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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H66N10O10S2
Molecular Weight 1019.2434
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OCTREOTIDE

SMILES

C[C@]([H])([C@@]([H])(CO)N=C([C@]1([H])CSSC[C@@]([H])(C(=N[C@@]([H])(Cc2ccccc2)C(=N[C@]([H])(Cc3c[nH]c4ccccc34)C(=N[C@@]([H])(CCCCN)C(=N[C@@]([H])([C@@]([H])(C)O)C(=N1)O)O)O)O)O)N=C([C@@]([H])(Cc5ccccc5)N)O)O)O

InChI

InChIKey=DEQANNDTNATYII-OULOTJBUSA-N
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)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2876507 https://www.ncbi.nlm.nih.gov/pubmed/6128648

Octreotide (SMS 201-995, Sandostatin) is an octapeptide that exerts pharmacologic actions similar to the natural hormone, somatostatin. It was developed by Bauer and co-authors at Sandoz. It is an even more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Like somatostatin, it also suppresses LH response to GnRH, decreases splanchnic blood flow, and inhibits release of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide. By virtue of these pharmacological actions, Sandostatin has been used to treat the symptoms associated with metastatic carcinoid tumors (flushing and diarrhea), and Vasoactive Intestinal Peptide (VIP) secreting adenomas (watery diarrhea). Sandostatin substantially reduces growth hormone and/or IGF-I (somatomedin C) levels in patients with acromegaly. A radioactively labelled analogue has been used to visualize somatostatin receptors in a GRF-secreting human tumour.

CNS Activity

Curator's Comment:: Octreotide (SMS 201-995, Sandostatin) passes blood-brain barrier in vitro https://www.ncbi.nlm.nih.gov/pubmed/8008714

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SANDOSTATIN

Approved Use

Acromegaly Sandostatin® (octreotide acetate) is indicated to reduce blood levels of growth hormone and IGF-I (somatomedin C) in acromegaly patients who have had inadequate response to or cannot be treated with surgical resection, pituitary irradiation, and bromocriptine mesylate at maximally tolerated doses.

Launch Date

5.9339519E11
Primary
SANDOSTATIN

Approved Use

Carcinoid Tumors Sandostatin is indicated for the symptomatic treatment of patients with metastatic carcinoid tumors where it suppresses or inhibits the severe diarrhea and flushing episodes associated with the disease.

Launch Date

5.9339519E11
Primary
SANDOSTATIN

Approved Use

Vasoactive Intestinal Peptide Tumors (VIPomas) Sandostatin is indicated for the treatment of the profuse watery diarrhea associated with VIP-secreting tumors.

Launch Date

5.9339519E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.2 ng/mL
100 μg single, subcutaneous
dose: 100 μg
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
OCTREOTIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OCTREOTIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.2 h
100 μg single, subcutaneous
dose: 100 μg
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
OCTREOTIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
100 μg single, subcutaneous
dose: 100 μg
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
OCTREOTIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak [IC50 116.6 uM]
weak [IC50 68 uM]
yes [IC50 23 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Review article: the relative effectiveness of somatostatin and octreotide therapy in pancreatic disease.
1995 Aug
Octreotide long-acting release (LAR). A review of its pharmacological properties and therapeutic use in the management of acromegaly.
1997 Apr
In vivo and in vitro efficacy of octreotide for treatment of enteric cryptosporidiosis.
1998 Feb
Systematic review: the use of somatostatin or octreotide in refractory diarrhoea.
2001 Dec
From somatostatin to octreotide LAR: evolution of a somatostatin analogue.
2009 Dec
Octreotide in chemotherapy induced diarrhoea in colorectal cancer: a review article.
2009 Jul-Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Sandostatin® (octreotide acetate) may be administered subcutaneously or intravenously. Subcutaneous injection is the usual route of administration of Sandostatin for control of symptoms.
Acromegaly: Dosage may be initiated at 50 mcg t.i.d. Beginning with this low dose may permit adaptation to adverse gastrointestinal effects for patients who will require higher doses. IGF-I (somatomedin C) levels every 2 weeks can be used to guide titration. Alternatively, multiple growth hormone levels at 0-8 hours after Sandostatin® (octreotide acetate) administration permit more rapid titration of dose. The goal is to achieve growth hormone levels less than 5 ng/mL or IGF-I (somatomedin C) levels less than 1.9 U/mL in males and less than 2.2 U/mL in females. The dose most commonly found to be effective is 100 mcg t.i.d., but some patients require up to 500 mcg t.i.d. for maximum effectiveness. Doses greater than 300 mcg/day seldom result in additional biochemical benefit, and if an increase in dose fails to provide additional benefit, the dose should be reduced. IGF-I (somatomedin C) or growth hormone levels should be re-evaluated at 6-month intervals. Carcinoid Tumors: The suggested daily dosage of Sandostatin during the first 2 weeks of therapy ranges from 100-600 mcg/day in 2-4 divided doses (mean daily dosage is 300 mcg). VIPomas: Daily dosages of 200-300 mcg in 2-4 divided doses are recommended during the initial 2 weeks of therapy (range 150-750 mcg) to control symptoms of the disease.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment:: The proliferation of A2780/Taxol cells was gradually inhibited with increasing octreotide concentration in a concentration-dependent and time-dependent manner.
1.25-20.0 nmol/ml (A2780/Taxol ovarian cancer cells)
Name Type Language
OCTREOTIDE
INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
OCTREOTIDE [WHO-DD]
Common Name English
L-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*))-
Common Name English
OCTREOTIDE [USAN]
Common Name English
OCTREOTIDE [EP MONOGRAPH]
Common Name English
SMS-995
Code English
D-PHENYLALANYL-L-HEMICYSTYL-L-PHENYLALANYL-D-TRYPTOPHYL-L-LYSYL-L-THREONYL-L-HEMICYSTYL-L-THREONINOL CYCLIC (2->7)-DISULFIDE
Common Name English
OCTREOTIDE [INN]
Common Name English
SMS995
Code English
SMS-201-995
Code English
OCTREOTIDE [MI]
Common Name English
OCTREOTIDE [VANDF]
Common Name English
D-PHENYLALANYL-L-CYSTEINYL-L-PHENYLALANYL-D-TRYPTOPHYL-L-LYSYL-L-THREONYL-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)PROPYL)-L-CYSTEINAMIDE CYCLIC (2->7)-DISULFIDE
Common Name English
SMS 201-995
Code English
Classification Tree Code System Code
WHO-ATC H01CB02
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
WHO-VATC QH01CB02
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
FDA ORPHAN DRUG 309310
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
FDA ORPHAN DRUG 116898
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
FDA ORPHAN DRUG 114698
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
NCI_THESAURUS C62799
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
FDA ORPHAN DRUG 114598
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
FDA ORPHAN DRUG 310710
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
NDF-RT N0000175904
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
LIVERTOX 702
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
NDF-RT N0000000194
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
Code System Code Type Description
EPA CompTox
83150-76-9
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
DRUG CENTRAL
1980
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
PUBCHEM
448601
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
FDA UNII
RWM8CCW8GP
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
LACTMED
Octreotide
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
MESH
D015282
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
INN
5656
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
DRUG BANK
DB00104
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
MERCK INDEX
M8121
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
OCTREOTIDE
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1680
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
NCI_THESAURUS
C711
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
EVMPD
SUB09417MIG
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY
RXCUI
7617
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY RxNorm
CAS
83150-76-9
Created by admin on Fri Jun 25 21:06:58 UTC 2021 , Edited by admin on Fri Jun 25 21:06:58 UTC 2021
PRIMARY