmacol. 1988 Mar 1;37(5):819-25. - Pubmed
DTHybrid score 1.1223

Enzymes


Cholinesterase
Name Cholinesterase
Gene Name BCHE
Actions inhibitor
References
  • Munoz-Delgado E, Vidal CJ: Kinetic behaviour of acetylcholinesterase from muscle microsomal membranes. Biochem Int. 1986 Oct;13(4):625-32. - Pubmed
  • Danilov AF: [Inhibition of cholinesterase in the myoneural synapses by decamethonium and ditilin]. Farmakol Toksikol. 1967 Nov-Dec;30(6):664-9. - Pubmed
DTHybrid score 0.7381

Predictions


Id Partner name Gene Name Score
617 Muscarinic acetylcholine receptor M2 CHRM2 0.1366
6145 Solute carrier family 22 member 1 SLC22A1 0.0558
1588 Multidrug resistance protein 1 ABCB1 0.0531
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0471
341 5-hydroxytryptamine 3 receptor HTR3A 0.0441
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0431
4119 Cytochrome P450 2D6 CYP2D6 0.0392
4512 Cytochrome P450 3A4 CYP3A4 0.0366
3454 Esterase estA 0.0353
198 Sodium channel protein type 10 subunit alpha SCN10A 0.034
5259 Transcriptional regulator ntrC1 0.0327
6699 Transcriptional regulator Cgl2612 0.0327
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0325
6144 Solute carrier family 22 member 2 SLC22A2 0.029
4264 Alpha-L-fucosidase, putative TM_0306 0.0278
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0255
766 Beta-2 adrenergic receptor ADRB2 0.0231
6794 Uncharacterized lipoprotein ybbD ybbD 0.0213
2662 Glutamate racemase murI 0.0213
6299 Glutamate racemase murI 0.0213
6641 Glutamate racemase murI 0.0213
6771 Glutamate racemase murI 0.0213
6892 Glutamate racemase murI 0.0213
6795 Phosphoenolpyruvate-protein phosphotransferase ptsP 0.0213
435 Kynureninase KYNU 0.0213
4654 Kynureninase kynU 0.0213
2433 Capsid protein P40 UL80 0.0213
3569 Capsid protein P40 BVRF2 0.0213
2049 Gastrin/cholecystokinin type B receptor CCKBR 0.0191
3076 Antigen 85-C fbpC 0.0187
723 Cytosolic phospholipase A2 PLA2G4A 0.0161
2517 Subtilisin BPN' apr 0.0155
4200 Cytochrome P450 1A2 CYP1A2 0.015
2796 Parathion hydrolase opd 0.0147
6539 Parathion hydrolase opd 0.0147
713 Sodium-dependent dopamine transporter SLC6A3 0.0147
6082 Neuronal acetylcholine receptor subunit beta-3 CHRNB3 0.0142
6080 Neuronal acetylcholine receptor subunit alpha-5 CHRNA5 0.0142
948 Neuronal acetylcholine receptor subunit beta-2 CHRNB2 0.0142
244 Angiotensin-converting enzyme ACE 0.0133
6081 Neuronal acetylcholine receptor subunit alpha-6 CHRNA6 0.0131
4097 Neuronal acetylcholine receptor subunit alpha-9 CHRNA9 0.0131
556 Alpha-1A adrenergic receptor ADRA1A 0.0126
2929 (S)-2-haloacid dehalogenase dhlB 0.0124
2995 (S)-2-haloacid dehalogenase Not Available 0.0124
6078 Neuronal acetylcholine receptor subunit beta-4 CHRNB4 0.0122
131 Synaptic vesicular amine transporter SLC18A2 0.0115
831 D(2) dopamine receptor DRD2 0.0113
6079 Neuronal acetylcholine receptor subunit alpha-3 CHRNA3 0.0111
118 Organic cation/carnitine transporter 2 SLC22A5 0.0108
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0107
290 Prostaglandin G/H synthase 2 PTGS2 0.0105
