2-hydroxydesipramine (BioDeep_00000018099)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C18H22N2O (282.1732042)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(urine) 12.5%
分子结构信息
SMILES: CNCCCN1C2=C(CCC3=CC=CC=C31)C=C(C=C2)O
InChI: InChI=1S/C18H22N2O/c1-19-11-4-12-20-17-6-3-2-5-14(17)7-8-15-13-16(21)9-10-18(15)20/h2-3,5-6,9-10,13,19,21H,4,7-8,11-12H2,1H3
描述信息
2-hydroxydesipramine is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
同义名列表
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:125680
- PubChem: 121249
- HMDB: HMDB0060992
- CAS: 1977-15-7
- PMhub: MS000002446
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(2)
- Desipramine Action Pathway:
Desipramine + Hydrogen Ion + NADPH + Oxygen ⟶ 2-hydroxydesipramine + NADP + Water
- Desipramine Metabolism Pathway:
Desipramine + Hydrogen Ion + NADPH + Oxygen ⟶ 2-hydroxydesipramine + NADP + Water
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Alice I Nichols, Madelyn Abell, Abell Madelyn, Yang Chen, Jessica A Behrle, Glen Frick, Jeffrey Paul. Effects of desvenlafaxine on the pharmacokinetics of desipramine in healthy adults.
International clinical psychopharmacology.
2013 Mar; 28(2):99-105. doi:
10.1097/yic.0b013e32835c1f49
. [PMID: 23221858] - Alice I Nichols, Penny Fatato, Magdy Shenouda, Jeffrey Paul, Jennifer A Isler, Ronald D Pedersen, Qin Jiang, Saeeduddin Ahmed, Albena Patroneva. The effects of desvenlafaxine and paroxetine on the pharmacokinetics of the cytochrome P450 2D6 substrate desipramine in healthy adults.
Journal of clinical pharmacology.
2009 Feb; 49(2):219-28. doi:
10.1177/0091270008326716
. [PMID: 19001559] - Albena Patroneva, Sandra M Connolly, Penny Fatato, Ron Pedersen, Qin Jiang, Jeffrey Paul, Christine Guico-Pabia, Jennifer A Isler, Michael E Burczynski, Alice I Nichols. An assessment of drug-drug interactions: the effect of desvenlafaxine and duloxetine on the pharmacokinetics of the CYP2D6 probe desipramine in healthy subjects.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Dec; 36(12):2484-91. doi:
10.1124/dmd.108.021527
. [PMID: 18809731] - K Shimoda, S Morita, G Hirokane, A Yokono, T Someya, S Takahashi. Metabolism of desipramine in Japanese psychiatric patients: the impact of CYP2D6 genotype on the hydroxylation of desipramine.
Pharmacology & toxicology.
2000 Jun; 86(6):245-9. doi:
10.1111/j.0901-9928.2000.860601.x
. [PMID: 10895986] - M E Van Dort, J H Kim, L Tluczek, D M Wieland. Synthesis of 11C-labeled desipramine and its metabolite 2-hydroxydesipramine: potential radiotracers for PET studies of the norepinephrine transporter.
Nuclear medicine and biology.
1997 Nov; 24(8):707-11. doi:
10.1016/s0969-8051(97)00109-1
. [PMID: 9428594] - A G Chen, Y K Wing, H Chiu, S Lee, C N Chen, K Chan. Simultaneous determination of imipramine, desipramine and their 2- and 10-hydroxylated metabolites in human plasma and urine by high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
1997 May; 693(1):153-8. doi:
10.1016/s0378-4347(97)00053-4
. [PMID: 9200529] - S L Stern, T B Cooper, L D Nelson, M H Johnson, R F Suckow. 2-Hydroxydesipramine and desipramine plasma levels: how are they related to antidepressant response?.
International clinical psychopharmacology.
1996 Dec; 11(4):219-27. doi:
10.1097/00004850-199612000-00002
. [PMID: 9031987] - E Spina, A Avenoso, G M Campo, A P Caputi, E Perucca. Phenobarbital induces the 2-hydroxylation of desipramine.
Therapeutic drug monitoring.
1996 Feb; 18(1):60-4. doi:
10.1097/00007691-199602000-00010
. [PMID: 8848823] - G Beauchamp, P A Lavoie, R Elie. Differential effect of desipramine and 2-hydroxydesipramine on depolarization-induced calcium uptake in synaptosomes from rat limbic sites.
Canadian journal of physiology and pharmacology.
