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Substance Name: Protirelin [USAN:INN:BAN:JAN]
RN: 24305-27-9
UNII: 5Y5F15120W
InChIKey: XNSAINXGIQZQOO-SRVKXCTJSA-N

Note

  • A tripeptide that stimulates the release of THYROTROPIN and PROLACTIN. It is synthesized by the neurons in the PARAVENTRICULAR NUCLEUS of the HYPOTHALAMUS. After being released into the pituitary portal circulation, TRH (was called TRF) stimulates the release of TSH and PRL from the ANTERIOR PITUITARY GLAND.

Molecular Formula

  • C16-H22-N6-O4

Molecular Weight

  • 362.3878
 

Classification Codes

  • Drug / Therapeutic Agent
  • Hormone
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Prothyrotropin
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Protirelin
  • Protirelin [USAN:INN:BAN:JAN]

MeSH Heading

  • Thyrotropin-releasing hormone

Synonyms

  • 5-Oxo-L-prolyl-L-histidyl-L-prolinamide
  • Abbott 38579
  • Abbott-38579
  • CCRIS 2593
  • EINECS 246-143-4
  • FDA 1725
  • L-Pyroglutamyl-L-histidyl-L-prolineamide
  • Lopremone
  • Protirelin
  • Protirelina
  • Protirelina [INN-Spanish]
  • Protireline
  • Protireline [INN-French]
  • Protirelinum
  • Protirelinum [INN-Latin]
  • Rifathyroin
  • Ro 8-6270/9
  • Synthetic TRH
  • Synthetic tsh-releasing factor
  • Synthetic tsh-releasing hormone
  • Thypinone
  • Thyrel TRH
  • Thyroid releasing hormone
  • Thyroliberin
  • Thyrothropin relasing hormone
  • Thyrotropic releasing hormone
  • Thyrotropic-releasing factor
  • Thyrotropin releasing hormone
  • Thyrotropin-releasing factor
  • Thyrotropin-releasing hormone
  • TRH
  • TSH-releasing factor
  • TSH-releasing hormone
  • UNII-5Y5F15120W

Systematic Names

  • L-Prolinamide, 5-oxo-L-prolyl-L-histidyl-
  • L-Pyroglutamyl-L-histidinyl-L-prolinamide
  • Protirelin

Registry Numbers

CAS Registry Number

  • 24305-27-9

FDA UNII

  • 5Y5F15120W

Other Registry Numbers

  • 22365-02-2
  • 22365-17-9
  • 39422-15-6
  • 77666-61-6
  • 9015-91-2

Related Registry Number

  • 53935-32-3 (1:1 tartrate)

System Generated Number

  • 0024305279

Structure Descriptors

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

InChIKey

XNSAINXGIQZQOO-SRVKXCTJSA-N

Smiles

NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@@H]3CCC(=O)N3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 5333ng/kg/2M- (0.005333mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
British Medical Journal. Vol. 287, Pg. 532, 1983.
man TDLo intravenous 5714ng/kg/1M- (0.005714mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: PULSE RATE

BEHAVIORAL: COMA
Medical Journal of Australia. Vol. 143, Pg. 264, 1985.
mouse LD50 intravenous 921mg/kg (921mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
mouse LD50 subcutaneous > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
rat LD50 intravenous 514mg/kg (514mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 727, 1982.
women TDLo intravenous 8ug/kg/2M-C (0.008mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Medical Journal. Vol. 287, Pg. 532, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.46E+00 (none)   EXP
Water Solubility 3.22E+04 mg/L 25 EST
Vapor Pressure 5.97E-19 mm Hg 25 EST
Henry's Law Constant 3.89E-25 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.54E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.