Carbetocin (BioDeep_00000012245)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S)-2-{[(2S)-1-[(3R,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide

化学式: C45H69N11O12S (987.4847634)
中文名称: 醋酸卡贝缩宫素
谱图信息: 最多检出来源 Homo sapiens(blood) 98.57%

分子结构信息

SMILES: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSCCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
InChI: InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64)

描述信息

Carbetocin is only found in individuals that have used or taken this drug. It is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is an analogue of oxytocin, and its action is similar to that of oxytocin, it causes contraction of the uterus.Carbetocin binds to oxytocin receptors present on the smooth musculature of the uterus, resulting in rhythmic contractions of the uterus, increased frequency of existing contractions, and increased uterine tone. The oxytocin receptor content of the uterus is very low in the non-pregnant state, and increases during pregnancy, reaching a peak at the time of delivery.
H - Systemic hormonal preparations, excl. sex hormones and insulins > H01 - Pituitary and hypothalamic hormones and analogues > H01B - Posterior pituitary lobe hormones > H01BB - Oxytocin and analogues
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone
D012102 - Reproductive Control Agents > D010120 - Oxytocics
Carbetocin, an oxytocin (OT) analogue, is an oxytocin receptor agonist with a Ki of 7.1 nM. Carbetocin has high affinity to chimeric N-terminus (E1) of the oxytocin receptor (Ki=1.17 μM). Carbetocin has the potential for postpartum hemorrhage research. Carbetocin can crosse the blood-brain barrier and produces antidepressant-like activity via activation of oxytocin receptors in the CNS[1][2][3].

同义名列表

15 个代谢物同义名

(2S)-2-{[(2S)-1-[(3R,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide; N-[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-butan-2-yl-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide; 1-Butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin; 1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin; 1-Butyrate-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin; 1-Butanoate-2-(O-methyl-L-tyrosine)-1-carbaoxytocin; 1-Deamino-1-monocarba-2-(tyr(ome))-oxytocin; Deamino-2-O-methyltyrosine-1-carbaoxytocin; Carbetocin Acetate; Duratocin (TN); Carbetocinum; Carbetocino; Carbetocin; Depotocin; Dcomot



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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代谢反应

0 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)

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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。

