Dibenzazepine
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MedKoo CAT#: 407112

CAS#: 209984-56-5

Description: Dibenzazepine, also known as YO-01027 and Iminostilbene, is a potent γ-secretase inhibitor. Dibenzazepine also potently blocks amyloid precursor protein-like (APPL) and Notch cleavage. γ-Secretase is a fascinating, multi-subunit, intramembrane cleaving protease that is now being considered as a therapeutic target for a number of diseases. Potent, orally bioavailable γ-secretase inhibitors (GSIs) have been developed and tested in humans with Alzheimer's disease (AD) and cancer.


Chemical Structure

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Dibenzazepine
CAS# 209984-56-5

Theoretical Analysis

MedKoo Cat#: 407112
Name: Dibenzazepine
CAS#: 209984-56-5
Chemical Formula: C26H23F2N3O3
Exact Mass: 463.17075
Molecular Weight: 463.48
Elemental Analysis: C, 67.38; H, 5.00; F, 8.20; N, 9.07; O, 10.36

Size Price Shipping out time Quantity
10mg USD 75 Same day
25mg USD 165 Same day
50mg USD 290 Same day
100mg USD 522 Same day
200mg USD 940 Same day
500mg USD 2115 Same day
1g USD 3450 Same day
2g USD 4950 2 weeks
5g USD 9850 2 weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-07. Prices are subject to change without notice.

Dibenzazepine, purity > 98%, is in stock. The same day shipping out after order is received

Synonym: YO-01027; YO 01027; YO01027; Dibenzazepine; DBZ; Iminostilbene; Deshydroxy LY-411575.

IUPAC/Chemical Name: (S)-2-(2-(3,5-difluorophenyl)acetamido)-N-((S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)propanamide

InChi Key: QSHGISMANBKLQL-OWJWWREXSA-N

InChi Code: InChI=1S/C26H23F2N3O3/c1-15(29-23(32)13-16-11-17(27)14-18(28)12-16)25(33)30-24-21-9-4-3-7-19(21)20-8-5-6-10-22(20)31(2)26(24)34/h3-12,14-15,24H,13H2,1-2H3,(H,29,32)(H,30,33)/t15-,24-/m0/s1

SMILES Code: C[C@H](NC(CC1=CC(F)=CC(F)=C1)=O)C(N[C@@H]2C(N(C)C3=CC=CC=C3C4=CC=CC=C24)=O)=O

Appearance:
Yellow to orange 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

Preparing Stock Solutions

The following data is based on the product molecular weight 463.48 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Sanabría CM, Palma A, Cobo J, Glidewell C. Three closely related dibenzazepine carboxylic acids: hydrogen-bonded aggregation in one, two and three dimensions. Acta Crystallogr C Struct Chem. 2014 Mar;70(Pt 3):332-7. doi: 10.1107/S2053229614003568. Epub 2014 Feb 22. PubMed PMID: 24594729.

2: Zheng YH, Li FD, Tian C, Ren HL, Du J, Li HH. Notch γ-secretase inhibitor dibenzazepine attenuates angiotensin II-induced abdominal aortic aneurysm in ApoE knockout mice by multiple mechanisms. PLoS One. 2013 Dec 16;8(12):e83310. doi: 10.1371/journal.pone.0083310. eCollection 2013. PubMed PMID: 24358274; PubMed Central PMCID: PMC3865307.

3: Tsoung J, Panteleev J, Tesch M, Lautens M. Multicomponent-multicatalyst reactions (MC)(2)R: efficient dibenzazepine synthesis. Org Lett. 2014 Jan 3;16(1):110-3. doi: 10.1021/ol4030925. Epub 2013 Dec 13. PubMed PMID: 24328339.

4: Al-Tel TH, Al-Qawasmeh RA, Schmidt MF, Al-Aboudi A, Rao SN, Sabri SS, Voelter W. Rational design and synthesis of potent dibenzazepine motifs as beta-secretase inhibitors. J Med Chem. 2009 Oct 22;52(20):6484-8. doi: 10.1021/jm9008482. PubMed PMID: 19788239.

5: Al-Qawasmeh RA, Lee Y, Cao MY, Gu X, Viau S, Lightfoot J, Wright JA, Young AH. 11-Phenyl-[b,e]-dibenzazepine compounds: novel antitumor agents. Bioorg Med Chem Lett. 2009 Jan 1;19(1):104-7. doi: 10.1016/j.bmcl.2008.11.001. Epub 2008 Nov 6. PubMed PMID: 19027297.

