Details of the Drug

General Information of Drug (ID: DMHIDCJ)

Drug Name

Octreotide

Synonyms

Longastatin; Octreotida; Octreotidum; Sandostatine; Octreotida [Spanish]; Octreotide Acetate Salt; Octreotidum [Latin]; DRG-0115; HS-2020; Octreotide-LAR; SAN 201-995; SM 201-995; SMS 201-995; Sandostatin (TN); Sandoz 201-995; Octreotide (USAN/INN); Octreotide [USAN:INN:BAN]; SMS-201-995; Zacycloicosane-4-carboxamide acetate; D-Phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-L-cysteinyl-L-threoninol cyclic (2-7)-disulfide; 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; L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-(2-hydroxy-1-(hydroxymethyl)propyl)-, cyclic (2->7)-disulfide; 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; 10-(4-Aminobutyl)-19-((2-amino-3-phenylpropanoyl)amino)-16-benzyl-7-(1-hydroxyethyl)-N-(2-hydroxy-1-(hydroxymethyl)propyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaa;10-(4-aminobutyl)-19-[(2-amino-3-phenylpropanoyl)amino]-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide; 10-(4-aminobutyl)-19-[(2-amino-3-phenylpropanoyl)amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Acromegaly	5A60.0	Approved	[1]
Carcinoid syndrome	5B10	Approved	[2]
Diabetic retinopathy	9B71.0	Approved	[2]
Neuroendocrine cancer	2B72.1	Investigative	[2]
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Therapeutic Class

Anabolic Agents

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

1019.2

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.67C2.5 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Clearance: The total body clearance of drug is 7-10 L/h [3]
Elimination: About 32% of an oral octreotide dose is excreted into the urine and 30-40% is excreted by the liver into the feces [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.2 hours [3]
Metabolism: The drug is metabolized via the liver [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.021 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.35% [7]
Vd: The volume of distribution (Vd) of drug is 13.6 L [3]

Chemical Identifiers

Formula: C49H66N10O10S2
IUPAC Name: (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
Canonical SMILES: C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)[C@@H](CC5=CC=CC=C5)N)C(=O)N[C@H](CO)[C@@H](C)O)O
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)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
InChIKey: DEQANNDTNATYII-OULOTJBUSA-N

Cross-matching ID

PubChem CID: 448601
CAS Number: 83150-76-9
DrugBank ID: DB00104
TTD ID: D02XIY
VARIDT ID: DR01163

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Somatostatin receptor type 2 (SSTR2)	TTZ6T9E	SSR2_HUMAN	Binder	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[10]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[11]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[12]
Cholecystokinin (CCK)	OT1GCG0L	CCKN_HUMAN	Protein Interaction/Cellular Processes	[13]
Glycoprotein hormones alpha chain (CGA)	OT00U3Y3	GLHA_HUMAN	Protein Interaction/Cellular Processes	[14]
Insulin (INS)	OTZ85PDU	INS_HUMAN	Gene/Protein Processing	[15]
Insulin-like growth factor I (IGF1)	OTIIZR61	IGF1_HUMAN	Gene/Protein Processing	[16]
Prolactin (PRL)	OTWFQGX7	PRL_HUMAN	Gene/Protein Processing	[17]
Somatostatin (SST)	OTY75GQH	SMS_HUMAN	Protein Interaction/Cellular Processes	[11]
Somatotropin (GH1)	OT92RTRD	SOMA_HUMAN	Gene/Protein Processing	[18]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Acromegaly

ICD Disease Classification

5A60.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Somatostatin receptor type 2 (SSTR2)	DTT	SSTR2	9.79E-07	-0.38	-0.65
Multidrug resistance-associated protein 2 (ABCC2)	DTP	MRP2	7.16E-01	-1.28E-02	-6.06E-02

