Octreotide acetate supplier | CasNO.83150-76-9

Name
Octreotide acetate
EINECS 1533716-785-6
CAS No. 83150-76-9
Article Data9
CAS DataBase
Density 1.395 g/cm³
Solubility
Melting Point
Formula C₄₉H₆₆N₁₀O₁₀S₂
Boiling Point 1447.228°C at 760 mmHg
Molecular Weight 1019.26
Flash Point 829.053 C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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?;
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

Conditions	Yield
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

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; Cyclization;
With air

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

: 83150-76-9
octreotide

Conditions

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

: C49H68N10O10S2

: 83150-76-9
octreotide

Conditions

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

: C55H78N12O12S2

: 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 View Scheme

: 18942-49-9
Boc-D-Phe-OH

: 83150-76-9
octreotide

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

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

...Expand

: C67H86N12O18S2

: 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; UV-irradiation; regioselective reaction;

: 28792-97-4
N-methyl-N-phenyl-vinylsulfonamide

: 83150-76-9
octreotide

: C58H77N11O12S3

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 4h;	89%

: Lys-Thr-Cys-Thr-ol

: 83150-76-9
octreotide

: C69H84N12O15S3

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃;	83%

: C30H34N2O8S

: 83150-76-9
octreotide

: C79H100N12O18S3

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃;	80%

: 24424-99-5
di-tert-butyl dicarbonate

: 83150-76-9
octreotide

: 119643-69-5
boc-octreotide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	70%

: 1034191-18-8
4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl acetate

: 83150-76-9
octreotide

: OctdiSIP

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	21%

: 83150-76-9
octreotide

: C49H65(18)FN10O10S2

Conditions

Conditions	Yield
With N-succinimidyl 4-[18F]fluorobenzoate In water at 20℃; pH=8.5;

: 83150-76-9
octreotide

A: C49H65(18)FN10O10S2

B: C49H64(18)F2N10O10S2

Conditions

Conditions	Yield
With N-succinimidyl 4-[18F]fluorobenzoate In water at 20℃; pH=7.0;

succinimidyl propionate-monomethoxy polyethylene glycol; MW 1000 Da: succinimidyl propionate-monomethoxy polyethylene glycol; MW 1000 Da

: 83150-76-9
octreotide

A octreotide, N-terminus mono(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate: octreotide, N-terminus mono(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate

B octreotide, Lys-mono(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate: octreotide, Lys-mono(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate

C octreotide, N-terminus, Lys di(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate: octreotide, N-terminus, Lys di(succinimidyl propionate-monomethoxy polyethylene glycol)conjugate

Conditions

Conditions	Yield
In phosphate buffer at 20℃; for 1h; pH=6.0 - 8.0; Product distribution;

...Expand

butyraldehyde-monomethoxy-polyethylene glycol; MW 2000: butyraldehyde-monomethoxy-polyethylene glycol; MW 2000

: 83150-76-9
octreotide

A mono-ALDPEG-2K-Phe1-octreotide: mono-ALDPEG-2K-Phe1-octreotide

B di-ALDPEG-2K-Phe1-octreotide: di-ALDPEG-2K-Phe1-octreotide

Conditions

Conditions	Yield
With sodium cyanoborohydride In acetate buffer at 4℃; pH=5; Product distribution;

...Expand

butyraldehyde-monomethoxy-polyethylene glycol; MW 5000: butyraldehyde-monomethoxy-polyethylene glycol; MW 5000

: 83150-76-9
octreotide

A mono-ALDPEG-5K-Phe1-octreotide: mono-ALDPEG-5K-Phe1-octreotide

B di-ALDPEG-5K-Phe1-octreotide: di-ALDPEG-5K-Phe1-octreotide

Conditions

Conditions	Yield
With sodium cyanoborohydride In acetate buffer at 4℃; pH=5; Product distribution;

...Expand

succinimidyl propionate-monomethoxy-polyethylene glycol; MW 2000: succinimidyl propionate-monomethoxy-polyethylene glycol; MW 2000

: 83150-76-9
octreotide

A mono-SPAPEG-2K-Phe1-octreotide: mono-SPAPEG-2K-Phe1-octreotide

B mono-SPAPEG-2K-Lys5-octreotide: mono-SPAPEG-2K-Lys5-octreotide

C di-SPAPEG-2K-Phe1, Lys5-octreotide: di-SPAPEG-2K-Phe1, Lys5-octreotide

Conditions

Conditions	Yield
In phosphate buffer at 20℃; for 1h; pH=6; Product distribution;

...Expand

: N-palmitoyl L-cysteinyl 2-pyridyl disulfide

: 83150-76-9
octreotide

: C87H138N12O16S4

Conditions

Conditions	Yield
Stage #1: octreotide With diothiothreitol In N,N-dimethyl-formamide at 37℃; for 0.666667h; Stage #2: N-palmitoyl L-cysteinyl 2-pyridyl disulfide In N,N-dimethyl-formamide at 25℃; for 0.5h;	5.6 mg

: 80307-12-6
4-maleimidobutyric acid N-hydroxysuccinimide ester

: 83150-76-9
octreotide

: GMB octreotide

Conditions

Conditions	Yield
With acetic acid In dimethyl sulfoxide for 1h;

: 112-31-2
caprinaldehyde

: 83150-76-9
octreotide

: decanal-octreotide

Conditions

Conditions	Yield
With sodium cyanoborohydride at 4℃; pH=5; Aqueous acetate buffer;

: 83150-76-9
octreotide

: C49H66N10O11S2

Conditions

Conditions	Yield
With oxygen In aq. acetate buffer pH=6.9; UV-irradiation;

: 83150-76-9
octreotide

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

Conditions

Conditions	Yield
With tris(2-carboxyethyl)phosphine at 20℃; for 1h; Inert atmosphere;

: 98026-79-0
3-bromo-1H-pyrrole-2,5-dione

: 83150-76-9
octreotide

: C57H70N12O14S2

Conditions

Conditions	Yield
Stage #1: octreotide With tris(2-carboxyethyl)phosphine In aq. phosphate buffer at 37℃; for 1h; pH=6.2; Stage #2: 3-bromo-1H-pyrrole-2,5-dione In aq. phosphate buffer at 20℃; for 0.583333h;	70 %Chromat.

: 83150-76-9
octreotide

: C59H76N12O14S4

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tris(2-carboxyethyl)phosphine / aq. phosphate buffer / 1 h / 37 °C / pH 6.2 1.2: 0.58 h / 20 °C 2.1: aq. phosphate buffer / 0.5 h View Scheme

Octreotide acetate History

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

Octreotide acetate 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.

Product Name

Octreotide acetate

Synthetic route

Octreotide acetate History

Octreotide acetate Specification

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