Oxytocin 50-56-6

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oxytocin

CAS: 50-56-6

Molecular Formula: C43H66N12O12S2

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50-56-6 - Names and Identifiers

Name	oxytocin
Synonyms	oxtocin atonino oxytocin nobitocins di-sipidin endopituitrina Oxytocin Solution oxytocin lyophilized (1-hemicystine)-oxytocin 3-isoleucine-8-leucinevasopressin H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 Disulfide bond H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (Disulfide bond) glycinamide,l-cysteinyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cys 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 (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-13-[(2s)-butan-2-yl]-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(1s)-1-(carbamoylmethylcarbamoyl)-3-methyl-butyl]pyrrolidine-2-carboxamide
CAS	50-56-6
EINECS	200-048-4
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
InChIKey	DSZOEVVLZMNAEH-BXUJZNQYSA-N

50-56-6 - Physico-chemical Properties

Molecular Formula	C43H66N12O12S2
Molar Mass	1007.19
Density	1.1086 (rough estimate)
Melting Point	192-194°C
Boling Point	1533.3°C at 760 mmHg
Specific Rotation(α)	D22 -26.2° (c = 0.53)
Flash Point	881.1°C
Water Solubility	Soluble in water.
Solubility	Very soluble in water. It dissolves in dilute solutions of acetic acid and of ethanol (96 per cent).
Vapor Presure	0mmHg at 25°C
Appearance	lyophilized powder
Color	White
Merck	13,7049
BRN	3586108
pKa	pKa ～6.1(free amino group on Cys) (Occasionally);～10(free phenol on Tyr) (Occasionally)
Storage Condition	2-8°C
Refractive Index	1.6700 (estimate)
Physical and Chemical Properties	White to yellow-brown powder, hygroscopic, soluble in water.
Use	Uterotonic drugs

50-56-6 - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing.
UN IDs	3249
WGK Germany	3
RTECS	RS7534000
FLUKA BRAND F CODES	3-8-10-23
HS Code	2937190000
Hazard Class	6.1(a)
Packing Group	II
Toxicity	LD50 oral in rat: > 20520ug/kg

50-56-6 - Nature

Open Data Verified Data

is a white amorphous powder with a slight abnormal odor and a specific optical rotation of 26.2. (22 °c). Soluble in water and acidic aqueous solution, soluble in acetone, butanol and acetic acid. The drying condition is stable, and heating at 9 0 ℃ for 30 min or below 5 0 ℃ for a long time is not inactivated. The solution between pH 3.5~4.4 is the most stable; The solution is unstable when the pH is 5; The solution of pH 6 will lose more vitality at room temperature. In glacial acetic acid at room temperature for 24h, the vitality is basically not lost.

Last Update：2024-01-02 23:10:35

50-56-6 - Preparation Method

Open Data Verified Data

• Both oxytocin and vasopressin are nonapeptides, and there is a basic amino acid residue in the vasopressin molecule, which is different in isoelectric point. Oxytocin has an isoelectric point of 7.7 and vasopressin has an isoelectric point of 10.9, indicating that vasopressin is more alkaline. When the extraction solution containing these two hormones is introduced into the artificial zeolite column, vasopressin easily forms positively charged ions and is largely adsorbed, and oxytocin flows out through the zeolite column. The eluted oxytocin solution was treated with bentonite to obtain relatively pure oxytocin.
• about 30g of the dry powder of the posterior pituitary and about 30g of the quartz powder were added to 1.4L of distilled water, ball-milled and extracted for 45min in a ball mill, centrifuged, and the supernatant was collected. The residue was further extracted 3 times by adding 1. 4L, 1.3L and 1.3L of water respectively. The supernatants of the 4 centrifugation were pooled. The treated artificial zeolite 0.25% G, 20L of acetic acid solution was added, stirred and then loaded into the exchange column. When the 25% acetic acid solution is lowered to 2-3cm below the zeolite surface, the extract solution is added immediately, and the flow rate is appropriately adjusted to collect the white turbid liquid from the adsorption column. When the liquid level of the extraction liquid was lowered to the surface of the zeolite, distilled water was immediately added, and the collection was stopped after the turbid liquid was exhausted. The extract flowing through the zeolite was adjusted to pH 3.5 with glacial acetic acid, then rapidly heated to 95 °c for 3min In a water bath, immediately cooled, and left overnight in a 0-5 °c cold chamber. The next day, the filtrate was clarified by filtration. Then add the filtrate with stirring, add pre-processed 10% bentonite slurry (usually 3ml per lOOmL), continuously stir th, the supernatant should be checked whether the adsorption is complete (check with 20% sulfosalicylic acid solution, precipitation should not occur), such as adsorption is not complete, should be added to bentonite slurry adsorption. 2 times of bentonite precipitation combined. The bentonite was then desorbed with 1% acetic acid solution. The total amount of 5L was desorbed 4 times, the amount was 1.6L, 1. 4L, 1.2L and 0.8L respectively, and the desorption solution was Combined 4 times. The content of oxytocin and vasopressin in The desorption solution was determined and calculated according to the potency of oxytocin. If vasopressin did not exceed the limit, the oxytocin solution was obtained.