2998 Sialic acid-binding Ig-like lectin 7 SIGLEC7 0.0104
6030 Cytochrome P450 2B6 CYP2B6 0.0103
4674 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase cumD 0.0097
4787 Envelope glycoprotein gp160 env 0.0094
4820 Envelope glycoprotein gp160 env 0.0094
5727 Envelope glycoprotein gp160 env 0.0094
947 Neuronal acetylcholine receptor subunit alpha-4 CHRNA4 0.0088
144 Hemoglobin subunit alpha HBA1 0.0087
3176 Trypsin-1 PRSS1 0.0086
3811 Cytochrome P450 19A1 CYP19A1 0.0085
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0085
4095 Neuronal acetylcholine receptor subunit alpha-7 CHRNA7 0.0083
1974 Oligopeptide transporter, kidney isoform SLC15A2 0.0082
4757 Cytochrome P450 2C9 CYP2C9 0.0081
124 Histamine H2 receptor HRH2 0.008
1539 Oligopeptide transporter, small intestine isoform SLC15A1 0.0079
275 Arachidonate 5-lipoxygenase ALOX5 0.0079
502 5-hydroxytryptamine 2A receptor HTR2A 0.0076
1178 Adenosine A2a receptor ADORA2A 0.0072
220 Sodium channel protein type 5 subunit alpha SCN5A 0.0071
6147 Solute carrier family 22 member 3 SLC22A3 0.0071
3626 Probable polysaccharide deacetylase pdaA pdaA 0.0071
20 Prostaglandin G/H synthase 1 PTGS1 0.0068
638 D(3) dopamine receptor DRD3 0.0068
85 Growth hormone receptor GHR 0.0065
6016 Cytochrome P450 2C19 CYP2C19 0.0063
4666 Fucose-binding lectin PA-IIL lecB 0.0062
833 Organic cation/carnitine transporter 1 SLC22A4 0.006
6013 Cytochrome P450 2E1 CYP2E1 0.006
23 D(1A) dopamine receptor DRD1 0.006
4785 Ig gamma-1 chain C region IGHG1 0.006
319 Opioid receptor, sigma 1 OPRS1 0.006
436 5-hydroxytryptamine 2B receptor HTR2B 0.0058
1373 Glucosylceramidase GBA 0.0056
824 Sodium-dependent serotonin transporter SLC6A4 0.0055
465 Calmodulin CALM1 0.0054
3480 Mannan endo-1,4-beta-mannosidase manA 0.0054
5878 Alpha-7 nicotinic cholinergic receptor subunit CHRFAM7A 0.0049
174 Sigma 1-type opioid receptor SIGMAR1 0.0048
737 Mineralocorticoid receptor NR3C2 0.0048
1656 CYP2B protein CYP2B 0.0047
4784 Beta-mannosidase manB 0.0046
6695 Beta-mannosidase BT_0458 0.0046
3947 Xanthine dehydrogenase/oxidase XDH 0.0044
318 Alpha-2A adrenergic receptor ADRA2A 0.0044
614 Progesterone receptor PGR 0.0043
232 Corticosteroid-binding globulin SERPINA6 0.0043
3941 Amine oxidase [flavin-containing] A MAOA 0.0042
606 Cytochrome P450 27, mitochondrial CYP27A1 0.0042
468 Cytochrome P450 4A11 CYP4A11 0.0041
146 Androgen receptor AR 0.0039
3929 Phosphoethanolamine/phosphocholine phosphatase PHOSPHO1 0.0039
549 Choline-phosphate cytidylyltransferase B PCYT1B 0.0039
264 Choline/ethanolamine kinase [Includes: Choline kinase beta CHKB 0.0039
861 Choline kinase alpha CHKA 0.0039
700 Choline dehydrogenase, mitochondrial CHDH 0.0039
3933 Choline/ethanolaminephosphotransferase CEPT1 0.0039
1686 Choline transporter-like protein 1 SLC44A1 0.0039
3927 Choline transporter-like protein 3 SLC44A3 0.0039
3926 Choline transporter-like protein 2 SLC44A2 0.0039
576 Choline O-acetyltransferase CHAT 0.0039
769 High-affinity choline transporter 1 SLC5A7 0.0039
3925 Choline transporter-like protein 4 SLC44A4 0.0039
