Oxytocin free acid Property

storage temp. 

-15°C

Water Solubility 

Soluble in water to 1mg/ml

InChI

InChI=1/C43H65N11O13S2/c1-5-22(4)35-42(66)48-26(12-13-32(45)56)38(62)50-29(17-33(46)57)39(63)52-30(20-69-68-19-25(44)36(60)49-28(40(64)53-35)16-23-8-10-24(55)11-9-23)43(67)54-14-6-7-31(54)41(65)51-27(15-21(2)3)37(61)47-18-34(58)59/h8-11,21-22,25-31,35,55H,5-7,12-20,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,61)(H,48,66)(H,49,60)(H,50,62)(H,51,65)(H,52,63)(H,53,64)(H,58,59)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/s3

InChIKey

NFBCSRNZYJJWNB-IEIRLNIENA-N

SMILES

N1(CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)O)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@H](C(N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N1)=O)CC1C=CC(O)=CC=1 |&1:4,8,22,27,32,35,36,43,52,r|

Hazard and Precautionary Statements (GHS)

Oxytocin free acid Chemical Properties,Usage,Production

Description

Oxytocin free acid (9-Deamidooxytocin) is an analog of oxytocin in which the glycinamide residue at position 9 in oxytocin has been replaced by a glycine residue. Oxytocin is a pleiotropic, peptide hormone with broad implications for general health, adaptation, development, reproduction, and social behavior.

Uses

Free acid form of oxytocin, which is a hormone involved in many aspects of mammalian reproduction as well as other physiological processes such as bond pairing and cardiovascular homeostasis.

Biological Functions

Oxytocin is a cyclic 9-peptide that, like somatostatin, contains a ring that encompasses a disulfide bridge. Oxytocin has uterotonic action, contracting the muscles of the uterus during gestation, and plays an important role in milk ejection (not milk secretion, which is regulated by the peptide hormone prolactin) from the mammary ducts into the nipples. Exogenous oxytocin most commonly is used for induction of labor, wherein it improves uterine contractions to achieve early vaginal delivery for fetal or maternal reasons (e.g., preeclampsia, Rh factor problems, pregnancy that has exceeded 42 weeks). It also finds use following delivery of the placenta, because it promotes contraction and vasoconstriction and helps to control postpartum bleeding.

Metabolism

In humans, estimates of median plasma half-life of oxytocin range from 3.2 min after a single 2 U bolus injection to 4.8 min during a 500 mU min^-1 infusion. Oxytocin is rapidly metabolised in the liver and kidneys, and also in the plasma during pregnancy by secreted oxytocinase (leucyl/cystinyl aminopeptidase), with some degree of metabolism also taking place in the mammary glands[1].

References

[1] C. Ding, F. Magkos, M. K.-S. Leow. “Oxytocin in metabolic homeostasis: implications for obesity and diabetes management.” Obesity Reviews 20 1 (2018): 22–40.