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MedKoo Cat#: 524953 | Name: Devazepide
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Description:

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

Devazepide is a potent, and orally active CCK1 (CCK-A) receptor antagonist that displays appetite-stimulant effects. It blocks the anorectic response to CCK-8 and increases food intake in rats following systemic and i.c.v administration.

Chemical Structure

Devazepide
Devazepide
CAS#103420-77-5

Theoretical Analysis

MedKoo Cat#: 524953

Name: Devazepide

CAS#: 103420-77-5

Chemical Formula: C25H20N4O2

Exact Mass: 408.1586

Molecular Weight: 408.45

Elemental Analysis: C, 73.51; H, 4.94; N, 13.72; O, 7.83

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 #
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Synonym
Devazepide; Devacade; L 364,718; L364,718; L-364,718; L 364718; L364718; L-364718; MK 329; MK329; MK-329; ZINC01847292; ZINC 01847292; ZINC-01847292;
IUPAC/Chemical Name
(S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)indole-2-carboxamide
InChi Key
NFHRQQKPEBFUJK-HSZRJFAPSA-N
InChi Code
InChI=1S/C25H20N4O2/c1-29-21-14-8-6-12-18(21)22(16-9-3-2-4-10-16)27-23(25(29)31)28-24(30)20-15-17-11-5-7-13-19(17)26-20/h2-15,23,26H,1H3,(H,28,30)/t23-/m1/s1
SMILES Code
CN1C(=O)[C@@H](NC(=O)c2cc3ccccc3[nH]2)N=C(c4ccccc4)c5ccccc15
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, not in water
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Devazepide (L-364,718) is a potent, competitive, selective and orally active nonpeptide antagonist of cholecystokinin (CCK) receptor, with IC50s of 81 pM, 45 pM and 245 nM for rat pancreatic, bovine gallbladder and guinea pig brain CCK receptors, respectively.
In vitro activity:
The proliferation of 5637 cells was significantly inhibited (P<0.001) after incubation with 12, 25, and 50 µM devazepide for 48 and 72 h. A treatment of 25 µM devazepide for 48 h induced G1-S cell cycle arrest and apoptosis (P<0.01), and inhibited cell migration (P<0.05). By western blot assay, it was found that devazepide can down-regulate CyclinD1 expression, and up-regulate Bax, PARP1, and Cleaved Caspase-3 expression. Reference: Transl Androl Urol. 2021 May;10(5):2113-2121. https://pubmed.ncbi.nlm.nih.gov/34159092/
In vivo activity:
The aim of the study was to determine if CCK plays a role in sleep responses to feeding. After the starvation period, sleep was recorded on 2 refeeding days when the control rats (n = 8) were injected with vehicle and the experimental animals (n = 8) received intraperitoneal injections of L-364,718 (500 microg/kg, on both refeeding days). In the control group, refeeding caused increases in rapid eye movement sleep (REMS) and non-REMS (NREMS) and decreases in NREMS intensity as indicated by the slow-wave activity (SWA) of the electroencephalogram. CCK-A receptor antagonist treatment completely prevented the SWA responses and delayed the NREMS responses to refeeding; REMS responses were not simply abolished, but the amount of REMS was below baseline after the antagonist treatment. These results suggest that endogenous CCK, acting on CCK-A receptors, may play a key role in eliciting postprandial sleep. Reference: Am J Physiol Regul Integr Comp Physiol. https://pubmed.ncbi.nlm.nih.gov/11294763/
