Octreotide

HCID 448601CAS 83150-76-9

基本情報

標準SMILES
C[C@@H](O)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@H](N)Cc2ccccc2)CSSC[C@@H](C(=O)N[C@H](CO)[C@@H](C)O)NC1=O
InChIKey
DEQANNDTNATYII-OULOTJBUSA-N
分子式
C49H66N10O10S2
平均分子量
1,019.2 g/mol
単同位体質量
1,018.44048031

概要

Acromegaly is a disorder caused by excess growth hormone (GH), increasing the growth of body tissues and causing metabolic dysfunction. In most cases, it results from an anterior pituitary growth hormone-releasing tumor. Typically, the feet, hands, and face grow abnormally large; organomegaly and insulin resistance may also occur. Acromegaly is a life-threatening disease requiring life-long management. Octreotide is a long-acting drug with pharmacologic activities that mimic those of the natural hormone, somatostatin, which inhibits the secretion of growth hormone. Additionally, it is used for the treatment of acromegaly and symptoms arising from various tumors, including carcinoid tumors and vasoactive intestinal tumors (VIPomas). In the past, octreotide has been administered solely by injection. On June 26, 2020, the first approved delayed-release oral somatostatin analog, Mycapssa, received FDA approval for the long term maintenance treatment of acromegaly. This drug was developed by Chiasma Inc.

名称と識別子

優先名称
Octreotide
IUPAC
(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

名称と別名

Octreotide83150-76-9OctreotidaOctreotidumRWM8CCW8GPSMS-201-995SMS995SMS-995DRG-0115D-Phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl)-L-cysteinamide cyclic (2->7)-disulfideDTXSID0048682L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-(2-hydroxy-1-(hydroxymethyl)propyl)-, cyclic (2-7)-disulfide, (R-(R*,R*))-
名称をさらに表示
CHEBI:7726Compound 201995Octreotide Acetate SaltRefChem:59031SMS 201995Compound 201 995Compound 201-995Sandoz 201995

データベース識別子

CAS
83150-76-9
PubChem CID
448601
DTXSID
DTXSID0048682
ChEMBL
CHEMBL1680
UNII
RWM8CCW8GP

物性

構造計算による物性

XLogP
1
極性表面積
383 Ų
水素結合供与体数
13
水素結合受容体数
14
回転可能結合数
17
重原子数
71

実験および物理化学的性質

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents, Hormonal; Gastrointestinal Agents

EMA approved medicines: Human medicine

Medicines for disorders of the pituitary hormone system

Melting Point153-156

安全と法規制

危険有害性情報

Regulatory InformationOctreotide: Does not have an individual approval but may be used under an appropriate group standard

毒性情報

Hepatotoxicity · 1 件

Mild, transient, asymptomatic elevations in serum aminotransferase levels occur in a small proportion of patients receiving octreotide, and in some individuals the elevations are persistent and worsen over time and may require drug discontinuation. In addition, several instances of acute, clinically apparent liver injury attributable to octreotide have been described. The onset is generally within 1 to 6 months of starting therapy and injury may be more frequent with higher doses. Most cases of liver injury associated with octreotide therapy have been asymptomatic and anicteric, and marked by prominent elevations in serum ALT and AST with normal or near normal serum alkaline phosphatase, GGT and bilirubin. In some instances, however, jaundice has arisen, particularly with rechallenge. There have been no instances of acute liver failure or vanishing bile duct syndrome associated with octreotide, and a characteristic feature of the injury is the rapidity of improvement upon stopping the injections or infusions. Several instances of marked aminotransferase elevations with rapid improvements on stopping have been reported in newborns and infants with congenital hyperinsulinemia who were treated with continuous infusions of high doses of octreotide.

Adverse Effects · 1 件

* Gastrointestinal abnormalities (34% to 61%) are transient and usually mild to moderate. They include diarrhea, nausea, abdominal discomfort, gallbladder abnormalities, such as cholelithiasis and microlithiasis, biliary sediment and sludge due to alteration of fat absorption, and possibly by decreasing motility of the gallbladder.

Toxicity Summary · 1 件

Limited studies have assessed octreotide toxicity. However, isolated studies have shown a mild degree of bone marrow suppression and impairment in spermatogenesis due to inhibition of serum inhibin B and concomitant increase in FSH in supratherapeutic doses. There is a need to conduct significantly larger studies and trials to define and establish the therapeutic index of octreotide and identify its toxic effects and its management.

Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

octreotide

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

ATC Code · 3 件

H - Systemic hormonal preparations, excl. sex hormones and insulins

QH - Systemic hormonal preparations, excl. sex hormones and insulin

H01CB02

Protein BindingApproximately 65% of the dose is bound in the plasma to lipoproteins and albumin.
Pharmacodynamics · 1 件

Octreotide mimics the naturally occurring hormone known as somatostatin. Like somatostatin, it demonstrates activity against growth hormone and glucagon, treating the disordered tissue growth and insulin regulation in patients with acromegaly. In addition, octreotide relieves the flushing and diarrhea associated with gastrointestinal tumors by reducing splanchnic blood flow and various gastrointestinal hormones associated with diarrhea. Product labeling warns that octreotide may reduce gallbladder contractility, bile secretion, and the release of thyroid-stimulating hormone (TSH) in healthy volunteers. In addition, reports of decreased vitamin B12 in patients treated with octreotide have been made. Ensure to monitor vitamin B12 levels in patients taking octreotide.

Mechanism of Action · 1 件

Octreotide binds to somatostatin receptors coupled to phospholipase C through G proteins and leads to smooth muscle contraction in the blood vessels. Downstream effects that stimulate phospholipase C, the production of 1, 4,5-inositol triphosphate, and action on the L-type calcium channels lead to the inhibition of growth hormone, treating the various growth-hormone and metabolic effects of acromegaly. Octreotide's suppression of luteinizing hormone (LH), reduction in splanchnic blood flow, and inhibition of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide provide relief for the gastrointestinal and flushing symptoms of carcinoid and/or VIPoma tumors.

Biological Half-Life · 1 件

After a subcutaneous dose, the plasma half-life is estimated to be 0.2 hours. The average elimination half-lives for subcutaneous and oral administration ranged from 2.3 - 2.7 hours and did not differ significantly. One pharmacokinetic study revealed a plasma half-life ranging from 72-113 minutes.

Metabolism/MetabolitesOctreotide has been reported to be heavily metabolized in the liver.

用途と製造

UsesUse (kg) in USA (2002): 1

関連反応

8 件

関連ノート

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