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MedKoo Cat#: 597824 | Name: Azetirelin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azetirelin is a TRH analog. Azetirelin has more potent effect than TRH on central nervous system.

Chemical Structure

Azetirelin
Azetirelin
CAS#95729-65-0

Theoretical Analysis

MedKoo Cat#: 597824

Name: Azetirelin

CAS#: 95729-65-0

Chemical Formula: C15H20N6O4

Exact Mass: 348.1546

Molecular Weight: 348.36

Elemental Analysis: C, 51.72; H, 5.79; N, 24.12; O, 18.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Azetirelin; Azetirelina; Azetirelinum;
IUPAC/Chemical Name
(S)-1-(((S)-4-oxoazetidine-2-carbonyl)-L-histidyl)pyrrolidine-2-carboxamide
InChi Key
WBGUMUGCONUXFK-DCAQKATOSA-N
InChi Code
InChI=1S/C15H20N6O4/c16-13(23)11-2-1-3-21(11)15(25)10(4-8-6-17-7-18-8)20-14(24)9-5-12(22)19-9/h6-7,9-11H,1-5H2,(H2,16,23)(H,17,18)(H,19,22)(H,20,24)/t9-,10-,11-/m0/s1
SMILES Code
O=C(N)[C@H]1N(C([C@H](CC2=CNC=N2)NC([C@H](C3)NC3=O)=O)=O)CCC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 348.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Sasaki I, Tamura T, Shibakawa T, Fujita T, Murakami M, Yamamoto A, Muranishi S. Metabolism of azetirelin, a new thyrotropin-releasing hormone (TRH) analogue, by intestinal microorganisms. Pharm Res. 1997 Aug;14(8):1004-7. PubMed PMID: 9279880. 2: Sasaki I, Tanaka K, Fujita T, Murakami M, Yamamoto A, Muranishi S. Intestinal absorption of azetirelin, a new thyrotropin-releasing hormone (TRH) analogue. II. In situ and in vitro absorption characteristics of azetirelin from the rat intestine. Biol Pharm Bull. 1995 Jul;18(7):976-9. PubMed PMID: 7581253. 3: Sasaki I, Tozaki H, Matsumoto K, Ito Y, Fujita T, Murakami M, Muranishi S, Yamamoto A. Development of an oral formulation of azetirelin, a new thyrotropin-releasing hormone (TRH) analogue, using n-lauryl-beta-D-maltopyranoside as an absorption enhancer. Biol Pharm Bull. 1999 Jun;22(6):611-5. PubMed PMID: 10408236. 4: Sasaki I, Fujita T, Murakami M, Yamamoto A, Nakamura E, Imasaki H, Muranishi S. Intestinal absorption of azetirelin, a new thyrotropin-releasing hormone (TRH) analogue. I. Possible factors for the low oral bioavailability in rats. Biol Pharm Bull. 1994 Sep;17(9):1256-61. PubMed PMID: 7841949. 5: Kagatani S, Inaba N, Fukui M, Sonobe T. Nasal absorption kinetic behavior of azetirelin and its enhancement by acylcarnitines in rats. Pharm Res. 1998 Jan;15(1):77-81. PubMed PMID: 9487550. 6: Azetirelin. YM 14673. Drugs R D. 1999 Aug;2(2):133-4. PubMed PMID: 10820659. 7: Urayama A, Yamada S, Deguchi Y, Ohmori Y, Kimura R. Studies on the transport of thyrotropin-releasing hormone (TRH) analogues in Caco-2 cell monolayers. J Pharm Pharmacol. 2003 May;55(5):603-8. PubMed PMID: 12831502. 8: Matsui K, Wada K, Kwak S. Ataxia-ameliorating effects of YM-14673, a potent analog of thyrotropin releasing hormone, in ataxic mutant mice. Eur J Pharmacol. 1994 Mar 21;254(3):295-7. PubMed PMID: 8013566. 9: Yamamoto M, Shimizu M. Effects of a new TRH analogue, YM-14673 on a passive avoidance test as a possible criterion of improvement in cognitive disturbance in rodents. Naunyn Schmiedebergs Arch Pharmacol. 1988 Sep;338(3):262-7. PubMed PMID: 3143078. 10: Mori M, Iriuchijima T, Yamada M, Murakami M, Kobayashi S. A novel TRH analog, YM14673, stimulates intracellular signaling systems in the brain more potently than predicted by its pituitary actions. Res Commun Chem Pathol Pharmacol. 1991 Jan;71(1):17-26. PubMed PMID: 1673800. 11: Faden AI. Comparison of single and combination drug treatment strategies in experimental brain trauma. J Neurotrauma. 1993 Summer;10(2):91-100. PubMed PMID: 8411221. 12: Yamamoto M, Shimizu M, Ozawa Y. Effects of YM-14673, a new TRH analogue, on responses to morphine in rodents. Arch Int Pharmacodyn Ther. 1989 Jul-Aug;300:29-36. PubMed PMID: 2515820. 13: Shimizu M, Yamamoto M, Kobayashi M. Effects of a new TRH analogue, YM-14673, on spontaneous motor activity in rats. Arch Int Pharmacodyn Ther. 1989 Sep-Oct;301:100-11. PubMed PMID: 2516440. 14: Puniak MA, Freeman GM, Agresta CA, Van Newkirk L, Barone CA, Salzman SK. Comparison of a serotonin antagonist, opioid antagonist, and TRH analog for the acute treatment of experimental spinal trauma. J Neurotrauma. 1991 Fall;8(3):193-203. PubMed PMID: 1803028. 15: Faden AI, Fox GB, Fan L, Araldi GL, Qiao L, Wang S, Kozikowski AP. Novel TRH analog improves motor and cognitive recovery after traumatic brain injury in rodents. Am J Physiol. 1999 Oct;277(4 Pt 2):R1196-204. PubMed PMID: 10516262. 16: Miwa Y, Koshikawa N, Miyata N, Koshida Y, Kobayashi M, Cools AR. YM-14673, a thyrotropin-releasing hormone analogue, injected into the nucleus accumbens and the striatum produces repetitive jaw movements in rats. Eur J Pharmacol. 1995 Apr 13;277(1):63-9. PubMed PMID: 7635174. 17: Kato S, Araki H, Kawauchi S, Takeuchi K. Body temperature dependency in baclofen-induced gastric acid secretion in rats relation to capsaicin-sensitive afferent neurons. Life Sci. 2001 Mar 16;68(17):1951-63. PubMed PMID: 11388698. 18: Behrmann DL, Bresnahan JC, Beattie MS. Modeling of acute spinal cord injury in the rat: neuroprotection and enhanced recovery with methylprednisolone, U-74006F and YM-14673. Exp Neurol. 1994 Mar;126(1):61-75. PubMed PMID: 8157127. 19: Yamamoto M, Iwai A, Ozawa Y. Effects of a new TRH analogue, YM-14673, on disturbance of passive avoidance learning in senescence-accelerated mice. Pharmacol Biochem Behav. 1990 Mar;35(3):727-9. PubMed PMID: 2111030. 20: Adachi K, Hirose N, Fujioka H, Yoneshige N, Koshikawa N. Effects of YM-14673, a thyrotropin-releasing hormone analogue, injected into the shell and the core of the nucleus accumbens on production of repetitive jaw movements in rats: comparison with the effects of a dopamine D1 and D2 receptor agonist combination. J Nihon Univ Sch Dent. 1997 Sep;39(3):142-6. PubMed PMID: 9354030.

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