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MedKoo Cat#: 562691 | Name: BIRT-377

Description:

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

BIRT-377 is a negative allosteric modulator of LFA-1.

Chemical Structure

BIRT-377
BIRT-377
CAS#213211-10-0

Theoretical Analysis

MedKoo Cat#: 562691

Name: BIRT-377

CAS#: 213211-10-0

Chemical Formula: C18H15BrCl2N2O2

Exact Mass: 439.9694

Molecular Weight: 442.13

Elemental Analysis: C, 48.90; H, 3.42; Br, 18.07; Cl, 16.04; N, 6.34; O, 7.24

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
BIRT-377; BIRT 377; BIRT377;
IUPAC/Chemical Name
(5R)-5-[(4-Bromophenyl)methyl]-3-(3,5-dichlorophenyl)-1,5-dimethyl-2,4-imidazolidinedione
InChi Key
FJNJHZQMQRVZEE-GOSISDBHSA-N
InChi Code
InChI=1S/C18H15BrCl2N2O2/c1-18(10-11-3-5-12(19)6-4-11)16(24)23(17(25)22(18)2)15-8-13(20)7-14(21)9-15/h3-9H,10H2,1-2H3/t18-/m1/s1
SMILES Code
O=C1N(C2=CC(Cl)=CC(Cl)=C2)C([C@@](C)(CC3=CC=C(Br)C=C3)N1C)=O
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
>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 442.13 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: Tazawa K, Koutsogiannaki S, Chamberlain M, Yuki K. The effect of different anesthetics on tumor cytotoxicity by natural killer cells. Toxicol Lett. 2017 Jan 15;266:23-31. doi: 10.1016/j.toxlet.2016.12.007. Epub 2016 Dec 8. PubMed PMID: 27940100; PubMed Central PMCID: PMC5209272. 2: Johnson A, Saunders MJ, Back TG. Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement. Org Biomol Chem. 2015 Feb 7;13(5):1463-9. doi: 10.1039/c4ob02303j. PubMed PMID: 25474271. 3: Hosseini BH, Louban I, Djandji D, Wabnitz GH, Deeg J, Bulbuc N, Samstag Y, Gunzer M, Spatz JP, Hämmerling GJ. Immune synapse formation determines interaction forces between T cells and antigen-presenting cells measured by atomic force microscopy. Proc Natl Acad Sci U S A. 2009 Oct 20;106(42):17852-7. doi: 10.1073/pnas.0905384106. Epub 2009 Oct 12. Erratum in: Proc Natl Acad Sci U S A. 2010 Feb 2;107(5):2373. PubMed PMID: 19822763; PubMed Central PMCID: PMC2764924. 4: Caviness GO, Labadia ME, Giblin PA, Woska JR Jr, Last-Barney K, Jeanfavre DD, Morelock MM. The determination and correlation of molecular and cellular equilibrium Kd and kinetic k(off) values for small molecule allosteric antagonists of LFA-1. Biochem Pharmacol. 2007 Jun 30;74(1):98-106. Epub 2007 Mar 12. PubMed PMID: 17482579. 5: Poria RB, Norenberg JP, Anderson TL, Erion J, Wagner CR, Arterburn JB, Larson RS. Characterization of a radiolabeled small molecule targeting leukocyte function-associated antigen-1 expression in lymphoma and leukemia. Cancer Biother Radiopharm. 2006 Oct;21(5):418-26. PubMed PMID: 17105416. 6: Patwardhan AP, Pulgam VR, Zhang Y, Wulff WD. Highly diastereoselective alkylation of aziridine-2-carboxylate esters: enantioselective synthesis of LFA-1 antagonist BIRT-377. Angew Chem Int Ed Engl. 2005 Sep 26;44(38):6169-72. Erratum in: Angew Chem Int Ed Engl. 2005 Dec 2;44(47):7661. PubMed PMID: 16118826. 7: Larson RS, Davis T, Bologa C, Semenuk G, Vijayan S, Li Y, Oprea T, Chigaev A, Buranda T, Wagner CR, Sklar LA. Dissociation of I domain and global conformational changes in LFA-1: refinement of small molecule-I domain structure-activity relationships. Biochemistry. 2005 Mar 22;44(11):4322-31. PubMed PMID: 15766261. 8: Chowdari NS, Barbas CF 3rd. Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter. Org Lett. 2005 Mar 3;7(5):867-70. PubMed PMID: 15727461. 9: Fraemohs L, Koenen RR, Ostermann G, Heinemann B, Weber C. The functional interaction of the beta 2 integrin lymphocyte function-associated antigen-1 with junctional adhesion molecule-A is mediated by the I domain. J Immunol. 2004 Nov 15;173(10):6259-64. PubMed PMID: 15528364. 10: Woska JR Jr, Last-Barney K, Rothlein R, Kroe RR, Reilly PL, Jeanfavre DD, Mainolfi EA, Kelly TA, Caviness GO, Fogal SE, Panzenbeck MJ, Kishimoto TK, Giblin PA. Small molecule LFA-1 antagonists compete with an anti-LFA-1 monoclonal antibody for binding to the CD11a I domain: development of a flow-cytometry-based receptor occupancy assay. J Immunol Methods. 2003 Jun 1;277(1-2):101-15. PubMed PMID: 12799043. 11: Asosingh K, Vankerkhove V, Van Riet I, Van Camp B, Vanderkerken K. Selective in vivo growth of lymphocyte function- associated antigen-1-positive murine myeloma cells. Involvement of function-associated antigen-1-mediated homotypic cell-cell adhesion. Exp Hematol. 2003 Jan;31(1):48-55. PubMed PMID: 12543106. 12: Winquist RJ, Desai S, Fogal S, Haynes NA, Nabozny GH, Reilly PL, Souza D, Panzenbeck M. The role of leukocyte function-associated antigen-1 in animal models of inflammation. Eur J Pharmacol. 2001 Oct 19;429(1-3):297-302. PubMed PMID: 11698049. 13: Woska JR Jr, Shih D, Taqueti VR, Hogg N, Kelly TA, Kishimoto TK. A small-molecule antagonist of LFA-1 blocks a conformational change important for LFA-1 function. J Leukoc Biol. 2001 Aug;70(2):329-34. PubMed PMID: 11493627. 14: Wasan KM, Ramaswamy M, Holtorf L, Jayaraj AA, Hauss DJ. Rat and rabbit plasma distribution of free and chylomicron-associated BIRT 377, a novel small molecule antagonist of LFA-1-mediated cell adhesion. Pharm Res. 2001 Apr;18(4):510-9. PubMed PMID: 11451039. 15: Kapadia SR, Spero DM, Eriksson M. An improved synthesis of chiral alpha-(4-bromobenzyl)alanine ethyl ester and its application to the synthesis of LFA-1 antagonist BIRT-377. J Org Chem. 2001 Mar 9;66(5):1903-5. PubMed PMID: 11262144. 16: Yee NK. Self-regeneration of stereocenters: a practical enantiospecific synthesis of LFA-1 antagonist BIRT-377. Org Lett. 2000 Sep 7;2(18):2781-3. PubMed PMID: 10964364. 17: Kelly TA, Jeanfavre DD, McNeil DW, Woska JR Jr, Reilly PL, Mainolfi EA, Kishimoto KM, Nabozny GH, Zinter R, Bormann BJ, Rothlein R. Cutting edge: a small molecule antagonist of LFA-1-mediated cell adhesion. J Immunol. 1999 Nov 15;163(10):5173-7. PubMed PMID: 10553036.