Oxytocin

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

CAS No.: 50-56-6

Molecular Weight：1007.18734

Modify Date.: 2022-10-26 09:23

Introduction: Oxytocin is the principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland. View more+

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1. Names and Identifiers

1.1 Name: Oxytocin
1.2 Synonyms: (1-hemicystine)-oxytocin (2S)-1-({(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-(4-hydroxybenzyl)-13-[(1S)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-N-{(1S)-1-[(2-amino-2-oxoethyl)carbamoyl]-3-methylbutyl}pyrrolidine-2-carboxamide 1-{[(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-2-butanyl]-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-leucylglycinamide 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-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-leucylglycinamide 3-isoleucine-8-leucinevasopressin Atonin O atonino cyclic(1-6)-di/// di-sipidin EINECS 200-048-4 endopituitrina Glycinamide, 1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-13-[(1S)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-yl]carbonyl]-L-prolyl-L-leucyl- glycinamide,l-cysteinyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cys L-Cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-leucylglycinamide cyclic (1®6)-disulfide MFCD00076731 Nobitocin S nobitocins Oxtocin Oxystin Oxytocin Acetate Partocon Pitocin Presoxin Synpitan Syntocin Syntocinon Syntocinone Utedrin Uteracon α-Hypophamine α-Hypophamine Oxytocic hormone

1.3 CAS No.: 50-56-6

1.4 CID: 439302

1.5 EINECS(EC#): 200-048-4

1.6 Molecular Formula: C43H66N12O12S2 (isomer)

1.7 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

1.8 InChkey: XNOPRXBHLZRZKH-DSZYJQQASA-N

1.9 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

1.10 Isomers Smiles: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

2. Properties

2.1 Density: 1.27

2.1 Melting point: 192-194 °C

2.1 Boiling point: 1533.3 °C at760mmHg

2.1 Refractive index: 1.6700 (estimate)

2.1 Flash Point: 881.1 °C

2.1 Precise Quality: 1006.44000

2.1 PSA: 450.13000

2.1 logP: 1.55630

2.1 Appearance: lyophilized powder

2.2 Storage: Store at -20°C.

2.3 Chemical Properties: White Solid

2.4 Color/Form: White powder

2.5 Decomposition: When heated to decomposition it emits toxic fumes of /sulfur oxide/ and /nitric oxide/.

2.6 pKa: pKa ～6.1(free amino group on Cys) (Occasionally);～10(free phenol on Tyr) (Occasionally)

2.7 Water Solubility: Soluble in water, butanol
In water, 1.2X10+4 mg/L at 25 deg C (est)

2.8 Spectral Properties: SPECIFIC OPTICAL ROTATION: -26.2 DEG @ 22 DEG C/D (0.53 G/100 ML WATER)

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is beleved to influence social cognition and behaviour.

3.2 Purification Methods: It is a cyclic nonapeptide which is purified by countercurrent distribution between solvent and buffer. It is soluble in H2O, n-BuOH and isoBuOH. [Bodanszky & du Vigneaud J Am Chem Soc 81 2504 1959, Cash et al. J Med Pharm Chem 5 413 1962, Sakakibara et al. Bull Chem Soc Jpn 38 120 1965; solid phase synthesis: Bayer & Hagenmyer Tetrahedron Lett 2037 1968.] It was also synthesised on a solid phase matrix and finally purified as follows: A Sephadex G-25 column is equilibrated with the aqueous phase of a mixture of 3.5% AcOH (containing 1.5% of pyridine)/n-BuOH/*C6H6 (2:1:1) and then the organic phase of this mixture is run through. A solution of oxytocin (100mg) in H2O (2mL) is applied to the column which is then eluted with the organic layer of the above mixture. The fractions containing the major peak [as determined by the Folin-Lowry protein assay: Fryer et al. Anal Biochem 153 262 1986] are pooled, diluted with twice their volume of H2O, evaporated to a small volume and lyophilised to give oxytocin as a pure white powder (20mg, 508 U/mg). [Ives Can J Chem 46 2318 1968, Beilstein 22 III/IV 82.] Oxytocin Preparation Products And Raw materials Raw materials

3.3 Usage: Oxytocin is the principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: 26-36

4.1 Exposure Standards and Regulations: 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.

4.2 Packing Group: II

4.2 Octanol/Water Partition Coefficient: log Kow = -6.27 (est)

4.3 Other Preventative Measures: This material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.
As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.
/Use/ safety goggles or glasses /and/ protect exposed skin.

