Oxytocin

OT · OXT · OXTOCIN · endopituitrina · pitocin · ocytocin · Oxytocin powder · CYS-TYR-ILE-GLN-ASN-CYS-PRO-LEU-GLY-NH2

https://huagongshe.com/de/chemical/439302

Identifikatoren & physikalische Daten

CAS No.	50-56-6
Summenformel	C43H66N12O12S2
Durchschnittliche Molmasse	1.007,2 g/mol
Monoisotopische Masse	1.006,43645755 g/mol
SMILES	CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O
InChIKey	XNOPRXBHLZRZKH-DSZYJQQASA-N
PubChem CID	439302
ChEMBL	CHEMBL395429
ChEBI	CHEBI:7872
EC No.	200-048-4
DTXSID	DTXSID8048361
Lokaler Name	Oxytocin

Chemische & physikalische Eigenschaften

XLogP	-2,6
Polarare Oberfläche (TPSA)	450
H-Brücken-Donoren	12
H-Brücken-Akzeptoren	15
Frei drehbare Bindungen	17
Schwere Atome	69
Formalladung	0
Komplexität	1.870
Color/Form	White powder
Löslichkeit	Soluble in water, butanolVery soluble in water. It dissolves in dilute solutions of acetic acid and of ethanol (96 per cent).Soluble in water.
Human Drugs	Breast FeedingLactationMilk, HumanOxytocicsPituitary Hormones, PosteriorFDA approved drugs -> Active ingredientUterotonics
Animal Drugs	FDA approved animal drugs -> Active ingredientPharmaceuticals -> UK Veterinary Medicines Directorate List
Decomposition	When heated to decomposition it emits toxic fumes of /sulfur oxide/ and /nitric oxide/.
Schmelzpunkt	192-194 ℃192-194°C
Optical Rotation	SPECIFIC OPTICAL ROTATION: -26.2 DEG @ 22 °C/D (0.53 G/100 ML WATER)
Collision Cross Section	294.98 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]298.97 Å² [M-H]- [CCS Type: DTMethod: stepped-field]297.9 Å² [M-H]-
Other Experimental Properties	Shows an activity of 450-500 USP units/mg when compared with USP posterior pituitary reference stdOxytocin from beef and hog sources shows no difference in amino acid composition
Siedepunkt	1533.3±65.0 °C(Predicted)
Dichte	1.1086 (rough estimate)
Brechungsindex	1.6700 (estimate)
Lagerbedingungen	2-8°C
Aggregatzustand	lyophilized powder
pKa (Säurekonstante)	pKa ~6.1(free amino group on Cys) (Occasionally)~10(free phenol on Tyr) (Occasionally)
Farbe	White
Biologische Quelle	synthetic (organic)
Merck	13,7049
BRN	3586108
InChIKey	DSZOEVVLZMNAEH-BXUJZNQYSA-N
SMILES	CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC1=O)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(N)=O
CAS Datenbank	50-56-6(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 79.6% (39 of 49) of all reports.WarningH302 (10.2%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 49 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Oxytocin: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - Oxytocin: Human health tier I assessment
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including oxytocin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Oxytocin is included on this list.Oxytocin may be used as a uterine contractor to precipitate and accelerate normal parturition and postpartum evacuation of uterine debris. In surgery it may be used postoperatively following cesarean section to facilitate involution and resistance to the large inflow of blood. It will contract smooth muscle cells of the mammary gland for milk letdown if the udder is in proper physiological state. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Hazard Classes and Categories	Acute Tox. 4 (10.2%)
Skin, Eye, and Respiratory Irritations	May cause irritation. Avoid contact. Avoid inhalation. Remove to fresh air.
Hazardous Reactivities and Incompatibilities	Oxytocin injection appears to be compatible with most iv infusion fluids but is reported to be physically incompatible with fibrinolysin, norepinephrine bitartrate, prochlorperazine edisylate, and warfarin sodium. Oxytocin injection has also been reported to be incompatible with various other drugs, but the compatibility depends on several factors (eg, the concentration of the drugs, resulting pH, temperature). Specialized references should be consulted for more specific compatibility information.

Anwendungen & Verwendung

Beschreibung

Oxytocin is a peptide hormone containing nine amino acids secreted and synthesized by the paraventricular and supraoptic nuclei of the hypothalamus and stored and released by the neurohypophysis. It acts in females by inducing uterine contractions during parturition and stimulating milk ejection by the mammary glands. No actions in males are known. Synthetic derivatives of oxytocin are used to induce labor and for therapeutic abortions. In recent years the safety of oxytocin has been greatly enhanced by the use of continuous maternal and fetal monitoring and by the use of controlled intravenous infusion of the drug.

History

Oxytocin was discovered by Sir Henry Dale in 1909 when he found that an extract from the human posterior pituitary gland contracted the uterus of a pregnant cat. (The hormone is found unchanged in every mammalian species.) Dale named the unknown substance oxytocin, using the Greek words for "quick" and "birth." As early as 1911, physicians began using the pituitary extract to stimulate childbirth contractions. Dale subsequently found that the same extract facilitates the release of mother's milk. In the early 1950s, American biochemist Vincent du Vigneaud found that oxytocin is made up of nine amino acids, and he identified its amino acid sequence. In 1953 du Vigneaud carried out the synthesis of oxytocin, making it the first polypeptide hormone to be synthesized. (Du Vigneaud received the Nobel Prize for Chemistry in 1955 for his breakthrough.)