 

50-56-6 - Preparation solution concentration reference

	1mg	5mg	10mg
1 mM	0.993 ml	4.964 ml	9.929 ml
5 mM	0.199 ml	0.993 ml	1.986 ml
10 mM	0.099 ml	0.496 ml	0.993 ml
5 mM	0.02 ml	0.099 ml	0.199 ml

 

50-56-6 - Use

Open Data Verified Data

has a stimulating effect on smooth muscle, can make the uterine smooth muscle contraction, so there is an effect of oxytocin. It can be used for induced labor, induced labor and uterine bleeding caused by Uterine inertia after abortion. Nasal drops can promote the discharge of milk. There is also a slight hemostatic effect.

 

50-56-6 - Reference Information

uterine contractile drug	oxytocin, also known as oxytocin, is a seed uterine contractile drug that can be extracted or chemically synthesized from the posterior lobe of the pituitary gland of animals. The chemically synthesized product does not contain vasopressin, has no pressor effect, has selective excitation effect on uterine smooth muscle, and strengthens its contraction. The uterus in labor is most sensitive to oxytocin (increased estrogen secretion), the immature uterus is not reactive to this product. The reactivity of the uterus to oxytocin in the early or second trimester of pregnancy is low, and it gradually increases in the late pregnancy, reaching the highest before labor. Small doses can strengthen the rhythmic contraction of the smooth muscle at the bottom of the uterus, strengthen its contractility, accelerate the frequency of contraction, and the nature of contraction is similar to natural childbirth, and maintain polarity and symmetry, so it is clinically used for induced labor and induced labor. Large doses make the uterine muscles contract ankylosing. It is clinically used to compress the blood vessels between muscle fibers, prevent postpartum hemorrhage and postpartum involution, and promote lactation, shrink the breast ducts, and promote the discharge of milk from the breast, but it cannot increase The secretion of milk can only promote milk excretion. It should be noted that the dosage and drip speed should be strictly controlled when used for induced labor or induced labor, so as not to cause tonic uterine contraction, resulting in fetal asphyxia death or uterine rupture. If there is no cephalopelvic, fetal position or other birth canal abnormalities, contraindicated, poor uterine contraction, history of cesarean section and more than 3 times of maternal contraindicated. Oxytocin preparations extracted from the pituitary gland of cattle and pigs occasionally cause allergic reactions, and intravenous drip too fast can cause mild vasodilation and blood pressure drop. The fastest dripping speed does not exceed 40~60 drops per minute. A slightly larger dose is also used for postpartum hemorrhage, fetal clothing, etc. In recent years, it has been found that this product has a good effect on pulmonary hemoptysis, and has a good effect on gastrointestinal function relaxation after vagus nerve resection or abdominal surgery. oral administration is ineffective and easy to be destroyed by digestive juice, but it can be absorbed by oral mucosa. intravenous drip of 0.01 IU can cause physiological contraction of uterus (rhythmic, polar and symmetrical) within 1-3 minutes, and the holding time is short, with a half-life of only 2.5-3 minutes and a large dose of myotonic contraction of uterine muscle. It has a synergistic effect with prostaglandins. Oxytocin is often combined with ergot preparations to treat postpartum hemorrhage; abortion is inevitable; it is mainly used for induction of labor in late pregnancy and delayed labor caused by uterine atony during labor; used for oxytocin sensitivity test; used for oxytocin irritation Test; assist postpartum milk discharge; hemoptysis; postoperative gastrointestinal motility delay.
biological activity	Oxytocin (α-Hypophamine; Oxytocic hormone) is a multi-effect hypothalamic peptide (hypothalamic peptide) that helps childbirth, breastfeeding and prosocial behavior. Oxytocin can be used as a stress response molecule with anti-inflammatory, antioxidant and protective effects, especially in the face of adversity or trauma.
Animal Model:	Fifty-six male Lister-hooded rats (150-200 g)
Dosage:	0.1 mg/kg-0.3 mg/kg
Administration:	Subcutaneousinjection; 0.1 mg/kg-0.3 mg/kg; single dose
Result:	Produced significantly greater hypothermia (at 0.3 mg/kg) than the saline group.
use	this product can be absorbed from oral mucosa and selectively act on uterine smooth muscle to promote uterine contraction. Suitable for birth and labor retardation. The effect is the same as that of oxytocin after intravenous drip. For pelvic stenosis, a history of uterine surgery (including caesarean section), excessive labor pains, obstruction of the birth canal, placental abruption, severe pregnancy poisoning maternal contraindicated. Uterine contractile drugs. Used for induced labor, induced labor, postpartum and after abortion due to uterine contraction weakness caused by uterine bleeding. Nose drops can promote milk discharge. Adverse reactions and contraindications: during delivery, obvious cephalopelvic disproportion, umbilical cord exposure or prolapse, complete placenta previa, too narrow pelvis, and too strong uterine contraction are prohibited. Placental abruption, heart disease, oversized uterus, pregnant women over 35 years old, history of caesarean section, history of myomectomy and breech delivery should be used with caution. With oxytocin in sacral block, severe hypertension and even cerebrovascular rupture can occur. It cannot be injected in the same solution with norepinephrine. There are incompatibility with hydrolyzed protein.