1995 May; 73(5):619-23. doi:
10.1139/y95-078
. [PMID: 7585328] - H Madsen, K K Nielsen, K Brøsen. Imipramine metabolism in relation to the sparteine and mephenytoin oxidation polymorphisms--a population study.
British journal of clinical pharmacology.
1995 Apr; 39(4):433-9. doi:
10.1111/j.1365-2125.1995.tb04473.x
. [PMID: 7640151] - G Villarreal. Desipramine plasma levels and treatment response in panic disorder.
Canadian journal of psychiatry. Revue canadienne de psychiatrie.
1995 Mar; 40(2):110-1. doi:
10.1177/070674379504000213
. [PMID: 7788615] - L L von Moltke, D J Greenblatt, M M Cotreau-Bibbo, S X Duan, J S Harmatz, R I Shader. Inhibition of desipramine hydroxylation in vitro by serotonin-reuptake-inhibitor antidepressants, and by quinidine and ketoconazole: a model system to predict drug interactions in vivo.
The Journal of pharmacology and experimental therapeutics.
1994 Mar; 268(3):1278-83. doi:
. [PMID: 8138941]
- M N Musa, K J Miescke. Pharmacogenetics of desipramine metabolism.
International journal of clinical pharmacology and therapeutics.
1994 Mar; 32(3):126-30. doi:
NULL
. [PMID: 8205373] - T E Wilens, J Biederman, R J Baldessarini, P R Puopolo, J G Flood. Electrocardiographic effects of desipramine and 2-hydroxydesipramine in children, adolescents, and adults treated with desipramine.
Journal of the American Academy of Child and Adolescent Psychiatry.
1993 Jul; 32(4):798-804. doi:
10.1097/00004583-199307000-00014
. [PMID: 8340301] - M L Dahl, L Iselius, C Alm, J O Svensson, D Lee, I Johansson, M Ingelman-Sundberg, F Sjöqvist. Polymorphic 2-hydroxylation of desipramine. A population and family study.
European journal of clinical pharmacology.
1993; 44(5):445-50. doi:
10.1007/bf00315541
. [PMID: 8359181] - T E Wilens, J Biederman, R J Baldessarini, P R Puopolo, J G Flood. Developmental changes in serum concentrations of desipramine and 2-hydroxydesipramine during treatment with desipramine.
Journal of the American Academy of Child and Adolescent Psychiatry.
1992 Jul; 31(4):691-8. doi:
10.1097/00004583-199207000-00017
. [PMID: 1644733] - J G Barnhill. Plasma desipramine levels and ECG changes in depressed young adults.
Journal of clinical psychopharmacology.
1992 Apr; 12(2):136-7. doi:
10.1097/00004714-199204000-00013
. [PMID: 1573037] - D J Hermann, T F Krol, G E Dukes, E K Hussey, M Danis, Y H Han, J R Powell, L J Hak. Comparison of verapamil, diltiazem, and labetalol on the bioavailability and metabolism of imipramine.
Journal of clinical pharmacology.
1992 Feb; 32(2):176-83. doi:
10.1002/j.1552-4604.1992.tb03823.x
. [PMID: 1613128] - R F Suckow, S P Roose, T B Cooper. Effect of fluoxetine on plasma desipramine and 2-hydroxydesipramine.
Biological psychiatry.
1992 Jan; 31(2):200-4. doi:
10.1016/0006-3223(92)90205-e
. [PMID: 1737080] - J P Foglia, D Sorisio, J M Perel. Determination of imipramine, desipramine and their hydroxy metabolites by reversed-phase chromatography with ultraviolet and coulometric detection.
Journal of chromatography.
1991 Dec; 572(1-2):247-58. doi:
10.1016/0378-4347(91)80489-y
. [PMID: 1818058] - S L Stern, H S Ribner, T B Cooper, L D Nelson, M H Johnson, R F Suckow. 2-Hydroxydesipramine and desipramine plasma levels and electrocardiographic effects in depressed younger adults.
Journal of clinical psychopharmacology.
1991 Apr; 11(2):93-8. doi:
NULL
. [PMID: 2056147] - R B Dell, K Hein, R Ramakrishnan, J Puig-Antich, T Cooper. Model for the kinetics of imipramine and its metabolites in adolescents.
Therapeutic drug monitoring.