6: Syeda A, Mahesh HR, Syed AA. 2,2'-Bipyridine as a new and sensitive spectrophotometric reagent for the determination of nanoamounts of certain dibenzazepine class of tricyclic antidepressant drugs. Farmaco. 2005 Jan;60(1):47-51. Epub 2004 Dec 24. PubMed PMID: 15652369.

7: Dardonville C, Jimeno ML, Alkorta I, Elguero J. Homoheteroaromaticity: the case study of azepine and dibenzazepine. Org Biomol Chem. 2004 Jun 7;2(11):1587-91. Epub 2004 May 11. PubMed PMID: 15162209.

8: Li R, Tränkle C, Mohr K, Holzgrabe U. Hexamethonium-type allosteric modulators of the muscarinic receptors bearing lateral dibenzazepine moieties. Arch Pharm (Weinheim). 2001 Apr;334(4):121-4. PubMed PMID: 11382147.

9: Brusova EG, Likhosherstov AM, Gritsenko AN. [The interaction of dialkylaminoacyl derivatives of phenothiazine, dibenzazepine and dibenzdiazepine with opiate receptors]. Eksp Klin Farmakol. 1996 Mar-Apr;59(2):20-3. Russian. PubMed PMID: 8974557.

10: Bruhwyler J, Liégeois JF, Lejeune C, Rogister F, Delarge J, Géczy J. New dibenzazepine derivatives with disinhibitory and/or antidepressant potential: neurochemical and behavioural study in the open-field and forced swimming tests. Behav Pharmacol. 1995 Dec;6(8):830-838. PubMed PMID: 11224387.

11: Radwańska A, Frackowiak T, Ibrahim H, Aubry AF, Kaliszan R. Chromatographic modelling of interactions between melanin and phenothiazine and dibenzazepine drugs. Biomed Chromatogr. 1995 Sep-Oct;9(5):233-7. PubMed PMID: 8593425.

12: Liégeois JF, Rogister F, Delarge J, Pincemail J. Peroxidase-catalysed oxidation of different dibenzazepine derivatives. Arch Pharm (Weinheim). 1995 Feb;328(2):109-12. PubMed PMID: 7726734.

13: Brusova EG. [Effects of phenothiazine and dibenzazepine derivatives on the muscarinic cholinergic system]. Biull Eksp Biol Med. 1992 Jan;113(1):60-2. Russian. PubMed PMID: 1391868.

14: Hussein SA, El-Kommos ME, Hassan HY, Mohamed AM. Spectrophotometric determination of some dibenzazepine drugs by electrophilic coupling. Talanta. 1989 Sep;36(9):941-4. PubMed PMID: 18964837.

15: Lavoie PA, Tiberi M. Inhibition of fast axonal transport in bullfrog nerves by dibenzazepine and dibenzocycloheptadiene calmodulin inhibitors. J Neurobiol. 1986 Nov;17(6):681-95. PubMed PMID: 2432170.

16: Senova ZP, Lyskovtsev VV, Grigor'eva EK, Gorbunova VV, Kaverina NV. [Anti-arrhythmia and antifibrillatory properties of dibenzazepine derivatives]. Kardiologiia. 1986 Aug;26(8):24-8. Russian. PubMed PMID: 3761845.

17: Berdiaev SIu, Marko R, Kelemen K, Darinskiĭ NV, Kaverina NV. [Electrophysiologic research on the anti-arrhythmia properties of bonnecor--a new dibenzazepine derivative]. Kardiologiia. 1986 Aug;26(8):16-9. Russian. PubMed PMID: 3531669.

18: Mori M, Fujita M, Kozuka H. The effect of phenothiazine and dibenzazepine pretreatment on the metabolism of methamphetamine in rats. J Pharm Pharmacol. 1985 Nov;37(11):819-20. PubMed PMID: 2867166.

19: Oxenkrug GF. Equal inhibitory effect of dimethyl- and monomethyl-beta-aminopropionylic derivatives of dibenzazepine on the uptake of [3H]noradrenaline by rat brain synaptosomes. Biochem Pharmacol. 1979 Mar 15;28(6):938-9. PubMed PMID: 454490.

20: Beyer KH, Wagemann A. [The influence of some carbamazepin metabolites on Nielsen's quantitative determination. 5th communication: on chemistry and analytics of dibenzazepine derivatives (author's transl)]. Arzneimittelforschung. 1978;28(2):246-8. German. PubMed PMID: 580385.