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Octreotide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylergonovine	DMBEX4O	Moderate	Decreased metabolism of Octreotide caused by Methylergonovine mediated inhibition of CYP450 enzyme.	Abortion [JA00]	[19]
Gilteritinib	DMTI0ZO	Moderate	Decreased metabolism of Octreotide caused by Gilteritinib mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[20]
Pexidartinib	DMS2J0Z	Major	Decreased metabolism of Octreotide caused by Pexidartinib mediated inhibition of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[21]
Palbociclib	DMD7L94	Moderate	Decreased metabolism of Octreotide caused by Palbociclib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[20]
Dofetilide	DMPN1TW	Moderate	Decreased metabolism of Octreotide caused by Dofetilide mediated inhibition of CYP450 enzyme.	Cardiac arrhythmia [BC9Z]	[22]
PF-04449913	DMSB068	Moderate	Decreased metabolism of Octreotide caused by PF-04449913 mediated inhibition of CYP450 enzyme.	Chronic myelomonocytic leukaemia [2A40]	[23]
Mifepristone	DMGZQEF	Moderate	Decreased metabolism of Octreotide caused by Mifepristone mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[24]
Ripretinib	DM958QB	Moderate	Decreased metabolism of Octreotide caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[25]
Avapritinib	DMK2GZX	Moderate	Decreased metabolism of Octreotide caused by Avapritinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[20]
177Lu-DOTATATE	DMT8GVU	Moderate	Interference of cell/tissue uptake of Octreotide by 177Lu-DOTATATE.	Hepatitis virus infection [1E50-1E51]	[26]
MK-1439	DM215WE	Minor	Decreased metabolism of Octreotide caused by MK-1439 mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[27]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Octreotide caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[28]
Lurbinectedin	DMEFRTZ	Moderate	Decreased metabolism of Octreotide caused by Lurbinectedin mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[29]
PF-06463922	DMKM7EW	Moderate	Decreased metabolism of Octreotide caused by PF-06463922 mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[30]
Pralsetinib	DMWU0I2	Moderate	Decreased metabolism of Octreotide caused by Pralsetinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[31]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Octreotide caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[20]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Octreotide caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[32]
Acalabrutinib	DM7GCVW	Moderate	Decreased metabolism of Octreotide caused by Acalabrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[33]
Ibrutinib	DMHZCPO	Moderate	Decreased metabolism of Octreotide caused by Ibrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[34]
Methysergide	DM1EF73	Moderate	Decreased metabolism of Octreotide caused by Methysergide mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[19]
Dihydroergotamine	DM5IKUF	Moderate	Decreased metabolism of Octreotide caused by Dihydroergotamine mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[35]
Ruxolitinib	DM7Q98D	Minor	Decreased metabolism of Octreotide caused by Ruxolitinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[20]
Oxycodone	DMXLKHV	Moderate	Decreased metabolism of Octreotide caused by Oxycodone mediated inhibition of CYP450 enzyme.	Pain [MG30-MG3Z]	[25]
Istradefylline	DM20VSK	Moderate	Decreased metabolism of Octreotide caused by Istradefylline mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[36]
Bromocriptine	DMVE3TK	Moderate	Decreased metabolism of Octreotide caused by Bromocriptine mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[37]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Octreotide caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[38]
Ergonovine	DM0VEC1	Moderate	Decreased metabolism of Octreotide caused by Ergonovine mediated inhibition of CYP450 enzyme.	Postpartum haemorrhage [JA43]	[19]
Lonafarnib	DMGM2Z6	Major	Decreased metabolism of Octreotide caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[39]
Darolutamide	DMV7YFT	Minor	Decreased metabolism of Octreotide caused by Darolutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[40]
Everolimus	DM8X2EH	Moderate	Decreased metabolism of Octreotide caused by Everolimus mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[41]
Upadacitinib	DM32B5U	Moderate	Decreased metabolism of Octreotide caused by Upadacitinib mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[42]
Fentanyl	DM8WAHT	Moderate	Decreased metabolism of Octreotide caused by Fentanyl mediated inhibition of CYP450 enzyme.	Sensation disturbance [MB40]	[43]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Octreotide caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[25]
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References

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