1990 Sep; 12(5):450-9. doi:
10.1097/00007691-199009000-00008
. [PMID: 2293407] - J T Kenney, P J Orsulak, R M Kolodner, M E Burton. Determination of serum desipramine and 2-hydroxydesipramine for pharmacokinetic applications by HPLC with ultraviolet detection.
Clinical chemistry.
1989 Oct; 35(10):2134-6. doi:
10.1093/clinchem/35.10.2134
. [PMID: 2791284] - S H Preskorn, S J Bupp, E B Weller, R A Weller. Plasma levels of imipramine and metabolites in 68 hospitalized children.
Journal of the American Academy of Child and Adolescent Psychiatry.
1989 May; 28(3):373-5. doi:
10.1097/00004583-198905000-00011
. [PMID: 2738003] - K Brøsen, L F Gram. Quinidine inhibits the 2-hydroxylation of imipramine and desipramine but not the demethylation of imipramine.
European journal of clinical pharmacology.
1989; 37(2):155-60. doi:
10.1007/bf00558224
. [PMID: 2792169] - J C Nelson, E Atillasoy, C Mazure, P I Jatlow. Hydroxydesipramine in the elderly.
Journal of clinical psychopharmacology.
1988 Dec; 8(6):428-33. doi:
NULL
. [PMID: 3235701] - J C Nelson, C Mazure, P I Jatlow. Antidepressant activity of 2-hydroxydesipramine.
Clinical pharmacology and therapeutics.
1988 Sep; 44(3):283-8. doi:
10.1038/clpt.1988.151
. [PMID: 3416551] - R F Suckow, T B Cooper. Isolation and identification of the glucuronide conjugate of 2-hydroxydesipramine by preparative liquid chromatography.
Journal of chromatography.
1988 Jun; 427(2):287-94. doi:
10.1016/0378-4347(88)80131-2
. [PMID: 3410912] - J C Nelson, P I Jatlow. Nonlinear desipramine kinetics: prevalence and importance.
Clinical pharmacology and therapeutics.
1987 Jun; 41(6):666-70. doi:
10.1038/clpt.1987.93
. [PMID: 3581650] - E Spina, A Arena, F Pisani. Urinary desipramine hydroxylation index and steady-state plasma concentrations of imipramine and desipramine.
Therapeutic drug monitoring.
1987 Jun; 9(2):129-33. doi:
10.1097/00007691-198706000-00001
. [PMID: 3617150] - H C Stancer, K L Reed. Desipramine and 2-hydroxydesipramine in human breast milk and the nursing infant's serum.
The American journal of psychiatry.
1986 Dec; 143(12):1597-600. doi:
10.1176/ajp.143.12.1597
. [PMID: 3789215] - K Brøsen, S V Otton, L F Gram. Imipramine demethylation and hydroxylation: impact of the sparteine oxidation phenotype.
Clinical pharmacology and therapeutics.
1986 Nov; 40(5):543-9. doi:
10.1038/clpt.1986.221
. [PMID: 3769385] - S P Kutcher, K I Shulman, K Reed. Desipramine plasma concentration and therapeutic response in elderly depressives: a naturalistic pilot study.
Canadian journal of psychiatry. Revue canadienne de psychiatrie.
1986 Nov; 31(8):752-4. doi:
10.1177/070674378603100812
. [PMID: 3791131] - S P Kutcher, K Reid, J D Dubbin, K I Shulman. Electrocardiogram changes and therapeutic desipramine and 2-hydroxy-desipramine concentrations in elderly depressives.
The British journal of psychiatry : the journal of mental science.
1986 Jun; 148(?):676-9. doi:
10.1192/bjp.148.6.676
. [PMID: 3779249] - K Brøsen, L F Gram, R Klysner, P Bech. Steady-state levels of imipramine and its metabolites: significance of dose-dependent kinetics.
European journal of clinical pharmacology.
1986; 30(1):43-9. doi:
10.1007/bf00614194
. [PMID: 3709631] - K Brøsen, R Klysner, L F Gram, S V Otton, P Bech, L Bertilsson. Steady-state concentrations of imipramine and its metabolites in relation to the sparteine/debrisoquine polymorphism.
European journal of clinical pharmacology.
1986; 30(6):679-84. doi:
10.1007/bf00608215
. [PMID: 3533565] - J D Amsterdam, D J Brunswick, L Potter, A Winokur, K Rickels. Desipramine and 2-hydroxydesipramine plasma levels in endogenous depressed patients. Lack of correlation with therapeutic response.
Archives of general psychiatry.
