Obinepitide

Identification

Generic Name

Obinepitide

DrugBank Accession Number

DB05045

Background

Obinepitide is a synthetic analogue of two natural human hormones, PYY and Pancreatic Polypeptide, which normally are released during a meal. These hormones are known to play a role in the regulation of food intake and appetite in man as satiety signal from the GI-tract to the CNS. In obinepitide, the properties of both of these hormones have been implanted into a single molecule.

Type

Small Molecule

Groups

Investigational

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Obinepitide (DB05045)

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Weight

Average: 4212.78
Monoisotopic: 4210.084051938

Chemical Formula

C₁₈₅H₂₈₈N₅₄O₅₅S₂

Synonyms

• (34-L-glutamine)pancreatic hormone (human)
• Obinepitide

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Pharmacology

Indication

Investigated for use/treatment in obesity.

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

TM30338 is a first-in-class compound, which in a single drug targets both the Y2 and the Y4 receptor with similar and very high potency. The Y2 and the Y4 receptors have both previously been validated in man as independent appetite suppressive drug targets through the use of the natural hormones. In pre-clinical studies in diet-induced obese animals the dual active TM30338 has demonstrated clear superiority in respect of long term reduction in body weight reduction as compared, for example, to the natural hormone PYY3-36, which only targets the Y2 receptor.

Target	Actions	Organism
UNeuropeptide Y receptor type 4	Not Available	Humans
UNeuropeptide Y receptor type 2	Not Available	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

Categories

Drug Categories

Not Available

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.

Kingdom

Organic compounds

Super Class

Organic Polymers

Class

Polypeptides

Sub Class

Not Available

Direct Parent

Polypeptides

Alternative Parents

Peptides / Tyrosine and derivatives / Arginine and derivatives / Phenylalanine and derivatives / Glutamic acid and derivatives / Glutamine and derivatives / Asparagine and derivatives / Aspartic acid and derivatives / Isoleucine and derivatives / Leucine and derivatives / Methionine and derivatives / Proline and derivatives / Valine and derivatives / N-acyl-alpha amino acids and derivatives / Tetracarboxylic acids and derivatives / Alpha amino acid amides / Alanine and derivatives / Amphetamines and derivatives / Pyrrolidinecarboxamides / N-acylpyrrolidines / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Tertiary carboxylic acid amides / Guanidines / Secondary alcohols / Amino acids / Secondary carboxylic acid amides / Primary carboxylic acid amides / Dialkylthioethers / Carboxylic acids / Carboximidamides / Azacyclic compounds / Sulfenyl compounds / Imines / Carbonyl compounds / Monoalkylamines / Organic oxides / Organopnictogen compounds / Hydrocarbon derivatives

show 29 more

Substituents

1-hydroxy-2-unsubstituted benzenoid / Alanine or derivatives / Alcohol / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amphetamine or derivatives / Arginine or derivatives / Aromatic heteromonocyclic compound / Asparagine or derivatives / Aspartic acid or derivatives / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid / Carboxylic acid derivative / Dialkylthioether / Fatty acyl / Fatty amide / Glutamic acid or derivatives / Glutamine or derivatives / Guanidine / Hydrocarbon derivative / Imine / Isoleucine or derivatives / Leucine or derivatives / Methionine or derivatives / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives / N-acyl-amine / N-acylpyrrolidine / N-substituted-alpha-amino acid / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Phenol / Phenylalanine or derivatives / Polypeptide / Primary aliphatic amine / Primary amine / Primary carboxylic acid amide / Proline or derivatives / Pyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Secondary alcohol / Secondary carboxylic acid amide / Sulfenyl compound / Tertiary carboxylic acid amide / Tetracarboxylic acid or derivatives / Thioether / Tyrosine or derivatives / Valine or derivatives

show 53 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

926PP306RV

CAS number

348119-84-6

InChI Key

LDUARVOCMXITCM-ILMFCTMOSA-N

InChI

InChI=1S/C185H288N54O55S2/c1-20-91(10)144(176(289)230-125(83-137(191)250)166(279)218-116(64-74-296-19)161(274)224-121(77-89(6)7)169(282)234-145(97(16)240)177(290)220-110(32-24-68-204-185(199)200)154(267)215-112(54-59-134(188)247)157(270)213-108(30-22-66-202-183(195)196)155(268)222-118(147(192)260)78-99-37-45-103(242)46-38-99)233-170(283)123(80-101-41-49-105(244)50-42-101)227-156(269)109(31-23-67-203-184(197)198)212-153(266)107(29-21-65-201-182(193)194)214-164(277)119(75-87(2)3)225-168(281)127(85-142(258)259)223-150(263)94(13)206-148(261)93(12)208-162(275)122(79-100-39-47-104(243)48-40-100)226-160(273)111(53-58-133(187)246)211-149(262)95(14)207-152(265)115(63-73-295-18)217-158(271)113(55-60-135(189)248)216-159(272)114(56-61-139(252)253)219-172(285)131-35-28-72-239(131)181(294)146(98(17)241)235-151(264)96(15)209-163(276)124(82-136(190)249)228-167(280)126(84-141(256)257)210-138(251)86-205-171(284)129-33-25-70-237(129)180(293)128(81-102-43-51-106(245)52-44-102)231-175(288)143(90(8)9)232-174(287)132-36-27-71-238(132)179(292)117(57-62-140(254)255)221-165(278)120(76-88(4)5)229-173(286)130-34-26-69-236(130)178(291)92(11)186/h37-52,87-98,107-132,143-146,240-245H,20-36,53-86,186H2,1-19H3,(H2,187,246)(H2,188,247)(H2,189,248)(H2,190,249)(H2,191,250)(H2,192,260)(H,205,284)(H,206,261)(H,207,265)(H,208,275)(H,209,276)(H,210,251)(H,211,262)(H,212,266)(H,213,270)(H,214,277)(H,215,267)(H,216,272)(H,217,271)(H,218,279)(H,219,285)(H,220,290)(H,221,278)(H,222,268)(H,223,263)(H,224,274)(H,225,281)(H,226,273)(H,227,269)(H,228,280)(H,229,286)(H,230,289)(H,231,288)(H,232,287)(H,233,283)(H,234,282)(H,235,264)(H,252,253)(H,254,255)(H,256,257)(H,258,259)(H4,193,194,201)(H4,195,196,202)(H4,197,198,203)(H4,199,200,204)/t91-,92-,93-,94-,95-,96-,97+,98+,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,143-,144-,145-,146-/m0/s1

