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MedKoo Cat#: 540011 | Name: Amastatin HCl
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Description:

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

Amastatin HCl is an aminopeptidase inhibitor that also induces vasoconstriction. Co-injection of microgram amounts of amastatin, an aminopeptidase inhibitor, prolonged the effect of both vasopressin and oxytocin. Amastatin did not induce large vasopressin-like behavioral effects by itself, nor did it significantly potentiate the action of 1-deamino[1,6-dicarba, 8-arginine] vasopressin (Asu-AVP), an analog that lacks the N-terminal amino group. The effect of Asu-AVP, but not that of vasopressin, was potentiated by phosphoramidon, an inhibitor of neutral metalloendopeptidase ("enkephalinase A").

Chemical Structure

Amastatin HCl
Amastatin HCl
CAS#100938-10-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 540011

Name: Amastatin HCl

CAS#: 100938-10-1 (HCl)

Chemical Formula: C21H39ClN4O8

Exact Mass: 0.0000

Molecular Weight: 511.01

Elemental Analysis: C, 49.36; H, 7.69; Cl, 6.94; N, 10.96; O, 25.05

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
67655-94-1 (free base) 100938-10-1 (HCl)
Synonym
BIMI-1803; J-000280; ZX-AFC000547; BIMI1803; J000280; ZXAFC000547; BIMI 1803; J 000280; ZX AFC000547; Amastatin HCl
IUPAC/Chemical Name
((2S,3R)-3-amino-2-hydroxy-5-methylhexanoyl)-L-valyl-L-valyl-L-aspartic acid hydrochloride
InChi Key
GBDUPCKQTDKNLS-PORDUOSCSA-N
InChi Code
InChI=1S/C21H38N4O8.ClH/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27;/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33);1H/t12-,13+,15+,16+,17+;/m1./s1
SMILES Code
O=C(O)[C@@H](NC([C@@H](NC([C@@H](NC([C@@H](O)[C@H](N)CC(C)C)=O)C(C)C)=O)C(C)C)=O)CC(O)=O.[H]Cl
Appearance
Solid powder
Purity
>95% (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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 511.01 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: Quirk WS, Harding JW, Wright JW. Amastatin and bestatin-induced dipsogenicity in the Sprague-Dawley rat. Brain Res Bull. 1987 Jul;19(1):145-7. doi: 10.1016/0361-9230(87)90178-x. PMID: 3651838. 2: Aoyagi T, Tobe H, Kojima F, Hamada M, Takeuchi T, Umezawa H. Amastatin, an inhibitor of aminopeptidase A, produced by actinomycetes. J Antibiot (Tokyo). 1978 Jun;31(6):636-8. doi: 10.7164/antibiotics.31.636. PMID: 681249. 3: Meisenberg G, Simmons WH. Amastatin potentiates the behavioral effects of vasopressin and oxytocin in mice. Peptides. 1984 May-Jun;5(3):535-9. doi: 10.1016/0196-9781(84)90083-4. PMID: 6540873. 4: Oka T, Hiranuma T, Liu XF, Ohgiya N, Iwao K, Matsumiya T. [Enkephalin- inactivating enzymes]. Nihon Yakurigaku Zasshi. 1993 Apr;101(4):197-207. Japanese. doi: 10.1254/fpj.101.4_197. PMID: 8390390. 5: Chen X, Pittman QJ. Vasopressin and amastatin induce V(1)-receptor-mediated suppression of excitatory transmission in the rat parabrachial nucleus. J Neurophysiol. 1999 Oct;82(4):1689-96. doi: 10.1152/jn.1999.82.4.1689. PMID: 10515959. 6: Sullivan MJ, Beltz TG, Johnson AK. Amastatin potentiation of drinking induced by blood-borne angiotensin: evidence for mediation by endogenous brain angiotensin. Brain Res. 1990 Mar 5;510(2):237-41. doi: 10.1016/0006-8993(90)91373-o. PMID: 2331601. 7: Tobe H, Kojima F, Aoyagi T, Umezawa H. Purification by affinity chromatography using amastatin and properties of aminopeptidase A from pig kidney. Biochim Biophys Acta. 1980 Jun 13;613(2):459-68. doi: 10.1016/0005-2744(80)90100-x. PMID: 7448199. 