1985 Apr; 42(4):361-4. doi:
10.1001/archpsyc.1985.01790270051005
. [PMID: 3977553] - E Spina, C Birgersson, C von Bahr, O Ericsson, B Mellström, E Steiner, F Sjöqvist. Phenotypic consistency in hydroxylation of desmethylimipramine and debrisoquine in healthy subjects and in human liver microsomes.
Clinical pharmacology and therapeutics.
1984 Nov; 36(5):677-82. doi:
10.1038/clpt.1984.239
. [PMID: 6488689] - R G Cooke, J J Warsh, H C Stancer, K L Reed, E Persad. The nonlinear kinetics of desipramine and 2-hydroxydesipramine in plasma.
Clinical pharmacology and therapeutics.
1984 Sep; 36(3):343-9. doi:
10.1038/clpt.1984.185
. [PMID: 6467794] - A I Barkai, R F Suckow, T B Cooper. Imipramine and its metabolites: relationship to cerebral catecholamines in rats in vivo.
The Journal of pharmacology and experimental therapeutics.
1984 Aug; 230(2):330-5. doi:
NULL
. [PMID: 6747838] - L H Price, J C Nelson, P I Jatlow. Effects of desipramine on clinical liver function tests.
The American journal of psychiatry.
1984 Jun; 141(6):798-800. doi:
10.1176/ajp.141.6.798
. [PMID: 6731623] - M V Rudorfer, E A Lane, W H Chang, M D Zhang, W Z Potter. Desipramine pharmacokinetics in Chinese and Caucasian volunteers.
British journal of clinical pharmacology.
1984 Apr; 17(4):433-40. doi:
10.1111/j.1365-2125.1984.tb02368.x
. [PMID: 6721989] - J D Amsterdam, D J Brunswick, L Potter, M J Kaplan. Cimetidine-induced alterations in desipramine plasma concentrations.
Psychopharmacology.
1984; 83(4):373-5. doi:
10.1007/bf00428548
. [PMID: 6436867] - T A Sutfin, C L DeVane, W J Jusko. The analysis and disposition of imipramine and its active metabolites in man.
Psychopharmacology.
1984; 82(4):310-7. doi:
10.1007/bf00427676
. [PMID: 6427820] - L F Gram, M Bjerre, P Kragh-Sørensen, B Kvinesdal, J Molin, O L Pedersen, N Reisby. Imipramine metabolites in blood of patients during therapy and after overdose.
Clinical pharmacology and therapeutics.
1983 Mar; 33(3):335-42. doi:
10.1038/clpt.1983.42
. [PMID: 6825388] - J L Bock, J C Nelson, S Gray, P I Jatlow. Desipramine hydroxylation: variability and effect of antipsychotic drugs.
Clinical pharmacology and therapeutics.
1983 Mar; 33(3):322-8. doi:
10.1038/clpt.1983.40
. [PMID: 6130865] - J C Nelson, J L Bock, P I Jatlow. Clinical implications of 2-hydroxydesipramine plasma concentrations.
Clinical pharmacology and therapeutics.
1983 Feb; 33(2):183-9. doi:
10.1038/clpt.1983.28
. [PMID: 6822031] - J C Nelson, P I Jatlow, J Bock, D M Quinlan, M B Bowers. Major adverse reactions during desipramine treatment: relationship to plasma drug concentrations, concomitant antipsychotic treatment, and patient characteristics.
Archives of general psychiatry.
1982 Sep; 39(9):1055-61. doi:
10.1001/archpsyc.1982.04290090045010
. [PMID: 6126171] - W Z Potter, H M Calil, T A Sutfin, A P Zavadil, W J Jusko, J Rapoport, F K Goodwin. Active metabolites of imipramine and desipramine in man.
Clinical pharmacology and therapeutics.
1982 Mar; 31(3):393-401. doi:
10.1038/clpt.1982.50
. [PMID: 7060321] - I Kitanaka, R J Ross, N R Cutler, A P Zavadil, W Z Potter. Altered hydroxydesipramine concentrations in elderly depressed patients.
Clinical pharmacology and therapeutics.
1982 Jan; 31(1):51-5. doi:
10.1038/clpt.1982.8
. [PMID: 7053304] - S H Wong, T McCauley, P A Kramer. Determination of 2-hydroxydesipramine by high-performance liquid chromatography.
Journal of chromatography.
1981 Nov; 226(1):147-54. doi:
10.1016/s0378-4347(00)84215-2
. [PMID: 7320140]