DT-Web

DB00366 - Doxylamine


Identification
Name Doxylamine
Accession Number DB00366 (APRD00937)
Type small molecule
Description Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in parkinsonism. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 270.3694
Groups approved
Monoisotopic Weight 270.173213336
Pharmacology
Indication Used alone as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug. Also used in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women.
Mechanism of action Like other antihistamines, doxylamine acts by competitively inhibiting histamine at H1 receptors. It also has substantial sedative and anticholinergic effects.
Absorption Readily absorbed via the gastrointestinal tract.
Protein binding Not Available
Biotransformation Hepatic.
Route of elimination Not Available
Toxicity Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Pramlintide May cause additive slowing of GI motility.
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Doxylamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available

Targets


Histamine H1 receptor
Name Histamine H1 receptor
Gene Name HRH1
Pharmacological action yes
Actions antagonist
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
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.5539
Muscarinic acetylcholine receptor M1
Name Muscarinic acetylcholine receptor M1
Gene Name CHRM1
Pharmacological action unknown
Actions antagonist
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
DTHybrid score 0.4503

Enzymes


CYP2B protein
Name CYP2B protein
Gene Name CYP2B
Actions inducer
References
  • Bookstaff RC, Murphy VA, Skare JA, Minnema D, Sanzgiri U, Parkinson A: Effects of doxylamine succinate on thyroid hormone balance and enzyme induction in mice. Toxicol Appl Pharmacol. 1996 Dec;141(2):584-94. - Pubmed
DTHybrid score 0.2468

