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Oxytocin

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Oxytocin is a mammalian neurohypophysial hormone. It plays an important role in the neuroanatomy of intimacy, specifically in sexual reproduction of both sexes, in particular during and after childbirth. It is released in large amounts after distension of the cervix and uterus during labor, facilitating birth, maternal bonding, and, after stimulation of the nipples, lactation.

Category
Peptide Inhibitors
Catalog number
BAT-010142
CAS number
50-56-6
Molecular Formula
C43H66N12O12S2
Molecular Weight
1007.19
Oxytocin
Size Price Stock Quantity
1 g $299 In stock
IUPAC Name
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
Synonyms
3-Isoleucine-8-leucine vasopressin; Alpha-hypophamine; Atonin O; Di-sipidin; Endopituitrina; Hyphotocin; Intertocine S; Nobitocin S; Orasthin; Partocon; Perlacton; Pitocin; Piton S; Presoxin; Synpitan; Synpitan forte; Synthetic oxytocin; Syntocin; Syntocinon; Syntocinone; Uteracon; Vasopressin, 3-L-isoleucine-8-L-leucine-; [1-Hemicystine]-oxytocin; a-Hypophamine; Oxytocin Acetate; Oxytocin Acetate USP30
Related CAS
112457-76-8 (Deleted CAS) 147207-13-4 (Deleted CAS) 1015760-67-4 (hydrate (1:7)) 6233-83-6 (acetate salt) 96089-82-6 (diacetate salt) 1122401-96-0 (monosodium salt) 874963-71-0 (x-sodium salt)
Appearance
White Solid
Purity
>98%
Density
1.270±0.06 g/cm3
Melting Point
192-194°C
Boiling Point
1533.3±65.0°C at 760 mmHg
Sequence
CYIQNCPLG-NH2 (Disulfide bridge: Cys1-Cys6)
Storage
Store at -20°C
Solubility
Soluble in water
Application
Oxytocics
InChI
InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
InChI Key
XNOPRXBHLZRZKH-DSZYJQQASA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
1.The Potential of Nasal Oxytocin Administration for Remediation of Autism Spectrum Disorders.
Okamoto Y, Ishitobi M, Wada Y, Kosaka H1. CNS Neurol Disord Drug Targets. 2016 Apr 13. [Epub ahead of print]
Administration of oxytocin has been proposed as a treatment for the core symptoms of autism spectrum disorder (ASD), including social-communicative deficit. Previous clinical trials have investigated the efficacy and safety of oxytocin intranasal single-dose and long-term administration for individuals with ASD. All studies suggest that single-dose and long-term administration are well tolerated, and no severe adverse events have been reported. However, the efficacy of long-term oxytocin administration is controversial. Some studies have reported significant improvement of the core symptoms of ASD by long-term oxytocin administration, while other studies showed no such improvement. To elucidate the factors influencing the efficacy of oxytocin administration, it is necessary to examine the effects of administration schedules (e.g., dosage amount, frequency per day) and participant characteristics (e.g., age, sex, intellectual ability). In addition to doubts about the efficacy of particular methods of administration, questions remain about the mechanism of action of intranasal oxytocin on the central nervous system.
2.Oxytocin for preventing postpartum haemorrhage (PPH) in non-facility birth settings.
Pantoja T1, Abalos E, Chapman E, Vera C, Serrano VP. Cochrane Database Syst Rev. 2016 Apr 14;4:CD011491. [Epub ahead of print]
BACKGROUND: Postpartum haemorrhage (PPH) is the single leading cause of maternal mortality worldwide. Most of the deaths associated with PPH occur in resource-poor settings where effective methods of prevention and treatment - such as oxytocin - are not accessible because many births still occur at home, or in community settings, far from a health facility. Likewise, most of the evidence supporting oxytocin effectiveness comes from hospital settings in high-income countries, mainly because of the need of well-organised care for its administration and monitoring. Easier methods for oxytocin administration have been developed for use in resource-poor settings, but as far as we know, its effectiveness has not been assessed in a systematic review.
3.Physiology of spontaneous [Ca2+]i oscillations in the isolated vasopressin and oxytocin neurones of the rat supraoptic nucleus.
Kortus S1, Srinivasan C2, Forostyak O3, Ueta Y4, Sykova E5, Chvatal A6, Zapotocky M7, Verkhratsky A8, Dayanithi G9. Cell Calcium. 2016 Apr 6. pii: S0143-4160(16)30038-0. doi: 10.1016/j.ceca.2016.04.001. [Epub ahead of print]
The magnocellular vasopressin (AVP) and oxytocin (OT) neurones exhibit specific electrophysiological behaviour, synthesise AVP and OT peptides and secrete them into the neurohypophysial system in response to various physiological stimulations. The activity of these neurones is regulated by the very same peptides released either somato-dendritically or when applied to supraoptic nucleus (SON) preparations in vitro. The AVP and OT, secreted somato-dendritically (i.e. in the SON proper) act through specific autoreceptors, induce distinct Ca2+ signals and regulate cellular events. Here, we demonstrate that about 70% of freshly isolated individual SON neurones from the adult non-transgenic or transgenic rats bearing AVP (AVP-eGFP) or OT (OT-mRFP1) markers, produce distinct spontaneous [Ca2+]i oscillations. In the neurones identified (through specific fluorescence), about 80% of AVP neurones and about 60% of OT neurones exhibited these oscillations.
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