4.4 Hazard Class: 6.1(a)

4.4 Cleanup Methods: Wipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.

4.5 DisposalMethods: SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

4.6 RIDADR: UN 3249

4.6 Fire Fighting Procedures: Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.

4.7 Safety Profile: Poison by intravenous route. Experimental reproductive effects. A pituitary hormone which stimulates uterine contraction and milk production. The principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland.Note: Unlike

4.8 Formulations/Preparations: Oxytocin injection, USP ... contains 10 USP units per mL and may be administered iv or im. All commercial preparations are now synthetic.
... injection, USP

4.9 WGK Germany: 3

4.9 RTECS: RS7534000

4.9 Protective Equipment and Clothing: Engineering controls such as exhaust ventilation are recommended.
Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.

4.10 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.

4.11 Skin, Eye, and Respiratory Irritations: May cause irritation. Avoid contact. Avoid inhalation. Remove to fresh air.

4.12 Safety: Poison by intravenous route. Experimental reproductive effects. A pituitary hormone which stimulates uterine contraction and milk production. The principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland. Note: Unlike vasopressin which occurs in at least two forms, oxytocin from beef and hog sources shows no difference in amino acid composition. When heated to decomposition it emits toxic fumes of SO_x and NO_x.
Hazard Codes:?Xi
Risk Statements:?36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:?26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
RIDADR:?3249
WGK Germany:?3
F:?3-8-10-23
HazardClass:?6.1(a)
PackingGroup: II
RTECS: RS7534000

4.13 Specification: ?Oxytocin (CAS NO.50-56-6), also named oxytocin lyophilized ; oxytocin acetate ; H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 Disulfide bond ; and H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (Disulfide bond) .?It is a mammalian hormone that also acts as a neurotransmitter in the brain.

4.14 Toxicity

???

ivn-mus LD₅₀:5800?μg/kg

???

NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),151.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

50-56-6Total: 5 Synthesis Route

27560-15-2

50-56-6 436 Suppliers

Literatures:
Wang, Ting; Danishefsky, Samuel J. Journal of the American Chemical Society, 2012 , vol. 134, # 32 p. 13244 - 13247
Yield: null

27610-07-7

50-56-6 436 Suppliers

Literatures:
Wang, Ting; Danishefsky, Samuel J. Journal of the American Chemical Society, 2012 , vol. 134, # 32 p. 13244 - 13247
Yield: null

41089-31-0

50-56-6 436 Suppliers

Literatures:
Wang, Ting; Danishefsky, Samuel J. Journal of the American Chemical Society, 2012 , vol. 134, # 32 p. 13244 - 13247
Yield: null

View all

8. Precursor and Product

precursor:

41089-31-0

118408-13-2

151937-33-6

27560-15-2

27610-07-7

product :

407-25-0

9. Other Information

9.0 Merck: 13,7049

9.1 BRN: 3586108

9.2 Animal Model:: Fifty-six male Lister-hooded rats (150-200?g)

9.3 Dosage:: 0.1?mg/kg-0.3 mg/kg

9.4 Result:: Produced significantly greater hypothermia (at 0.3 mg/kg) than the saline group.

9.5 Indications and Usage: Oxytocin (OT) is a type of uterine contraction drug and can be derived from the animal posterior pituitary or chemically synthesized.
Oxytocin is a uterine contraction drug that is mostly used in late pregnancy induction and stagnant birth due to weak uterine contractions. Suitable for inducing labor and alleviating pain. Commonly used with ergot preparations to be used in inducing labor, expediting labor, and in uterine bleeding due to weak uterine contractions following birth or still birth. Nose drops can be used to promote lactation.