3922 Phospholipase D2 PLD2 0.0039
3924 Phospholipase D1 PLD1 0.0039
587 Serum albumin ALB 0.0037
871 Glucocorticoid receptor NR3C1 0.0036
4924 Cytochrome P450 2C8 CYP2C8 0.0035
2297 Genome polyprotein Not Available 0.0034
2322 Genome polyprotein Not Available 0.0034
2694 Genome polyprotein Not Available 0.0034
2719 Genome polyprotein Not Available 0.0034
2860 Genome polyprotein Not Available 0.0034
2928 Genome polyprotein Not Available 0.0034
3160 Genome polyprotein Not Available 0.0034
3260 Genome polyprotein Not Available 0.0034
4783 Genome polyprotein Not Available 0.0034
5726 Genome polyprotein Not Available 0.0034
5779 Genome polyprotein Not Available 0.0034
5867 Genome polyprotein Not Available 0.0034
6253 Genome polyprotein Not Available 0.0034
6301 Genome polyprotein Not Available 0.0034
6380 Genome polyprotein Not Available 0.0034
6381 Genome polyprotein Not Available 0.0034
6437 Genome polyprotein Not Available 0.0034
6520 Genome polyprotein Not Available 0.0034
6521 Genome polyprotein Not Available 0.0034
6652 Genome polyprotein Not Available 0.0034
6734 Genome polyprotein Not Available 0.0034
6735 Genome polyprotein Not Available 0.0034
6736 Genome polyprotein Not Available 0.0034
6737 Genome polyprotein Not Available 0.0034
6738 Genome polyprotein Not Available 0.0034
6739 Genome polyprotein Not Available 0.0034
6744 Genome polyprotein Not Available 0.0034
6748 Genome polyprotein Not Available 0.0034
6894 Genome polyprotein Not Available 0.0034
6898 Genome polyprotein Not Available 0.0034
6107 Cytochrome P450 3A7 CYP3A7 0.0034
677 Choline-phosphate cytidylyltransferase A PCYT1A 0.0033
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0033
1517 Beta-3 adrenergic receptor ADRB3 0.0033
3426 Glutamine synthetase glnA 0.0033
3987 Glutamine synthetase GLUL 0.0033
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0032
1064 DNA (cytosine-5)-methyltransferase 1 DNMT1 0.0032
4118 Cytochrome P450 3A5 CYP3A5 0.0032
3437 Eosinophil lysophospholipase CLC 0.003
5449 Hypothetical gliding protein mglB 0.003
5443 UPF0189 protein ymdB ymdB 0.003
5440 UPF0067 protein yebR yebR 0.003
5439 33 kDa chaperonin hslO 0.003
4705 Manganese catalase Not Available 0.003
2720 Copper-containing nitrite reductase nirK 0.003
3781 Thiol:disulfide interchange protein dsbC precursor dsbC 0.003
5446 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase HI_1679 0.003
5448 Ribonuclease Z rnz 0.003
332 Beta-lactamase blaZ 0.003
2478 Beta-lactamase ampC 0.003
2613 Beta-lactamase ampC 0.003
2635 Beta-lactamase ampC 0.003
2700 Beta-lactamase penP 0.003
5445 Beta-lactamase blaB 0.003
6019 Beta-lactamase SHV-7 0.003
6701 Beta-lactamase cphA 0.003
5447 Lethal(3)malignant brain tumor-like protein L3MBTL1 0.003
5454 Internalin-A inlA 0.003
4498 Ornithine cyclodeaminase PP3533 0.0029
5450 Prolyl endopeptidase Pep pep 0.0026
6131 Carbonic anhydrase 14 CA14 0.0026
3736 Glyceraldehyde-3-phosphate dehydrogenase A gapA 0.0026
3356 Diaminopimelate decarboxylase lysA 0.0026
4771 Dissimilatory copper-containing nitrite reductase nir 0.0026
