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
Weight
Average: 4212.78
Monoisotopic: 4210.084051938
Chemical Formula
C185H288N54O55S2
Synonyms
  • (34-L-glutamine)pancreatic hormone (human)
  • Obinepitide

Pharmacology

Indication

Investigated for use/treatment in obesity.

Reduce drug development failure rates
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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.

TargetActionsOrganism
UNeuropeptide Y receptor type 4Not AvailableHumans
UNeuropeptide Y receptor type 2Not AvailableHumans
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
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
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
PubChem Compound
131704295
PubChem Substance
347827706
ChemSpider
44241190

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
logP3.53ChemAxon
pKa (Strongest Acidic)2.81ChemAxon
pKa (Strongest Basic)12.48ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count105ChemAxon
Hydrogen Donor Count66ChemAxon
Polar Surface Area1900.21 Å2ChemAxon
Rotatable Bond Count131ChemAxon
Refractivity1172.81 m3·mol-1ChemAxon
Polarizability441.47 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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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
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

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