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Octreotide acetate
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83150-76-9 Usage

Manufacturing Process

Synthesis of octreotide and derivative thereof can be carried out by two methods. The first method is synthesized initially by fragment condensation solution phase procedures. The synthetic process of octreotide has been described by Bauer et al. (1). The second method is the synthese by solidphase procedures. Edward et al. (2) isolated side chain protected octreotide with a total yield of 14% by cleaving the protected peptide from the resin with threoninol. Arano et al. (3) carried out another solid phase method for octreotide. and produced it in overall 31.8% yield based on the starting FmocThr(tBu)-ol-resin. The basic difference from the other procedures already described is that the introduction of the threoninol is carried out upon the protected peptidic structure (resin-free), which, when appropriately activated, leads quantitatively and without needing to make temporary protections upon the threoninol, to the protected precursor of octreotide, which in turn, with a simple acid treatment leads to octreotide with very high yields.At first the Fmoc-Cys-Cl-trityl-resin was prepared. The incorporation of the Fmoc-Cys(trt)-OH residue upon 2Cl-Trt resin is accomplished with an excess of 1 eq. of Fmoc-Cys(Trt) and 2.5 eq. of N,N'-diisopropylethylamine (DIEA).2.93 g (5.0 mmol) of Fmoc-Cys(Trt) are incorporated upon 5 g of resin (f = 1.28 mmol/g of resin, 6.4 mmol). The resin and the amino acid are weighed in separate containers and left to dry in a vacuum with KOH, for a minimum of two hours. A 1/1 solution of DIEA and CH2Cl2 (DCM) (dry on a 4A sieve) is prepared. The already dry amino acid is dissolved with dry DCM at a concentration of 0.1 g of resin per ml, adding the minimum quantity of dry DMF to complete the dissolution. 1/3 of the 1.8 ml (12.5 mmol) DIEA solution is added to this transparent solution in 1.8 ml of DCM. This is thoroughly homogenized and added to the dry resin. It is subjected to vigorous magnetic agitation for five minutes and the rest of the DIEA is added to the reaction; the mixture is allowed to react for forty minutes more. Then, 4 ml of dry MeOH are added and allowed to react for 10 minutes, after which the resin is filtered and the washings described below are carried out.

Clinical Use

Octreotide acetate is used by SC injection in the palliative treatment of patients with metastatic carcinoid tumors, which are tumors of the endocrine system, GI tract, and lung (gastroenteropancreatic). Carcinoid tumors secrete increasing amounts of vasoactive substances, including histamine, serotonin, bradykinin, and prostaglandins. Octreotide acetate inhibits or suppresses the release of these vasoactive substances and, thus, is useful in treating the severe diarrhea, facial flushing, and wheezing episodes that accompany carcinoid tumors. In addition, it finds use in the palliative management of VIP-secreting tumors (VIPomas, usually pancreatic tumors). Patients with VIPomas suffer a profuse, watery diarrhea syndrome, and octreotide acetate is able to help by decreasing the release of damaging intestinal tumor cell secretions. Octreotide also helps to reduce hypokalemia by correcting electrolyte imbalances.An excessive secretion of GH from the pituitary can cause the disorder known as acromegaly, which is characterized by a progressive enlargement of the head, face, hands, feet, and thorax. Inasmuch as octreotide acetate is able to decrease the secretion of GH from the pituitary, it is used in treating patients with acromegaly who are unresponsive to previous pituitary radiation therapy or surgery. It is used in the treatment of acromegaly, because it reduces the blood levels of both GH and insulin-like growth factor-I (IGF-I). The long-acting repository form of octreotide acetate also is used in treating acromegaly, carcinoid tumors, and VIPomas, but in monthly depot injections.Octreotide for IV injection is used in the treatment of acute bleeding from esophageal varices. Variceal bleeding occurs in about half the patients with cirrhosis of the liver and is responsible for about one-third of deaths in these patients. Octreotide is a potent vasoconstrictor that reduces portal and collateral blood flow by constricting visceral vessels, which leads to reduced portal blood pressure and decreases the bleeding.

Originator

Sandoz (Switzerland)

Veterinary Drugs and Treatments

Octreotide may be useful in the adjunctive treatment of hyperinsulinemia in patients with insulinomas (especially dogs, ferrets). Response is variable, presumably dependent on whether the tumor cells have receptors for somatostatin. Octreotide may also be useful in the diagnosis and symptomatic treatment of gastrinomas in dogs or cats. It may be of use in the treatment of acute pancreatitis, but more research is needed before it can be recommended for this use in veterinary patients.

Biological Functions

Octreotide acetate, a long-acting octapeptide analogue of somatostatin, has a half-life of approximately 100 minutes. A comparison of the primary structures of octreotide and somatostatin suggests little similarity, but from earlier work at the Salk Institute it was known that not all the residues in somatostatin were necessary to elicit its full biological activity. Other studies suggested that the essential fragment for its activity was the tetrapeptide Phe7-Trp8- Lys9-Thr10. These earlier studies helped in the design of the potent drug now known as octreotide acetate. This drug suppresses the secretion of gastroenteropancreatic peptides, such as gastrin, vasoactive intestinal peptide (VIP), insulin, and glucagon, as well as pituitary GH. Furthermore, it is more potent than natural somatostatin in inhibiting the release of glucagon, insulin, and GH.

Indications

Octreotide acetate (Sandostatin) is a synthetic peptide analogue of the hormone somatostatin. Its actions include inhibition of the pituitary secretion of growth hormone and an inhibition of pancreatic islet cell secretion of insulin and glucagon. Unlike somatostatin, which has a plasma half-life of a few minutes, octreotide has a plasma elimination half-life of 1 to 2 hours. Excretion of the drug is primarily renal.