2714 Chorismate mutase aroH 0.0026
4611 Chorismate mutase aroG 0.0026
3274 Hydroxylamine reductase hcp 0.0026
4804 Hydroxylamine reductase hcp 0.0026
6014 Cytochrome P450 2A13 CYP2A13 0.0026
4113 Voltage-dependent L-type calcium channel subunit alpha-1F CACNA1F 0.0025
6106 Cytochrome P450 2C18 CYP2C18 0.0025
904 Glutathione S-transferase P GSTP1 0.0024
590 5-hydroxytryptamine 2C receptor HTR2C 0.0024
2207 Rhodopsin RHO 0.0024
597 Dihydropteridine reductase QDPR 0.0024
3462 Tyrosine-protein kinase transforming protein Abl ABL 0.0024
3399 Limonene-1,2-epoxide hydrolase limA 0.0024
3697 Bifunctional protein glmU [Includes: UDP-N-acetylglucosamine pyrophosphorylase glmU 0.0024
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0024
5180 L(+)-mandelate dehydrogenase mdlB 0.0023
4608 Putative cytochrome P450 SCO1207 0.0023
4963 Putative cytochrome P450 SCO2884 0.0023
6254 Putative cytochrome P450 SCO6998 0.0023
3500 Putative family 31 glucosidase yicI yicI 0.0023
577 Argininosuccinate lyase ASL 0.0022
1615 Chymase CMA1 0.0022
4115 Voltage-dependent L-type calcium channel subunit alpha-1D CACNA1D 0.0021
4111 Voltage-dependent L-type calcium channel subunit alpha-1S CACNA1S 0.0021
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.0021
2597 Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] glmS 0.0021
365 Dihydrofolate reductase DHFR 0.0021
2381 Dihydrofolate reductase DFR1 0.0021
2833 Dihydrofolate reductase Not Available 0.0021
2931 Dihydrofolate reductase folA 0.0021
3544 Dihydrofolate reductase folA 0.0021
3682 Dihydrofolate reductase folA 0.0021
6642 Dihydrofolate reductase folA 0.0021
6756 Dihydrofolate reductase dfrA 0.0021
287 Beta-1,4-galactosyltransferase 1 B4GALT1 0.002
102 DNA topoisomerase I, mitochondrial TOP1MT 0.002
1353 DNA topoisomerase 1 TOP1 0.0017
3552 DNA topoisomerase 1 topA 0.0017
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0017
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0017
364 Corticosteroid 11-beta-dehydrogenase isozyme 1 HSD11B1 0.0016
4604 Liver carboxylesterase 1 CES1 0.0016
3939 Amine oxidase [flavin-containing] B MAOB 0.0016
5718 Cytochrome P450 2A6 CYP2A6 0.0014
6161 Probable low affinity copper uptake protein 2 SLC31A2 0.0014
6024 Cytochrome P450 1A1 CYP1A1 0.0014
6163 Copper-transporting ATPase 2 ATP7B 0.0013
6165 Copper-transporting ATPase 1 ATP7A 0.0013
6146 High affinity copper uptake protein 1 SLC31A1 0.0012
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0012
4152 Superoxide dismutase [Cu-Zn] SOD1 0.0012
776 Bile salt export pump ABCB11 0.0012
908 Glutathione S-transferase theta-1 GSTT1 0.0012
632 Alpha-1B adrenergic receptor ADRA1B 0.0012
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0011
320 5-hydroxytryptamine 1A receptor HTR1A 0.0011
896 Glutathione S-transferase Mu 1 GSTM1 0.0011
6137 Multidrug resistance-associated protein 6 ABCC6 0.001
862 Multidrug resistance-associated protein 1 ABCC1 0.001
492 Histamine H1 receptor HRH1 0.001
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.001
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.001
