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Cas Database

83150-76-9

83150-76-9

Identification

  • Product Name:Octreotide acetate

  • CAS Number: 83150-76-9

  • EINECS:1533716-785-6

  • Molecular Weight:1019.26

  • Molecular Formula: C49H66N10O10S2

  • HS Code:3004909090

  • Mol File:83150-76-9.mol

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?;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:Usbiological
  • Product Description:Octreotide Acetate
  • Packaging:1mg
  • Price:$ 319
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Octreotide ≥98%(HPLC)
  • Packaging:500 μg
  • Price:$ 240
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Octreotide ≥98% (HPLC)
  • Packaging:500ug
  • Price:$ 231
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Octreotide Acetate Pharmaceutical Secondary Standard; Certified Reference Material
  • Packaging:10 mg
  • Price:$ 256
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Octreotide ≥98% (HPLC)
  • Packaging:1mg
  • Price:$ 338
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Octreotide acetate United States Pharmacopeia (USP) Reference Standard
  • Packaging:4.37 mg
  • Price:$ 1300
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:(4R,7S,10S,13R,16S,19R)-13-((1H-Indol-3-yl)methyl)-19-((R)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-((R)-1-hydrox 95%
  • Packaging:500mg
  • Price:$ 678
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:(4R,7S,10S,13R,16S,19R)-13-((1H-Indol-3-yl)methyl)-19-((R)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-((R)-1-hydrox 95%
  • Packaging:100mg
  • Price:$ 198
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  • Manufacture/Brand:Crysdot
  • Product Description:Octreotide 95+%
  • Packaging:25mg
  • Price:$ 355
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  • Manufacture/Brand:ChemScene
  • Product Description:Octreotide 98.84%
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Relevant articles and documentsAll total 9 Articles be found

Use of trichloroacetimidate linker in solid-phase peptide synthesis

Yan, Liang Zeng,Mayer, John P.

, p. 1161 - 1162 (2003)

A solid-phase method for the preparation of C-terminal amino-alcohol-containing peptides using activated Wang resin is presented. A diverse set of (fluorenylmethoxy)carbonyl (Fmoc) protected amino alcohols was found to load rapidly and efficiently. The synthetic utility of this approach was demonstrated through the direct synthesis of the peptide drug octreotide with excellent yield and purity. These results suggest that the use of trichloroacetimidate activated resins offers an attractive alternative in the preparation of this class of peptides.

Rapid Photolysis-Mediated Folding of Disulfide-Rich Peptides

Patil, Nitin A.,Karas, John A.,Wade, John D.,Hossain, Mohammed Akhter,Tailhades, Julien

, p. 8599 - 8603 (2019/06/04)

Structure–activity relationship studies are a highly time-consuming aspect of peptide-based drug development, particularly in the assembly of disulfide-rich peptides, which often requires multiple synthetic steps and purifications. Therefore, it is vital to develop rapid and efficient chemical methods to readily access the desired peptides. We have developed a photolysis-mediated “one-pot” strategy for regioselective disulfide bond formation. The new pairing system utilises two ortho-nitroveratryl protected cysteines to generate two disulfide bridges in less than one hour in good yield. This strategy was applied to the synthesis of complex disulfide-rich peptides such as Rho-conotoxin ρ-TIA and native human insulin.

METHOD FOR PRODUCTION OF OCTREOTIDE

-

Paragraph 0060, (2016/10/08)

PROBLEM TO BE SOLVED: To provide a method for producing high-purity octreotide with high yields in a liquid phase synthesis method. SOLUTION: The present invention provides a method for producing octreotide or a salt thereof by using an acetal compound represented by formula (3) or a salt thereof as an intermediate, desorbing the amino protective group R1a, repeating condensation reaction with a protected amino acid and desorption of a protective group, and further performing oxidation reaction thereof. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction

Tailhades, Julien,Gidel, Marie-Aude,Grossi, Benjamin,Lecaillon, Jennifer,Brunel, Luc,Subra, Gilles,Martinez, Jean,Amblard, Muriel

experimental part, p. 117 - 120 (2010/04/04)

(Figure Presented) Getting the better of troublemakers: C-terminal peptide alcohols cannot be synthesized by conventional solidphase peptide synthesis (SPPS) because of the absence of a free carboxylic group to attach to the resin. This problem was circumvented by anchoring a β-amino alcohol residue to the resin to provide a starting point for SPPS. An intramolecular O-N acyl shift completed the synthesis of the desired peptides (see scheme).