Solvent mg/mL mM
Solubility
DMSO 120.0 293.79
Ethanol 20.4 50.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 408.45 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
Formulation protocol:
1. Xu MY, Yang XP, Jin HB, Yang CX, Yang LZ. Devazepide reversed effect of sincalide against morphine on rat jejunal activities. Zhongguo Yao Li Xue Bao. 1999 May;20(5):419-22. PMID: 10678088. 2. Zhang H, Bao X, Zhang J, Hu Q, Wei B. Devazepide suppresses cell proliferation and migration, and induces apoptosis in bladder carcinoma. Transl Androl Urol. 2021 May;10(5):2113-2121. doi: 10.21037/tau-21-409. PMID: 34159092; PMCID: PMC8185656. 3. Shemyakin A, Kapás L. L-364,718, a cholecystokinin-A receptor antagonist, suppresses feeding-induced sleep in rats. Am J Physiol Regul Integr Comp Physiol. 2001 May;280(5):R1420-6. doi: 10.1152/ajpregu.2001.280.5.R1420. PMID: 11294763. 4. Carrillo J, Agra N, Fernández N, Pestaña A, Alonso J. Devazepide, a nonpeptide antagonist of CCK receptors, induces apoptosis and inhibits Ewing tumor growth. Anticancer Drugs. 2009 Aug;20(7):527-33. doi: 10.1097/CAD.0b013e32832c3a4f. PMID: 19407653.
In vitro protocol:
1. Xu MY, Yang XP, Jin HB, Yang CX, Yang LZ. Devazepide reversed effect of sincalide against morphine on rat jejunal activities. Zhongguo Yao Li Xue Bao. 1999 May;20(5):419-22. PMID: 10678088. 2. Zhang H, Bao X, Zhang J, Hu Q, Wei B. Devazepide suppresses cell proliferation and migration, and induces apoptosis in bladder carcinoma. Transl Androl Urol. 2021 May;10(5):2113-2121. doi: 10.21037/tau-21-409. PMID: 34159092; PMCID: PMC8185656.
In vivo protocol:
1. Shemyakin A, Kapás L. L-364,718, a cholecystokinin-A receptor antagonist, suppresses feeding-induced sleep in rats. Am J Physiol Regul Integr Comp Physiol. 2001 May;280(5):R1420-6. doi: 10.1152/ajpregu.2001.280.5.R1420. PMID: 11294763. 2. Carrillo J, Agra N, Fernández N, Pestaña A, Alonso J. Devazepide, a nonpeptide antagonist of CCK receptors, induces apoptosis and inhibits Ewing tumor growth. Anticancer Drugs. 2009 Aug;20(7):527-33. doi: 10.1097/CAD.0b013e32832c3a4f. PMID: 19407653.
1: Wang HH, Portincasa P, Wang DQ. The cholecystokinin-1 receptor antagonist devazepide increases cholesterol cholelithogenesis in mice. Eur J Clin Invest. 2016 Feb;46(2):158-69. doi: 10.1111/eci.12580. Epub 2016 Jan 12. PubMed PMID: 26683129. 2: Carrillo J, Agra N, Fernández N, Pestaña A, Alonso J. Devazepide, a nonpeptide antagonist of CCK receptors, induces apoptosis and inhibits Ewing tumor growth. Anticancer Drugs. 2009 Aug;20(7):527-33. doi: 10.1097/CAD.0b013e32832c3a4f. PubMed PMID: 19407653. 3: Butera PC, Briffa CF, Whitaker EE. Devazepide fails to reverse the inhibitory effect of interleukin-1beta on food intake in female rats. Physiol Behav. 2004 Oct 15;82(5):777-83. PubMed PMID: 15451641. 4: Ebenezer IS. Effects of intracerebroventricular administration of the CCK(1) receptor antagonist devazepide on food intake in rats. Eur J Pharmacol. 2002 Apr 19;441(1-2):79-82. PubMed PMID: 12007923. 5: Xu MY, Lu HM, Wang SZ, Shi WY, Wang XC, Yang DX, Yang CX, Yang LZ. Effect of devazepide reversed antagonism of CCK-8 against morphine on electrical and mechanical activities of rat duodenum in vitro. World J Gastroenterol. 