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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H22N6O4
Molecular Weight 362.3837
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTIRELIN

SMILES

NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H]3CCC(=O)N3

InChI

InChIKey=XNSAINXGIQZQOO-SRVKXCTJSA-N
InChI=1S/C16H22N6O4/c17-14(24)12-2-1-5-22(12)16(26)11(6-9-7-18-8-19-9)21-15(25)10-3-4-13(23)20-10/h7-8,10-12H,1-6H2,(H2,17,24)(H,18,19)(H,20,23)(H,21,25)/t10-,11-,12-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H22N6O4
Molecular Weight 362.3837
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12683933

Protirelin is the pharmaceutically available synthetic analogue of the endogenous peptide thyrotropin-releasing hormone (TRH). It is a tri-peptide tropic hormone, released by the hypothalamus, which stimulates the release of Thyroid Stimulating Hormone (TSH) and prolactin from the anterior pituitary. Although not currently available in any FDA-approved product, protirelin is a component of the TRH Test where it is used to test the response of the anterior pituitary gland in conditions such as secondary hypothyroidism and acromegaly. TRH is indicated as an adjunctive agent in the diagnostic assessment of thyroid function. As an adjunct to other diagnostic procedures, testing with TRH (protirelin) may yield useful information in patients with pituitary or hypothalamic dysfunction. TRH is indicated as an adjunct to evaluate the effectiveness of thyrotropin suppression with a particular dose of T4 in patients with nodular or diffuse goiter. A normal TSH baseline value and a minimal difference between the 30 minute and baseline response to TRH injection would indicate adequate suppression of the pituitary secretion of TSH. TRH may be used, adjunctively, for adjustment of thyroid hormone dosage given to patients with primary hypothyroidism. A normal or slightly blunted TSH response, thirty minutes following TRH injection, would indicate adequate replacement therapy. Side effects have been reported in about 50% of the patients tested with TRH. Generally, the side effects are moor, have occurred promptly, and have persisted for only a few minutes following injection. Cardiovascular reactions: Marked changes in blood pressure, including both hypertension and hypotension with or without syncope, have been reported in a small number of patients. Endocrine reaction: Breast enlargement and leakage in lactating women for up to two or three days. Other reactions: Headaches, sometimes severe, and transient amaurosis in patients with pituitary tumors. Rarely, convulsions may occur in patients with predisposing conditions, e.g., epilepsy, brain damage. Nausea; urge to urinate; flushed sensation; light-headedness; bad taste in mouth; abdominal discomfort; and dry mouth. Less frequently reported were: Anxiety; sweating; tightness in the throat; pressure in the chest; tingling sensation; drowsiness; and allergic reactions. Pharmacologically, TRH increases the release of the thyroid stimulating hormone (TSH) from the anterior pituitary. Prolactin release is also increased. It has recently been observed that approximately 65% of acromegalic patients tested respond with a rise in circulating growth hormone levels; the clinical significance is as yet not clear. Following intravenous administration, the mean plasma half-life of protirelin in normal subjects is approximately five minutes. TSH levels rise rapidly and reach a peak at 20 to 30 minutes. The decline in TSH levels takes place more slowly, approaching baseline levels after approximately three hours.

CNS Activity

Curator's Comment: thyrotropin-releasing hormone molecule may slowly penetrate the blood-brain barrier Known to be CNS penetrant in guinea pig. Human data not available

Originator

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/4982117

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Thyrel TRH

Approved Use

Protirelin is used to test the response of the anterior pituitary gland in people who may have certain medical conditions involving the thyroid gland. Testing with this medicine may help to identify the problem or may ensure that the dose of medicine being used is correct.
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular and cellular biology of thyrotropin-releasing hormone receptors.
1996 Jan
Effects of acute prolactin manipulation on sexual drive and function in males.
2003 Dec
Neuroendocrine predictors of the evolution of depression.
2005
Treatments in depression.
2006
Attenuation of kindled seizures by intranasal delivery of neuropeptide-loaded nanoparticles.
2009 Apr
Patents

Sample Use Guides

Adults: 500 μg. Doses between 200 and 500 μg have been used. 500 μg is considered the optimum dose to give the maximum response in the greatest number of patients. Doses greater than 500 μg are unlikely to elicit a greater TSH response. Children age 6 to 16 years: 7 μg/kg body weight up to a dose of 500 μg. Infants and children up to 6 years: Experience is limited in this age group; doses of 7μg/kg have been administered.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: The effects of thyrotropin-releasing hormone (TRH) on growth hormone (GH) and gonadotropin (GtH) release, and the influences of somatostatin (SRIF), the dopamine agonist apomorphine (APO) and extracellular calcium on basal and TRH-induced GH release were examined using an in vitro perifusion system for pituitary fragments of common carp (Cyprinus carpio). Five minute pulses of different dosages of TRH stimulated a rapid and dose-dependent increase in GH release from the perifused pituitary fragments with an ED50 of 9.7 ± 2.3 nM. TRH was ineffective on GtH release.
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:00:56 GMT 2023
Edited
by admin
on Sat Dec 16 18:00:56 GMT 2023
Record UNII
5Y5F15120W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROTIRELIN
EP   INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
TRH [MI]
Common Name English
SYNTHETIC TRH
Code English
L-PYROGLUTAMYL-L-HISTIDYL-L-PROLINE-AMIDE
Common Name English
L-PROLINAMIDE, 5-OXO-L-PROLYL-L-HISTIDYL-
Systematic Name English
RELEFACT TRH
Brand Name English
THYROID RELEASING HORMONE
Common Name English
PROTIRELIN [JAN]
Common Name English
THYROLIBERIN
Common Name English
LOPREMONE
Common Name English
PROTIRELIN [ORANGE BOOK]
Common Name English
NSC-760113
Code English
THYROTROPIN-RELEASING HORMONE
Common Name English
ABBOTT-38579
Code English
THYROTROPIN RELEASING HORMONE
Common Name English
TRH
MI  
Common Name English
PROTIRELIN [USAN]
Common Name English
5-OXO-L-PROLYL-L-HISTIDYL-L-PROLINAMIDE
Systematic Name English
Protirelin [WHO-DD]
Common Name English
PROTIRELIN [MART.]
Common Name English
PROTIRELIN [VANDF]
Common Name English
THYROTROPIN-RELEASING FACTOR
Common Name English
5-OXO-PRO-HIS-PRO-NH2
Common Name English
PROTIRELIN [EP MONOGRAPH]
Common Name English
protirelin [INN]
Common Name English
PROTIRELIN, SYNTHETIC
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 75093
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
WHO-VATC QV04CJ02
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
WHO-ATC V04CJ02
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
FDA ORPHAN DRUG 5184
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
NCI_THESAURUS C76367
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
LOINC 70096-3
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
LOINC 3018-9
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C66495
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
SMS_ID
100000092191
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
MERCK INDEX
m11020
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY Merck Index
PUBCHEM
638678
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
DRUG CENTRAL
2316
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
NSC
760113
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
MESH
D013973
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
CAS
24305-27-9
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
DRUG BANK
DB09421
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
DAILYMED
5Y5F15120W
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
IUPHAR
2139
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
CHEBI
35940
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL1472
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
WIKIPEDIA
Thyrotropin-releasing hormone
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID0023533
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
INN
3335
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
EVMPD
SUB10142MIG
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
RXCUI
10580
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY RxNorm
FDA UNII
5Y5F15120W
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
246-143-4
Created by admin on Sat Dec 16 18:00:57 GMT 2023 , Edited by admin on Sat Dec 16 18:00:57 GMT 2023
PRIMARY
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