Tesamorelin

Identification

Name
Tesamorelin
Accession Number
DB08869
Description

Tesamorelin is a stabilized synthetic peptide analogue of the hypothalamic peptide, Growth Hormone Releasing Hormone (GHRH) indicated for the reduction of excess abdominal fat in HIV-infected patients with lipodystrophy. Lipodystrophy is a metabolic condition characterized by insulin resistance, fat redistribution, and hyperlipidemia associated with antiretroviral therapy for HIV infection.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 5005.76
Monoisotopic: 5002.690032114
Chemical Formula
C216H360N72O63S
Synonyms
  • GHRH(1-44)
  • N-[(3E)-1-oxo-3-hexenyl]Somatoliberin (human pancreatic islet)
  • Tesamorelin
External IDs
  • TH-9507
  • TH9507

Pharmacology

Indication

Tesamorelin acetate is a synthetic analogue of human hypothalamic Growth Hormone Releasing Factor (hGRF) indicated to induce and maintain a reduction of excess abdominal fat in HIV-infected patients with lipodystrophy.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Tesamorelin stimulates growth hormone secretion, and subsequently increases IGF-1 and IGFBP-3 levels.

Mechanism of action

By acting on the pituitary cells in the brain, tesamorelin stimulates production and release of the endogenous hormone (hGRF). Tesamorelin therapy predisposes the patient to glucose intolerance and can also increase the risk of type 2 diabetes, so the drug is contraindicated in pregnancy.

TargetActionsOrganism
AGrowth hormone-releasing hormone receptor
binder
Humans
Absorption

The absolute bioavailability was determined to be less than 4% in healthy adult subjects following a 2 mg subcutaneous dose.

Volume of distribution

9.4±3.1 L/kg in healthy subjects. 10.5±6.1 L/kg in HIV-infected patients.

Protein binding
Not Available
Metabolism

No formal metabolism studies have been performed in humans.

Route of elimination
Not Available
Half-life

26 and 38 minutes in healthy subjects and HIV-infected patients, respectively.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Diarrhea, congestive heart failure, peripheral neuropathy, and loss of mobility were the four serious adverse events reported during the clinical studies

Affected organisms
  • Humans and other mammals
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.
DrugInteraction
Cortisone acetateThe serum concentration of the active metabolites of Cortisone acetate can be reduced when Cortisone acetate is used in combination with Tesamorelin resulting in a loss in efficacy.
PrednisoloneThe serum concentration of the active metabolites of Prednisolone can be reduced when Prednisolone is used in combination with Tesamorelin resulting in a loss in efficacy.
PrednisoneThe serum concentration of the active metabolites of Prednisone can be reduced when Prednisone is used in combination with Tesamorelin resulting in a loss in efficacy.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Tesamorelin acetateLGW5H38VE3901758-09-6Not applicable
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EgriftaKit1 mg/1mLSubcutaneousEmd Serono2010-12-162014-11-30US flag
EgriftaKit; Powder, for solution2 mgSubcutaneousTheratechnologiesNot applicableNot applicableCanada flag
EgriftaKit2 mg/0.5mLSubcutaneousTheratechnologies Inc.2019-07-012019-07-01US flag
EgriftaKit2 mg/2mLSubcutaneousTheratechnologies2014-04-162014-08-25US flag
EgriftaKit; Powder, for solution1 mgSubcutaneousTheratechnologies2015-06-23Not applicableCanada flag
EgriftaKit1 mg/1mLSubcutaneousTheratechnologies Inc.2014-07-142020-07-31US flag
Egrifta SvKit2 mg/0.5mLSubcutaneousTheratechnologies Inc.2019-11-04Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EgriftaTesamorelin acetate (2 mg/2mL) + Water (1 mL/1mL)KitSubcutaneousEMD Serono, Inc.2012-09-052016-10-31US flag

Categories

ATC Codes
H01AC06 — Tesamorelin
Drug Categories
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 / Glutamine and derivatives / Asparagine and derivatives / Aspartic acid and derivatives / Isoleucine and derivatives / Leucine and derivatives / Methionine and derivatives
show 25 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 46 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
polypeptide, peptide hormone (CHEBI:63626)