production method	method 1. extraction method (currently used in our country, the purity is low, but the cost is low) extraction of oxytocin solution 100g of leaf dry powder and 30g of quartz powder are put into a ball mill, distilled water is added, and the same method is used for extraction four times. The amount of distilled water added was 1.4L twice and 1.3L twice. Each extraction for 45min, centrifugation, liquid collection, residue extraction. Merge four extracts to obtain oxytocin solution. After leaf dry powder [water, ball mill] → chromatography separation of oxytocin extract 1500g of pre-treated artificial zeolite, adding 20L of 0.25% acetic acid solution, stirring and pouring into an exchange column, adding the extract when the acetic acid solution drops to 2-3cm above the surface of zeolite, and collecting white turbid solution at an appropriate flow rate (mainly containing oxytocin, because of its pI7.7, while vasopressin pI10.9 is easy to become a positive ion and is adsorbed). When the liquid level of the extract drops to the surface of the zeolite, immediately add distilled water and continue to collect the turbid liquid until it runs out. The turbid liquid was adjusted to 3.5 with glacial acetic acid, heated to 95 ℃ in a water bath for 3min, cooled quickly and refrigerated overnight. Oxytocin extract [HAc, artificial zeolite column] → turbid solution [HAc, heating] → adsorption and elution of the separation solution the next day, the refrigerated solution is filtered, the filtrate is added with 10% bentonite slurry (3ml per 100ml) under stirring, adsorption for 1h, centrifugation. The supernatant was checked with sulfosalicylic acid test solution, and no precipitation occurred for complete adsorption. If it is not complete, it is adsorbed again and precipitated twice. The bentonite is eluted four times with 1% acetic acid (1.6L, 1.4L, 1.2L and 0.8L respectively). When the eluate is heated to 80 ℃, trichlorotert-butanol is added, the temperature is raised to 95 ℃, the temperature is quickly cooled to 25 ℃, the filtrate is filtered or centrifuged, the filtrate is combined four times, and the titer and vasopressin limit are detected. Cold storage solution [filtration] → filtrate [bentonite slurry] → adsorbate [1% HAc]→ preparation of eluate oxytocin injection the measured qualified oxytocin solution is diluted to 5U/ml or 10U/ml, filtered by No. 4 or No. 5 vertical melting funnel, potted, and sterilized by circulating steam at 100 ℃ for 30min to obtain the finished product. Oxytocin solution (qualified for determination) [filter potting, sterilization] → Oxytocin injection. Note: After the artificial zeolite treats the new boiling stone through a 60-80 mesh sieve, add 2L of distilled water every 500g, adjust sodium hydroxide to pH9, keep it for half an hour, pour out the supernatant, add 2L of water, adjust to pH9, pour out the supernatant, add water, stir and add dilute sulfuric acid to lower the pH to 5.8-6, stir for half an hour, pour out the supernatant, and then use child water every time, repeatedly wash 7-8 times. Add 1L of water and dilute sulfuric acid, stir for half an hour, pour out the supernatant, wash with water to pH7, filter to dry, and dry for later use. Regeneration of Artificial Zeolite Wash artificial zeolite twice with distilled water, then add 1.5L of water (calculated by zeolite 500g) and 150g of sodium chloride to stir for 2 hours, wash to remove vasopressin, and then wash with distilled water until there is no chloride ion. Add a proper amount of water, adjust the pH to 9 with sodium hydroxide, stir for half an hour, pour out the supernatant, wash with distilled water, adjust the pH to 5.5-6 with sulfuric acid, then wash with water to near neutral, filter dry, and dry at 105 ℃ for later use. Add appropriate amount of water before use, adjust with glacial acetic acid, stir and soak. The preparation of 10% bentonite slurry is mixed according to the volume ratio of bentonite mass to water of 1:10, grinding for about 1h, and adjusting pH with acetic acid in grinding to stabilize at 3.5, and placing it in refrigerator for later use. Methods Seven-peptide amide (3-9 segment) was synthesized from benzyloxycarboyl leucine p-nitrophenyl ester by 2. chemical synthesis method, then benzyloxycarbonyl-S-benzylcysteine tyrosyl azide (1-2 segment) was synthesized, and oxytocin was synthesized in the third step.
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)

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