Predictions


Id Partner name Gene Name Score
617 Muscarinic acetylcholine receptor M2 CHRM2 0.1525
51 Muscarinic acetylcholine receptor M3 CHRM3 0.1377
4119 Cytochrome P450 2D6 CYP2D6 0.1188
4512 Cytochrome P450 3A4 CYP3A4 0.0956
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0851
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0741
824 Sodium-dependent serotonin transporter SLC6A4 0.0585
1588 Multidrug resistance protein 1 ABCB1 0.057
502 5-hydroxytryptamine 2A receptor HTR2A 0.0523
713 Sodium-dependent dopamine transporter SLC6A3 0.0505
556 Alpha-1A adrenergic receptor ADRA1A 0.0501
4200 Cytochrome P450 1A2 CYP1A2 0.0471
6016 Cytochrome P450 2C19 CYP2C19 0.0461
4757 Cytochrome P450 2C9 CYP2C9 0.0442
6030 Cytochrome P450 2B6 CYP2B6 0.0433
3923 Cholinesterase BCHE 0.0417
590 5-hydroxytryptamine 2C receptor HTR2C 0.0388
831 D(2) dopamine receptor DRD2 0.0347
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0346
318 Alpha-2A adrenergic receptor ADRA2A 0.0323
4118 Cytochrome P450 3A5 CYP3A5 0.0318
320 5-hydroxytryptamine 1A receptor HTR1A 0.0289
3947 Xanthine dehydrogenase/oxidase XDH 0.027
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0267
23 D(1A) dopamine receptor DRD1 0.0263
632 Alpha-1B adrenergic receptor ADRA1B 0.0263
3811 Cytochrome P450 19A1 CYP19A1 0.0245
290 Prostaglandin G/H synthase 2 PTGS2 0.0223
6107 Cytochrome P450 3A7 CYP3A7 0.0187
6013 Cytochrome P450 2E1 CYP2E1 0.018
1341 Histamine H3 receptor HRH3 0.0175
516 Neurotensin receptor type 2 NTSR2 0.0168
124 Histamine H2 receptor HRH2 0.0167
432 D(4) dopamine receptor DRD4 0.0159
3941 Amine oxidase [flavin-containing] A MAOA 0.0148
789 Alpha-1D adrenergic receptor ADRA1D 0.0136
638 D(3) dopamine receptor DRD3 0.0136
4924 Cytochrome P450 2C8 CYP2C8 0.0136
587 Serum albumin ALB 0.0131
3939 Amine oxidase [flavin-containing] B MAOB 0.0127
378 Alpha-2C adrenergic receptor ADRA2C 0.012
629 Alpha-2B adrenergic receptor ADRA2B 0.0119
118 Organic cation/carnitine transporter 2 SLC22A5 0.0119
833 Organic cation/carnitine transporter 1 SLC22A4 0.0118
716 5-hydroxytryptamine 7 receptor HTR7 0.0104
436 5-hydroxytryptamine 2B receptor HTR2B 0.0099
813 Neuronal acetylcholine receptor subunit alpha-2 CHRNA2 0.0094
1256 5-hydroxytryptamine 6 receptor HTR6 0.0093
6144 Solute carrier family 22 member 2 SLC22A2 0.0088
6024 Cytochrome P450 1A1 CYP1A1 0.0087
1275 Estrogen sulfotransferase SULT1E1 0.0086
6145 Solute carrier family 22 member 1 SLC22A1 0.0083
341 5-hydroxytryptamine 3 receptor HTR3A 0.0076
6154 Multidrug and toxin extrusion protein 1 SLC47A1 0.0076
5718 Cytochrome P450 2A6 CYP2A6 0.0076
725 5-hydroxytryptamine 1D receptor HTR1D 0.0076
528 5-hydroxytryptamine 1E receptor HTR1E 0.0074
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0068
163 D(1B) dopamine receptor DRD5 0.0068
6098 Potassium voltage-gated channel subfamily D member 2 KCND2 0.0063
6099 Potassium voltage-gated channel subfamily D member 3 KCND3 0.0063
885 5-hydroxytryptamine 1B receptor HTR1B 0.0062
723 Cytosolic phospholipase A2 PLA2G4A 0.0057
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0053
6104 Dimethylaniline monooxygenase [N-oxide-forming] 1 FMO1 0.0053
465 Calmodulin CALM1 0.0052
6182 Cytochrome P450 2J2 CYP2J2 0.005
6097 Protein S100-A2 S100A2 0.005
1810 Protein S100-A1 S100A1 0.005
5878 Alpha-7 nicotinic cholinergic receptor subunit CHRFAM7A 0.0044
2129 Sucrase-isomaltase, intestinal SI 0.0043
1729 Solute carrier family 22 member 6 SLC22A6 0.0043
1048 Protein S100-A13 S100A13 0.0043
2226 Protein S100-A12 S100A12 0.0043
6106 Cytochrome P450 2C18 CYP2C18 0.0041
2132 Protein S100-B S100B 0.004
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.004
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.004
164 Histamine H4 receptor HRH4 0.0039
6147 Solute carrier family 22 member 3 SLC22A3 0.0039
15 Voltage-dependent T-type calcium channel subunit alpha-1I CACNA1I 0.0037
94 5-hydroxytryptamine 4 receptor HTR4 0.0036
6432 Transporter snf 0.0036
535 Voltage-dependent T-type calcium channel subunit alpha-1G CACNA1G 0.0035
6217 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B PDE8B 0.0035
964 Voltage-dependent T-type calcium channel subunit alpha-1H CACNA1H 0.0034
6023 Cytochrome P450 11B2, mitochondrial CYP11B2 0.0033
198 Sodium channel protein type 10 subunit alpha SCN10A 0.0033
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0033
380 Cytochrome P450 17A1 CYP17A1 0.0032
6216 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A PDE8A 0.003
220 Sodium channel protein type 5 subunit alpha SCN5A 0.003
805 Cytochrome P450 11B1, mitochondrial CYP11B1 0.0029
691 cAMP-specific 3',5'-cyclic phosphodiesterase 7B PDE7B 0.0029
779 High-affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A PDE7A 0.0026
696 Kappa-type opioid receptor OPRK1 0.0026
439 Glutamate [NMDA] receptor subunit epsilon-4 GRIN2D 0.0026
20 Prostaglandin G/H synthase 1 PTGS1 0.0025
1360 Sphingomyelin phosphodiesterase SMPD1 0.0024
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0024
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0024
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0024
4109 cAMP-specific 3',5'-cyclic phosphodiesterase 4C PDE4C 0.0024
591 Glutamate [NMDA] receptor subunit 3B GRIN3B 0.0023
401 Glutamate [NMDA] receptor subunit zeta-1 GRIN1 0.0023
4115 Voltage-dependent L-type calcium channel subunit alpha-1D CACNA1D 0.0022
6100 BDNF/NT-3 growth factors receptor NTRK2 0.0022
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.0021
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0021
6040 6-phosphogluconate dehydrogenase, decarboxylating PGD 0.0021
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0021
215 Sodium channel protein type 11 subunit alpha SCN11A 0.0021
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.002
1971 cAMP-specific 3',5'-cyclic phosphodiesterase 4A PDE4A 0.002
2358 cAMP-specific 3',5'-cyclic phosphodiesterase 4D PDE4D 0.0019
4203 Histamine N-methyltransferase HNMT 0.0019
193 Beta-1 adrenergic receptor ADRB1 0.0018
766 Beta-2 adrenergic receptor ADRB2 0.0018
541 cAMP-specific 3',5'-cyclic phosphodiesterase 4B PDE4B 0.0018
1618 High affinity nerve growth factor receptor NTRK1 0.0017
1086 Potassium voltage-gated channel subfamily KQT member 2 KCNQ2 0.0016
474 Acetylcholinesterase ACHE 0.0016
4113 Voltage-dependent L-type calcium channel subunit alpha-1F CACNA1F 0.0016
872 Gamma-aminobutyric-acid receptor subunit alpha-1 GABRA1 0.0015
734 D1 dopamine receptor-interacting protein calcyon CALY 0.0014
4111 Voltage-dependent L-type calcium channel subunit alpha-1S CACNA1S 0.0013
858 Potassium voltage-gated channel subfamily A member 1 KCNA1 0.0013
6047 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A PDE1A 0.0012
5692 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B PDE1B 0.0011
467 Delta-type opioid receptor OPRD1 0.0011
776 Bile salt export pump ABCB11 0.001
762 Voltage-dependent calcium channel subunit alpha-2/delta-1 CACNA2D1 0.0009
1898 Cytochrome P450 1B1 CYP1B1 0.0009
4110 Voltage-dependent L-type calcium channel subunit beta-2 CACNB2 0.0009
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