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83150-76-9

Basic Information
CAS No.: 83150-76-9
Name: Octreotide acetate
Article Data: 9
Molecular Structure:
Molecular Structure of 83150-76-9 (Octreotide acetate)
Formula: C49H66N10O10S2
Molecular Weight: 1019.26
Synonyms: 11: PN:US20030229017 PAGE: 13 claimed protein;14: PN: DE10147056 PAGE: 40 claimedprotein;17: PN: US6268342 SEQID: 18 claimed protein;1: PN: EP1118336 SEQID: 1claimed protein;1: PN: WO2005007122 TABLE: 22 claimed protein;25: PN:WO2007081792 SEQID: 40 claimed protein;2: PN: EP1358890 TABLE: A claimedprotein;Longastatin;L-Cysteinamide,D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[2-hydroxy-1-(hydroxymethyl)propyl]-, cyclic (2?;
EINECS: 1533716-785-6
Density: 1.395 g/cm3
Boiling Point: 1447.228°C at 760 mmHg
Flash Point: 829.053 C
Appearance: white powder
PSA: 382.82000
LogP: 3.02100
Synthetic route

H-D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-OH

83150-76-9

octreotide

Conditions
ConditionsYield
With ammonium acetate; pyrographite In tetrahydrofuran; water at 20℃;85.6%

D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr(ol)

83150-76-9

octreotide

Conditions
ConditionsYield
In water at 20℃; for 47.5h; pH=7.4; aq. phosphate buffer;80%
With phosphate buffer; air at 25℃; for 48h; Yield given;
With ammonium acetate for 48h; pH=7.0; Cyclization;
With air

H-DPhe-Cys(SO3Na)-Phe-DTrp-Lys-Thr-Cys-Thr-ol

83150-76-9

octreotide

Conditions
ConditionsYield
for 24 - 72h; pH=3 - 9.2; Product distribution / selectivity;76.4%

C49H68N10O10S2

83150-76-9

octreotide

Conditions
ConditionsYield
With ammonia; dihydrogen peroxide In methanol at 25℃; for 1h; pH=7.5 - 8;

C55H78N12O12S2

83150-76-9

octreotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: mercury acetate; acetic acid / H2O
2: H2O2; ammonia / methanol / 1 h / 25 °C / pH 7.5 - 8
View Scheme
18942-49-9

Boc-D-Phe-OH

83150-76-9

octreotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: air
View Scheme

2TFA.H-DPhe-Cys(SO3Na)-Phe-DTrp-Lys-Thr-Cys-Thr-ol

83150-76-9

octreotide

Conditions
ConditionsYield
With disodium hydrogenphosphate; phosphoric acid In water; acetonitrile at 23℃; pH=8.3;
887144-97-0

Togni's reagent

CF3CO2H*H2N-(D)-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-ol

A

CF3CO2H*H2N-(D)-Phe-[Cys-Phe-D-(2-CF3)Trp-Lys-Thr-Cys]-Thr-ol

B

CF3CO2H*H2N-(D)-Phe-Cys(CF3)-Phe-D-Trp-Lys-Thr-Cys(CF3)-Thr-ol

C

CF3CO2H*H2N-(D)-Phe-Cys(CF3)-Phe-D-(2-CF3)Trp-Lys-Thr-Cys(CF3)-Thr-ol

D

83150-76-9

octreotide

Conditions
ConditionsYield
In methanol at -78 - 25℃; Inert atmosphere;A 0.4 mg
B 3 mg
C 3 mg
D n/a
887144-94-7

Togni's reagent II

CF3CO2H*H2N-(D)-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-ol

A

CF3CO2H*H2N-(D)-Phe-[Cys-Phe-D-(2-CF3)Trp-Lys-Thr-Cys]-Thr-ol

B

83150-76-9

octreotide

Conditions
ConditionsYield
In methanol at -78℃; for 12h;

C67H86N12O18S2

83150-76-9

octreotide

Conditions
ConditionsYield
With O-Methylhydroxylamin; 2,2'-dipyridyldisulphide In aq. phosphate buffer; acetonitrile at 30℃; for 0.5h; pH=7.4; UV-irradiation; regioselective reaction;
Raw Materials
18942-49-9
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History

 Octreotide was first synthesized in 1979 by the chemist Wilfried Bauer.

Specification

1. Introduction of Octreotide acetate
Octreotide acetate is one kind of white powder. The IUPAC Name of this chemical is 7-(4-Aminobutyl)-16-[(2-amino-3-phenylpropanoyl)amino]-13-benzyl-N-(1,3-dihydroxybutan-2-yl)-4-(1-hydroxyethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15-pentaoxo-18,19-dithia-2,5,8,11,14-pentazacycloicosane-1-carboxamide. The Product Categories of it is Peptide;API. The Classification Code of Octreotide acetate is Antineoplastic Agents; Antineoplastic agents, hormonal; Antisecretory [gastric]; Gastrointestinal agents. Besides, Octreotide acetate can soluble in water or 10% acetic acid at a concentration of ≥1mg/ml.

2. Properties of Octreotide acetate
Physical properties about Octreotide acetate are:
(1)Storage Temp.: -20 °C; (2)Density: 1.395 g/cm3; (3)Boiling Point: 1447.228 °C at 760 mmHg; (4)Flash Point: 829.053 °C; (5)Index of Refraction: 1.673; (6)Molar Refractivity: 273.948 cm3; (7)Molar Volume: 730.708 cm3; (8)Surface Tension: 79.098 dyne/cm; (9)Enthalpy of Vaporization: 231.842 kJ/mol; (10)XLogP3-AA: 1; (11)H-Bond Donor: 13; (12)H-Bond Acceptor: 12; (13)Rotatable Bond Count: 17; (14)Tautomer Count: 972; (15)Exact Mass: 1018.44048; (16)MonoIsotopic Mass: 1018.44048; (17)Topological Polar Surface Area: 332; (18)Heavy Atom Count: 71.

3. Structure Descriptors of Octreotide acetate
(1)InChI: InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)
(2)InChIKey: DEQANNDTNATYII-UHFFFAOYSA-N
(3)Canonical SMILES: CC(C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)C(CC5=CC=CC=C5)N)C(=O)NC(CO)C(C)O)O
(4)Smiles: C1(=O)N[C@@H](C(N[C@@H](C(=O)N[C@@H](C(N[C@@H]([C@@H](C)O)CO)=O)CSSC[C@@H](C(N[C@@H](Cc2ccccc2)C(=O)N[C@@H]1Cc1c[nH]c2c1cccc2)=O)NC(=O)[C@@H](Cc1ccccc1)N)[C@@H](C)O)=O)CCCCN

4. Uses of Octreotide acetate
Octreotide acetate (CAS NO.83150-76-9) has been used off-label for the treatment of severe, refractory diarrhea from other causes. It has also been used with varying degrees of success in infants with nesidioblastosis to help decrease insulin hypersecretion. Octreotide may be useful in the treatment of thymic neoplasms. It has been used in the treatment of malignant bowel obstruction. Octreotide may be used in conjunction with midodrine to partially reverse peripheral vasodilation in the hepato-renal syndrome.