9.6 Mechanisms of Action: Oxytocin does not contain vasopressin and has no pressure-boosting effects. It can be absorbed through oral mucosa, selectively excite smooth uterine muscle, and intensify its contractions. The uterus is most sensitive to oxytocin when in labor (due to increased estrogen secretion), and an immature uterus will not respond to this drug. During early or mid-term pregnancy, the uterus has a relatively low reactivity to oxytocin, which gradually increases during late-stage pregnancy and peaks during labor. Small doses can strengthen the rhythmic contractions of smooth uterine muscles, increase their contractibility, increase their contraction speed, ensure similar contraction characteristics to that of a natural birth, and maintain polarity and symmetry. Thus, it is used clinically to expedite and induce labor. Large doses cause tonic contractions in the uterine muscles, so it is used clinically to burst blood vessels between muscle fibers, prevent postpartum hemorrhage, and ensuring postpartum recovery. It can also promote lactation by causing the breast ducts to contract and expel milk from the breasts, but it cannot increase the lactation amount.

9.7 Pharmacokinetics: Ineffective when taken orally, as it can be damaged by digestive fluids, although it can be absorbed through oral mucosa. 1-3 minutes of venous infusion 0.01 IU can induce physiological uterine contractions (Rhythmic, polar, symmetrical) with a short time span, as its half-life is only 2.5-3 minutes. Large doses cause tonic uterine contractions.

9.8 Adverse reactions: Oxytocin derived from cow or pig’s pituitary occasionally causes allergic reactions, and infusing too quickly may lead to mild vasodilation and hypotension. Patients who suffer from abruptio placentae, heart disease, or enlarged uterus, are over 35 years old, have a history of cesarean section or uterine muscle tumor removal, or are experiencing a breech birth should use with caution. Using oxytocin while experiencing a sacral block may lead to severe hypertension and even cerebrovascular rupturing. Cannot be injected in the same solution with norepinephrine. Incompatible with hydrolyzed proteins.

9.9 Contradictions: Do not use during birth if there are obvious signs of an unsymmetrical head, incorrect fetal position, exposed umbilical cord, prolapse, complete placenta previa, narrow pelvis, or overly intense uterine contractions. Not to be used by patients with overly narrow pelvises, histories of uterine surgery (including C-sections), excessive pains, blocked birth canals, abruptio placentae, or pregnancy poisoning.

9.10 Warnings and Precautions: Dosage and infusion speed must be strictly monitored when used to expedite or induce labor to prevent tonic contractions, which can suffocate the fetus or rupture the uterus.

9.11 Description: 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.

9.12 Chemical Properties: White Solid

9.13 Originator: Syntocinon,Sandoz,US,1957

9.14 Uses: Oxytocin is the principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland.

9.15 Uses: Oxytocin is a nonapeptide hormone primarily synthesized in magnocellular neurons of the paraventricular and supraoptic nuclei of the hypothalamus. It is known best for its role in stimulating uterine contraction and lactation and is important for social memory and attachment, sexual and maternal behavior, and aggression. Also, it has been implicated in various non-social behaviors, including learning, anxiety, feeding, and pain perception.

9.16 Definition: ChEBI: A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is bel eved to influence social cognition and behaviour.

