Corticorelin ovine triflutate

Identification

Summary

Corticorelin ovine triflutate is a synthetic corticotropin-releasing hormone used for diagnostic purposes in differentiating pituitary and ectopic production of ACTH in patients with ACTH-dependent Cushing's syndrome.

Brand Names
Acthrel
Generic Name
Corticorelin ovine triflutate
DrugBank Accession Number
DB09067
Background

Corticorelin, available commercially as corticorelin ovine triflutate (tradename Acthrel), is a synthetic form of the peptide human corticotropin-releasing hormone (hCRH), a potent stimulator of adrenocorticotropic hormone (ACTH) release from the anterior pituitary. Endogenous forms hCRH are involved in the stress response and its main function is stimulation of the pituitary to release ACTH.

It is used as a diagnostic agent to evaluate the status of the pituitary-adrenal axis in the differentiation of a pituitary source from an ectopic source of excessive ACTH secretion. It provides a differential diagnosis for Cushing's disease (a pituitary source of ACTH excess) or of ectopic ACTH syndrome (an ectopic source of ACTH excess). If corticorelin injection results in an increase of plasma ACTH and cortisol, the patient is diagnosed with Cushing's disease. However, if corticorelin injection does not result in an increase of plasma ACTH and cortisol, the patient is diagnosed with ectopic ACTH syndrome.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 4670.38
Monoisotopic: 4667.485744386
Chemical Formula
C205H339N59O63S
Synonyms
  • Corticorelin ovine
  • Corticorelin ovine triflutate
  • Corticorelin triflutate
  • Corticotropin-releasing factor (sheep hypothalamus)
  • Corticotropin-releasing factor (sheep)
  • Ovine ACTH releasing factor
  • Ovine corticotropin-releasing factor
  • Ovine CRF 41
  • Ovine CRH
  • Sheep corticotropin-releasing factor
  • Sheep corticotropin-releasing factor (1-41)

Pharmacology

Indication

Corticorelin is indicated for use in differentiating pituitary and ectopic production of ACTH in patients with ACTH-dependent Cushing's syndrome.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

In normal subjects, intravenous administration of corticorelin results in a rapid and sustained increase of plasma ACTH levels and a near parallel increase of plasma cortisol. In addition, intravenous administration of corticorelin to normal subjects causes a concomitant and prolonged release of the related proopiomelanocortin peptides β- and γ-lipotropins (β -and γ-LPH) and β-endorphin (β -END).

Mechanism of action

Corticorelin is a potent stimulator of adrenocorticotropic hormone (ACTH) release from the anterior pituitary. It is used as a diagnostic agent to evaluate the status of the pituitary-adrenal axis in the differentiation of a pituitary source from an ectopic source of excessive ACTH secretion.

TargetActionsOrganism
ACorticotropin-releasing factor receptor 1
ligand
Absorption

Plasma ACTH levels in normal subjects increased 2 minutes after injection of corticorelin doses of ≥0.3 mcg/kg and reached peak levels after 10-15 minutes. Plasma cortisol levels increased within 10 minutes and reached peak levels at 30 to 60 minutes.

Volume of distribution

The mean volume of distribution for IR-corticorelin is 6.2 ± 0.5 L

Protein binding

Corticorelin does not appear to be bound specifically by a circulating plasma protein.

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Plasma half-lives for IR-corticorelin are 11.6 ± 1.5 minutes (mean ± SE) for the fast component and 73 ± 8 minutes for the slow component.

Clearance

95 ± 11 L/m2/day

Adverse Effects
Medicalerrors
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Toxicity

The severity of adverse effects to a corticorelin injection appear to be dose-dependent. Dosages above 1 mcg/kg are not recommended. While few adverse effects have been observed at the 1 mcg/kg or 100 mcg dose, higher doses have been associated with transient tachycardia, decreased blood pressure, loss of consciousness, and asystole.

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
ArdeparinThe risk or severity of hypotension and sinus node depression can be increased when Ardeparin is combined with Corticorelin ovine triflutate.
Beclomethasone dipropionateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Beclomethasone dipropionate.
BemiparinThe risk or severity of hypotension and sinus node depression can be increased when Bemiparin is combined with Corticorelin ovine triflutate.
BetamethasoneThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Betamethasone.
Betamethasone phosphateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Betamethasone phosphate.
BudesonideThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Budesonide.
CiclesonideThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Ciclesonide.
ClobetasolThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Clobetasol.
Clobetasol propionateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Clobetasol propionate.
CorticotropinThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Corticotropin.
Interactions
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Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Corticorelinunknown305OE8862Y86784-80-7Not applicable
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ActhrelInjection, powder, lyophilized, for solution100 ug/2mLIntravenousFerring Pharmaceuticals Inc.1996-05-23Not applicableUS flag