IUPAC Name

(4S)-4-({[(2S)-1-[(2S,3R)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[2-({[(2S)-1-[(2S)-2-{[(2S)-2-({[(2S)-1-[(2S)-2-{[(2S)-2-({[(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-4-carboxybutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyethylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxypropylidene]amino}-3-hydroxybutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}butyl]-C-hydroxycarbonimidoyl}-3-(C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}butyl]-C-hydroxycarbonimidoyl}-2-hydroxypropyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-C-hydroxycarbonimidoyl}-2-(C-hydroxycarbonimidoyl)ethyl]-C-hydroxycarbonimidoyl}-2-methylbutyl]-C-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}butyl]-C-hydroxycarbonimidoyl}butyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}-2-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}-3-(C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-C-hydroxycarbonimidoyl}-3-(C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}butanoic acid

SMILES

CC[C@H](C)[C@H](N=C(O)[C@H](CC1=CC=C(O)C=C1)N=C(O)[C@H](CCCNC(N)=N)N=C(O)[C@H](CCCNC(N)=N)N=C(O)[C@H](CC(C)C)N=C(O)[C@H](CC(O)=O)N=C(O)[C@H](C)N=C(O)[C@H](C)N=C(O)[C@H](CC1=CC=C(O)C=C1)N=C(O)[C@H](CCC(O)=N)N=C(O)[C@H](C)N=C(O)[C@H](CCSC)N=C(O)[C@H](CCC(O)=N)N=C(O)[C@H](CCC(O)=O)N=C(O)[C@@H]1CCCN1C(=O)[C@@H](N=C(O)[C@H](C)N=C(O)[C@H](CC(O)=N)N=C(O)[C@H](CC(O)=O)N=C(O)CN=C(O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=C(O)C=C1)N=C(O)[C@@H](N=C(O)[C@@H]1CCCN1C(=O)[C@H](CCC(O)=O)N=C(O)[C@H](CC(C)C)N=C(O)[C@@H]1CCCN1C(=O)[C@H](C)N)C(C)C)[C@@H](C)O)C(O)=N[C@@H](CC(O)=N)C(O)=N[C@@H](CCSC)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H]([C@@H](C)O)C(O)=N[C@@H](CCCNC(N)=N)C(O)=N[C@@H](CCC(O)=N)C(O)=N[C@@H](CCCNC(N)=N)C(O)=N[C@@H](CC1=CC=C(O)C=C1)C(O)=N

References

General References

Not Available

External Links

PubChem Compound

131704295

PubChem Substance

347827706

ChemSpider

44241190

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
logP	3.53	Chemaxon
pKa (Strongest Acidic)	2.81	Chemaxon
pKa (Strongest Basic)	12.48	Chemaxon
Physiological Charge	-4	Chemaxon
Hydrogen Acceptor Count	105	Chemaxon
Hydrogen Donor Count	66	Chemaxon
Polar Surface Area	1900.21 Å2	Chemaxon
Rotatable Bond Count	131	Chemaxon
Refractivity	1172.81 m3·mol-1	Chemaxon
Polarizability	441.47 Å3	Chemaxon
Number of Rings	8	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Neuropeptide Y receptor type 4

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Peptide yy receptor activity

Specific Function

Receptor for neuropeptide Y and peptide YY. The rank order of affinity of this receptor for pancreatic polypeptides is PP, PP (2-36) and [Ile-31, Gln-34] PP > [Pro-34] PYY > PYY and [Leu-31, Pro-34...

Gene Name

NPY4R

Uniprot ID

P50391

Uniprot Name

Neuropeptide Y receptor type 4

Molecular Weight

42194.55 Da

Details2. Neuropeptide Y receptor type 2

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Receptor activity

Specific Function

Receptor for neuropeptide Y and peptide YY. The rank order of affinity of this receptor for pancreatic polypeptides is PYY > NPY > PYY (3-36) > NPY (2-36) > [Ile-31, Gln-34] PP > [Leu-31, Pro-34] N...

Gene Name

NPY2R

Uniprot ID

P49146

Uniprot Name

Neuropeptide Y receptor type 2

Molecular Weight

42730.69 Da

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Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51