8: Rich DH, Moon BJ, Harbeson S. Inhibition of aminopeptidases by amastatin and bestatin derivatives. Effect of inhibitor structure on slow-binding processes. J Med Chem. 1984 Apr;27(4):417-22. doi: 10.1021/jm00370a001. PMID: 6142952. 9: Patacchini R, Maggi CA. Amastatin interferes with the antagonist properties of MEN 10,208 in the rabbit pulmonary artery but not in the hamster trachea. Eur J Pharmacol. 1993 May 12;236(1):31-7. doi: 10.1016/0014-2999(93)90223-5. PMID: 8391454. 10: Wilkes SH, Prescott JM. The slow, tight binding of bestatin and amastatin to aminopeptidases. J Biol Chem. 1985 Oct 25;260(24):13154-62. PMID: 2865258. 11: Weissmann N, Leyhausen G, Maidhof A, Tanaka W, Umezawa H, Müller WE. Mitogenic potentials of bestatin, amastatin, arphamenines A and B, FK-156 and FK-565 on spleen lymphocytes. J Antibiot (Tokyo). 1985 Jun;38(6):772-8. doi: 10.7164/antibiotics.38.772. PMID: 4019321. 12: Astolfi M, Treggiari S, Giachetti A, Meini S, Maggi CA, Manzini S. Characterization of the tachykinin NK2 receptor in the human bronchus: influence of amastatin-sensitive metabolic pathways. Br J Pharmacol. 1994 Feb;111(2):570-4. doi: 10.1111/j.1476-5381.1994.tb14775.x. PMID: 8004400; PMCID: PMC1909962. 13: Sullivan MJ, Johnson AK. Amastatin potentiates drinking elicited by osmotic stimuli: evidence for peptidergic mediation of intracellular dehydration-induced thirst. Brain Res. 1992 Sep 11;590(1-2):271-6. doi: 10.1016/0006-8993(92)91105-n. PMID: 1422835. 14: Hiranuma T, Oka T. Effects of peptidase inhibitors on the [Met5]-enkephalin hydrolysis in ileal and striatal preparations of guinea-pig: almost complete protection of degradation by the combination of amastatin, captopril and thiorphan. Jpn J Pharmacol. 1986 Aug;41(4):437-46. doi: 10.1254/jjp.41.437. PMID: 3534399. 15: Orawski AT, Simmons WH. Dipeptidase activities in rat brain synaptosomes can be distinguished on the basis of inhibition by bestatin and amastatin: identification of a kyotorphin (Tyr-Arg)-degrading enzyme. Neurochem Res. 1992 Aug;17(8):817-20. doi: 10.1007/BF00969018. PMID: 1641064. 16: Kishioka S, Miyamoto Y, Fukunaga Y, Nishida S, Yamamoto H. Effects of a mixture of peptidase inhibitors (amastatin, captopril and phosphoramidon) on Met-enkephalin-, beta-endorphin-, dynorphin-(1-13)- and electroacupuncture- induced antinociception in rats. Jpn J Pharmacol. 1994 Nov;66(3):337-45. doi: 10.1254/jjp.66.337. PMID: 7869621. 17: Hiranuma T, Kitamura K, Taniguchi T, Kobayashi T, Tamaki R, Kanai M, Akahori K, Iwao K, Oka T. Effects of three peptidase inhibitors, amastatin, captopril and phosphoramidon, on the hydrolysis of [Met5]-enkephalin-Arg6-Phe7 and other opioid peptides. Naunyn Schmiedebergs Arch Pharmacol. 1998 Mar;357(3):276-82. doi: 10.1007/pl00005168. PMID: 9550299. 18: Kim H, Lipscomb WN. X-ray crystallographic determination of the structure of bovine lens leucine aminopeptidase complexed with amastatin: formulation of a catalytic mechanism featuring a gem-diolate transition state. Biochemistry. 1993 Aug 24;32(33):8465-78. doi: 10.1021/bi00084a011. PMID: 8357796. 19: Harding JW, Felix D. The effects of the aminopeptidase inhibitors amastatin and bestatin on angiotensin-evoked neuronal activity in rat brain. Brain Res. 1987 Oct 27;424(2):299-304. doi: 10.1016/0006-8993(87)91474-0. PMID: 3676828. 20: Hiranuma T, Kitamura K, Taniguchi T, Kanai M, Arai Y, Iwao K, Oka T. Protection against dynorphin-(1-8) hydrolysis in membrane preparations by the combination of amastatin, captopril and phosphoramidon. J Pharmacol Exp Ther. 1998 Aug;286(2):863-9. PMID: 9694943.