Categories

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
Hexacarboxylic acids and derivatives / Peptides / Arginine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Glutamic acid and derivatives / Glutamine and derivatives / Asparagine and derivatives / Aspartic acid and derivatives / Isoleucine and derivatives
show 32 more
Substituents
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
show 56 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
56X54T817Q
CAS number
121249-14-7
InChI Key
QEEJLLNYQOBRRM-KSHGRFHLSA-N
InChI
InChI=1S/C205H339N59O63S/c1-30-104(21)159(198(322)225-106(23)163(214)287)259-193(317)142(87-157(285)286)253-184(308)132(77-99(11)12)246-182(306)130(75-97(7)8)244-172(296)117(46-36-38-67-207)231-170(294)118(47-39-68-221-204(215)216)233-189(313)139(84-151(213)274)251-194(318)143(91-266)256-188(312)137(82-113-88-219-93-223-113)241-165(289)108(25)227-169(293)120(51-58-147(209)270)234-173(297)121(52-59-148(210)271)229-164(288)107(24)228-179(303)128(73-95(3)4)243-176(300)123(54-61-150(212)273)236-190(314)140(85-155(281)282)242-166(290)109(26)226-168(292)116(45-35-37-66-206)239-200(324)161(110(27)268)261-178(302)126(65-72-328-29)238-174(298)124(55-62-152(275)276)237-181(305)134(79-101(15)16)254-197(321)158(103(19)20)258-177(301)125(56-63-153(277)278)235-171(295)119(48-40-69-222-205(217)218)232-180(304)129(74-96(5)6)245-183(307)131(76-98(9)10)247-187(311)138(83-114-89-220-94-224-114)250-186(310)136(81-112-43-33-32-34-44-112)255-201(325)162(111(28)269)262-192(316)135(80-102(17)18)248-191(315)141(86-156(283)284)252-185(309)133(78-100(13)14)249-195(319)144(92-267)257-199(323)160(105(22)31-2)260-196(320)145-49-41-70-263(145)203(327)146-50-42-71-264(146)202(326)127(57-64-154(279)280)240-175(299)122(53-60-149(211)272)230-167(291)115(208)90-265/h32-34,43-44,88-89,93-111,115-146,158-162,265-269H,30-31,35-42,45-87,90-92,206-208H2,1-29H3,(H2,209,270)(H2,210,271)(H2,211,272)(H2,212,273)(H2,213,274)(H2,214,287)(H,219,223)(H,220,224)(H,225,322)(H,226,292)(H,227,293)(H,228,303)(H,229,288)(H,230,291)(H,231,294)(H,232,304)(H,233,313)(H,234,297)(H,235,295)(H,236,314)(H,237,305)(H,238,298)(H,239,324)(H,240,299)(H,241,289)(H,242,290)(H,243,300)(H,244,296)(H,245,307)(H,246,306)(H,247,311)(H,248,315)(H,249,319)(H,250,310)(H,251,318)(H,252,309)(H,253,308)(H,254,321)(H,255,325)(H,256,312)(H,257,323)(H,258,301)(H,259,317)(H,260,320)(H,261,302)(H,262,316)(H,275,276)(H,277,278)(H,279,280)(H,281,282)(H,283,284)(H,285,286)(H4,215,216,221)(H4,217,218,222)/t104-,105-,106-,107-,108-,109-,110+,111+,115-,116-,117-,118-,119-,120-,121-,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-,158-,159-,160-,161-,162-/m0/s1
IUPAC Name
corticorelin
SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CO)[C@@H](C)CC)[C@@H](C)O)C(C)C)[C@@H](C)O)C(=O)N[C@@H](C)C(N)=O

References

General References
Not Available
KEGG Drug
D03592
PubChem Compound
16132344
PubChem Substance
310265000
ChemSpider
17289003
RxNav
74671
ChEBI
65307
ChEMBL
CHEMBL1201591
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Corticorelin
FDA label
Download (2.56 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic ScienceSleep Restriction1
1CompletedBasic ScienceStress1
0CompletedDiagnosticPituitary Neoplasms1
0RecruitingBasic ScienceSleep Restriction1
Not AvailableCompletedNot AvailableDependence, Cocaine1
Not AvailableNot Yet RecruitingDiagnosticCushing's Disease / Pituitary Adenomas1
Not AvailableWithdrawnBasic ScienceFunctional Dyspepsia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous100 ug/2mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-27ChemAxon
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)12.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count74ChemAxon
Hydrogen Donor Count66ChemAxon
Polar Surface Area1989.13 Å2ChemAxon
Rotatable Bond Count159ChemAxon
Refractivity1178.82 m3·mol-1ChemAxon
Polarizability485.81 Å3ChemAxon
Number of Rings5ChemAxon
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

Drugtargets
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Kind
Protein
Organism
Not Available
Pharmacological action
Yes
Actions
Ligand
General Function
G-protein coupled receptor for CRH (corticotropin-releasing factor) and UCN (urocortin). Has high affinity for CRH and UCN. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and down-stream effectors, such as adenylate cyclase. Promotes the activation of adenylate cyclase, leading to increased intracellular cAMP levels. Inhibits the activity of the calcium channel CACNA1H. Required for normal embryonic development of the adrenal gland and for normal hormonal responses to stress. Plays a role in the response to anxiogenic stimuli.
Specific Function
Corticotrophin-releasing factor receptor activity
Gene Name
CRHR1
Uniprot ID
P34998
Uniprot Name
Corticotropin-releasing factor receptor 1
Molecular Weight
50718.755 Da

Drug created on May 11, 2015 22:48 / Updated on February 21, 2021 18:52