Electrophilic S-trifluoromethylation of cysteine side chains in α- and β-peptides: Isolation of trifluoromethylated sandostatin (octreotide) derivatives

Caponea, Stefania,Kieltschb, Iris,Floegela, Oliver,Lelaisa, Gerald,Togni, Antonio,Seebach, Dieter

experimental part, p. 2035 - 2056 (2009/02/08)

The new electrophilic trifluoromethylating 1-(trifluoromethyl)-benziodoxole reagents A and B (Scheme 1) have been used to selectively attach CF3 groups to the S-atom of cysteine side chains of α- and β-peptides (up to 13-residues-long; products 7-14). Other functional groups in the substrates (amino, amido, carbamate, carboxylate, hydroxy, phenyl) are not attacked by these soft reagents. Depending on the conditions, the indole ring of a Trp residue may also be trifluoromethylated (in the 2-position). The products are purified by chromatography, and identified by 1H-, 13C-, and 19F-NMR spectroscopy, by CD spectroscopy, and by high-resolution mass spectrometry. The CF3 groups, thus introduced, may be replaced by H (Na/NH3), an overall Cys/Ala conversion. The importance of trifluoromethylations in medicinal chemistry and possible applications of the method (spin-labelling, imaging, PET) are discussed.

Process for the formation of disulfide bonds in cyclic peptides

-

Page/Page column 3-4, (2008/06/13)

A non-oxidative process is described for the formation of an intramolecular disulfide bond in precursors of the peptide or peptidomimetic type; said process comprises the preparation of a linear intermediate containing an —SH group in the S-sulfonate form and a second —SH group which is obtainable in the free form by means of acid treatment.

Process route upstream and downstream products

Process route

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

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
With ammonium acetate; pyrographite; In tetrahydrofuran; water; at 20 ℃;
85.6%
D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr(ol)

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
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;
With air;
2TFA<sub>.</sub>H-DPhe-Cys(SO<sub>3</sub>Na)-Phe-DTrp-Lys-Thr-Cys-Thr-ol

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
With disodium hydrogenphosphate; phosphoric acid; In water; acetonitrile; at 23 ℃; pH=8.3;
C<sub>49</sub>H<sub>68</sub>N<sub>10</sub>O<sub>10</sub>S<sub>2</sub>

C49H68N10O10S2

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
With ammonia; dihydrogen peroxide; In methanol; at 25 ℃; for 1h; pH=7.5 - 8;
C<sub>67</sub>H<sub>86</sub>N<sub>12</sub>O<sub>18</sub>S<sub>2</sub>

C67H86N12O18S2

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
With O-Methylhydroxylamin; 2,2'-dipyridyldisulphide; In aq. phosphate buffer; acetonitrile; at 30 ℃; for 0.5h; pH=7.4; regioselective reaction; UV-irradiation;
H-DPhe-Cys(SO<sub>3</sub>Na)-Phe-DTrp-Lys-Thr-Cys-Thr-ol

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
for 24 - 72h; pH=3 - 9.2; Product distribution / selectivity;
76.4%
C<sub>55</sub>H<sub>78</sub>N<sub>12</sub>O<sub>12</sub>S<sub>2</sub>

C55H78N12O12S2

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: mercury acetate; acetic acid / H2O
2: H2O2; ammonia / methanol / 1 h / 25 °C / pH 7.5 - 8
With mercury(II) diacetate; ammonia; dihydrogen peroxide; acetic acid; In methanol; water;
Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: air
With air;
Togni's reagent II
887144-94-7

Togni's reagent II

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-ol

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

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-[Cys-Phe-D-(2-CF<sub>3</sub>)Trp-Lys-Thr-Cys]-Thr-ol

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
In methanol; at -78 ℃; for 12h;
Togni's reagent
887144-97-0

Togni's reagent

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-ol

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

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-[Cys-Phe-D-(2-CF<sub>3</sub>)Trp-Lys-Thr-Cys]-Thr-ol

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

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-Cys(CF<sub>3</sub>)-Phe-D-Trp-Lys-Thr-Cys(CF<sub>3</sub>)-Thr-ol

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

CF<sub>3</sub>CO<sub>2</sub>H*H<sub>2</sub>N-(D)-Phe-Cys(CF<sub>3</sub>)-Phe-D-(2-CF<sub>3</sub>)Trp-Lys-Thr-Cys(CF<sub>3</sub>)-Thr-ol

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

octreotide
83150-76-9

octreotide

Conditions
Conditions Yield
In methanol; at -78 - 25 ℃; Inert atmosphere;
3 mg
3 mg
0.4 mg

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  • Hangzhou Hysen Pharma co.,Ltd.
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  • Shanghai Apeptide Co., Ltd.
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