9.17 Manufacturing Process: BocGly resin (3.0 g, 3 meq) was placed in the reaction vessel of a Vega Model 50 semiautomatic peptide synthesizer.Activation of the amino acid was carried out by dissolving 10 meq of a suitably protected amino acid, 15 meq of hydroxy benzotriazole and 10 meq of dicyclohexylcarbodiimide in DMF (70 ml), whereupon the mixture was left at room temperature for 1 h (asparagine and glutamine were activated at 0°C for 15 min), whereupon the precipitate was filtered off, and the filtrate was treated the activated amino acid in Table 1 (step 7). The completion of the coupling step was checked by the method of Kaiser (Anal. Biochem. 34, 595 (1970)) after the cycle had been completed (step 9). If the test was positive (coupling yield below 99%), the cycle was repeated starting from step 7. If the test was negative, the termination procedure was performed according to Table 2. When the whole sequence had been coupled, the resin was placed on a filter and washed repeatedly with methanol. The dried product was placed in a glass vessel and cooled in an ethanol-dry ice bath and suspended in methanol (about 100 ml). The mixture was then saturated with sodium-dried ammonia to achieve approximately 50% concentration. Then the vessel was placed in a steel cylinder and left at room temperature for two days. After the pressure had been relieved, the product was filtered, and the residue was extracted with hot (about 100°C) DMF (2x100 ml). The filtrate and the extract were combined and evaporated. The residue was dissolved in a small amount of hot DMF, and methanol was added to the coupling point. The precipitate was collected by filtration and washed on the filter with methanol. After drying in vacuum, the purity was checked by thin-layer chromatography. Yield about 2.8 g.
100 mg of the above described protected peptide were placed in a 100 ml round-bottom flask, and dry nitrogen was flushed through for about 15 min. 50 ml of sodium-dried ammonia were distilled in, and the protective group was removed from the product by adding sodium until blue color remained in the solution for 15 sec. The excess of sodium was destroyed by adding of ammonium chloride. Ammonia was removed in a nitrogen stream, and the residue was dissolved in 1 liter of methanol. The pH of the solution was adjusted to about 4 with concentrated acetic acid, and the solution was then titrated with 0.1 mM of iodine in methanol to brownish color. The mixture was stirred with 3 g of Dowex 50x2 ion exchanger in chloride form for 10 min at room temperature. The ion exchanger was removed by filtration, and the filtrate was evaporated to dryness. The residue was dissolved in 3 ml of 20% acetic acid and purified by chromatography on Sephadex G-25 with 20% acetic acid as eluent. The final purification was achieved by reverse phase HPLC. The purity of the product was determined on a HPCL column μ- Bondapak C-18 in 45% ethanol and 55% 5 mM trifluoroacetic acid in water. The column was supplied by Water Associates, Inc., Millford, Mass., U.S.A. The purity of the product was also shown by amino acid analysis.

9.18 Usage: Oxytocin is used as a peptide hormone that acts predominantly as a neurotransmitter; stimulates uterine contraction and lactation, increases Na+ excretion; stimulates myometrial GTPase and phospholipase C.

9.19 Brand name: Pitocin (Parkdale); Syntocinon (Novartis);Oxytocin;Pituitrin.

9.20 Therapeutic Function: Oxytocic

9.21 General Description: Oxytocin (OXT) is a potent natriuretic hormone encoded by the gene mapped to human chromosome 20p13. It is synthesized along with its carrier protein neurophysin I from its inactive precursor prepro-OXT. OXT gene consists of three exons and two introns, where first exon codes for hormone OXT while other exon codes for neurophysin I.

10. Computational chemical data

Molecular Weight: 1007.18734g/mol
Molecular Formula: C₄₃H₆₆N₁₂O₁₂S₂
Compound Is Canonicalized: True
XLogP3-AA: -2.6
Exact Mass: 1006.43645793
Monoisotopic Mass: 1006.43645793
Complexity: 1870
Rotatable Bond Count: 17
Hydrogen Bond Donor Count: 12
Hydrogen Bond Acceptor Count: 15
Topological Polar Surface Area: 450
Heavy Atom Count: 69
Defined Atom Stereocenter Count: 9
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB//ABgAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgQQCAAADSzF2ASyBoPAAgCIAiFSEAACAAAgIAAIiIGOCIgIZjqC0TOUcAAk1hGImAedy6COIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What does "oxy" mean in chemicals such as oxycontin and oxytocin? Apr 04 2022
What does "oxy" mean in chemicals such as oxycontin and oxytocin? Oxycontin® is a trade name. The company that sells the drug (Purdue Pharma) can call it pretty much anything they want as long as it doesn’t fall afoul of FDA restrictions (so Higher Than A Kite ® probably would not fly). It may mea...
Do emotional chemicals such as oxytocin contain a color when in a large amount, or are they colorless? Jan 16 2022
Biological hormones are so powerful that microscopic amounts have great effects. In the body, they are always in solution ( the bloodstream) for delivery. Crystalized, it is white. Why do you want to know?

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CAS: 50-56-6 Oxytocin atonino endopituitrina nobitocins