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文献列表

  • Lobna A Abdelwahab, Omneya O Galal, Sahar S Abd El-Rahman, Amany I El-Brairy, Mahmoud M Khattab, Aiman S El-Khatib. Targeting the Oxytocin System to Ameliorate Early Life Depressive-Like Behaviors in Maternally-Separated Rats. Biological & pharmaceutical bulletin. 2021 Oct; 44(10):1445-1457. doi: 10.1248/bpb.b21-00247. [PMID: 34349049]
  • Wen Ai, Yanfei Zeng, Yubo Ma, Li Liu, Dazhi Fan, Song Wu, Yinghui Zhang. Side-effects of carbetocin to prevent postpartum hemorrhage: A systematic review and meta-analysis of randomized controlled trials. Pharmacology research & perspectives. 2021 04; 9(2):e00745. doi: 10.1002/prp2.745. [PMID: 33723868]
  • Maria Bekkenes, Marte Morin Jørgensen, Anne Flem Jacobsen, Morten Wang Fagerland, Helene Rakstad-Larsen, Ole Geir Solberg, Lars Aaberge, Olav Klingenberg, Trude Steinsvik, Leiv Arne Rosseland. A study protocol for the cardiac effects of a single dose of either oxytocin 2.5 IU or carbetocin 100 µg after caesarean delivery: a prospective randomized controlled multi-centre trial in Norway. F1000Research. 2021; 10(?):973. doi: 10.12688/f1000research.73112.2. [PMID: 34745566]
  • Ali S Imami, Sinead M O'Donovan, Justin F Creeden, Xiaojun Wu, Hunter Eby, Cheryl B McCullumsmith, Kerstin Uvnäs-Moberg, Robert E McCullumsmith, Elissar Andari. Oxytocin's anti-inflammatory and proimmune functions in COVID-19: a transcriptomic signature-based approach. Physiological genomics. 2020 09; 52(9):401-407. doi: 10.1152/physiolgenomics.00095.2020. [PMID: 32809918]
  • Elsa Pflimlin, Zhihong Zhou, Zaid Amso, Qiangwei Fu, Candy Lee, Avinash Muppiddi, Sean B Joseph, Vân Nguyen-Tran, Weijun Shen. Engineering a Potent, Long-Acting, and Periphery-Restricted Oxytocin Receptor Agonist with Anorexigenic and Body Weight Reducing Effects. Journal of medicinal chemistry. 2020 01; 63(1):382-390. doi: 10.1021/acs.jmedchem.9b01862. [PMID: 31850759]
  • Sophia A Ward, R N Kirkwood, K L Plush. Effects of oxytocin and carbetocin on farrowing performance. Animal reproduction science. 2019 Jun; 205(?):88-93. doi: 10.1016/j.anireprosci.2019.04.007. [PMID: 31047762]
  • B Nucci, Agm Aya, E Aubry, J Ripart. Carbetocin for prevention of postcesarean hemorrhage in women with severe preeclampsia: a before-after cohort comparison with oxytocin. Journal of clinical anesthesia. 2016 Dec; 35(?):321-325. doi: 10.1016/j.jclinane.2016.08.017. [PMID: 27871550]
  • I Passoni, M Leonzino, V Gigliucci, B Chini, M Busnelli. Carbetocin is a Functional Selective Gq Agonist That Does Not Promote Oxytocin Receptor Recycling After Inducing β-Arrestin-Independent Internalisation. Journal of neuroendocrinology. 2016 04; 28(4):. doi: 10.1111/jne.12363. [PMID: 26751410]
  • Panos Zanos, Polymnia Georgiou, Sherie R Wright, Susanna M Hourani, Ian Kitchen, Raphaëlle Winsky-Sommerer, Alexis Bailey. The oxytocin analogue carbetocin prevents emotional impairment and stress-induced reinstatement of opioid-seeking in morphine-abstinent mice. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2014 Mar; 39(4):855-65. doi: 10.1038/npp.2013.285. [PMID: 24129263]
  • Iuliia A Karpenko, Rémy Kreder, Christel Valencia, Pascal Villa, Christiane Mendre, Bernard Mouillac, Yves Mély, Marcel Hibert, Dominique Bonnet, Andrey S Klymchenko. Red fluorescent turn-on ligands for imaging and quantifying G protein-coupled receptors in living cells. Chembiochem : a European journal of chemical biology. 2014 Feb; 15(3):359-63. doi: 10.1002/cbic.201300738. [PMID: 24449564]
  • Ken-Ichi Yayou, Shuichi Ito, Etsuko Kasuya, Madoka Sutoh, Naoyuki Yamamoto. Effects of intracerebroventricularly administered carbetocin on social behavior in Holstein steers. The Journal of veterinary medical science. 2013; 75(9):1147-52. doi: 10.1292/jvms.12-0560. [PMID: 23603880]
  • Wengang Cao, Christopher Pavlinec, Nikolaus Gravenstein, Christoph N Seubert, Anatoly E Martynyuk. Roles of aldosterone and oxytocin in abnormalities caused by sevoflurane anesthesia in neonatal rats. Anesthesiology. 2012 Oct; 117(4):791-800. doi: 10.1097/aln.0b013e318266c62d. [PMID: 22854980]
  • D Steckler, V Naidoo, D Gerber, W Kähn. Ex vivo influence of carbetocin on equine myometrial muscles and comparison with oxytocin. Theriogenology. 2012 Aug; 78(3):502-9. doi: 10.1016/j.theriogenology.2012.02.030. [PMID: 22538009]
  • A R Schramme, C R F Pinto, J Davis, C S Whisnant, M D Whitacre. Pharmacokinetics of carbetocin, a long-acting oxytocin analogue, following intravenous administration in horses. Equine veterinary journal. 2008 Nov; 40(7):658-61. doi: 10.2746/042516408x334343. [PMID: 19165935]
  • Christian Elabd, Armelle Basillais, Hélène Beaupied, Véronique Breuil, Nicole Wagner, Marcel Scheideler, Laure-Emmanuelle Zaragosi, Florence Massiéra, Emmanuel Lemichez, Zlatko Trajanoski, Georges Carle, Liana Euller-Ziegler, Gérard Ailhaud, Claude-Laurent Benhamou, Christian Dani, Ez-Zoubir Amri. Oxytocin controls differentiation of human mesenchymal stem cells and reverses osteoporosis. Stem cells (Dayton, Ohio). 2008 Sep; 26(9):2399-407. doi: 10.1634/stemcells.2008-0127. [PMID: 18583541]
  • Johannes Handler, Danielle Hoffmann, Frank Weber, Dieter Schams, Christine Aurich. Oxytocin does not contribute to the effects of cervical dilation on progesterone secretion and embryonic development in mares. Theriogenology. 2006 Sep; 66(5):1397-404. doi: 10.1016/j.theriogenology.2006.04.032. [PMID: 16769107]
  • T Engstrøm, T Barth, P Melin, H Vilhardt. Oxytocin receptor binding and uterotonic activity of carbetocin and its metabolites following enzymatic degradation. European journal of pharmacology. 1998 Aug; 355(2-3):203-10. doi: 10.1016/s0014-2999(98)00513-5. [PMID: 9760035]
  • J Silcox, P Schulz, G L Horbay, W Wassenaar. Transfer of carbetocin into human breast milk. Obstetrics and gynecology. 1993 Sep; 82(3):456-9. doi: NULL. [PMID: 8355953]
  • W Tian, D E Noakes. Effects of four hormone treatments after calving on uterine and cervical involution and ovarian activity in cows. The Veterinary record. 1991 Jun; 128(24):566-9. doi: 10.1136/vr.128.24.566. [PMID: 1887557]
  • A Atke, H Vilhardt. Uterotonic activity and myometrial receptor affinity of 1-deamino-1-carba-2-tyrosine(O-methyl)-oxytocin. Acta endocrinologica. 1987 May; 115(1):155-60. doi: 10.1530/acta.0.1150155. [PMID: 3035851]