Chemical Identifiers

UNII
MQG94M5EEO
CAS number
218949-48-5
InChI Key
LAJJBLZKAIOLRM-YHAVXTEWSA-N
InChI
InChI=1S/C216H360N72O63S/c1-25-28-30-53-161(304)256-142(90-118-54-58-120(294)59-55-118)193(334)251-114(21)175(316)271-147(94-165(308)309)194(335)252-115(22)176(317)286-168(109(16)26-2)209(350)279-144(89-117-43-31-29-32-44-117)201(342)288-170(116(23)293)210(351)280-146(93-160(226)303)200(341)284-152(102-292)205(346)275-143(91-119-56-60-121(295)61-57-119)198(339)263-128(51-41-81-244-215(236)237)182(323)262-124(46-34-36-76-218)192(333)285-167(108(14)15)207(348)278-138(85-104(6)7)179(320)248-98-164(307)254-131(63-69-154(220)297)186(327)273-141(88-107(12)13)197(338)283-149(99-289)203(344)253-113(20)174(315)258-126(49-39-79-242-213(232)233)181(322)261-123(45-33-35-75-217)185(326)272-140(87-106(10)11)196(337)274-139(86-105(8)9)195(336)267-135(67-73-158(224)301)190(331)277-148(95-166(310)311)202(343)287-169(110(17)27-3)208(349)269-136(74-83-352-24)191(332)282-150(100-290)204(345)264-129(52-42-82-245-216(238)239)183(324)266-133(65-71-156(222)299)189(330)265-130(62-68-153(219)296)178(319)247-97-163(306)255-132(64-70-155(221)298)187(328)281-151(101-291)206(347)276-145(92-159(225)302)199(340)268-134(66-72-157(223)300)188(329)260-122(47-37-77-240-211(228)229)177(318)246-96-162(305)249-111(18)172(313)257-125(48-38-78-241-212(230)231)180(321)250-112(19)173(314)259-127(50-40-80-243-214(234)235)184(325)270-137(171(227)312)84-103(4)5/h28-32,43-44,54-61,103-116,122-152,167-170,289-295H,25-27,33-42,45-53,62-102,217-218H2,1-24H3,(H2,219,296)(H2,220,297)(H2,221,298)(H2,222,299)(H2,223,300)(H2,224,301)(H2,225,302)(H2,226,303)(H2,227,312)(H,246,318)(H,247,319)(H,248,320)(H,249,305)(H,250,321)(H,251,334)(H,252,335)(H,253,344)(H,254,307)(H,255,306)(H,256,304)(H,257,313)(H,258,315)(H,259,314)(H,260,329)(H,261,322)(H,262,323)(H,263,339)(H,264,345)(H,265,330)(H,266,324)(H,267,336)(H,268,340)(H,269,349)(H,270,325)(H,271,316)(H,272,326)(H,273,327)(H,274,337)(H,275,346)(H,276,347)(H,277,331)(H,278,348)(H,279,350)(H,280,351)(H,281,328)(H,282,332)(H,283,338)(H,284,341)(H,285,333)(H,286,317)(H,287,343)(H,288,342)(H,308,309)(H,310,311)(H4,228,229,240)(H4,230,231,241)(H4,232,233,242)(H4,234,235,243)(H4,236,237,244)(H4,238,239,245)/b30-28+/t109?,110?,111-,112-,113-,114-,115-,116?,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,167-,168-,169-,170-/m0/s1
IUPAC Name
SMILES
CC\C=C\CC(=O)N[[email protected]@H](CC1=CC=C(O)C=C1)C(=O)N[[email protected]@H](C)C(=O)N[[email protected]@H](CC(O)=O)C(=O)N[[email protected]@H](C)C(=O)N[[email protected]@H](C(C)CC)C(=O)N[[email protected]@H](CC1=CC=CC=C1)C(=O)N[[email protected]@H](C(C)O)C(=O)N[[email protected]@H](CC(N)=O)C(=O)N[[email protected]@H](CO)C(=O)N[[email protected]@H](CC1=CC=C(O)C=C1)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)N[[email protected]@H](CCCCN)C(=O)N[[email protected]@H](C(C)C)C(=O)N[[email protected]@H](CC(C)C)C(=O)NCC(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CC(C)C)C(=O)N[[email protected]@H](CO)C(=O)N[[email protected]@H](C)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)N[[email protected]@H](CCCCN)C(=O)N[[email protected]@H](CC(C)C)C(=O)N[[email protected]@H](CC(C)C)C(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CC(O)=O)C(=O)N[[email protected]@H](C(C)CC)C(=O)N[[email protected]@H](CCSC)C(=O)N[[email protected]@H](CO)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CCC(N)=O)C(=O)NCC(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CO)C(=O)N[[email protected]@H](CC(N)=O)C(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)NCC(=O)N[[email protected]@H](C)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)N[[email protected]@H](C)C(=O)N[[email protected]@H](CCCNC(N)=N)C(=O)N[[email protected]@H](CC(C)C)C(N)=O