6136 Multidrug resistance-associated protein 5 ABCC5 0.001
1757 Myeloperoxidase MPO 0.001
4878 Glycoprotein hormones alpha chain CGA 0.0009
1052 Cytotoxic T-lymphocyte protein 4 CTLA4 0.0009
1072 Granzyme B GZMB 0.0009
4889 Ig epsilon chain C region IGHE 0.0009
4877 Beta-mannanase man 0.0009
4871 Endo-beta-N-acetylglucosaminidase F3 endOF3 0.0009
4189 Alpha-galactosidase A GLA 0.0009
4850 Beta-2-glycoprotein 1 APOH 0.0009
4880 Membrane cofactor protein CD46 0.0009
4856 CD209 antigen CD209 0.0009
1354 Beta-glucuronidase GUSB 0.0009
757 Fusion glycoprotein F0 F 0.0009
4875 Fusion glycoprotein F0 F 0.0009
4869 Major capsid protein A430L 0.0009
4852 Reticulon-4 receptor RTN4R 0.0009
4845 ADAM 33 ADAM33 0.0009
1563 Platelet glycoprotein Ib alpha chain GP1BA 0.0009
442 Envelope glycoprotein gp41 0.0009
4859 Envelope glycoprotein env 0.0009
4882 Dipeptidyl aminopeptidase-like protein 6 DPP6 0.0009
4721 Beta-1,4-mannanase manA 0.0009
3352 Structural polyprotein Not Available 0.0009
3628 Structural polyprotein Not Available 0.0009
4892 Structural polyprotein Not Available 0.0009
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0009
4861 Interleukin-6 receptor alpha chain IL6R 0.0008
793 T-cell surface antigen CD2 CD2 0.0008
119 Carcinoembryonic antigen-related cell adhesion molecule 1 CEACAM1 0.0008
4193 Atrial natriuretic peptide clearance receptor NPR3 0.0008
3837 Cytokine receptor common beta chain CSF2RB 0.0008
4890 Hemagglutinin HA 0.0007
6566 Hemagglutinin Not Available 0.0007
1379 Interleukin-12 subunit beta IL12B 0.0007
4857 Zinc-alpha-2-glycoprotein AZGP1 0.0007
6858 Inactive carboxylesterase 4 CES1P1 0.0007
1184 Interferon beta IFNB1 0.0007
6120 Cation-independent mannose-6-phosphate receptor IGF2R 0.0007
18 High affinity immunoglobulin epsilon receptor subunit alpha FCER1A 0.0006
554 Low-density lipoprotein receptor LDLR 0.0006
852 Heparin cofactor 2 SERPIND1 0.0006
1859 Prostatic acid phosphatase ACPP 0.0006
3444 Cyanovirin-N Not Available 0.0006
3140 Hemagglutinin-neuraminidase HN 0.0006
3609 Hemagglutinin-neuraminidase HN 0.0006
595 Fibrinogen alpha chain FGA 0.0006
3258 Mannosyl-oligosaccharide alpha-1,2-mannosidase MSDC 0.0006
2372 Bifunctional tail protein 9 0.0005
958 Insulin-like growth factor 1 receptor IGF1R 0.0005
2577 Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase MAN1B1 0.0005
3814 Complement C1r subcomponent C1R 0.0005
64 Neuraminidase NA 0.0005
641 Neuraminidase NA 0.0005
2676 Neuraminidase NA 0.0005
3026 Neuraminidase NA 0.0005
3519 Neuraminidase NA 0.0005
6007 Neuraminidase NA 0.0005
1243 Cathepsin D CTSD 0.0005
1439 Lactotransferrin LTF 0.0005
1782 Neutrophil gelatinase-associated lipocalin LCN2 0.0005
309 Antithrombin-III SERPINC1 0.0005
2430 Chondroitinase B cslB 0.0004
6307 Ig gamma-2 chain C region IGHG2 0.0004
2581 Chondroitinase AC cslA 0.0004
6847 Lactase-phlorizin hydrolase LCT 0.0004
6500 Phospholipase A2 PLA2G1B 0.0004
76 Nitric-oxide synthase, brain NOS1 0.0003
952 Dipeptidyl peptidase 4 DPP4 0.0003
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