Description

Octreotide is a long-acting somatostatin analog indicated for symptomatic control in acromegaly and gastroenteropancreatic tumors. Other potential uses under investigation include diabetes, psoriasis and Alzheimer's disease.

Therapeutic Function

Antiulcer, Growth hormone inhibitor

Brand name

Sandostatin (Novartis).

Uses

Antisecretory (gastric).
InChI:InChI=1/C49H66N10O10S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+;/m1./s1

83150-76-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name Octreotide acetate

1.2 Other means of identification

Product number -
Other names ctreotide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:83150-76-9 SDS

83150-76-9Synthetic 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
ConditionsYield
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
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

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

octreotide
83150-76-9

octreotide

Conditions
ConditionsYield
for 24 - 72h; pH=3 - 9.2; Product distribution / selectivity;76.4%
C49H68N10O10S2

C49H68N10O10S2

octreotide
83150-76-9

octreotide

Conditions
ConditionsYield
With ammonia; dihydrogen peroxide In methanol at 25℃; for 1h; pH=7.5 - 8;
C55H78N12O12S2

C55H78N12O12S2

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

Boc-D-Phe-OH

octreotide
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

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

octreotide
83150-76-9

octreotide

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

Togni's reagent

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

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

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

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

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

D

octreotide
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
Togni's reagent II
887144-94-7

Togni's reagent II

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

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

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

B

octreotide
83150-76-9

octreotide

Conditions
ConditionsYield
In methanol at -78℃; for 12h;
C67H86N12O18S2

C67H86N12O18S2

octreotide
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;
N-methyl-N-phenyl-vinylsulfonamide
28792-97-4

N-methyl-N-phenyl-vinylsulfonamide

octreotide
83150-76-9

octreotide

C58H77N11O12S3

C58H77N11O12S3

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 4h;89%
Lys-Thr-Cys-Thr-ol

Lys-Thr-Cys-Thr-ol

octreotide
83150-76-9

octreotide

C69H84N12O15S3

C69H84N12O15S3

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃;83%
C30H34N2O8S

C30H34N2O8S

octreotide
83150-76-9

octreotide

C79H100N12O18S3

C79H100N12O18S3

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃;80%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

octreotide
83150-76-9

octreotide

boc-octreotide
119643-69-5

boc-octreotide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h;70%
4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl acetate
1034191-18-8

4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl acetate

octreotide
83150-76-9

octreotide

OctdiSIP

OctdiSIP

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;21%
octreotide
83150-76-9

octreotide

C49H65(18)FN10O10S2

C49H65(18)FN10O10S2

Conditions
ConditionsYield
With N-succinimidyl 4-[18F]fluorobenzoate In water at 20℃; pH=8.5;
octreotide
83150-76-9

octreotide

A

C49H65(18)FN10O10S2

C49H65(18)FN10O10S2

B

C49H64(18)F2N10O10S2

C49H64(18)F2N10O10S2

Conditions
ConditionsYield
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

octreotide
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
ConditionsYield
In phosphate buffer at 20℃; for 1h; pH=6.0 - 8.0; Product distribution;
butyraldehyde-monomethoxy-polyethylene glycol; MW 2000

butyraldehyde-monomethoxy-polyethylene glycol; MW 2000

octreotide
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
ConditionsYield
With sodium cyanoborohydride In acetate buffer at 4℃; pH=5; Product distribution;
butyraldehyde-monomethoxy-polyethylene glycol; MW 5000

butyraldehyde-monomethoxy-polyethylene glycol; MW 5000

octreotide
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
ConditionsYield
With sodium cyanoborohydride In acetate buffer at 4℃; pH=5; Product distribution;
succinimidyl propionate-monomethoxy-polyethylene glycol; MW 2000

succinimidyl propionate-monomethoxy-polyethylene glycol; MW 2000

octreotide
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
ConditionsYield
In phosphate buffer at 20℃; for 1h; pH=6; Product distribution;
N-palmitoyl L-cysteinyl 2-pyridyl disulfide

N-palmitoyl L-cysteinyl 2-pyridyl disulfide

octreotide
83150-76-9

octreotide

C87H138N12O16S4

C87H138N12O16S4

Conditions
ConditionsYield
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
4-maleimidobutyric acid N-hydroxysuccinimide ester
80307-12-6

4-maleimidobutyric acid N-hydroxysuccinimide ester

octreotide
83150-76-9

octreotide

GMB octreotide

GMB octreotide

Conditions
ConditionsYield
With acetic acid In dimethyl sulfoxide for 1h;
caprinaldehyde
112-31-2

caprinaldehyde

octreotide
83150-76-9

octreotide

decanal-octreotide

decanal-octreotide

Conditions
ConditionsYield
With sodium cyanoborohydride at 4℃; pH=5; Aqueous acetate buffer;
octreotide
83150-76-9

octreotide

C49H66N10O11S2

C49H66N10O11S2

Conditions
ConditionsYield
With oxygen In aq. acetate buffer pH=6.9; UV-irradiation;
octreotide
83150-76-9

octreotide

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

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

Conditions
ConditionsYield
With tris(2-carboxyethyl)phosphine at 20℃; for 1h; Inert atmosphere;
3-bromo-1H-pyrrole-2,5-dione
98026-79-0

3-bromo-1H-pyrrole-2,5-dione

octreotide
83150-76-9

octreotide

C57H70N12O14S2

C57H70N12O14S2

Conditions
ConditionsYield
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.
octreotide
83150-76-9

octreotide

C59H76N12O14S4

C59H76N12O14S4

Conditions
ConditionsYield
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
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