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Argipressine

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Name

Argipressine

EINECS 204-035-4
CAS No. 113-79-1 Density 1.59 g/cm3
PSA 512.03000 LogP 1.16100
Solubility N/A Melting Point N/A
Formula C46H65N15O12S2 Boiling Point N/A
Molecular Weight 1084.25 Flash Point 113℃
Transport Information N/A Appearance White powder
Safety 36 Risk Codes 20
Molecular Structure Molecular Structure of 113-79-1 (Argipressine) Hazard Symbols HarmfulXn
Synonyms

3-(Phenylalanine)-8-arginineoxytocin;8-L-Arginine-vasopressin;AVP;Arg8-vasopressin;Arginine antidiuretic hormone;Arginine-8-vasopressin;Arginine-vasopressin;1,2-Dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide,19-amino-13-benzyl-7-(carbamoylmethyl)-4-[2-[[1-[(carbamoylmethyl)carbamoyl]-4-guanidinobutyl]carbamoyl]-1-pyrrolidinylcarbonyl]-16-p-hydroxybenzyl-6,9,12,15,18-pentaoxo-(6CI);

Article Data 8

Argipressine Synthetic route

63-91-2

L-phenylalanine

71989-31-6

Fmoc-Pro-OH

113-79-1

cyclo(L-Cysteinyl-L-Tyrosyl-L-Phenylalanyl-L-Glutaminyl-L-Asparaginyl-L-Cysteinyl)-L-Prolyl-L-Arginyl-L-Glycinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / Automated synthesizer
1.2: 0.17 h / Automated synthesizer
2.1: oxygen / aq. buffer / 72 h / 20 °C / pH 8
View Scheme

C46H67N15O12S2

113-79-1

cyclo(L-Cysteinyl-L-Tyrosyl-L-Phenylalanyl-L-Glutaminyl-L-Asparaginyl-L-Cysteinyl)-L-Prolyl-L-Arginyl-L-Glycinamide

Conditions
ConditionsYield
With oxygen In aq. buffer at 20℃; for 72h; pH=8;

Argipressine Specification

1. Introduction of Argipressin

Argipressin is one kind of white powder. The IUPAC Name of Argipressin is 1-[16-Amino-4-(2-amino-2-oxoethyl)-7-(3-amino-3-oxopropyl)-10-benzyl-13-[(4-hydroxyphenyl)methyl]-3,6,9,12,15-pentaoxo-18,19-dithia-2,5,8,11,14-pentazacycloicosane-1-carbonyl]-N-[1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide. The Product Categories of this chemical is Amino Acid Derivatives;Peptide;Vasopressin and Oxytocin receptor;Peptide Receptors;Intermediates & Fine Chemicals;Peptides;Pharmaceuticals. Argipressine can soluble in water or acetic acid at a concentration of ≥1mg/ml to give a clear, colorless solution.

2. Properties of Argipressine

Physical properties about Argipressine are:
(1)Index of Refraction: 1.724; (2)Molar Refractivity: 270.08 cm3; (3)Molar Volume: 680.6 cm3; (4)Surface Tension: 76.5 dyne/cm ; (5)XLogP3-AA: -4.8 ; (6)H-Bond Donor: 14; (7)H-Bond Acceptor: 16; (8)Rotatable Bond Count: 19; (9)Tautomer Count: 1001; (10)Exact Mass: 1083.437854; (11)MonoIsotopic Mass: 1083.437854; (12)Topological Polar Surface Area: 464; (13)Heavy Atom Count: 75; (14)Storage Temp.: 2-8 °C.

3. Structure Descriptors of Argipressine

(1) InChI: InChI=1S/C46H65N15O12S2.C2H4O2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25;1-2(3)4/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53);1H3,(H,3,4);
(2) InChIKey: ZHFGXNMADRRGQP-UHFFFAOYSA-N;
(3) Canonical SMILES : CC(=O)O.C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N.

4. Toxicity of Argipressine

1.    

ivn-pig TDLo:40 ng/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 293 (2000),852.

5. Safety information of Argipressine

Hazard Codes: HarmfulXn
Risk Statements: 20 
R20:Harmful by inhalation.
Safety Statements: 36 
S36:Wear suitable protective clothing.
WGK Germany: 3
A poison by intravenous route. When heated to decomposition it emits toxic vapors of NOx and SOx.

6. Uses of Argipressine

Argipressine, also known as vasopressin, antidiuretic hormone by the hypothalamus supraoptic nucleus and paraventricular nucleus cells, is stored in the neurohypophysis. Physiological functions in the central nervous system can adjust the intracranial pressure and brain tissue metabolism. Argipressine is an anti-diuretic vasoconstrictor and can enhance memory. Argipressine is involved in body temperature and immunomodulatory.

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