References

General References
  1. Spooner LM, Olin JL: Tesamorelin: a growth hormone-releasing factor analogue for HIV-associated lipodystrophy. Ann Pharmacother. 2012 Feb;46(2):240-7. doi: 10.1345/aph.1Q629. Epub 2012 Jan 31. [PubMed:22298602]
  2. McLarnon A: Neuroendocrinology: Tesamorelin can improve cognitive function. Nat Rev Endocrinol. 2012 Oct;8(10):568. doi: 10.1038/nrendo.2012.151. Epub 2012 Aug 28. [PubMed:22926095]
  3. Bedimo R: Growth hormone and tesamorelin in the management of HIV-associated lipodystrophy. HIV AIDS (Auckl). 2011;3:69-79. doi: 10.2147/HIV.S14561. Epub 2011 Jul 10. [PubMed:22096409]
  4. Dhillon S: Spotlight on tesamorelin in HIV-associated lipodystrophy. BioDrugs. 2011 Dec 1;25(6):405-8. doi: 10.2165/11208290-000000000-00000. [PubMed:22050344]
  5. Garg A: Acquired and inherited lipodystrophies. N Engl J Med. 2004 Mar 18;350(12):1220-34. [PubMed:15028826]
  6. Patel A, Gandhi H, Upaganlawar A: Tesamorelin: A hope for ART-induced lipodystrophy. J Pharm Bioallied Sci. 2011 Apr;3(2):319-20. doi: 10.4103/0975-7406.80763. [PubMed:21687371]
  7. Campbell RM, Lee Y, Rivier J, Heimer EP, Felix AM, Mowles TF: GRF analogs and fragments: correlation between receptor binding, activity and structure. Peptides. 1991 May-Jun;12(3):569-74. [PubMed:1656403]
UniProt
P01286
KEGG Drug
D09015
PubChem Compound
56928011
PubChem Substance
347827804
ChemSpider
34999256
RxNav
1044584
ChEBI
63626
ChEMBL
CHEMBL1237026
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tesamorelin
AHFS Codes
  • 68:30.04 — Somatotropin Agonists*
FDA label
Download (1.53 MB)
MSDS
Download (568 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentBody Composition / HIV Lipodystrophy Syndrome / Human Growth Hormone Deficiency1
4TerminatedPreventionDiabetic Retinopathy (DR) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies2
2CompletedTreatmentAging / Mild Cognitive Impairment (MCI)1
2CompletedTreatmentHuman Growth Hormone Deficiency / Obesity, Abdominal1
2CompletedTreatmentType 2 Diabetes Mellitus1
2RecruitingTreatmentBMI >30 kg/m2 / Fatty Liver / Liver Fat / Non-Alcoholic Fatty Liver Disease (NAFLD) / Obesity, Abdominal1
2RecruitingTreatmentMild Cognitive Impairment (MCI)1
2RecruitingTreatmentPeripheral Nerve Injury (PNI)1
2TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitSubcutaneous
KitSubcutaneous1 mg/1mL
KitSubcutaneous2 mg/2mL
Kit; powder, for solutionSubcutaneous1 mg
Kit; powder, for solutionSubcutaneous2 mg
KitSubcutaneous2 mg/0.5mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7144577No2006-12-052020-07-14US flag
US7316997No2008-01-082023-08-14US flag
US5861379No1999-01-192020-05-26US flag
US8314066No2012-11-202023-08-14US flag
US8435945No2013-05-072023-08-14US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
Predicted Properties
PropertyValueSource
logP-35ChemAxon
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)12.7ChemAxon
Physiological Charge6ChemAxon
Hydrogen Acceptor Count83ChemAxon
Hydrogen Donor Count81ChemAxon
Polar Surface Area2278.76 Å2ChemAxon
Rotatable Bond Count176ChemAxon
Refractivity1314.56 m3·mol-1ChemAxon
Polarizability505.02 Å3ChemAxon
Number of Rings3ChemAxon
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

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Binder
General Function
Peptide hormone binding
Specific Function
Receptor for GRF, coupled to G proteins which activate adenylyl cyclase. Stimulates somatotroph cell growth, growth hormone gene transcription and growth hormone secretion.
Gene Name
GHRHR
Uniprot ID
Q02643
Uniprot Name
Growth hormone-releasing hormone receptor
Molecular Weight
47401.53 Da
References
  1. Spooner LM, Olin JL: Tesamorelin: a growth hormone-releasing factor analogue for HIV-associated lipodystrophy. Ann Pharmacother. 2012 Feb;46(2):240-7. doi: 10.1345/aph.1Q629. Epub 2012 Jan 31. [PubMed:22298602]

Drug created on April 30, 2013 18:36 / Updated on October 26, 2020 22:41

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