1998 Dec;4(6):524-526. PubMed PMID: 11819361; PubMed Central PMCID: PMC4723444. 6: Xu MY, Yang XP, Jin HB, Yang CX, Yang LZ. Devazepide reversed effect of sincalide against morphine on rat jejunal activities. Zhongguo Yao Li Xue Bao. 1999 May;20(5):419-22. PubMed PMID: 10678088. 7: Woltman TA, Hulce M, Reidelberger RD. Relative blood-brain barrier permeabilities of the cholecystokinin receptor antagonists devazepide and A-65186 in rats. J Pharm Pharmacol. 1999 Aug;51(8):917-20. PubMed PMID: 10504030. 8: Wang L, Cardin S, Martínez V, Taché Y, Lloyd KC. Duodenal loading with glucose induces fos expression in rat brain: selective blockade by devazepide. Am J Physiol. 1999 Sep;277(3 Pt 2):R667-74. PubMed PMID: 10484482. 9: Ohlsson B, Borg K, Rehfeld JF, Ihse I, Axelson J. The effect of intermittent injections of CCK-8S and the CCK-A receptor antagonist devazepide on cell proliferation in exocrine rat pancreas. Int J Pancreatol. 1998 Dec;24(3):211-8. PubMed PMID: 9873956. 10: Ohlsson B, Rehfeld JF, Axelson J. An evaluation of the influence of devazepide and CCK-8S on the intact and resected rat liver. Eur Surg Res. 1998;30(6):378-84. PubMed PMID: 9838229. 11: Pérez C, Lucas F, Sclafani A. Devazepide, a CCK(A) antagonist, attenuates the satiating but not the preference conditioning effects of intestinal carbohydrate infusions in rats. Pharmacol Biochem Behav. 1998 Feb;59(2):451-7. PubMed PMID: 9476995. 12: Francis J, Dourish CT, Cooper SJ. Devazepide attenuates dl-fenfluramine-induced suppression of gastric emptying but not food intake in the 17 h food-deprived rat. Physiol Behav. 1997 Sep;62(3):545-50. PubMed PMID: 9272662. 13: Smeets RL, IJzerman AP, Hermsen HP, Ophorst OJ, Van Emst-de Vries SE, De Pont JJ, Willems PH. Mutational analysis of the putative devazepide binding site of the CCK(A) receptor. Eur J Pharmacol. 1997 Apr 23;325(1):93-9. PubMed PMID: 9151944. 14: Matto V, Harro J, Allikmets L. The effects of cholecystokinin A and B receptor antagonists, devazepide and L 365260, on citalopram-induced decrease of exploratory behaviour in rat. J Physiol Pharmacol. 1996 Dec;47(4):661-9. PubMed PMID: 9116333. 15: Forgue-Lafitte ME, Coudray AM, Aubert JP, Gespach C, Bara J. Devazepide (L-364718) inhibits growth and increases expression of tumor markers in HT29-S-B6 cells. C R Acad Sci III. 1996 Dec;319(12):1133-8. PubMed PMID: 9091185. 16: Francis J, Dourish CT, Cooper SJ. Lack of interaction between devazepide and 8-OH-DPAT-induced hyperphagia in the rat. Physiol Behav. 1996 Nov;60(5):1337-40. PubMed PMID: 8916191. 17: Ohlsson B, Axelson J, Rehfeld JF, Ihse I. Devazepide-induced hyperplasia in the rat liver and bile ducts. Eur Surg Res. 1996 Jul-Aug;28(4):299-305. PubMed PMID: 8813655. 18: Strohmayer AJ, Greenberg D. Devazepide increases food intake in male but not female Zucker rats. Physiol Behav. 1996 Jul;60(1):273-5. PubMed PMID: 8804675. 19: Hernando F, Fuentes JA, Ruiz-Gayo M. Impairment of stress adaptive behaviours in rats by the CCKA receptor antagonist, devazepide. Br J Pharmacol. 1996 May;118(2):400-6. PubMed PMID: 8735644; PubMed Central PMCID: PMC1909625. 20: Furuse M, Choi YH, Satoh S, Okumura J. The action of the cholecystokinin-A receptor antagonist, devazepide, on the digestive system of the chicken. Experientia. 1996 Apr 15;52(4):353-6. PubMed PMID: 8620940.